• Martins Lasmanis, the founder of Supliful, struggles with balancing startup growth and family time.
• Supliful quickly gained traction, and Lasmanis began working 16-hour days with three young kids.
• He now schedules family time and delegates work to manage 'dad guilt' and improve work-life balance.

My youngest son turned 3 this year — the same age as my startup, Supliful. As I watched my toddler playing on his birthday, I felt a strong sense of guilt creep up inside me. He wasn't a baby anymore, and I realized I'd missed out on him growing up.

"They grow up so fast!" is what all parents say. That day, this cliché suddenly felt terrifyingly real. Even worse — it felt as if, over the past three years, I'd spent more time growing my startup than paying attention to my children growing up.

That feeling was torturous

I've always wanted two things in life: a big family and my own business. Family is where I find peace and joy, and I find self-fulfillment in business. I've never been able to sit still and must be in constant motion.

In 2021, when I became a father of three and founder of a newly launched startup, I felt I was on the right path. My life goals were being met. I was nailing it.

While I didn't expect raising three kids and building a company from scratch would be easy, I didn't worry much either. I had already been there — a few years prior, I was running a successful online store while raising two preschoolers. I thought I had the experience necessary to handle the new responsibilities.

I was wrong

I soon realized my new venture had much more potential and was more complex and demanding than anything I had built before.

When I attracted serious interest from VC investors, my company was still in its ideation phase. We onboarded hundreds of users just three weeks after making our product public. By our second year in business, we were already making over $1M in revenue.

Success came with challenges and new responsibilities. I had to quickly grow our team, onboard new partners, and open a new fulfillment center on the other side of the world to ensure quality service to our clients — all while ensuring we didn't run out of money.

I spent my days on back-to-back calls with investors, business partners, and new hires. In the evenings, I sometimes had to help my colleagues pack and send out orders. I'd regularly travel between our office in Europe and the fulfillment center in Denver, feeling guilty for leaving my family behind every time.

My wife was extremely understanding

Throughout our 13 years together, my wife has always supported me. Although she wasn't happy about me staying late in the office or leaving for another business trip, she always encouraged me to pursue my career goals.

Without realizing it, my working days got longer. At one point, I worked 12 hours a day and sometimes as many as 16 hours.

I still tried to be as hands-on as possible with my kids. My wife and I had our own caregiving "shifts" — I covered mornings and after-work, taking the kids to and from school and day care. My wife handled the evening, taking care of dinner and putting the three to bed. We all tried to spend time together between dinner and my late work calls.

Eventually, a dreaded day came

"Daddy, you're working too much." My 7-year-old daughter caught me off guard. We had just finished our dinner one evening in September, and I prepared to disappear into my home office for another round of calls and emails. I responded "I know. I'm trying to build this business, but I should be more present with you."

I realized I was experiencing an enormous feeling of guilt — the feeling of failing as a parent because I wasn't there for my kids. While I saw my tight work schedule as a sprint that would eventually end, my kids only saw me working.

I had heard about "mom guilt," a term often used to describe the feeling women have when they believe they're not meeting their own or others' expectations in their role as parents.

I felt "dad guilt" — the dark side of entrepreneurship and many other demanding jobs requiring long hours. Every day, I feel guilty for not prioritizing my children or failing to build my startup.

I wish I had an easy fix to make this all balance out

I don't have a solution, but I have found a few things that make the weight easier to carry.

I make it a point to schedule family time on my calendar and never cancel it. I treat it as seriously as any work meeting and make a real effort to be present.

I set high standards, but I've had to remind myself that perfection isn't real. Sometimes, I take stock of the good I've done, balancing it against the areas I wish to improve. Reminding myself of these positives helps me feel more at peace with where I am.

I've delegated more work to my team, allowing me to spend more time with my kids this past month. We're moving to the US next year, so that will be another adventure.

Through it all, I'm beyond grateful for my wife. She's my best friend, and her unwavering support allows me to pursue my entrepreneurial dreams.

• Nicole Chan Loeb is a 38-year-old photographer, videographer, and a mother-of-two.
• She and her husband prioritize experiences over gifts, so they invest for their kids in lieu of toys.
• They want to teach their children financial literacy and set them up for a secure financial future.

