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Meet the Americans secretly working multiple remote jobs to afford early retirement — and making up to $300K

22 May 2025 at 01:03
Rear view of a young woman sitting at a desk and working online from home on a computer
Β Secretly juggling multiple remote jobs is helping some Americans get closer to early retirement.

AJ_Watt/Getty Images

  • Some Americans are secretly working multiple remote jobs so they can retire early.
  • Four job jugglers shared how working multiple jobs has helped pad their retirement savings.
  • They also shared the downsides of working multiple jobs, including burnout.

To retire early, some Americans aren't climbing the corporate ladder to earn more β€” they're secretly working multiple remote jobs simultaneously and banking the surplus earnings.

Last year, Daniel earned about $280,000 juggling two remote roles in the medical field. Before becoming overemployed in 2021, he wasn't sure retirement was even realistic: With expenses like his children's college tuition looming, he said it was hard to put enough toward long-term savings. However, his net worth grew to $1.6 million from $1 million since 2022, and he's aiming to retire around the age of 59.

"I will be able to retire when I want, and perhaps earlier, if everything continues to fall into place," said Daniel, who's in his late 40s and based in Texas. "Before this, retirement was looking like wishful thinking."

Over the past two years, BI has interviewed more than two dozen overemployed workers like Daniel who've used their extra income to travel the world, pay down debt, and accelerate their retirement plans. These workers hope to escape the retirement challenges many Americans face β€” and protect themselves from rising costs, stock market volatility, and the potential threat of layoffs.

Four current and former job-jugglers shared how their strategies are giving them the financial means to retire earlier than initially planned. All did so on the condition that pseudonyms would be used, citing fears of professional repercussions. BI has verified their identities and earnings.

To be sure, working multiple jobs without employer approval could have professional repercussions and lead to other consequences, like burnout. But many job jugglers have told BI that the financial benefits generally outweigh the downsides and risks.

Job juggling is making early retirement possible

George, who's 39 and based in the Southeast, is on track to earn about $250,000 this year by secretly working two full-time remote IT roles. Early retirement has long been his "north star" because he hasn't enjoyed working.

Before he started job juggling about two years ago, George said he and his wife had a net worth of about $1 million, and he hoped they could reach $2.1 million by age 55. He said their net worth has since grown to $1.5 million, and he's now projecting they'll hit $3.2 million by age 48. His goal is to retire at age 50.

"I don't know that I would really stop before 50," he said. "I think I'd rather just pad the account, because I'd rather have too much than not enough."

Burnout and spending can impede overemployment

For some overemployed workers, holding multiple jobs isn't a perfect fix.

Adrian, a California-based data analyst in his early 40s, earned about $110,000 in 2023 by secretly working two full-time remote jobs. When the contract for one of his jobs came to an end last year, he decided not to look for a new role: Job juggling had become too stressful.

However, Adrian's roughly yearlong overemployment stint allowed him to make significant progress toward his retirement goals: He said he earned about $50,000 in additional income, all of which he invested in index funds that he's allocating for his retirement.

Adrian, who has about $323,000 in savings, said he's started exploring retirement plans that fit within his and his partner's budget.

"My partner and I are hoping to retire in about three years and move to a cheaper cost-of-living area," he said.

Kelly, who's in her late 40s and based in Arizona, also hopes to retire soon, but several hurdles stand in her way.

She's on track to earn nearly $300,000 this year by secretly working two full-time remote engineering jobs. However, she said her stock market investments have underperformed lately, and that she's had to support several family members financially.

"I am pretty much the sole provider for a lot of my family members," she said. "So I'm basically working to support others."

Kelly has about $42,000 in savings. Still, she's hopeful that her multiple income streams will make an early retirement possible.

"I would like to retire in five years from now," she said. "I'm trying to pay down all of my bills and invest more."

Do you have a story to share about secretly working multiple jobs or discovering an employee is doing so? Contact this reporter via email at [email protected] or Signal at jzinkula.29.

Read the original article on Business Insider

I started waking up at 5 a.m. to apply for jobs. It helped me land a tech role after a yearlong search.

21 May 2025 at 01:03
Preeti Ladwa
Preeti Ladwa said waking up early to apply for jobs helped her land a tech role.

Preeti Ladwa

  • When Preeti Ladwa was job-hunting, she woke up at 5 a.m. to apply for roles.
  • She also focused on roles that had been posted within the last 24 hours.
  • She believes those strategies helped her land interviews and a job offer.

This as-told-to essay is based on a conversation with Preeti Ladwa, a 30-year-old platform manager who lives in New Jersey. The following has been edited for length and clarity.

I graduated with a master's in information systems in May 2023, and spent the rest of the year applying to dozens of jobs. After about 30 interviews, I still hadn't received an offer.

In January 2024, I decided to try something different: I began waking up at 5 a.m. every weekday, and after getting some coffee and taking my dog for a walk, I applied to jobs from about 6 a.m. to 10 or 11 a.m., focusing on roles that had been posted in the last 24 hours. I spent the rest of my days networking, attending events, and researching companies to see how my skills might align with their work.

This strategy worked wonders for me. From January to May, after I became more selective in my job search, I submitted seven applications and landed three interviews. On one occasion, I applied for a job at around 7 a.m. and got an interview request two hours later. The role I ultimately landed β€” a technical projects manager position at the American Association for Cancer Research β€” was one I applied for during my usual morning window. I believe my strategy didn't just improve my visibility β€” it helped me get hired.

I accepted the offer in May, and about four months later, I was promoted to platform manager, with my salary increasing into the six-figure range.

Applying early helped me get noticed by recruiters

My job search strategy was partly an experiment, but it was also shaped by conversations I had with recruiters.

I learned that timing can play a big role in whether your application gets seen. When a job posting attracts a lot of applicants, hiring teams may review the first batch of submissions and pause to evaluate those before looking at newer ones. If they find strong candidates early, they might not go back. That's why I decided to start applying to jobs soon after they were posted.

But I decided to take it a step further. I figured that if recruiters start reviewing applications around 8 or 9 a.m. when they log on for the day, then applying early in the morning could help me land at the top of the applicant list β€” right where they might be looking first. I didn't want my rΓ©sumΓ© to get buried under hundreds of others, so I started waking up early to apply to the newest job postings.

I focused on roles that had been posted within the past 24 hours, whether they went up that morning or the night before, but always applied during my 6 to 11 a.m. window. The only exception was if I had a strong referral, in which case I'd sometimes apply even if the posting was older.

Visa needs shaped the employers I chased

I first started exploring job opportunities in January 2023 while I was finishing up my master's degree at Pace University. However, most companies I interviewed with said they needed someone who could start immediately.

This was a problem for me because I had moved to the US from India in 2021, and like many international students, couldn't begin working full time until I received my employment authorization. Once I received my authorization in July, I began applying more seriously.

As my search continued, I realized I needed to be highly strategic. The large tech companies and startups I applied to were subject to the H-1B visa lottery, and many had limited sponsorship opportunities for candidates who required a visa. However, I learned that some nonprofit organizations β€” including some universities and research institutions β€” are H-1B cap exempt, which means they can sponsor international applicants at any time of year without going through the lottery.

That was a game changer. I had overlooked nonprofits at first, but I soon realized they had real IT needs and could have far less competition than other tech roles. I noticed some nonprofit job postings had fewer than 30 applicants on LinkedIn β€” compared to hundreds for similar roles in the private sector β€” which made me feel like I had a better shot. So I decided to focus on nonprofit opportunities.

Cover letters could be more helpful than referrals

In addition to waking up early to apply, I only applied for roles where I met at least 80% of the qualifications listed in the posting. I used the same rΓ©sumΓ© for every application, which was about a page and a half long.

While I pursued employee referrals early in my search, they didn't lead to interviews unless my experience was a strong match. What I think made a bigger difference was submitting a cover letter. I was also volunteering at a nonprofit during my search, and I made sure to leverage that experience in my applications. It helped me show that I understood the space and was already contributing in a meaningful way.

I didn't have any income during my job search. I had saved money from my on-campus job, and my fiancΓ© β€” who had started working β€” supported me and our dog. I'm so grateful for that support.

After months of experimenting, refining my approach, and waking up early, I finally found a strategy that worked.

Read the original article on Business Insider

How baby boomers on a budget are fighting loneliness

Two men playing Checkers and games in a park.
Some retirees are finding ways to socialize on a budget.

FG Trade/Getty Images

  • Many older Americans are seeking budget-friendly ways to fend off loneliness.
  • Some are finding community in new places; others are building ties after the death of loved ones.
  • Low-cost activities and returning to the workforce have helped some stay social.

During the colder months, Barbara O'Keeffe, 79, her husband, and their friends journey into the rocky deserts of Arizona. With the intense sun shining on their sunscreen-covered faces, they take walks and admire the vastness.

When May hits and the blistering heat traps them inside, O'Keeffe occasionally wakes up early, tries a new breakfast spot, and bookmarks it for when her snowbird friends return in the winter.

Their finances are stable, but the O'Keeffes have tried to keep costs down while maintaining a healthy social life, though they will splurge on concerts.

But because of rising costs, they've slowed their search for new restaurants and embraced being homebodies during the summer, taking up projects like sewing and going through old photographs. Their over-55 community often holds events in the evenings, and they've maintained online connections with friends from their travels and work. Still, balancing social activities on a budget isn't easy.

Barbara O'Keeffe
Barbara O'Keeffe said her social life is busy during the cooler months.

Barbara O'Keeffe

"One of the hardest things at our age is that we are starting to lose close friends of 30 to 40 years, and each time it happens, it reinforces our own mortality," said O'Keeffe, who retired over 18 years ago from her role as a university department head.

O'Keeffe is one of dozens of retirees who recently told Business Insider they're trying to stay socially connected despite having limited retirement savings. Some said it's difficult to make friends later in life, especially without workplace connections to fall back on. Others said spending on food, housing, and other essentials has already strained their monthly budgets, making it harder to prioritize relationships and fend off loneliness. Many older Americans, particularly those with lower incomes, have been caught in the nation's broader "loneliness crisis."

What's more, fears about the future of government benefits like Social Security and Medicaid because of federal staffing and budget cuts, along with the stock market's ups and downs, have added to their financial stress. This story is part of a series on older workers.

Some retirees are going back to work to seek connections

For some retirees, going back to work has been the most practical way to address their financial and social challenges.

Carolyn Evans, 71, worked at a Big Four accounting firm for two decades before retiring in 2021 to care for her terminally ill husband. Despite having a pension and 401(k), she didn't have enough saved to retire comfortably β€” she lost much of her $400,000 in savings during the 2008 recession and paid hefty bills to repair her house after a natural disaster. When her husband died in 2022, she felt isolated and returned to work.

"I wanted to be around people because of the loneliness that I encountered after my husband passed away," Evans said.

Evans, who lives in Texas, said she couldn't find many part-time openings, so she became a full-time accountant for a real estate company. She's enjoyed working with younger people, property managers, and clients. Evans isn't sure when she might be able to retire again, though she's hopeful work will keep her fulfilled and financially stable for the time being.

"I enjoy work because it is very community-connected with various social activities such as bowling and pickleball," Evans said. "My children often entertain with barbecues and other family gatherings, there are church gatherings, and activities where it is often potluck and less expensive."

Finding low-cost activities and returning to work haven't fully solved the social challenges many retirees, like Libby Mintzer, face.

Mintzer, 73, retired from her job as a paralegal in 2022. She relies on her monthly Social Security income, which she says is barely enough to get by. As a result, Mintzer said she's been actively searching for part-time employment β€” preferably an office job β€” but hasn't had any luck yet.

The financial strain has also made it harder for her to build new friendships since she relocated from New York to Tampa, Florida, about three years ago. She's tried joining local meetup groups β€” some of which involved going out to dinner β€” but said they haven't been a good fit.

"I ended up broke every month because I'd spend $60 on dinner, and I didn't click with anybody," she said.

When a social opportunity catches her interest β€” even an expensive one β€” it can be hard to pass on it. If she overspends, she said she typically cuts back on food.

"To me, it's worth spending money or even going over my budget once in a while," she said.

Read the original article on Business Insider

A millennial couple who grew their net worth to $1 million before turning 30 share the 'house-hacking' strategy that made it possible

14 May 2025 at 01:01
Lauren and Ian Simpson
Lauren and Ian Simpson are living a FIRE lifestyle in the hopes of retiring by age 35.

Lauren Simpson

  • A Utah-based couple who are 29 years old are trying to retire by age 35.
  • Aggressive saving and a "house-hacking" strategy helped them increase their net worth to over $1 million.
  • They're pursuing a FIRE lifestyle with the goal of eventually becoming full-time parents.

In 2019, at the age of 23, Lauren Simpson and her husband Ian decided to pursue an ambitious goal: retire by age 35.

Over the last five years, the Utah-based couple, now 29, has grown their net worth from less than $100,000 to roughly $1,095,000. Through a combination of savings, investments, and passive income via rental properties, they hope to be able to spend up to $150,000 a year in their retirement.

Simpson said the FIRE movement, which she first learned about in 2019, inspired her and Ian's retirement goal. FIRE stands for "financial independence, retire early."

"The way we see it, 50-year-olds panic that they have not yet saved enough and that they have only 10 to 15 years before retirement β€” they aggressively save and end up retiring," Simpson said. "Rather than panicking at 50, we did it at 23."

Many Americans are struggling to save for retirement, but the FIRE movement has offered some a blueprint for achieving financial security. The methods and goals of FIRE advocates vary widely, with some saving most of their income, taking on side hustles, or delaying costly life milestones like having kids. While the FIRE movement isn't for everyone, financial experts say some of its general principles β€” like the benefits of saving and investing at a young age to take advantage of compounded investment returns β€” are applicable to a wide audience.

Simpson shared her and Ian's top strategies for improving their finances and why one of their ultimate goals is to become "full-time parents."

'House hacking' has helped them grow their wealth

Simpson works in financial services as a chief marketing officer, and Ian works in IT as an asset manager β€” they both earn six figures annually. More than half of the couple's net worth is from the equity they've built in the five properties they've purchased over roughly the last four years: one primary residence and four rental properties.

Between June 2024 and May, the couple's equity in their properties increased 37%, to about $641,000 from $467,000, based on Zillow estimates of property values. Simpson said the increase in their real estate equity came from principal payments and growth in their property values. These properties also provide the couple with rental income that they put toward their savings.

In 2021, the couple, both of whom work remotely, moved from Florida to New Hampshire. Simpson said Florida's lack of state income tax was a perk, but New Hampshire offered an even more appealing combination: no income or sales tax and an escape from Florida's "way too hot" climate. Because the housing market was so competitive, they made an offer on a home sight unseen β€” their first time visiting New Hampshire was for the inspection. Despite New Hampshire's tax benefits, the couple moved to Utah within the last year to be closer to family β€” buying a new home and turning their New Hampshire property into a rental. Unlike New Hampshire, Utah has both state income and sales taxes.

In addition to their primary residence in Utah, the couple owns four rental properties β€” two multi-family and two single-family homes β€” all of which they rent out with the assistance of a property manager. To afford their four rental properties β€” each of which is located in New Hampshire β€” Simpson said she and Ian have used a "house hacking" strategy to minimize their down payments.

When someone buys a second home or investment property, mortgage lenders often require a down payment of at least 10%. But when someone buys a property they plan to live in β€” known as an owner-occupied home β€” they can sometimes qualify for a down payment of 5% or lower. To qualify for a lower, owner-occupied down payment, the couple had to live in each property for at least one year. Once they met that requirement, they used the same strategy to buy and move into a new home β€” turning the previous one into a rental. This strategy required them to move three times in a three-year span.

"Moving was a necessary evil to get so many properties for so little down," Simpson said.

While this strategy requires taking on a significant debt burden and can come with hefty private mortgage insurance costs, Simpson said the rental income from their properties and rising home values have helped make it profitable.

However, Simpson said their strategy has become harder to execute in recent years due to high mortgage rates. Last year, they didn't find any properties they considered profitable, so they increased their 401(k) contributions and focused more on saving.

"That cash is there to be deployed if we do find a property that's going to be profitable," Simpson said.

They're playing the 'long game' with the stock market

Roughly $438,000 of the couple's net worth is in stock market investments, including retirement accounts like a 401(k) and Roth IRA. Between June 2024 and May, their investments grew by 22%. Simpson said around $78,000 of that increase came from new contributions, with the rest driven by market growth. The couple also had about $19,000 in cash savings.

While the stock market has been a roller coaster in recent months, this hasn't stopped the couple from continuing to invest.

"When the stock market's down, we just look at it as an opportunity β€” we look at it like everything's on sale." Simpson said, adding, "I know that we're playing the long game."

Simpson said their strategy is to invest in index funds with a roughly 90-10 allocation β€” 90% in stocks and 10% in bonds.

"I think trying to guess or bet on individual companies is just a losing game," she said.

Retiring early would make it possible to become 'full-time parents'

Despite their financial progress, the couple has encountered some changes to their lifestyles along the way. They had their first child in 2023, something that has put pressure on their savings. They're expecting their second child this summer.

However, Simpson said one of the biggest reasons she and her husband want to retire early is so they can be "full-time parents."

Growing up, she said her parents dedicated "all of their time" to her and her siblings. In comparison, Ian's parents spent more time prioritizing their relationship. When the couple discussed the merits of both parenting styles, they decided they wanted to do both. By retiring early, they'd have enough time to dedicate to their children and each other.

"We see money as a means to build connections and foster family," Simpson said. "Money isn't meant to be buried under a mattress or hoarded like acorns."

Editor's note: This story was originally published in July 2024.

Read the original article on Business Insider

I asked ChatGPT to grade my rΓ©sumΓ© on a scale of 10. It helped me land a six-figure tech job.

11 May 2025 at 01:03
Malhar Shah
Malhar Shah says asking the AI tools ChatGPT and Gemini to grade his rΓ©sumΓ© helped him land a tech job.

Malhar Shah

  • Malhar Shah used AI tools like ChatGPT and Gemini to score his rΓ©sumΓ© on a scale of 10.
  • He said the AI helped him improve the wording and formatting of his rΓ©sumΓ©.
  • However, the feedback from the AI tools was sometimes inconsistent.

This as-told-to essay is based on a conversation with Malhar Shah, a 34-year-old technical lead who lives in New Jersey. The following has been edited for length and clarity.

When I started applying for jobs earlier this year, I figured my best shot at landing interviews was to optimize my rΓ©sumΓ© as much as possible.

One of the most effective strategies I used was asking AI tools like ChatGPT and Gemini to rate my rΓ©sumΓ© β€” both overall and by section β€” on a scale from one to 10 (one being the worst and 10 being the best). I also asked the AI to suggest targeted improvements.

I wanted to find ways to cut through the noise of applicant tracking systems β€” the automated filters some companies use to screen and rank rΓ©sumΓ©s. I felt confident I could make a strong impression once I reached the interview stage.

My job search spanned around 120 companies and led to 10 to 15 interviews. I believe that incorporating rΓ©sumΓ© feedback from AI tools played a key role in helping me land a technical lead position with a six-figure salary. My original rΓ©sumΓ© scored around a seven or seven-and-a-half, while the version that ultimately got me the job earned a nine-and-a-half from ChatGPT and a nine from Gemini.

ChatGPT and Gemini helped me optimize my rΓ©sumΓ©

I started by uploading my rΓ©sumΓ© to ChatGPT and asking for feedback and a rΓ©sumΓ© grade. Then, to gather a broader range of insights, I did the same with Gemini.

While I didn't spend much time tailoring my rΓ©sumΓ© to each individual job description, I did create separate versions for the four main types of roles I was targeting: technical lead, staff engineer, engineering manager, and principal engineer. I asked the AI tools to help me craft rΓ©sumΓ©s for each of these roles and rate my rΓ©sumΓ©s along the way. My target score was eight or better.

Things got a bit confusing at times. For instance, ChatGPT might rate one version of my rΓ©sumΓ© a nine, while Gemini gave it a seven β€” and it wasn't always clear why. The feedback could also be inconsistent. If I asked ChatGPT to suggest improvements to a rΓ©sumΓ© it had scored as a seven, applying those changes might raise the score to a nine. But if I uploaded that revised rΓ©sumΓ© to a new ChatGPT chat, I'd sometimes get a different score.

Over time, it became clear that these tools didn't follow a consistent scoring system. Their ratings were based on the context of each conversation I'd have with the AI tool: which rΓ©sumΓ© version I shared, how I framed my questions, and what criteria were being applied.

Receiving a perfect 10 was difficult, though I managed it at certain points. I never asked the AI tools to generate a rΓ©sumΓ© that would score a perfect 10, because I wanted to ensure they wouldn't hallucinate or include inaccurate information. Instead, I focused on refining my rΓ©sumΓ© using the tools' suggestions.

In the end, it didn't matter much whether all my rΓ©sumΓ©s scored a perfect 10. What mattered was that I felt the AI feedback was helping me keep improving my rΓ©sumΓ©.

Once I felt I had a solid rΓ©sumΓ© on hand, I started applying to a few jobs to see how I'd fare. If I didn't hear back from employers, I'd revisit the AI tools to make additional tweaks. When I began having more success, I felt confident that my rΓ©sumΓ© was in a strong place.

AI also helped organize and format my rΓ©sumΓ©

The most helpful part of using AI tools to improve my rΓ©sumΓ© was getting clear, real-time feedback and practical suggestions for how to make it better. The AI helped me reword things to sound clearer and more effective, include the right keywords to get past applicant tracking systems, and organize my experience in a way that made my accomplishments stand out. It also made it easy to go through multiple rΓ©sumΓ© drafts quickly, adjusting the language and layout until my rΓ©sumΓ© felt polished. If I had to pick the AI tool I found most useful, I'd say Gemini.

Besides asking the AI tools to rate my rΓ©sumΓ©, I also asked for advice on formatting, help comparing different versions, and suggestions for how to tailor it for specific jobs β€” including senior roles and applications to top tech companies. I also got tips on how to rewrite sections like my professional summary to sound more focused, impactful, and leadership-oriented.

Overall, using AI this way helped make sure my rΓ©sumΓ© matched what companies were looking for and gave me a better shot at landing competitive roles.

Human connections and internet research were also helpful

In addition to using AI tools to improve my rΓ©sumΓ©, I also used them to refine my cover letters and run mock interviews to sharpen both my behavioral and technical responses.

However, I can't credit all of my job search success to AI tools. When I first set out to improve my rΓ©sumΓ©, I started by conducting research on the latest trends for tech role applications. I found out that simply listing my skills wasn't enough: To make it through applicant tracking systems, I needed to highlight concrete accomplishments from my past roles.

Some of the best feedback I got during my job search didn't come from an AI tool, but from a former coworker. He suggested I limit my job search to no more than two hours a day, set aside time to stay sharp on job-related skills β€” including some involving AI β€” and then spend the rest of the day with my family. Looking back, I think that was very wise advice.

Read the original article on Business Insider

A millennial who couldn't find a job for 4 years revamped his family's meal planning and childcare to make it work

11 May 2025 at 01:01
Dan Colflesh
Dan Colflesh, 43, found a job after searching for four years and going back to school.

Dan Colflesh

  • Dan Colflesh spent four years looking for a job after leaving the workforce to attend college.
  • He said his cost-cutting measures helped ease the financial stress during his job hunt.
  • It's become harder for some Americans, like Colflesh, to find work in recent years.

Editor's note: In May 2024, Business InsiderΒ wrote about Dan ColfleshΒ and his difficulty finding a job after earning his bachelor's degree. Read more here.

During the four years Dan Colflesh struggled to find work, he often thought about his upbringing in rural Appalachia.

Colflesh was used to "pinching pennies" as a young person, he told Business Insider. And as his job search dragged on in adulthood, he began actively looking for ways to cut costs.

"It's the advice you get when you grow up poor," he said. "If you don't have a lot of money, you can't spend a lot of money."

Colflesh is one of many Americans who have struggled to find work in recent years. While he landed a job last year, hundreds of others have shared their stories with BI about their long searches and how they've settled for lower-paying roles. Although the unemployment rate remains low by historical standards, businesses are hiring at nearly the slowest pace since 2013, excluding a temporary dip in 2020. In response, some job seekers have found creative ways to pay the bills, adjust their application strategies, and stay motivated.

"It's easier not to be stressed about finding a job if you don't have to stress about finances at the same time," said Colflesh, 43, who's based in Massachusetts.

Cutting costs eased some pressure

Colflesh said he was fortunate that both his wife and mother-in-law β€” who they live with β€” have jobs, which helped ease the financial pressure on the household. Still, his family made a number of adjustments to cut costs during his job search.

For one, they bought a deep freezer, which allowed them to buy in bulk and freeze meals that Colflesh cooked in large batches β€” a purchase he believes will save them money in the long run. They also grew some of their own produce in a vegetable garden and smoke-cured store-bought bacon at home to cut grocery costs. Additionally, the family decided to stop using one of their two vehicles and dropped the insurance on it β€” a choice that was feasible because Colflesh wasn't commuting to work.

Colflesh added that YouTube videos helped him handle basic car maintenance himself, so he could save money on mechanic bills. And because he was home more, he was able to help care for his children, which reduced his family's childcare expenses. Colflesh said taking these steps helped him feel less pressure during his job search.

A positive mindset helped him persevere

In 2015, when he was 34, Colflesh quit his job in the customer service industry to pursue a college degree, hoping it would help him with career growth. Six years later, he held an associate degree in physics from Holyoke Community College in Massachusetts and a bachelor's in political science from the University of Massachusetts Amherst.

However, Colflesh said the additional education didn't seem to help him much in the job market and saddled him with student loans. Despite applying to more than 100 jobs, he said he struggled to find work, which led him to pause his search for a few months at a time.

Colflesh said he tried common job search strategies, like tailoring his rΓ©sumΓ© and cover letter to each role, but nothing seemed to work. Then, last year, a friend referred him for a job at a tech company, that would involve answering phones, scheduling, and triaging customer support tickets. He said the referral helped him land an interview, and by May 2024, he'd accepted a job offer.

"This isn't really what I was looking for, but it's far from the worst job I've had," he said.

During his job search, Colflesh managed stress by hanging out with friends, engaging with his hobbies, and spending time with his family. While he felt discouraged at times, he did his best to retain a positive mindset, which he said was key to staying motivated.

"Staying positive has to be a choice the person makes," he said. "Waiting for the situation to create positivity will likely cause you to feel unmotivated and upset. You keep moving forward because what other option is there?"