This as-told-to essay is based on a conversation with Nicole Chan Loeb, a photographer and videographer from Boston. It's been edited for length and clarity.

My kids are 1.5 and 4 years old, and I've never bought them any physical presents for birthdays and holidays.

For birthdays, I'll make a cake, and instead of buying toys and clothing, I invest money for them to set them up for a more secure financial future. Plastic toys and knickknacks are temporary fun, but they cause clutter and landfill waste.

My mom taught me about stocks when I was growing up

Growing up, my mom used to tell me about the stocks or funds she invested in for me. Every week, we'd take the figures in the newspaper, chart them on graph paper, and stick them on the fridge. We mostly invested in mutual funds. That was fun, and I especially loved the special time my mom and I spent together. I similarly want to teach my kids financial responsibility and literacy.

My husband and I met in college in 2004. We both worked in the finance and accounting industry — I was in management consulting, and he was in internal audits — before deciding it wasn't for us. I quit in 2010, and he quit shortly afterward, and we both became entrepreneurs. I'm a photographer and videographer, and he owns an escape room company.

It was a considerable risk and I was absolutely terrified. But since my parents taught me financial literacy, I've learned how to save to be comfortable no matter what. Plus, the flexibility and fulfillment this lifestyle provides is very worth it.

We gift our kids investments instead of physical gifts

My husband and I don't exchange gifts in general. If we want something, we'll just purchase it for ourselves — after all, our money is pooled — so I find gift-giving challenging. Instead, we share and enjoy dinners, experiences, shows, and vacations. We give each other cards — it's more about the sentiment.

This year, my husband and I maxed out our kids' custodial Roth IRAs and deposited $7,000 each. My kids have been models for children's clothing lines, toy companies, and hospitality campaigns in my work as a commercial and advertising photographer, so the money is considered their earned income.

We decided to start investing for the kids last year because, from conversations with friends, we realized that we all wished topics like taxes, saving for retirement, and smart investing were taught in high school or earlier. We decided not to wait and agreed to start teaching these concepts as soon as our kids could grasp the basics.

Also, both my husband and I were lucky to leave school without a massive amount of debt because of our parents. These investments will allow our kids to graduate from college without an insurmountable amount of debt.

We're focused on Roth IRAs for now, but we plan to open investment accounts for them within the following year. If they don't have earned income in future years, we will set up a custodial brokerage account and invest for them that way. Because we both own our businesses, our salaries and incomes fluctuate, so we look at our finances each year and decide how much to invest.

Our kids are happy with spending time together

My kids are young, so the concept of expecting gifts has yet to solidify. And they don't really need anything. We're lucky to live in a great neighborhood where the parents pass on toys when their kids have outgrown them. I rarely purchase large toys or gifts, but I don't hold back from ad hoc purchases of crayons, markers, kids' card games, and board games.

Our children are happiest when we spend time together, doing things like lunch dates, playing board games, and baking. Happiness comes from experiences and relationships, and fewer material things promote creativity.

They spend a lot of time outside making up their own games, and we often play with things like sticks, stones, water, acorns, and pinecones. We want contented, balanced kids who aren't overwhelmed with things and toys and chasing the next new shiny object.

My husband and I find a lot of interest and joy in investments, and we hope our kids will as well. My four-year-old is very bright, and in the next year or so, he'll understand that you can put money in specific vehicles to grow, learning the concept of delayed gratification.

I'm hopeful that our kids will start making their own side income in high school and start to learn to invest for themselves as teenagers, just as I did while growing up.

If you have a unique way of teaching your children financial literacy and would like to share your story, email Jane Zhang at [email protected].

• Michael Allen stopped buying pricey Christmas presents for his friends and family in college.
• His financial priorities changed after leaving the Marine Corps and working toward his degree.
• Allen values time with loved ones over material gifts and emphasizes memories over money.

This as-told-to essay is based on a conversation with Michael Allen, a 54-year-old author from Titusville, Florida. It has been edited for length and clarity.

In 1995, I realized I couldn't give expensive gifts anymore. I was used to buying gifts to impress my loved ones, and I received nice gifts as well. At a younger age, I would get things like an Atari with games, boxing gloves, or a football. Gift cards, nice clothes, and even a watch were more common presents as I grew older.