Read the original article on Business Insider

5 people who made up to $470,000 secretly juggling multiple jobs explain the best roles for making it work

8 May 2025 at 01:01
A woman sits in a desk working on a computer.
Workers who have secretly juggled multiple remote jobs (not pictured) said some roles are better for overemployment.

Alex Potemkin/Getty Images

  • Some people secretly work multiple remote jobs to increase their earnings and build job security.
  • Five current and former job-jugglers shared the roles that are best suited for overemployment.
  • They said software engineers, data analysts, and sales roles can work well.

If you want to secretly work multiple remote jobs, some roles are easier to juggle than others.

Tom Wedding held multiple remote marketing jobs until last year, when he founded LVRGD β€” a company that helps people land remote roles and outsource the work, charging $3,000 to $5,000 per placement, he told Business Insider. Wedding said some of his clients aim to juggle multiple jobs at once.

He said the best roles for overemployed workers tend to involve minimal meetings, low communication demands, and repeatable tasks that can be done independently, such as software development, IT, and tech support jobs. He added that certain marketing, sales, and creative support roles β€” such as video editing and graphic design β€” could also work.

"It's best to find something that is remote, has simple repetitive workloads, and is highly systemisable," said Wedding, 25, who's based in Australia.

Wedding is one of more than two dozen job-jugglers BI has interviewed in the past two years who balance multiple roles to increase their earnings or ensure job security. While many of these workers hold tech and IT positions, others work in communications, healthcare, or engineering.

Five current and former job-jugglers shared insights based on their experiences and research into the world of overemployment. Aside from Wedding, all did so on the condition that pseudonyms would be used, for fear of professional repercussions. BI has verified their identities and earnings.

To be sure, holding multiple jobs without employer approval could have professional repercussions and lead to burnout. But many job-jugglers told BI the financial benefits have generally outweighed the downsides and risks.

The ideal overemployed job has few meetings and lots of independent work

Adam earned roughly $170,000 in 2023, secretly working two remote jobs as a security risk professional. This helped him pay off more than $100,000 in student loan debt, and he said he continues to juggle two full-time gigs.

Based on his experience in the tech industry, Adam said three job categories stood out as good fits for job juggling: software engineers, data analysts, and third-party risk analysts β€” the field where he works. He said these roles are often remote, involve independent work, come with reasonable deadlines, and have manageable communication demands.

"If the job allows for independent management and communication isn't overly demanding or time-sensitive, these roles can be juggled," he said.

Kelly, who's on track to earn nearly $300,000 this year by secretly working two full-time remote engineering jobs, said it helps to be in a management role β€” particularly in project management and software quality assurance.

"These types of positions don't require you to sit around and produce much," she said. "Your team will do the work and provide you with the inputs."

Maximizing time is a key factor for Harrison, who holds six full-time remote jobs and has a team of seven workers who assist him. He works as a quality assurance professional in the IT sector and estimates he'll earn roughly $800,000 this year.

Harrison said roles involving automation testing β€” where software automatically checks for functionality β€” can be ideal for job-jugglers, since tests often take time to run, giving workers a window to focus on other jobs. Regardless of the role, he said it's important to find jobs with relatively few meetings.

"I think it's best to stay away from jobs that have a lot of meetings or that need you on camera a lot," he said. "This reduces the times you can work other jobs."

For George, who's secretly working two remote IT jobs in the finance industry and earning about $250,000 a year, the company and sector matter as much as the job title when assessing whether a role suits job juggling.

"I think it's about finding the right industry where the demands on the employee's specific role are lower," he said.

Productivity hacks can make job juggling easier

Having jobs that suit overemployment is only half the battle: The job-jugglers BI interviewed said it's just as important to find ways to increase productivity.

Kelly said she tries to plan her workdays to stay as efficient as possible. She uses several AI tools to streamline her workload, including ChatGPT for writing emails and QuillBot to make her writing sound more professional. When reviewing code, she inputs it into GitHub Copilot, an AI-powered coding assistant, which she said cuts her workload in half.

"These tools are life-changing and make my job a lot easier," she said.

Since job-juggling can make it difficult to focus during meetings, Harrison said he uses Zoom's AI-generated meeting summaries to help him catch up on the key talking points.

Adam said he relies on keyboard shortcuts, reuses templates instead of starting from scratch, and turns to AI tools like ChatGPT and Gemini for "mundane" tasks such as writing emails.

"I automate my work as much as I can," he said.

In addition to these strategies, Adam said there's one low-tech way to reduce his workload: just say "no."

"I'm not afraid to say no to some special tasks or projects," he said. "I don't try to be Superman all the time."

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The 25 richest American families, ranked

Rob, Alice, and Jim Walton are part of America's richest family.
Rob, Alice, and Jim Walton are part of America's richest family.

Rick T. Wilking/Getty Images

  • The US may not have royals, but it does have family empires worth billions.
  • They've accumulated fortunes in a variety of ways, such as publishing, cosmetics, retail, and hotels.
  • The richest families in the US include the Waltons, the Kochs, the Hearsts, and the Lauders.

Billionaires' wealth has been growing exponentially over the past few years.

And even though the United States doesn't have any royal families, it does have family empires with enormous fortunes.

There are the Hearst and Newhouse families, who built publishing powerhouses; EstΓ©e Lauder, the founder of the cosmetics giant that generated the Lauder family fortune; and the families who created their wealth with retail and hotel empires, such as the Waltons with Walmart and the Pritzkers with Hyatt Hotels.

But not all of America's richest families began as entrepreneurs; some were also savvy investors.

Below, meet the 25 richest families in the US, ranked from lowest estimated net worth to highest estimated net worth. The rankings were determined using the most up-to-date estimated net worths available from Forbes, which were determined in February 2024.

The ranking excluded first-generation fortunes, like those of Jeff Bezos and Bill Gates, as well as fortunes controlled by a single heir.

Spoiler alert: The Roy family, of HBO's "Succession," didn't make the cut.

25. Kohler family
Herbert V. Kohler, Jr. and his wife, Natalie
Longtime CEO Herbert V. Kohler reportedly bought out shareholders in efforts to consolidate the company under the family's ownership.

Pool/Getty Images

Net worth: $16.2 billion

Source of wealth: Kohler Company

The Kohler family's legacy traces back to 1873, when John Michael Kohler founded the Kohler Company as a farm tools manufacturer. Since 1883, the company has focused on manufacturing bathroom fixtures and plumbing. Leadership of the company has been passed down from its founder to his son, former Wisconsin governor Walter J. Kohler Sr., and most recently to longtime CEO Herbert Kohler Jr.'s son, David Kohler. In 2024, the company made $9 billion in revenue, Forbes reported.

24. The Brown family
Owsley Brown
The Brown-Forman Corporation was founded in 1870 by pharmaceutical salesman George Garvin Brown.

Noam Galai/Getty Images

Net worth: $16.5 billion

Source of wealth: Brown-Forman Corp.

The Brown family is behind Jack Daniel's, Woodford Reserve, and Old Forester, among other alcohol brands. Forbes estimated 25 family members own more than half of Brown-Forman Corp., which began with pharmaceuticals salesman George Garvin Brown in 1870.

23. The Dorrance family
Campbell's Soup
The family is behind Campbell's Soup.

Justin Sullivan/Getty Images

Net worth: $17 billion

Source of wealth: Campbell Soup Company

An estimated 11 members of the Dorrance family own more than 50% of Campbell's Soup. John T. Dorrance invented the process for condensing soup in the late 1800s. Today, the company owns more than soup, including the brands V8, Pepperidge Farm, and Snyder's, generating more than $9 billion in annual revenue, per the company's latest earnings report. At least three of Dorrance's descendants are board members.Β 

22. The du Pont family
DuPont
Members of the du Pont family own the majority of shares in the company, although none take part in its management.

Laurent Gillerion/AP Images

Net worth: $18.1 billion

Source of wealth: DuPont

The du Pont fortune is one of the oldest and most widely shared fortunes on this list. Chemicals giant DuPont was founded in 1802 as a gunpowder manufacturer. Over time, it evolved into producing everything from dynamite to plastics and invented nylon and Teflon. Forbes estimates about 3,500 family members control the majority of shares in the company, although none take part in running the company.

21. The Ziff family
dirk ziff
The Ziff family grew its wealth through Ziff Davis Inc., which published PC Magazine.

Getty/Scott Olson

Net worth: $18.5 billion

Source of wealth: Ziff Davis Inc.

William Ziff Jr. sold the magazine publisher his father created, Ziff Davis Inc., which published PC Magazine, for $1.4 billion in 1994. Forbes report his sons, Daniel, Robert, and Dirk, grew their inheritance through Ziff Brothers Investments and reportedly invested some of their billions with managers who used to work at their hedge funds.

The brothers own several homes in Aspen and have put their money toward philanthropic efforts.

20. The Butt family
HEB store
Charles Butt is the current majority shareholder of the H.E. Butt Grocery Company.

Courtesy of H-E-B

Net worth: $18.8 billion

Source of wealth: H.E. Butt

Florence Butt founded H-E-B grocery store in Texas in 1905, which her son, Howard, expanded throughout the state when he took over the company in the 1920s. His son Charles is the majority shareholder and currently runs the company, which has over 400 stores in Texas and Mexico and generated over $46 billion in revenue in 2024, Forbes reported. Charles' siblings and two nephews also have stakes in the business.

19. The Taylor family
Chrissy Taylor, President and CEO of Entreprise Mobility
The Taylor family controls Enterprise Mobility, which reported $35 billion in revenue in 2023.

CHARLY TRIBALLEAU / AFP

Net worth: $19 billion

Source of wealth: Enterprise Rent-A-Car, National Car Rental, and Alamo Rent a Car

The Taylor family controls Enterprise Mobility, the parent company of National Car Rental, Alamo Rent a Car, and Enterprise Rent-A-Car, which was founded by Jack C. Taylor in 1957. Since then, the Taylor family has acquired competitors National Car Rental and Alamo Rent a Car and grown into a powerhouse, with Enterprise Mobility reporting $35 billion in revenue in the 2023 fiscal year, Forbes reported.

18. Millstone-Winter-Heyman families
David Millstone and Jennifer Millstone at a New York City gala
Standard Industries brought in $11 billion in revenue in 2024, according to Forbes.

Sylvain Gaboury/Paul Bruinooge/Patrick McMullan via Getty Images

Net worth: $19.2 billion

Source of wealth: Standard Industries

Currently led by David Millstone and David Winter, the Standard Industries conglomerate dates its family ties back to a 1938 proxy battle in which businessman Sam Heyman acquired GAF Corporation, which is the country's largest roofing manufacturer, perΒ Forbes.

17. The Smith family
Illinois Tool Works logo
The family owns shares of both Illinois Tool Works and Northern Trust.

Illustration by Pavlo Gonchar/SOPA Images/LightRocket via Getty Images

Net worth: $19.8 billion

Source of wealth: Illinois Tool Works

Dating back to Byron Smith's 1889 founding of the financial services company Northern Trust Corporation and his 1912 co-founding of the manufacturing firm Illinois Tool Works, the Smith family has ties to both the tools manufacturing and finance industries. The family now holds at least 9% of Illinois Tool Works and 1% of Northern Trust's shares, according to Forbes.

16. The Reyes Family
Coca Cola truck
The family owns a group of major distributors in the US and globally.

Artur Widak/NurPhoto

Net worth: $19.9 billion

Source of wealth: Reyes Holdings

Led by chairmen Chris and Jude Reyes and CEO Duke Reyes, Reyes Holdings is a leading food-and-beverage distributor, according to Forbes. It owns Martin-Brower, McDonald's's main global food distributor, Reyes Beverage Group, the largest beer distributor in the US, and Reyes Coca-Cola Bottling, which serves the Midwest and the West Coast.

15. The Busch family
Haley Busch
Despite having extensive ties to the beer industry, the family's many descendants aren't currently involved with major beer firms.

Paul A. Hebert/Getty Images

Net worth: $20 billion

Source of wealth: Anheuser-Busch

The Busch family roots in the beer industry date back to 1876, when Adolphus Busch created what is now known as Budweiser. While the company passed through each family generation, an estimated 25% of the business was sold between 1989 and 2008, and it was fully bought out for $52 billion in 2008, as reported by The New York Times. Roughly 30 members of the family split the fortune.

Part of the family got back into the beer business with William K. Busch Brewing, but the company shut down in 2019.

14. The Hearst family
Hearst cousins
The Hearst fortune dates back to William Randolph Hearst's purchase of the San Francisco Examiner in 1887.

Bryan Bedder/Getty Images

Net worth: $22.4 billion

Source of wealth: Hearst Corporation

About 67 family members share the fortune that William Randolph Hearst created when he took over the San Francisco Examiner in the late 1800s, Forbes reported. Soon after, Hearst acquired other newspapers and expanded into radio and TV, creating the foundation for the media giant, Hearst Corporation, which owns 76 newspapers, nearly 260 magazines, television stations, and stakes in cable TV channels that include A&E and ESPN.Β 

Hearst used to own what is now one of the most expensive homes in America. His grandson, William R. Hearst III, is currently the chairman of the company's board.

13. The Newhouse family
donald and victoria newhouse
Advance Publications' holdings include CondΓ© Nast Publications, the publisher of magazines like Vogue and The New Yorker.

Ben Gabbe/Getty Images

Net worth: $24.1 billion

Source of wealth: Advance Publications

The Newhouse family's wealth derives from the publishing giant Sam Newhouse created. Advance Publications owns CondΓ© Nast Publications, whose media properties include Vogue, Vanity Fair, and GQ. As of 2021, the company owned a 30% to 35% stake in Reddit.Β 

In April 2016, Sam's sons sold the cable-TV company Bright House Networks for roughly $11.4 billion in cash and stock, per reports.

12. The Hunt family
Caroline Rose Hunt
The Hunt family owns the Kansas City Chiefs.

Amanda Edwards/Getty Images

Net worth: $24.8 billion

Source of wealth: Hunt Oil Company

H.L. Hunt laid the foundation for his family's fortune with Hunt Oil Company. His many heirs (he had 14 children) command several fortunes, from Hunt Oil and Petro-Hunt to Rosewood Hotels & Resorts. His children spend their billions on real estate, like the 6 million-square-foot underground business park SubTropolis, and sports teams. The Hunt family owns the Kansas City Chiefs, which won its fourth Super Bowl in 2024, and they have a minority stake in the Chicago Bulls.Β 

11. The Lauder family
Lauder family
The family controls the cosmetics giant EstΓ©e Lauder, which owns MAC and Clinique.

Dimitrios Kambouris/Getty Images

Net worth: $25.9 billion

Source of wealth: EstΓ©e Lauder

In 1947, EstΓ©e Lauder received her first major order for $800 of skincare products from Saks Fifth Avenue, Bloomberg reported. The company, which sells cosmetics and fragrances through over 20 brands that include MAC and Clinique, brought in over $15 billion of revenue in fiscal year 2024, the company reported.

The Lauders are active philanthropists, and EstΓ©e Lauder's sons, Leonard and Ronald, are major art collectors. Leonard donated $1 billion worth of paintings and sculptures to the Metropolitan Museum of Art. The family also owns a significant amount of real estate.

10. The Cox family
Jim Cox Kennedy
The family owns firms in cable and broadcast, publishing, and the automobile industry.

AP Photos

Net worth: $26.8 billion

Source of wealth: Cox Enterprises

Since its founding in 1898, Cox Enterprises has a hand in a number of industries β€” cable and broadband (Cox Communications), newspapers and radio stations (Cox Media Group), and the automotive industry. It generates about $20 billion in revenue per year, per Forbes.

The company's CEO is Alex Taylor, the great-grandson of the founder, James Cox.

9. The Duncan family
randa williams
The family's fortune dates back to Dan L. Duncan's 1968 founding of Enterprise Products Partners.

Bob Levey/Getty Images

Net worth: $30 billion

Source of wealth: Enterprise Products Partners

Dan L. Duncan founded the gas and oil company Enterprise Products Partners in 1968 with just $10,000, per Forbes. After he died in 2010, the company remained under family control, and his four children inherited a nearly $10 billion estate. The family fortune has since more than doubled.

Randa Duncan Williams is the only one of the children actively involved with the company, serving as a non-executive chairwoman.

8. The Cathy family
Dan Cathy
The fast-food chain Chick-fil-A has remained in the hands of Cathy family members since its founding by Samuel Truett Cathy in 1967.

Gustavo Caballero/Getty Images for Pinewood Studios Group

Net worth: $33.6 billion

Source of wealth: Chick-fil-A

Samuel Truett Cathy founded the fast-food chain Chick-fil-A in 1967. Since then, the business has remained in the hands of second- and third-generation family members. In 2021, Andrew Truett Cathy, the founder's grandson, took over as CEO from his father, Dan.Β 

As of May 2025, Samuel Truett Cathy's sons, Dan and Bubba, each have a net worth of more than $10 billion, per Forbes.

Members of the Cathy family have previously generated controversy for donating to causes considered to have anti-LGBTQ+ stances.

7. The SC Johnson family
Herbert Fisk Johnson III
SC Johnson was founded by its namesake in 1882.

Theo Wargo/Getty Images

Net worth: $38.5 billion

Source of wealth: SC Johnson

The Johnson family is behind SC Johnson, which produces cleaning products such as Pledge, Glade, and Windex. The company was founded by its namesake, S.C. Johnson, in 1882 and was eventually taken over by his son Herbert Fisk Johnson. Herbert died in 1928 without a will, and the family feuded over the inheritance until it was eventually divided between his two children, Herbert Fisk Johnson Jr. and Henrietta Johnson Louis.

Herbert Fisk Johnson III, a fifth-generation member of the family, is the current CEO and chairman of the company.

6. The Pritzker family
Penny Pritzker
The family's fortune dates back to Jay Pritzker's 1957 purchase of the Hyatt House hotel in Los Angeles.

Pool/Getty Images

Net worth: $41.6 billion

Source of wealth: Hyatt hotels

A.N. Pritzker and his sons Jay, Donald, and Robert created the family's wealth by founding the Hyatt Hotel chain and investing in holdings such as Marmon Group. Today, the fortune is split among 13 family members, 11 of whom are billionaires, per Forbes. They reportedly spent much of the 2000s arguing over trusts, ultimately dividing up the fortune at the end.

Members of the Pritzker family have also been involved in politics. Penny Pritzker, Donald's daughter, is the former US Secretary of Commerce. Her brother, J.B. Pritzker, has served as the governor of Illinois since 2019.Β 

Hyatt Hotels reported over $6.65 billion in annual revenue in 2024.Β 

5. The (Edward) Johnson family
Abigail Johnson
The Johnson family owns 49% of the mutual fund company Fidelity, which generated $32 billion in revenue in 2024.

Brian Snyder/Reuters

Net worth: $44.8 billion

Source of wealth: FidelityΒ 

Edward C. Johnson founded one of the world's largest mutual-fund companies, Fidelity, in 1946, which has been run by three Johnson generations since. It's currently helmed by his granddaughter Abigail Johnson.

As of 2020, the family owns 49% of the company, which is shared among six family members, according to Forbes. In 2024, the company generated over $32 billion in revenue, it reported.

4. The Cargill-MacMillan family
Martha MacMillan
The family has over 100 shareholding members, owning a total of 88% of Cargill Inc.

Jemal Countess/Getty Images

Net worth: $60.6 billion

Source of wealth: Cargill Inc.

William W. Cargill founded agribusiness giant Cargill Inc. in 1865. As of 2020, roughly 23 members of the Cargill-MacMillan family owned 88% of the company, Forbes reported, which generated over $160 billion in revenue in 2024.

Bloomberg reported in 2022 that the family keeps 80% of Cargill Inc.'s net income inside the company for reinvestment annually.

3. The Koch family
Charles Koch
The family's fortune dates back to Fred C. Koch's 1940 confounding of Wood River Oil and Refining Company.

Business Insider/Julie Bort

Net worth: $116 billion

Source of wealth: Koch

Brothers Charles and David Koch expanded their father's oil-refinery firm into the conglomerate Koch Industries, Inc. β€” later shortened to Koch, Inc. β€” after their other brothers, Frederick and William, left the business following a failed takeover. Today, Koch generates roughly $125 billion in revenue annually.

David Koch stepped down from a leadership position in the company in 2018 and died the following year. Charles Koch became the company's chairman and CEO in 1967, and he has been the chairman and co-CEO since 2023.

David Koch's foundation has pledged to contribute more than $1.2 billion to cancer research, hospitals, education, and cultural institutions, Koch's external relations team told Barron's in 2019.

The Koch brothers have also used their wealth to reshape conservative politics in a substantial way over the past few decades. Since the 1970s, they donated at least $100 million to fund the fiscally conservative Tea Party movement and fortify the Republican Party, The New York Times reported in 2019.

2. The Mars family
Jacqueline Mars
The family owns the largest candy and pet food companies, according to Forbes.

Pool/Getty Images

Net worth: $117 billion

Source of wealth: Mars Inc.

Jacqueline and John Mars inherited a stake in the candy empire Mars Inc., which invented M&Ms, Milky Way, and Mars Bars, when their father died in 1999.

The company also owns other food brands, such Ben's Original and Dolmio, and petcare brands. In 2024, the company brought in over $50 billion in revenue, per Forbes.

The siblings run the Mars Foundation, which donates to educational, environmental, cultural, and health-related causes.

1. The Walton family
Walton family
Aside from the retailer, the family also owns a total of seven sports teams, according to Forbes.

Rick Wilking/Reuters

Net worth: $267 billion

Source of wealth: Walmart

Sam and Bud Walton founded Walmart in 1962. Following its success, they founded Sam's Club in 1983. In 2024, Walmart brought in $648.1 billion in revenue, the company reported, making it the largest retailer by revenue in the world.

The Walton family fortune is dispersed among seven family members, including cofounder Sam Walton's three children, Rob, Jim, and Alice, who is the richest woman in the world.

Correction β€”Β May 6, 2025: An earlier version of this article misstated the name of Koch, Inc. and Charles Koch's role. As of August 2024, the conglomerate is called Koch, not Koch Industries, and as of March 2023, Charles Koch is its chairman and co-CEO.

Read the original article on Business Insider

I landed my dream job at Adobe after applying to the company 12 times. A video cover letter helped me stand out.

4 May 2025 at 01:01
Curtis Ying
Curtis Ying said making a video cover letter helped him land his "dream job" at Adobe.

Curtis Ying

  • Curtis Ying applied to Adobe 12 times before landing a user experience designer role.
  • He said a video cover letter helped him stand out among other applicants.
  • He shared his tips for making a video cover letter.

This as-told-to essay is based on a conversation with Curtis Ying, a 30-year-old user experience designer at Adobe who lives in California. The following has been edited for length and clarity. Adobe did not respond to a request for comment from Business Insider.

In January 2023, I was laid off from my product designer job. I had a few months of severance and some savings, so it didn't feel like the world was crashing down.

Rather than immediately applying to various employers, I decided to focus on landing a job at one company in particular: Adobe.

About a month before I was laid off, my friend who works at Adobe gave me a tour of the company's headquarters in San Jose, California. I fell in love with graphic design after my cousin taught me how to use Adobe Illustrator, and I was already using the company's products on a regular basis. Working at Adobe became a dream job of mine. After I was laid off, landing a job at Adobe became my top priority.

I figured the best way to make this happen was to do something unique in my application that would help me stand out: creating a video cover letter. For about a month, I only applied to one position β€” a role at Adobe that I didn't get β€” while I worked on the video.

After finishing the video in February, I kept a close eye on Adobe's job postings. Over a six-month period, I applied to 10 Adobe jobs β€” including some I was probably underqualified for β€” and was rejected from all of them. Then, in December 2023, I applied for my 12th Adobe role of the year β€” a user experience designer position β€” and landed an interview. After going through the process, I accepted an offer for a full-time contract role with a six-figure salary. Thirteen months after my layoff, I'd accomplished my goal.

Video cover letters can "humanize your application"

I first became intrigued by video cover letters after seeing a YouTube video in which someone sang about why they wanted to work at a particular company. They ended up getting the job, and the video left a strong impression on me. I decided to create my own video cover letter to include with my Adobe applications.

In the video, which ran about a minute and a half, I talked about how I got interested in graphic and UX design, my education and work experience, the design tools and techniques I knew well, a few fun facts about myself, and why I wanted to work at Adobe. While I didn't have a professional microphone, I recorded myself using a Canon DSLR camera set up on a tripod. I edited the footage with Adobe Premiere Pro.

I used two different methods to include my video cover letter in my application. First, I uploaded the video to YouTube as an unlisted video and hyperlinked it at the top of my rΓ©sumΓ© with the text "watch my video cover letter." I also embedded a snapshot of the video in a PDF titled "video cover letter," added the same hyperlink, and attached that document as well.

Some people told me not to focus exclusively on Adobe β€” that I shouldn't put all my eggs in one basket. But I was hesitant to change my approach. Applying to other jobs felt a little like admitting that landing a job at Adobe might not be possible.

Several months into my job search, I started applying to some companies other than Adobe using a second video cover letter I made that was more generic. But Adobe remained my target employer.

In addition to creating a customized video cover letter, I pursued a second strategy: networking with Adobe employees. In June 2023, I posted my Adobe video cover letter on LinkedIn. I wasn't sure how it would be received, but it proved to be a good decision, as it helped me grow my Adobe network. Even as the rejections came in, I felt I'd built so many connections at Adobe that it was probably easier to land a job there than anywhere else β€” and that kept me motivated.

I think my video cover letter definitely helped me land a job at Adobe. The hiring manager I interviewed with told me it gave them a sense of my personality and helped me stand out among other applicants. Posting the video on LinkedIn also led to some connections that I believe boosted my application.

I don't think a video cover letter has to be as highly produced as mine to be helpful for job seekers. It doesn't have to have a beautiful background or the perfect lighting, but if you can be concise and speak naturally, I think it can work.

One of the reasons I highly advocate for video cover letters is that they humanize your application, which is typically just lines of text in a rΓ©sumΓ© and cover letter. When you're competing with sometimes thousands of applicants in a challenging job market, I think having a video cover letter can help you stand out. I see absolutely no downsides to it.

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Servers share their top strategies for getting gratuity amid a tipping backlash

2 May 2025 at 01:04
A sign on a tip bowl that says "Tips, show some love. - Baristas"
Some servers and bartenders are turning to customer service strategies to help them land tips.

Al Drago/Bloomberg via Getty Images

  • Workers are finding ways to land tips even as some Americans cut back on gratuity spending.
  • Three workers said offering freebies and connecting with customers have helped them land tips.
  • Some Americans are tipping less due to rising prices and frustrations about widespread tip requests.