As a college student and a recently retired Marine, my priorities were school and food. My next goal after serving in the Marine Corps was to get a degree. Not wanting to participate in the "who bought the most expensive present" game made sense.

I was getting by on side jobs

I tutored other college students and worked as a bouncer. Although I was only making enough money to cover my necessities, I was looking forward to achieving my goals of becoming an English teacher and a writer.

Buying extravagant things at the expense of putting myself in huge debt didn't seem attractive. I knew my financial situation had changed throughout my life, and I had to spend and save accordingly.

Reflecting on the hard work I put in made me extremely proud rather than ashamed of my financial background.

I decided to have a conversation with my friends and family

One day before Christmas, I asked my friends and family to lower their expectations regarding future gifts. I told them about my financial situation, what I could spend on, and what I was trying to accomplish.

Spending exorbitant amounts on Christmas was out of the question. Being open and honest about my struggles and primary issues worked out in my favor. I wasn't nervous to have this conversation.

Most of them understood, and I was truly relieved once I confessed. It immediately broke the needless superficial confinement I had put myself in to conform to the norms.

I also prepared myself to receive less of what I had previously

While some family members would still buy me costly gifts, some limited their splurging on me after this conversation. I was satisfied with getting whatever they would get me, even if it was nothing sometimes. Some even joined me in setting this boundary for themselves.

I started enjoying Christmas even more without having to impress people with my gift-giving superpowers. I became accustomed to speaking my mind and being truthful at all times. When you embrace life in that manner, many burdens are lifted.

Even as I make more money, gifts still don't seem important to me

My financial situation has improved, but I now sometimes only hand out one present per person. I make sure it's something meaningful and not just anything.

I once made my mother a loving video, and she still plays it often. On another occasion, I built a website for my daughter and made her a book. Personalization goes a long way.

Focusing on getting together with your loved ones and spending purposeful time with them are the only significant things of concern to me. Gifts are a component of Christmas, not the foundation.

Memories matter, not money. Food, drinks, old movies, and a good time is all I care about getting from anyone.

• Jamie Jackson worked in HR for over 20 years and is now a podcaster and consultant.
• Jackson said when you're no longer engaged or growing at work, it could be time for a new role.
• Updating skills and preparing a job search toolkit can aid in career transitions.

This as-told-to essay is based on a conversation with Jamie Jackson, a 43-year-old podcaster and consultant in Nashville. It has been edited for length and clarity.

As someone who has worked in HR for over 20 years, I've had this conversation countless times. People often confide in me, saying, "Jamie, I don't know what to do next."

They feel stuck in their roles, want to advance, or are considering a new job — but that can be just as scary because it means stepping outside their comfort zones. I've been there, too, wondering whether it's time to quit my job for something new.

If this is you, here are four key signs you've been in your role too long and what you can do next if you need to make a change.

1. You no longer feel motivated

Your engagement level is a good indicator of whether you've been in your role for too long.

For example, you may have previously felt engaged in meetings but now find it harder to do so because you no longer feel motivated.

Or, perhaps you once enjoyed conversations with coworkers at the watercooler or over coffee — asking about their weekends or holiday plans — but now you simply do what you need to do and move on.

2. There's no room for growth

Another sign is feeling stagnant in your growth.

For example, I once worked at a company for five years and kept being promised a promotion. Over time, it became clear it wasn't going to happen — they didn't see me moving up.

For a long time, I believed their promise was coming, but it never did. To advance, I realized I'd need to change companies because the growth I wanted wasn't going to happen there.

Sometimes, there simply isn't room for growth, and when that's the case, it's a clear sign that it's time to make your next move.

3. Your feedback has plateaued

Or, you might find yourself hitting a feedback plateau.

For instance, you may consistently receive the same performance reviews, with your manager saying that you're meeting expectations but not exceeding them — suggesting you've reached a stopping point.

If you're thinking to yourself, "I don't have anything else to offer. I'm doing the same job I was doing three years ago without additional constructive feedback or recognition," it might be time to switch roles.

4. You're burned out

Another sign is burnout. In the past, I had a job where I felt physically sick going into work.

I remember one time needing to pull over to the side of the road to puke because I was so stressed.

As I sat in a parking lot trying to compose myself, I thought, I have to find another job. I knew my mental health was more important — but as I didn't have the luxury of quitting on the spot, I found another job first.

For others, there are times when environments are insanely toxic, and they need to get out immediately — and they should, but when possible, it's important to have a plan in place.

Either way, burnout or feeling physically sick from work might be a sign that it's time for a change.

If you realize you're no longer happy in your role, you need to do some self-reflection

Ask yourself, what are my goals? Where do I want to be? In your mind, try to understand where you want to be in six months, a year, or even further into the future.

Do you need a new title or a promotion, and if so, how do you get there? Before doing anything, it's really important to understand what you want. Then it's time to take aligned action.

Brush up on your skills

Maybe you're perfectly content with your current role; you just need to be challenged more. By learning new skills, you can push for more responsibilities.

You can use resources like LinkedIn or YouTube to brush up on skills like Excel or explore additional training or certifications offered by your current company. New skills can help you stand out in your current role or make you more appealing to potential employers.

Get your tool kit ready

If you're looking to land a new job, you need to learn new skills and prepare your toolkit.

This includes updating your résumé, refreshing your LinkedIn profile, and researching the salary you should be making.

When you start looking for a new job, knowing your market value is key — especially if you've been in your current role for a while and aren't sure what the going rate is. From there, talk to your mentors, colleagues, and friends, and let them know you're looking for something new.

You might say something like, "Hey, I think by March, I'm really going to start looking for another job — so can you keep your eyes and ears open?"

That can really help.

December isn't the easiest month to get a new job, with the holidays and people taking time off. However, January can be a better time as companies enter the new fiscal year — new budgets and new positions are being rolled out. But you can always be passively looking.

Some of us are content where we're at, but if you're no longer interested in stepping up or taking on new challenges, it might be time to reassess your role.

If you're an HR professional with unique career advice you would like to share, please email Manseen Logan at [email protected].

• Erwin Jacob Miciano left the Navy in 2021 to focus on his real estate business full-time.
• Miciano and his wife used VA loans to buy a triplex and start their business, Semi Homes.
• Semi Homes helps homeowners avoid foreclosure and launched Miciano's real estate career.

This as-told-to essay is based on a conversation with Erwin Jacob Miciano, a 27-year-old real-estate investor and the owner of Semi Homes in South El Monte, California. It has been edited for length and clarity.

I'm a dedicated dad, a committed husband, a real-estate investor, and the co-owner of Semi Homes, a real-estate company specializing in direct-to-seller transactions and marketing strategies. I co-own the company with my wife, Theressa.

I don't have a college degree. I graduated from high school in 2015 and first worked at Wetzel's Pretzels. I decided to join the Navy to support my family abroad in the Philippines and my mom and brother in the US.

In March 2016, after three months of boot camp, I completed the basic training to become a photojournalist. Until September 2021, I served as a mass communication specialist, with most of my overseas years based in Japan, stationed on the USS Ronald Reagan.

I separated from the military in 2021 to pursue real estate full-time

My Navy job included writing press releases, aerial photography, videography, and printing. In later years, I was stationed at the Naval Hospital Balboa in San Diego, where we covered COVID-19, and I was deployed with USNS Mercy to San Pedro in Los Angeles during the pandemic.

I was presented with an "early out" program because of overmanning in my job, and it allowed me to complete my contract a couple of years early. I had already started my business, but leaving the military allowed me to pursue it full-time.

I also wanted to spend more time with my young family. My eldest was born in January 2020.

My wife and I met on the day I arrived on the USS Ronald Reagan in 2016

We became friends through the first-response/firefighting team, where she worked as an electrician. We also noticed each other at church services, and she invited me to her baptism ceremony, where she was baptized inside an open jet fuel tank.

Early in our relationship, we lived together in a small Japanese apartment. Then, we spent about a year doing long-distance, with me still deploying on the carrier and her based in San Diego.

After a year of dating, we got married, and soon after some vacation in the US, we discovered we were expecting our first child. During most of her pregnancy, Theressa lived alone until I got stationed in San Diego around her seventh month.