When Maddy Joss gets a table of patrons, she typically asks if they're celebrating anything. If they are, she often offers "freebies," which could boost her chances of earning a big tip.

"You're using the restaurant's resources to get more money in your pocket," said Joss, 27, a part-time restaurant server in Brooklyn. She added that her restaurant is fairly relaxed about what freebies servers can offer β€” such as a dessert or drink β€” though other establishments can have stricter policies.

While Joss said she hasn't noticed any big changes in tipping habits β€” she thinks people are dining out less, which can lead to fewer tips β€” other servers are facing a tougher tipping environment as some Americans scale back their gratuity due to rising prices and frustrations about being asked to tip more often. Data shared with Business Insider by the point-of-sale platform Toast β€” drawn from more than a billion transactions at roughly 134,000 restaurants β€” showed that the average tip at full-service restaurants fell to 19.3% by the end of last year from 19.9% in early 2021. On a $50 meal, that means a server's tip dropped to $9.65 from $9.95.

While there's limited data on bartender tipping specifically, 53% of Americans said they always tip when buying a drink at a bar, per a Pew Research survey from 2023.

Overall, 35% of Americans said that tipping culture was out of control last year, up from 30% in 2023, per Bankrate.

Three tipped workers who spoke with BI said they rely heavily on tips because a chunk of their hourly earnings, which range from roughly $8 to $12 an hour, go toward federal and state taxes.

Making an impression on customers can help combat "tipping fatigue"

Amy Burke, a bartender in New Orleans, said that over her 30 years in the industry, she's developed some strategies to nudge people toward bigger tips.

Burke said it's easier to connect with customers and get tips if they know your name, but that introducing herself or wearing a name tag wasn't enough to make her name stick. That's why she decided to buy light-up letters from Amazon that spell out her name β€” and display these letters behind the bar where she works.

"It's a big conversation piece," she said of the letters. "I get a lot of compliments on them."

Amy Burke
Amy Burke said the light-up letters behind the bar that spell her name have helped her connect with customers.

Amy Burke

Burke, 49, said this strategy has helped her land tips. She estimated that 98% of her customers leave a tip and said many tip at least 20%.

Another one of Burke's favorite strategies is the stamp she puts on customers' bills that says, "Thank you :) Amy B." She said the hotel where she works encouraged staff to write a thank-you note on bills, but she thought a stamp would be faster and more personalized.

"I pop it on the bill when I hand it to people," she said. "It adds a personal touch that people appreciate."

Amy Burke's stamp
Amy Burke has a customized stamp that she puts on customers' bills.

Amy Burke

Providing exceptional service to customers helps Lindsay Ruck, a server at a restaurant in Phoenix's Sky Harbor airport, combat some of the "tipping fatigue" she's seen in recent years.

She believes some of this tipping resistance comes from customers who are often asked to tip at more businesses. She said her restaurant provides customers with a checkout machine that suggests a tip of 18%, 20%, or 22% β€” and that many people choose 18%.

"They're still tipping, but they're not necessarily tipping what a lot of us consider standard, which is 20%," said the 42-year-old.

However, Ruck said she hasn't seen a significant decline in customer tipping and that, in her typical workweek, only a couple of customers don't leave a tip.

She said the key to earning big tips is building a connection with customers. Since many are travelers passing through the airport, it's often their first time at the restaurant, which provides the opportunity to offer them a unique experience.

"It's almost like being on a stage," she said. "You're guiding them through this process at a new restaurant they've probably never been to."

While some restaurants have introduced screens for placing orders, Ruck said many customers still prefer to interact with her and ask questions about the menu.

"You start to develop a relationship with these people within a 45-minute timeframe," she said. "I like to make sure that people have what they need before they think they need it."

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Older Americans who need to unretire are starting businesses, earning $15 an hour, or struggling to find anything at all

Diann Witherspoon
Diann Witherspoon is preparing to restart her fiber art and quilting business to supplement her Social Security income amid economic uncertainty.

Rich-Joseph Facun for BI

Sharon Tagle thought her finances were in order when she retired seven years ago. However, she recently returned to work.

In December, the 68-year-old got a job at Home Depot as a cashier working 20 hours a week. She said her concerns about inflation and a failed home sale influenced her decision. She earns $15 hourly and expects to work for the next few months, longer if her financial conditions remain tight.

"I'm sorry that I left my job as soon as I did, but things were getting to me, and I just didn't want to work anymore," Tagle, who lives in Tampa, Florida, said. "I was not as frugal as I could have been. We're still having a good time, just not having it as much."

She retired from her role as a personal injury claims adjuster from an insurance company with about $250,000 in savings. She and her husband receive about $3,400 monthly in combined Social Security. The couple hoped to sell their home in Florida two years ago and move to a state with a lower cost of living, but they couldn't secure a buyer.

Tagle is one of dozens of older Americans who told Business Insider recently that they're either holding on to their jobs or unretiring because of economic uncertainty and pessimism about their financial futures. Those who are unretiring said they're nervous about the fate of Social Security, Medicaid, and other government benefits amid federal budget cuts. Others fear how their retirement savings and investments will fare as tariff policies continue to roil the stock market. This story is part of a series on older workers.

To be sure, returning to work is often out of the question for many older Americans. Geoffrey Sanzenbacher, a research fellow at the Center for Retirement Research at Boston College, said many older Americans couldn't return to work or had limited options because they worked physical jobs that they're no longer capable of doing. These workers often lacked employer-based retirement systems like 401(k)s, which hurt their retirement plans.

Uncertainty about Social Security and Medicaid has fueled some fears

Earlier in April, House Republicans voted to pass a GOP budget plan that included $880 billion in cuts for the House Energy and Commerce Committee over the next decade, whose main programs are Medicaid and Medicare. As part of reconciliation, GOP lawmakers are set to add details to the proposal, such as whether federal Medicaid funding would be reduced and by how much.

Trump has said that he will not cut Social Security benefits or touch Medicare. But the Social Security Administration has outlined plans to cut as many as 7,000 employees, which could increase wait times for recipients seeking assistance. Former SSA Commissioner Martin O'Malley, along with staff inside the agency, told BI that disruptions could lead to interrupted benefits.

While investors and economists have grown more concerned about a recession this year, they remain divided on whether it will happen. That hasn't eased some older Americans' fears, prompting some to reenter the workforce.

But for many older Americans, finding the perfect job may be out of the question. Amanda Clayman, a financial therapist, said many older job seekers have to deal with rejections from employers due to factors including ageism. She said people should be open to a wide variety of jobs, as any boost to their finances could be worthwhile.

"The goal may no longer be finding the right job or what the right job might be," Clayman said, adding older Americans should consider taking temporary or part-time positions even if they're not desirable.

Some are unretiring to start businesses

Diann Witherspoon
Diann Witherspoon.

Rich-Joseph Facun for BI

Diann Witherspoon, 72, said recent financial insecurities had pushed her to prepare to restart her fiber art and quilting business.

Witherspoon, who lives in Ohio, said she's always lived paycheck to paycheck, raising two special needs children and "working myself to death" to provide for them. She held accounting and property management jobs while sewing on the side. After back and knee surgeries, Witherspoon said there weren't many jobs she could do now.

She was laid off in 2017 the day she returned to her office after surgery, and her husband died of lung cancer a few years later. She shuttered her quilting company in December 2022 after a period of grief and had more back surgeries a year later.

She lives off half her husband's retirement income, which is $467 monthly, and $2,137 in monthly Social Security. It's enough to cover her $1,700 monthly house payment but not enough to have much left after other expenses. Her son, who lives with her, helps pay the bills.

Witherspoon said she's working to make new patterns to sell online and start teaching. She hopes to sell a few pieces a month and earn between $2,000 and $5,000, but she doesn't want to scale so large that she'll need employees.

"I just want to be able to sustain it myself so that we can survive, and I'd like to get something going so it just keeps producing income," Witherspoon said. "For the first time in 72 years living in this country, I am afraid."

Diann Witherspoon
Diann Witherspoon in front of her home.

Rich-Joseph Facun for BI

Some retirees are struggling to find work

Moira MacLean, 69, retired as a social assistance case manager 2 Β½ years ago, though she knew she would have to return to work at some point. The former lawyer, who lives in a community for older folks, left her position when she feared her company wouldn't let her work part time because she was fatigued.

MacLean, who lives in Washington, was getting by with savings and her $2,280 monthly Social Security payments, but with her money dwindling, she put herself back on the job market over the past few months in search of a similar role. She hasn't had luck yet, and she feels her age and time away from the office haven't helped her applications.

She also tried starting a third-party seller business for household products on Amazon, which put her into debt as the business didn't take off.

"There is zero room for investing anything differently than I already have," MacLean said of her long-term planning. "I live too close to the edge to do anything about that."

Pam Hovland, 70, is also struggling to find work and fears a recession would make it even more difficult.

"It scares me to death," Hovland said of the prospect of an economic downturn. "So I'd like to try to get a job before it all takes effect."

Hovland, who also lives in Washington, worked as a medical transcriber until around 2005 when a health issue put her in a coma for three months and forced her into retirement. She relied on disability income until around 2020, when her benefits converted to Social Security income β€” she said she gets a check for $1,099 monthly.

But by 2022, Hovland began struggling to pay the bills and, at times, afford birthday cards for her grandchildren. While she was able to reduce her rent through a Department of Housing and Urban Development program, she's still searching for customer service or fast food roles.

"I desperately need to get back to work," she said, "but because I didn't build up enough money when I became disabled, I'm very much scraping by."

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A Gen Zer swears by a LinkedIn trick that helped him be among the first to apply for roles. Experts say he's onto something.

25 April 2025 at 01:25
Michael Yan
Michael Yan said a LinkedIn trick helped him apply to internships soon after they were posted.

Michael Yan

  • A LinkedIn trick helped a Gen Zer be among the first applicants for tech internships.
  • He was offered internships at Microsoft and Meta, and accepted the latter.
  • Career experts said applying early can give candidates an edge in a competitive labor market.

Being among the first to apply for a job can increase your chances for success. A LinkedIn trick helped a Gen Zer in tech beat the rush of other applicants.

In 2018, when Michael Yan was a freshman computer science major at Stanford University, he wanted a competitive edge when applying to internships. After searching for his desired job and using LinkedIn's feature that sorts roles posted in the last day, he changed the numbers at the end of the website's URL from 86400 β€” the number of seconds in 24 hours β€” to 3600 β€” the number of seconds in one hour.

"It was extremely helpful in shortlisting jobs that were posted recently that I could basically prioritize applying to," Yan, 25, told Business Insider.

Yan said this trick helped him focus on the newest job postings, and he thinks it was one of the reasons he landed internships after his first two years in college. During his sophomore year, in 2019, he was offered internships at Microsoft and Meta β€” and accepted the latter.

In 2020, Yan dropped out of Stanford to start Simplify, which offers an AI copilot that aims to help people find and apply for jobs. He said applying early remains one of his top tips for job seekers.

Hundreds of Americans have told BI that they've struggled to find work in the last year. While the unemployment rate remains low compared to historical levels, businesses are hiring at nearly the lowest rate since 2013, excluding a temporary dip in 2020. In response to these challenges, some Americans are looking for ways to stand out. Career experts from LinkedIn, Indeed, and ZipRecruiter told Business Insider that applying to jobs early could give candidates an edge in today's challenging job market.

When asked about Yan's job filter trick, LinkedIn told BI that keyword and search filter restrictions frustrate some job seekers, but that the company was working to reduce those limitations.

Applying early could "change your odds"

There are several perks to being among the early wave of job applicants.

Andrew McCaskill, a LinkedIn career expert, suggested that job seekers set up alerts for specific types of roles so they can apply quickly after the listing goes live. He added that applying to a job on LinkedIn within the first 10 minutes of receiving an alert can increase a person's chances of hearing back from the company by up to four times.

"Being among the first to apply, especially for jobs you really want or are super qualified for, should certainly be part of a job search strategy," he said.

Sam DeMase, a career expert at ZipRecruiter, agreed and added that some employers close job postings after receiving a certain number of applications, which can happen fast. When possible, she recommends applying within three days of a job being posted.

"Employers are more likely to interview, extend an offer to, and hire earlier applicants, so moving fast can literally change your odds," she said.

DeMase said applying early could be particularly important for entry-level positions, which tend to see a large number of applicants. She added that roles at startups and in the retail and customer service sectors tend to be filled fairly quickly.

Jennifer Herrity, a career trends expert at Indeed, said that an early application can demonstrate enthusiasm and promptness, and that it's best to apply to a job no more than a week or two after it's been posted.

To be sure, the timing of an application is only one factor in a job search. The career experts Business Insider spoke with said job seekers shouldn't sacrifice application quality just to be early. They added that applicants should tailor their rΓ©sumΓ©s for each role and ensure the positions they apply for match their skills and experience.

"More important than applying quickly β€” whether that's within 24 hours or one hour β€” is that you're a good fit for the job you're applying to, and that your application shows you off in the best light," McCaskill said.

Have you landed a new job in the last year and are open to sharing your story? Please fill out this quick Google Form.

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A Gen Xer making $300,000 secretly working 2 remote roles says the 12-hour days are worth the job security

22 April 2025 at 01:02
A woman working on her laptop on a messy desk.
A Gen Xer (not pictured) earning $300,000 by secretly working two remote jobs says the 12-hour days are worth it for the extra income and job security.