That same year, I became deeply interested in personal finance and real-estate investing, inspired by stories of blue-collar workers achieving financial freedom through real estate. I learned the most from the BiggerPockets podcasts.

We were motivated to become first-time homebuyers

We were eager to apply what we had learned and planned to use the VA loan entitlement from our military service. VA entitlement is how much lenders can lend to a veteran or active duty member without providing a down payment.

We aimed to buy a multifamily property — ideally a duplex, triplex, or fourplex — so we could live in one unit and rent the others to offset our mortgage. Today, this strategy is known as house hacking.

Being stationed in San Diego gave us a few key advantages

The housing allowance we received as military members was higher than in most US locations, boosting our household income to about $10,000-$12,000 monthly. This allowance was discontinued once we both left the military. Theressa left the Navy almost a year before I did at the end of 2020.

Second, the VA loan allowed us to buy a multifamily property with zero down payment.

Third, we included 75% of the gross rental income from the property in our loan application, increasing our approved loan amount. On paper, our monthly gross increased to $15,000-$17,000.

Finally, new legislation removed local VA loan limits for first-time users, giving us more purchasing power.

After months of searching, we found a triplex listed for $1.2 million

We offered $1 million and settled at $1.1 million. By March 2020, we had moved into a three-bedroom unit while renting out the other two for about $4,000 a month, reducing our housing costs to less than what one-bedroom rentals were going for at the time. This was the start of Semi Homes.

After living in the triplex for two years, we moved in with my mom and brother in September 2021 in the San Gabriel Valley. The triplex is now fully a rental property generating $1,500 to $2,000 monthly profit.

My day-to-day work involves meeting with homeowners who are looking for support in selling their properties

We now buy properties and resell them for a profit. We also help sellers in deep foreclosure and save them from it. My role is to get my team in front of our target audience and guide clients through the entire process, all the way to the closing table.

There are also late-night administrative hours and business-building, which I work on three to four nights a week. The biggest change from my Navy days is that I'm no longer away from my family for long periods — a small freedom I cherish.

I feel both fulfilled and successful

While Semi Homes started as a way to build wealth and achieve financial freedom for my family, it's grown into something more.

We stay in this tough business because we truly believe in the value we provide to the individuals we work with. I'm focused on building our online presence and spreading the word that foreclosing is not the only option.

I see myself in real estate for the rest of my life.

Want to share your story about getting on the property ladder? Email Lauryn Haas at [email protected].

• Samantha Shih sold her custom clothing company 9Tailors to join LookSky as chief brand officer.
• Shih founded 9Tailors in 2008, growing it through challenges like the financial crisis and pandemic.
• Her C-suite role both doubled her salary and allowed her to balance her work and family life.

This as-told-to essay is based on a conversation with Samantha Shih, a 43-year-old chief brand officer from Boston. It's been edited for length and clarity.

After graduating from Brown University in 2003, I worked as a consultant at Deloitte for three years before spending a year in China. There, I started making custom clothing, which inspired me to open a custom suiting and shirting company. I founded 9Tailors in Boston in 2008.

Launching a business was challenging because I had little experience in retail and fashion and had to learn everything from scratch. I had some business strategy knowledge from working at Deloitte but didn't have operational knowledge.

I learned and grew the company for 14 years. In 2022, I sold 9Tailors and jumped ship to work for a startup.

Launching a company in 2008 was tough

I had a lot of friends who were getting laid off, but I was optimistic. You can only go up from the bottom, so I thought it was an excellent time to start a business.

The company started online, keeping no inventory and making everything to order. This allowed us to identify our target customer — young professional males looking to dress up for work or weddings.

We've been profitable since year two, winning awards and garnering press until the pandemic threw everything off track. Running a high-touch custom clothing company that needed in-person contact and relationships was stressful. We pivoted toward making masks and sold out immediately.

Around this time, my brother called me one day out of the blue

My brother told me his former boss was advising LookSky — an Asian direct-to-consumer fashion brand looking to enter the US market — and they wanted to speak to a fashion industry expert. I had no set expectations for these calls — I enjoy helping people and sharing industry and fashion insights.

What started as one call turned into three or four calls. I met with the chairman, CEO, and the rest of the C-suite team. The company's chairman asked if I was interested in joining them.

I had to think about it. 9Tailors was never busier after the pandemic; there was so much pent-up demand for suits, shirts, and dressing up, and our revenue kept growing.

Two things made the decision easy for me

LookSky allowed me six months to transition out of my business and design my dream job description from scratch. Although I suggested the position of creative director, they offered to hire me as the chief brand officer. I was pleasantly surprised they wanted me at the C-suite level.

I loved running my own business but wanted to make more impact, so the opportunity arose at the optimal time. At LookSky, I would have the opportunity to scale a personalized experience to potentially millions of users.

Also, I had my first child in 2017 and wanted to spend more time with him instead of working crazy retail hours. I had started feeling worn down.

I accepted their offer and nearly doubled my salary at 9Tailors.

Balancing both jobs for a while was tough

During the six-month transition, I worked about eight hours daily, six days a week on 9Tailors. Then, after my son went to bed, I dedicated time to LookSky, often for team meetings or marketing and branding projects. I thrive on being busy, so it was manageable.

LookSky asked me to sell my business, but I couldn't talk about it until we signed the papers and closed because it could destabilize my clients and team if it didn't go through.

The final sale was to my CMO. Even though several businesses expressed interest in buying, I preferred to sell to someone who knew the company, our clients, and how we operate.

My last day at 9Tailors was the same day I announced my departure and the sale of the business to the team. To help transition, my husband, who worked at the company for a good chunk of the 14 years that I did, stayed on for another six months.

I work remotely for LookSky, as most of my team is in Asia

Working remotely was initially a shock because I'm an extrovert who loves being around people, but one of the biggest advantages is having more control over my schedule.

Mornings and evenings are typically dedicated to team calls. Afternoons provide a window for productive personal time — I might work out, dive into a business book (I'm reading "Good to Great" by James C. Collins), or listen to a startup or tech podcast like Lenny's Podcast, Hard Fork, or How I Built This. Best of all, I can attend my son's events and activities.

Last summer, I was diagnosed with breast cancer, which was a shock

After hearing of my diagnosis, my team could not have been more supportive, telling me to take as much time as needed. I like being busy and productive, and work actually allowed me some reprieve.

I've found a company that nurtures my strengths and encourages and supports me in learning new skills. I'm surrounded by bright people who motivate me to do my best work. I've grown and developed tremendously.

I don't miss running 9Tailors, though I'm incredibly grateful for the experience. While I might consider running another startup in the distant future, I'm genuinely happy with where I've landed.

Have you been poached and want to share your story? Email Lauryn Haas at [email protected].

• Dan Weiss, 79, earns up to $47 per hour on Taskrabbit assembling furniture in Minnesota.
• Weiss, a retired mortgage manager, joined Taskrabbit in 2021 for both the income and structure.
• He completes tasks almost daily, earning $3,000 to $5,000 monthly and supplementing his retirement.

This as-told-to essay is based on a conversation with Dan Weiss, a 79-year-old Tasker on Taskrabbit in Oakdale, Minnesota. It has been edited for length and clarity.

I joined Taskrabbit in 2021 and have completed nearly 1,200 tasks at around $47 per hour for my services in Ikea furniture and general furniture assembly in and around Minneapolis.

I have a bachelor's degree in business administration and management and two master's degrees. Before I retired in November 2014, I managed several residential mortgage branches for a major bank.

Retirement was fine initially, but I quickly realized I needed to add structure to my life. Now, I fill my days building furniture, meeting new people, and supplementing my retirement income.

Going from 100 MPH to zero was a very abrupt change for me

One can only do so much gardening and reading without feeling unfulfilled.

I stayed "retired" for about six months and then had to find something that gave me more enjoyment and provided additional income to avoid chipping away at all of my retirement savings, which I began saving for in my mid-40s.

Before Taskrabbit, my other part-time jobs included stints at Costco, customer service work, and driving for Uber and Lyft.

I read an article in my local newspaper about a young woman who had discovered Taskrabbit. It intrigued me, so I immediately went online to create a Tasker account and have them run a background check on me. That was completed in a matter of days, and I was ready to go.

I've now been Tasking for 3 years

I've always enjoyed assembling things, but there was a learning curve. Although I had previously worked with Ikea furniture, there was much to figure out about some of the "tricks" associated with Ikea products.