Justin Paget/Getty Images

  • A Gen Xer will earn $300,000 annually by secretly juggling two remote IT jobs.
  • She said the 12-hour days can be stressful, but worth it for the added job security.
  • Rewarding herself for her hard work helps keep her motivated.

Sarah secretly works 12-hour days across two jobs, and while that leaves little downtime, she said it's a worthwhile effort.

"I want to ride this out until I retire," said Sarah, whose identity was verified by Business Insider but who asked to use a pseudonym, citing fears of professional repercussions.

So far, the strategy has paid off: Sarah worked two remote IT jobs simultaneously until December, when she was laid off from one. She said she was relieved to have the second income.

"It really gave me a sense of security, knowing that I had another job," Sarah said.

In February, Sarah landed a second full-time remote IT job and is on track to earn about $300,000 this year across her jobs. Over the last four years, Sarah said the extra income from job juggling has allowed her to save more than $100,000 in her 401(k)s, pay off $17,000 in credit card debt, and furnish her home. She said these benefits offset the downsides of juggling, including that she has less time and energy for her family and hobbies.

Sarah, who's in her 50s and lives in the Southeast, is among some of the Americans who have secretly juggled multiple remote roles to increase their incomes. Over the past two years, BI has interviewed more than two dozen "overemployed" workers who've used their extra cash to travel the world, buy expensive weight-loss drugs, and pay down their student debt.

To be sure, holding multiple jobs without employer approval could have professional repercussions and lead to burnout. However, most job jugglers have told BI that the financial benefits have generally outweighed the downsides and risks.

Limiting burnout from a 12-hour workday

Sarah said job juggling requires long hours, but she's figured out how to make it work.

She works Eastern hours for one job, and since she lives in the same time zone, she works from roughly 8 a.m. to 5 p.m. Her other job follows Pacific Standard Time, so her hours are 12 p.m. to 8 p.m. ET.

"There is a level of stress because I am connected from 8 a.m. to 8 p.m.," she said, adding that she sometimes has work calls as late as 7:30 p.m. ET.

However, Sarah said the schedule works in her favor. She doesn't have to think about her West Coast job until noon and can focus solely on it after logging off from her East Coast job around 5 p.m. She said the most demanding stretch is between 1 p.m. and 3 p.m., when both jobs are busy.

To avoid burnout, Sarah said she travels with her family when she can, watches her favorite TV shows, and rewards herself for her hard work. Sometimes, that means splurging on clothes, shoes, special dinners, or spa days.

"Having something to look forward to is a great motivator," she said.

Still, she tries to stay realistic: Working 12-hour days means giving up time she might otherwise spend with her family or on her hobbies.

Return-to-office mandates haven't stopped her job juggling

In December 2020, Sarah was working remotely when a headhunter reached out about a full-time contract job that paid about $30,000 more than the position she held. The job was remote at the time due to the pandemic, but it was based in another state and could eventually require in-office work. When Sarah said she wouldn't be willing to relocate, the headhunter told her she could accept the job β€” and then quit if working from the office became mandatory.

Later that month, Sarah accepted the job offer and, in January 2021, began juggling two roles for the first time. She worked both jobs until last December.

Sarah said the employer of her contract job implemented a return-to-office policy over the past year, but because her contract specifies remote work, she hasn't been affected. However, her contract is up for its annual reassessment this summer, but she's hopeful she'll be allowed to continue working remotely.

"There's a need to have me there," she said, adding, "I told them that if I ever had to come in, I probably would quit."

Looking ahead, Sarah said she plans to keep job-juggling for the foreseeable future. If she quits her contract role, she's confident that she'll be able to land a new remote job.

While her workload can be tough to manage at times, she said she'd rather work the occasional weekend than give up one of her gigs.

"I will do what I need to do to get the work done," she said.

Do you have a story to share about secretly working multiple jobs or discovering an employee is doing so? Contact this reporter via email at [email protected] or Signal at jzinkula.29.

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Beating the system or cheating it? I set out to learn the ethics of secretly working multiple remote jobs.

21 April 2025 at 01:03
Rear view of a man working in front of two monitors.
Secretly juggling multiple full-time remote jobs raises ethical concerns.

Morsa Images/Getty Images

  • Over the past two years, I've interviewed more than two dozen people secretly working multiple remote jobs.
  • In response, I often get emails from readers who believe the practice is unethical.
  • Ethics academics and consultants said overemployment raises ethical concerns and may create conflicts of interest.

Some Americans are secretly working multiple full-time remote jobs simultaneously. Whether it's beating the system or cheating depends on who you ask.

Over the past two years, I've interviewed more than two dozen "overemployed" people, many of whom work in the IT and tech sectors. These people have doubled and tripled their earnings by juggling multiple roles simultaneously, and used their extra income to travel the world, buy expensive weight loss drugs, and pay off their student debt.

These stories have drawn a wide range of reactions from readers. Some people have commended these job jugglers for finding a way to maximize their earnings and job security. Others have argued that these workers are taking advantage of their employers β€” getting full-time pay without giving full-time attention β€” and holding jobs that unemployed Americans need.

I asked four ethics academics and consultants to weigh in on the debate. The consensus: Secretly juggling multiple full-time remote jobs isn't ethical, but the motivations behind it are understandable.

A question of contracts

Several of the sources Business Insider spoke with said the ethics question often starts with whether an employee has a contract and what it says.

Todd Haugh, an associate professor of business law and ethics at Indiana University, said that if an employee's contract stipulates that they must work exclusively for their employer, it'd be hard to argue that it's ethical for them to work another job.

However, Haugh said most workers in the US are "at will" employees who don't have formal employee contracts, which generally allows them to be fired or quit at any time. He thinks many job jugglers are likely breaching their employer's implied expectation that they'll focus fully on only one job during work hours. Even if a worker doesn't have a formal contract that prohibits job juggling, Haugh said they could be fired if they're found out.

"We expect that if you took a job with one company, you work for just that company," he said. "You're going to give your full attention, time, and energy to that particular company."

Jeffrey Moriarty, executive director of the Hoffman Center for Business Ethics at Bentley University, feels similarly.

"When you promise to work during certain hours for an employer, you implicitly promise not to work for another employer during that time period," he said, adding that job juggling likely involves lying and deception, behaviors generally frowned upon from an ethical standpoint.

Moriarty said workers likely wouldn't appreciate it if their employer started violating implicit agreements without their consent. For example, by paying them in a "wheelbarrow full of pennies" instead of the direct deposit they assumed was a given, he said.

Elizabeth Anderson, a professor of public philosophy at the University of Michigan and author of "Value in Ethics and Economics," said she believes lying is generally wrong, but an employer isn't entitled to know whether someone is working multiple jobs unless it's explicitly prohibited in an employment contract.

"As long as the salaried employee is working hard enough not to get fired, the employee has done everything they owe to their employer and is not obligated to reveal that they are moonlighting for someone else," she said.

Additionally, she doesn't think it would be unethical for an employee to evade a question about their work status or offer "truthful but misleading" information.

In the case of contract workers, who are often hired temporarily for a specific purpose, Anderson said job juggling is ethically acceptable unless it is explicitly prohibited in a formal contract.

"Their employer has no loyalty to them β€” else they'd be permanent β€” so no loyalty is owed back," she said.

The possibility of conflicts of interest

Overemployment could open the door to other ethical trouble, along with questions about loyalty.

Chris MacDonald, an associate professor at Toronto Metropolitan University who also consults on ethics, said it could create a conflict of interest if a person juggles multiple jobs and the employers are in the same field, presenting a different set of ethical concerns.

Meanwhile, Anderson said it would be wrong to work for a second employer from the first employer's office, rather than from a separate workspace, she added. And if an employee is paid by the hour, they should only bill for the time actually spent working for that employer.

While some job jugglers might think it's fine to have multiple jobs if the work gets done, MacDonald said it's probably wrong unless they've asked their employers first. Additionally, he said there could be times when performing well at two or more jobs isn't realistic.

"When two bosses both give you urgent deadlines on a Friday afternoon, who will you be loyal to?" he said. "You're likely going to have to lie to one of them, and probably fail in your responsibilities to them as well."

However, not every overemployed person will agree. In fact, Haugh said job jugglers likely have little trouble coming up with their own justifications for their working arrangements.

"Individuals are very good at viewing their own behavior as ethical," he said. "They come up with lots of good stories about why it's OK to do a thing, when really, if you step back objectively and look at it, oftentimes it's a lot harder to defend."

Do you have a story to share about secretly working multiple jobs or discovering an employee is doing so? Contact this reporter via email at [email protected] or Signal at jzinkula.29.

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How these 80-somethings are stitching together work, savings, and Social Security to get through the month

Photo collage of older couple over an image of money

Richard Stephen/Getty, Ricky John Molloy/Getty, BI

  • Some older Americans are working past 80 to supplement Social Security and cover their expenses.
  • Rising inflation and health issues are driving some older workers to seek part-time jobs.
  • The number of workers 80 and older increased by 25% since 2022, per Gusto, sometimes in risky jobs.

Jim Uhrinyak, 82, doesn't know if he'll ever have enough money to retire.

Uhrinyak is gearing up to work part time as a driver inspector at the traffic control company his son manages. He could have to work in areas where the traffic poses safety hazards. The Navy veteran said the extra money he makes will help him afford groceries, medications, and the bills he shares with his son, with whom he lives.

"I never saved for retirement," said Uhrinyak, who lives in Arizona. "It is miserable at an older age not to have funds to enjoy the last years of your life."

Uhrinyak is one of dozens of Americans in their 80s who spoke to Business Insider about needing to work well past retirement age. Many said they need income to supplement their Social Security checks, while others said a health scare, job loss, or rising inflation have eaten into the savings they hoped would carry them through retirement. This story is part of an ongoing series on older workers.

An analysis by Gusto, a small-business payment and HR platform, found that since 2022, the number of workers 80 and older has increased by about 25%, compared to 4% growth in the overall workforce. To be sure, that number represents a fraction of the workforce β€” about one in 1,000 US workers. The analysis was based on payroll records from over 400,000 small business customers.

"The economy and current prices are in a place where they're really forcing folks to reconsider or even rejoin the labor force," Nich Tremper, a senior economist at Gusto, said. "These are folks who are just likely looking to earn a little bit extra to have their money last as long as the month does."

Navigating work amid health challenges

Some workers in their 80s and older, including Uhrinyak, said they've taken on new jobs amid health issues, as they had few other options to stay afloat financially.

In February, Uhrinyak resigned from his role as a construction coordinator because of side effects he experienced from taking Ozempic. He said working with his son will make his transition back to the workforce easier.

Uhrinyak said the $800 a week he'll earn from the driver inspector job will supplement his $2,800 a month Social Security payment. He spends roughly $350 a month on medications β€” including $120 for a blood thinner β€” which, along with various medical expenses, has hurt his financial planning.

"The worry of having funds just to survive is sometimes overwhelming," Uhrinyak said. He has about $6,000 in total savings, he said.

Jim Uhrinyak
Jim Uhrinyak said working will help him pay for medications and household bills.

Jim Uhrinyak

Some older Americans have told BI that the only jobs they could find have put them at potential risk of injury, including jobs where they have to stand for hours at a time or lift heavy items. Some said their jobs have taken a toll on their bodies or mental health.

Monique Morrissey, a senior economist at the Economic Policy Institute who researches Social Security, found that older workers' jobs fall into, on average, 2.6 of six dangerous work categories, including physical demands and high pressure. She told BI that many older workers approaching or past retirement age have had to take blue-collar jobs that are lower-paying and riskier.

"You have slightly less dangerous jobs for older workers than for prime-age workers, but the dangers that they face are much worse," Morrissey said.

Diane Knaus, 82, broke her ankle in September, and she temporarily stopped working as a freelance writer to focus on her recovery. After a couple of months with limited income, Knaus said she began thinking about how to generate some additional cash. She's about to start a desk job for a trucking company.

"I'm on my Social Security, but that's not much," said Knaus, who lives near Annapolis, Maryland. "I'm just taking life year by year."

A tough job market for older Americans

Dozens of workers in their 60s and older told BI this year that finding a well-paying job feels nearly impossible amid a tight job market and reduced white-collar hiring. It's leading many to seek blue-collar roles and other part-time positions that pay a bit more than minimum wage.

Pamela Levier, 81, recently resigned from her full-time service department job at the car dealership where she'd worked since 2013. While she has four pensions tied to her and her late husband, she said they're "not large amounts" and that she's not in a position to retire.

Pamala Levier
Pamala Levier said she doesn't have enough in savings to stop working.

Pamala Levier

The dealership was sold, and the new owner was expected to make changes that Levier felt would negatively affect her work experience and could put her job at risk. She said she's been looking for positions at other car dealerships but hasn't had much luck. She's hoping to find a job to supplement her $2,100 monthly Social Security check.

"I live paycheck to paycheck," said Levier, who lives in the Tampa area. "No savings, no stocks, or bonds."

While she's in need of additional income, Levier said working would also help her stay busy.

"I don't want to be sitting around just not doing anything," she said. "I enjoy being out and about and learning things. It helps me stay young."

Working partly for the fun of it

To be sure, some older Americans who need work to supplement Social Security said financial stability and fulfillment are their main motivators.

Lawrence Dugan, 80, said he isn't desperate for the wages he earns and could live minimally on his savings and retirement income. While he and his wife value working, Dugan said they have some concerns, including knowing they could be "screwed" if an economic disaster comes.

"Working is probably 30% to 35% financial to get extras in life," said Dugan, who lives in Grand Rapids, Michigan.

Dugan said he works as a psychology consultant and earns roughly $3,000 monthly. He also sells paintings for extra income. Meanwhile, his wife works 15 to 20 hours a week as a home-care agency nurse. Dugan receives about $2,800 monthly in Social Security, while his wife gets about $2,100. Their combined net worth is less than $250,000.

"I knew when I was 25 I wouldn't retire and would die with my boots on," Dugan said. But he values work because it keeps him feeling younger. "Unless you keep using your brain, you use it or lose it."

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Fight, flight, or freeze: What kind of recession prepper are you?

woman sorting through bills
Β 

Getty Images

  • Americans are dealing with a palpable sense of uncertainty about the economy.
  • Most react to money fears in three ways: fight, flight, or freeze.
  • Which are you? Identifying your reaction can help regain a sense of control when anxiety strikes.

Job applications, panic buying, and tuning out the news: Which one's closest to your reaction to economic anxiety?

"We want the economy to keep rolling smoothly in the background while we live our lives," Joseph Coughlin, director of the Massachusetts Institute of Technology AgeLab told Business Insider. "So when we see this great uncertainty, it only adds to the stress that we're already trying to manage."

Coughlin said that many people cope in three ways: fight, flight, or freeze. In other words, Americans' money anxiety mirrors their natural reactions to other fears.

In recent months, BI has heard from dozens of Americans who are dealing with uncertainty regardless of their age, financial situation, or political affiliation.

The US isn't in a recession yet, but most of the people we spoke to are worried about short-term price increases, their student loan payments, or their 401(k)s. Some fear a more dire scenario of job losses and a downturn in the months to come.

Amid flip-flopping trade policies, stock market fluctuations, and DOGE cuts, consumer sentiment fell again in April, reaching its second-lowest level since 1952. Consumer spending trends indicate households are feeling the heat of high prices and tariffs.

If you feel powerless in the current financial environment, focus on what you can control and be aware of your own natural fear reaction, said Bradley Klontz, psychologist and professor at Creighton University's business school. He added that the US economy has faced downturns before andΒ always recovers.

"We have a fight, flight, freeze response," Klontz said. "You need to point it in the right direction."

Do you have a story to share about your finances? Fill out this survey.

People in 'fight' mode are busy making plans

Those with a fight mentality toward uncertainty are working hard to make plans. As Coughlin said, they are likely calling their financial advisors, reading news articles, saving extra money, and doing anything else they can to prepare for a potential downturn.

Robert Kistler, 71, retired a decade ago from his career as a product engineer. He and his wife built a seven-figure net worth and strong nest egg, but they're working to dial back their spending. With the long-term future of the Social Security trust fund in question and current staffing turmoil at the Social Security Administration, Kistler said they aren't confident benefits will support them as they age.

"It turns out our annual spending is roughly 20-25% more than in our plan β€” I am certain this is going to impact our retirement plan confidence level somewhat," Kistler said, adding that he met with his financial advisor this month to make a plan.

Similarly, 65-year-old professor Gail Lisenbard recently paid off her car and started grooming her mini golden doodle at home to save more money. She hopes to retire in the next few months and said she's carefully planned her nest egg, but is now concerned about rising prices.

Haylee Bachman
Haylee Bachman, 30, is worried about affording groceries because her family lives on a low income.

Photo courtesy Haylee Bachman

Younger Americans are taking action to protect their finances, too. Millennial mom Jen Miller had planned to buy a new car before May because her family has a third baby on the way, and they need more room. But, concerned about new tariffs on auto imports, she moved up her timeline because she's worried US car inventory will decline: "We certainly felt spurred into action," she said.

Haylee Bachman, a 30-year-old mother of three near Seattle, said her family lives on a low income and receives some government aid, but their budget has been especially tight lately. Her fiancΓ©'s job in car manufacturing became less stable in recent months because the industry is in turmoil with the auto tariffs.

Bachman said she's teaching herself to bake bread, cinnamon rolls, and other kitchen staples from scratch because it's cheaper and has visited food banks to pick up groceries. She's trying to save enough to afford rent and pay for activities like soccer and tumbling that make her kids happy.

"I know that things could get very bad for us since we are low-income and a one-income household," she said. "I'm not sure what the future holds, so I'm just trying to make those tiny changes."

People with a 'flight' reaction make snap financial decisions

A "flight" reaction to economic turmoil can take a few different forms. To protect their finances, Coughlin and Klontz said people with this response are likely panic buying or pulling their investments out of the stock market β€” snap financial decisions that may not be the wisest, but make people feel better in the moment. Coughlin refers to it as the "I need to get out of here" feeling.

BI has heard from teachers cashing out their pensions, families with tariff nerves overstocking their pantries, and investors primed to sell at the first sign of trouble. Some Americans are considering literal 'flight' β€” they're moving to other states or countries to escape high costs or policies they disagree with. Others are anxiously stepping back from newspapers or social media to tune it all out.

Klontz said when people get scared, "our survival brain tends to take over."

"Our instincts are great if we're being chased by a rabid dog," Klontz said, "but our instincts are not good when it comes to investing and spending." He advised people to avoid major or impulsive purchases where possible.

Still, Olivia Iverson, 28, doesn't regret choosing to "panic buy" a new MacBook laptop in early April. She pulled the trigger because many laptops are imported from China, and tariffs are likely to raise prices. Trump has since announced a pause on tariffs on electronics for now.

"A laptop is a one-time purchase," Iverson said, adding, "there's some stuff people panic buy that you're going to have to keep buying week to week, even if prices of these items change."

Olivia Iverson
Olivia Iverson, 28, said she panic bought a laptop after Trump's tariff announcement.

Photo courtesy Olivia Iverson

A flight response can lead to moves and major purchases, but it can also be a much-needed emotional break. As a busy mom balancing a household budget, Bachman said she often turns off the news. She said it can be stressful to constantly be on alert for changes in politics or the economy that might affect her family.

"I try to take care of myself as much as possible, just because I can't be the best mom without doing that," she said. "I do self-care, skincare, like face masks, or I sit in silence. That's a big one. I just sit in silence, in the dark sometimes, and just relax."

People who 'freeze' don't know what to do with uncertainty

The most common reaction to economic uncertainty is freezing, Coughlin said. Freezers are looking at the economy β€” the tariffs, stock ups-and-downs, the tough white-collar job market, and DOGE cuts β€” and they don't know what to do.

Christopher Smith
Christopher Smith, 41, is anxious about his job search.

Photo courtesy: Christopher Smith

The slow job market has left Christopher Smith's financial plans on ice. The 41-year-old has been looking for a job for about two years, but hasn't found the right fit. He's trying to stay optimistic, but he's "admittedly terrified" of what will happen to his employment prospects if there's a recession. He's taken on a roommate to help with bills.

"I am begging the universe to send me a job ASAP," he said. "I really hoped to be working by now, and I am slowly drowning under my finances."

Michael Salvatore
Michael Salvatore isn't sure how tariffs will impact his small business.

Photo courtesy Melissa Salvatore, Field Creatives

Michael Salvatore, similarly, isn't sure what to do next. He operates several bars and coffee shops in Chicago. His businesses are at risk of higher costs on everything from eggs to coffee beans. He said he's put all kinds of decisions on hold, including hiring and opening a new location.

"Especially as a small-business owner, the unknown makes it impossible to have a vision that you can execute on," he said, adding, "I'd rather the market crash and know that, 'hey, we're on a level playing field."

Rebecca Walriven-Lawson, 74, is also feeling stuck. She recently lost Medicaid because her Social Security cost-of-living increase put her over the qualification threshold. Without health insurance, she can't afford the surgery she needs to walk comfortably. She isn't sure what to do next.

"There's nothing for any of us to do but wait," she said.

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Don't call it DEI: Recruiters explain the hiring landscape under Trump 2.0

17 April 2025 at 01:03
Line in a job fair.
Some recruiters said hiring managers have continued to prioritize DEI in the hiring process, despite rollbacks.

Joe Raedle/Getty Images

  • Since returning to office, Trump signed an executive order to end DEI programs across the federal government.
  • Despite DEI rollbacks, some hiring managers are still prioritizing diversity, recruiters said.
  • Firms that continue commitments to DEI could get a leg up when competing for workers.

For some recruiters, DEI initiatives look different these days.

Some employers have scaled back or dropped their DEI programs, in part due to President Donald Trump's executive order to end DEI programs across the federal government. Additionally, Trump directed all departments and agencies to "take strong action to end private sector DEI discrimination."

However,Β fourΒ recruitingΒ professionals told Business Insider that many of the hiring managers they work with, including some at companies that have rolled back DEI initiatives, remain committed toΒ hiring a diverse workforce. They view this as the best way to find the most qualified person for the job.

"At some of the biggest major companies that you have seen on these lists, the same hiring managers are telling me, 'Okay, we're doubling down on my team, I don't care,'" said Den Mondejar β€” director of enterprise and talent solutions at the recruiting firm Aquent β€” referring to lists of companies that have rolled back their DEI initiatives.

Deepali Vyas said there appeared to be a "quiet commitment" to DEI among the companies that she worked with at the consulting firm Korn Ferry. Vyas was a senior partner, focused on building leadership teams, until she joined the talent advisory firm ZRG Partners this month. She said hiring managers who value interviewing and hiring diverse candidates have continued doing so, and their employers aren't getting in their way. Meanwhile, companies that have rolled back DEI policies aren't telling hiring managers to ignore diversity, Vyas said. They're just taking a hands-off approach and letting hiring managers take the lead.

"Companies that roll back their DEI policies aren't going to hiring managers and saying, 'Don't do this,'" she said. "What they're saying is, 'We don't really care if you do this or not.'"

Recruiters say DEI hiring looks different now

Julia Pollak, chief economist at the US Department of Labor, said she hasn't seen "broad evidence of a decline in the hiring of diverse candidates," adding that unemployment rates across demographics like race and gender haven't changed much in recent months.

Of course, not all hiring managers will prioritize diversity when they aren't being assessed on it. The recruiting professionals BI spoke with said that the absence of top-down pressure to meet DEI initiatives would likely lead to fewer diverse candidates being hired.

Matt Stabile, the founder of the recruitment firm Stabile Search, agreed that specific demographic "quotas" have "all but gone away," but that many hiring managers have continued to prioritize diversity in hiring.

For example, Stabile said one hiring manager he worked with in the past year had a team of about six people β€” all white males β€” and was looking to hire someone new. They asked him to make sure he introduced female candidates during the interview process.

However, some recruiters β€” like Vyas and Mondejar β€” said they aren't waiting for hiring managers to request a diverse pool of candidates.

"Regardless of what the client says, I think our commitment is to still continue to make sure that we are casting the widest net possible to make sure that we are bringing in the most qualified folks," Mondejar said.

Cautiously approaching DEI

Anuradha Hebbar, President of SHRM CEO Action for Inclusion and Diversity, said DEI has become a polarizing topic, creating a "chilling effect" that's made some companies more cautious about how they talk about diversity. However, she said many companies remain committed to having a diverse workforce while ensuring their hiring practices don't expose them to legal challenges.

"I think leading organizations are looking to optimize their diverse workforce to ensure fairness and making sure that they're lawful β€” but also really trying to drive meaningful business outcomes," she said, adding that companies that don't consider a diverse slate of candidates are likely to miss out on talented candidates.

Vyas said some companies have embraced "skills-based hiring," which focuses more on a candidate'sΒ capabilitiesΒ rather than their education and experience, in part so they can prioritize diversity without the DEI label. With this approach, she said it's easier to make the case for a wider range of candidates.

Reuben Hurst, assistant professor of management and organization at the University of Maryland, said there's one reason many companies are continuing their commitments to DEI, even if they're not as vocal about them as they used to be: It could help them compete for workers.

Hurst said that many of the college-educated workers that employers are competing for have values that align with the goals of DEI initiatives.

"I think the current narrative about firms abandoning DEI is overstated," he said, adding, "What's changed is that companies may now need more subtle ways to signal their continued commitment to DEI values."

Do you have a story to share about DEI practices at your employer? Contact this reporter at [email protected] or Signal at jzinkula.29.

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A video cover letter could help you stand out in a tough job market. Here's how to make one.

13 April 2025 at 01:01
Photo collage of a person in front of a cell phone and ring light
Β 

Raul Ortin/Getty, undefined undefined/Getty, Julia Pautova/Getty, Tyler Le/BI

  • Video cover letters could help applicants stand out in a competitive job market.
  • Career experts said video cover letters can showcase your personality and enthusiasm for a role.
  • However, you may want to avoid making one if you're not comfortable speaking on camera.

If you're struggling to get hired, it could be worth submitting a video cover letter.

"Unlike traditional cover letters, a video cover letter lets you showcase your personality, skills, and experience in a way that's unexpected, which can really help you stand out and make an impression," Andrew McCaskill, a career expert at LinkedIn, told Business Insider.

Hundreds of Americans told BI how they've struggled to find work in the last year. While the unemployment rate remains low compared to historical levels, businesses are hiring at nearly the lowest rate since 2013, excluding a temporary dip in 2020. In response to these challenges, some Americans are trying alternative ways to stand out, such as recording video cover letters. McCaskill, along with career experts from Indeed and ZipRecruiter, told Business Insider that video cover letters could give candidates an edge in a challenging job market.

Similar to written cover letters, video versions allow applicants to introduce themselves, explain why they're interested in the role, and share their qualifications. There isn't much data on the prevalence of video cover letters, but the career experts BI spoke with said they've become more common since the pandemic β€” when employees grew more accustomed to virtual work.

To be sure, there's some debate over how important a traditional cover letter is for today's job seekers. However, the career experts BI spoke to said that for many, the potential rewards of a video cover letter are likely to outweigh the downsides.

What to consider when making a video cover letter

Sam DeMase, a career expert at ZipRecruiter, said that including an unprompted video cover letter isn't "mainstream" yet but has become more common in recent years. She said the rise may have been driven by younger job seekers who may prefer video content β€” like TikTok and YouTube videos β€” to the written word.

"It lets candidates showcase personality, communication style, and presence β€” things that a rΓ©sumΓ© or even a written cover letter can't fully capture," DeMase said.

However, a video cover letter should supplement β€” not replace β€” a written cover letter, particularly when a company has a specific requirement for the latter, the career experts told BI.

DeMase said a video cover letter should be between 60 and 90 seconds and include a brief introduction of yourself, an explanation of how your skills and experience align with the job description β€” including a couple of specific examples β€” and why you're excited about the role and company.

"Our data shows that the No. 1 thing employers care about is that you have aligned experience and skills," DeMase said. "So that's going to be the priority."

DeMase and Priya Rathod, a career expert at Indeed, encouraged job seekers to write out a script but avoid reading directly from it. And be mindful of how quickly they're speaking.

"You don't want to speak too fast," DeMase said. "That can come across as nervous, low confidence, and unprofessional."

See below for an example video cover letter DeMase created and shared with Business Insider.

McCaskill stressed the importance of aesthetics: Make sure the video's background isn't distracting and that you're dressed professionally. Additionally, he said it's important to show your excitement for the role.

"The reality is companies want to hire people who want to work there," he said. "Be yourself, show some passion, and clearly share why this specific role and company speak to you, your values, and where you want to take your career next."

DeMase said you should film the video vertically on your phone and speak to the camera like you would on a video call. She recommended uploading the video to YouTube as an unlisted video, which can only be viewed by someone with the link.

While speaking to the camera should suffice, DeMase said people who have video editing skills could consider including visual representations of their work β€” or finding other ways to get creative. McCaskill pointed to a "standout example" of a highly produced video cover letter posted last year on LinkedIn by Marta Puerto, a job seeker who was looking for a product marketing position.

"Her video went viral and landed her hundreds of interview requests and a job," he said.

For applicants who include a written cover letter, DeMase suggested putting the link at the top of their cover letter with a note saying something like, "If you prefer to watch a short video of me highlighting why I think I'm a great fit for this position, click here." For applicants who decide not to include a written cover letter, she said placing the link at the top of their rΓ©sumΓ© next to their contact information is a good option.

Video cover letters may not be a fit for everyone

The career experts BI spoke to said video cover letters could be particularly helpful for customer-facing roles or jobs that require strong communication skills.

"For those in media, marketing, or creative industries, a high-quality video cover letter can also double as a portfolio piece, showcasing your skills in film production or content creation," Rathod said.

A LinkedIn representative shared an example video cover letter made by Curtis Ying, a graphic and web design professional who applied for β€” and landed β€” a job at Adobe last year.

DeMase said video cover letters could also be helpful for applicants in industries like business consulting, marketing, and tech. However, she cautioned against the practice for some older job seekers.

"I think when you're older, sending a video could open you up to potential age discrimination, which a lot of folks deal with," she said.

Lastly, use your judgment when deciding to submit a video cover letter. If an employer is "super old school" or you're not confident speaking on camera, you may want to reconsider, DeMase said.

"Done well, a video cover letter can help you stand out and leave a lasting impression with hiring managers," Rathod said.

Have video cover letters or other creative job search strategies helped you land interviews or a job offer? Contact this reporter at [email protected].

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The anti-aging secret these 80-somethings swear by: work

A collage of an older worker.
Β Some Americans are working in their 80s for fulfillment and social benefits.

Getty Images; Rebecca Zisser/BI

  • Some Americans in their 80s are working past retirement age, but not because they need the money.
  • They told BI their jobs bring them fulfillment and social connections.
  • The number of US workers over 80 has grown 24% since 2022, but is still a small amount.

As he approaches 90, Al Faber often works 50-hour weeks. But he's not doing it for the money.

"I'm 87 going on 67," said Faber, who hopes to work into his 90s. "Being a resource for as many people as you can be a resource for, including family and friends, is why I work."

Faber is one of dozens of Americans in their 80s who told Business Insider that they're working past retirement age for fulfillment and social connections β€” not because they need the money. Some of the people BI spoke with said they're still running companies they created decades ago, while others remain at a business or in an industry they love. The money they make has contributed to vacations or emergency medical expenses β€” but isn't the driving force keeping them employed.

Workers in their 80s and 90s represent a sliver of the US workforce, but their numbers have grown in recent years. Americans in their 80s and 90s account for about one in 1,000 of all US workers, per an analysis by the small business payroll and HR platform Gusto. The analysis was based on payroll records from over 400,000 small business customers.

However, the number of workers ages 80 and older has increased by 24% between January 2022 and February of this year. In comparison, total employment grew about 4% in that same time period.

Nich Tremper, a senior economist at Gusto, said this growth has likely been driven by two factors: People are living longer and the cost of living has risen in recent years.

"Things are still really expensive for folks who have retired," he said. "They might be considering going back into the workforce to start earning a little bit of extra money."

While the older Americans BI spoke to don't fall into this category, many people work past the retirement age of 66 or 67 due to financial reasons. Some previously told BI that a health scare or job loss ate into the savings that they hoped would carry them through retirement β€” and that their Social Security checks aren't enough to live on.

Tremper said workers 80 and older are most likely employed in education and health services. He added that the most employment growth since 2022 in this 80s and older cohort has come in retail and wholesale trade, where he thinks many people have found part-time work. Additionally, 85% of workers over the age of 80 were employed part-time, per Gusto.

Finding joy through the social connections of work

Faber, who lives in the Boston area, said that every day brings new conversations and lessons that improve his quality of life.

For most of his career, Faber worked in public accounting and held management positions in development counseling. In his 70s, Faber founded the consulting organization Alan Faber Growth Strategies and still runs it but works shorter hours these days.

Faber said he values meeting people face-to-face and remains physically strong by lifting weights and running. Some days are longer and more stressful than others, but Faber said regular interactions keep him fresh.

"If it was strictly for money, I wouldn't be doing a lot of the pro bono work," Faber said. "I see people who are 60 and 70 walking around like they're 10 years older than me not doing anything, not interacting with people, and it's sad."

Helping people is one of the main reasons Charles Mango is still working. He's been a retinal specialist for 53 years and works five days a week.

"I could retire tomorrow if I wanted to," said the 82-year-old, who's based in Syracuse, New York. "I don't really have to work."

Charles Mango
Charles Mango said he enjoys working and that it keeps him busy.

Charles Mango

Mango said he continues to work because it keeps him busy and he loves his job β€” in particular, talking with and caring for patients. He's cut back on performing major surgeries in hospitals since the pandemic but will do minor surgeries in his office.

"As long as my health allows, I'm going to continue," he said. "I have no reason to stop."

Passion for a business can make it difficult to stop working

Andrea Hutchinson doesn't want to stop working at the restaurant where she's devoted the last 40 years of her career.

The 82-year-old works about five hours a day, twice a week, as a director of operations at Pierce's Pitt Bar-B-Que in Williamsburg, Virginia. She's held different roles at the restaurant and said she's seen it go through ups and downs. But her commitment to its success has, at times, been an "obsession."

"The friendships, the activity, keeping myself busy, also the pride I have in what we have been able to do," she said. "That's a lot to give up."

Hutchinson said if her restaurant job ended, she doubts she'd look for work elsewhere.

"If you have someplace you can go where you feel needed and people listen to you, it's wonderful," she said.

Jay Crisford, 83, is also deeply invested in a business β€” one he started in 1993. Crisford, who's based in the Dallas area, continues to run Front Desk Office Furniture, an eight-person company that sells new and used furniture for professional settings.

Jay Crisford
Jay Crisford still works for the company he created decades ago.

Jay Crisford

He said he's gearing up for a "pre-retirement," which would mean fewer hours at work and more leisure time, but doesn't think he'll ever stop working.

When people tell him he should retire, Crisford replies, "I'm retired on the weekends." Crisford said he works to remain social and continue hitting professional and personal goals. He added that he has too many connections and deep knowledge of the industry to call it quits.

"I don't know what age has to do with retirement, and I think there's a lot of people who shouldn't be working if they don't enjoy it," he said.

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4 tax-reduction tips from 6-figure earners secretly juggling multiple jobs

11 April 2025 at 01:02
A woman sits in a desk and makes a call in the phone while holding a paper.
Some Americans who secretly work multiple remote jobs are using tax strategies to reduce their tax burdens.

10'000 Hours/Getty Images

  • Americans who secretly work multiple remote jobs are finding ways to reduce their tax burdens.
  • Some said establishing an S-Corp and maxing out their 401(k)s are among their top tax strategies.
  • Others contribute to charities or deduct business expenses from their incomes.

Damien has secretly worked multiple remote jobs, earning six figures on and off for years. To reduce his hefty tax burden, he's used several strategies, including maxing out his 401(k).

Damien, who works in IT support, is on track to earn $386,000 this year from three full-time remote jobs, two of which are 1099 contractor roles. The earnings from his contract positions flow to an LLC he established in 2022, which he elected to be taxed as an S Corporation. This helps him reduce the amount he owes in self-employment taxes, he said.

"Tax wise, it's a substantial difference," said Damien, whose identity was verified by Business Insider but who asked to use a pseudonym, citing a fear of professional repercussions. "I would have to guess it's tens of thousands of dollars that I'm saving."

Damien is among the Americans who have secretly juggled multiple remote jobs to boost their incomes and who have found strategies to reduce their tax burdens. Others make charitable donations and deduct business expenses from their incomes. Over the past two years, BI has interviewed more than two dozen "overemployed" workers who've used their additional earnings to travel the world, buy weight-loss drugs, and pay down debt.

Six job jugglers shared their experiences on the condition that pseudonyms would be used, for fear of professional repercussions. BI has verified their identities and earnings.

To be sure, what works for these job jugglers may not make sense for everyone. Tax professionals can provide advice for specific situations.

S-corps and business deductions help job jugglers reduce their taxes

John, who works in IT, earned more than $300,000 in 2023 secretly working two remote jobs. His earnings from one contract job flow into his S-Corp, which he also uses to deduct business expenses, reducing his taxable income.

Business expenses include software subscriptions to ChatGPT, online programming courses, and the home office deduction, which allows him to deduct $5 per square foot of his home office.

"If I needed a new computer desk or chair, I'd run that through my business," said John, who is based in California.

To reduce his taxable income further, John said he donates to charitable organizations and makes significant 401(k) contributions.

Harrison also has an S-Corp, but his tax situation is more complicated. Harrison has six full-time remote jobs as a quality assurance professional in the IT sector and estimates he'll earn roughly $800,000 this year. He's built a team of seven workers who help him complete his duties.

Three of Harrison's jobs are contract roles, and he said the income for these flows into his S-Corp, which he said helps reduce his taxable income.

Lisa Greene-Lewis, a CPA and tax expert with TurboTax, said that S-Corps can help people legally reduce the amount they owe in self-employment taxes. Individuals are required to pay themselves a "reasonable" salary β€” which is subject to employment taxes β€” but then can take additional distributions from profits their companies generate that are not subject to these taxes. But she said there are limits to an S-Corp's tax benefits.

"In the eyes of the IRS, you could not pay yourself a majority of your business income to avoid more self-employment taxes," she said, adding, "If you pay yourself too little, the IRS could determine the amount they think you should be paid based on your business profit."

She added that S-Corp owners tend to have more tax prep-related expenses and must file a business tax return by March 1st, rather than the April 15 deadline for personal tax returns.

Despite the tax benefits that come with his S-Corp, Harrison said he tends to owe a significant amount of money in taxes. But he said he's still coming out ahead financially.

"Making more and paying more in taxes is better than making less and paying less," he said.

Some job jugglers accept their higher taxes

Adam earns roughly $170,000 annually secretly working two remote security risk jobs. He plans on reducing his taxable income this year by contributing $23,500 to his 401(k) β€” the maximum amount allowed by the IRS β€” and donating about $1,200 to charitable organizations.

However, not every job juggler is taking significant steps to reduce their taxable income. Daniel earns about $250,000 annually working two remote IT gigs in the finance industry. He said his main focus is withholding enough in taxes to ensure his tax payment isn't too steep.

"I've never had an issue with paying taxes," he said.

Kelly is on track to earn nearly $300,000 this year secretly working two full-time remote jobs as an engineer. She said her taxes aren't too complicated and finding ways to lower her taxable income isn't something she thinks too much about.

"I don't mind paying taxes on both jobs even if I owe," she said.

Do you have a story to share about secretly working multiple jobs or discovering an employee is doing so? Contact this reporter via email at [email protected] or Signal at jzinkula.29.

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