I made over $47,000 in 2023, my highest year in earnings yet. I average $3,000 to $5,000 in earnings monthly. I could live on my retirement savings if I had to, but Taskrabbit income helps.

I do tasks almost daily

I complete between one and three tasks daily, averaging about four to five days a week. Most of my tasks are no more than a half-hour away, but I spend a fair amount of time driving. I can expense the mileage and gas.

My time spent with clients is highly enjoyable. I meet people from all walks of life and find their stories interesting. I enjoy this aspect of tasking the most.

I've realized how fulfilling and also challenging retirement can be

The lack of structure and income flow in retirement is challenging. We're told to save, save, save for retirement, and that's what I did. When I made the change from saving to spending, I was mind-blown. It didn't feel comfortable or natural.

Taskrabbit has allowed me to continue to generate income while also providing structure and allowing me to maintain contact with a variety of people.

I've discovered the importance of superb reviews in growing my business

When I was young, there were no such things as digital reviews. Today, they're critical because everyone checks them before booking a service or going to a restaurant. I secure generally excellent reviews by doing the following steps:

• Always communicate openly with your client. Confirm the date and time and set expectations in advance.
• Arrive on time or slightly early. If you will be late, even by a few minutes, it's important to let them know.
• Upon arriving, be friendly and cordial. A handshake usually gets things off to a good start to establish a line of trust.
• Be efficient and ensure the task is completed properly and precisely. Having the correct tools is also mandatory for this aspect of the task.
• If there are problems such as missing or defective parts, let the client know as soon as possible and provide suggestions on how to remedy the problem so as not to add stress to their plate.
• Thank them for the work opportunity and share how they can save you as a favorite for future tasks, leave a review and, if they choose, tip you, which happens about 25-40% of the time. I'm very focused during the actual task, but if the client engages me in conversation or has questions, I stop and focus on them.

I expect to continue to task as long as the compensation is commensurate with the job

I will continue to do this as long as my body holds up.

Tasking has given me both fulfillment and help funding trips and vacations. My wife and I love Maui and intend to return soon.

I'm still in the planning phase of deciding on our next vacation destination. There are many other places that we wish to visit while we're still healthy and relatively mobile.

Are you a retiree with a side hustle who wants to share your story? Email Lauryn Haas at [email protected].

• Alexis Ohanian shared three books that shaped his career in 2024.
• Ohanian cofounded Reddit with Steve Huffman and currently serves as founder of 776 VC firm.
• He said "Unreasonable Hospitality" is a must-read for anyone trying to build a brand.

Alexis Ohanian has been recognized as an innovator since cofounding Reddit in 2005 and selling it a year later to Condé Nast. That sale was reportedly between $10 to $20 million.

In the 20 years since then, Ohanian has vastly multiplied his wealth and business portfolio with investments in tech, sports, and other innovative ideas.

The tech founder and investor, who launched his venture firm Seven Seven Six in 2020 after officially leaving Reddit's leadership team, shared with Business Insider the top three books that shaped his career in 2024.

Ohanian said these are his must-reads for various reasons. His quotes have been edited for clarity.

"Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration" by Ed Catmull and Amy Wallace

My founding partner at 776, Katelin Holloway, helped produce "Creativity Inc." based on her time at Pixar. This book informed a lot of how we turned around Reddit and how I'm building 776.

"Never Split the Difference: Negotiating as if Your Life Depended on It" by Chris Voss with Tahl Raz

Zachariah Reitano, the founder/CEO of Ro — one of my 776 investments — recommended the book "Never Split the Difference: Negotiating as if Your Life Depended on it." It's a must-read for anyone, not just CEOs and founders. I re-read it every year to refresh my memory.

"Unreasonable Hospitality: The Remarkable Power of Giving People More Than They Expect" by Will Guidara

Maggi from the 776 team recommended "Unreasonable Hospitality," written by Will Guidara who achieved fame as former coowner and leader of Eleven Madison Park. EMP is one of my favorite restaurants. The methods and mindset here are imperative for anyone trying to build an exceptional brand, even outside of food and hospitality.

• Regina Grogan is a tech exec who says high stress once impacted her mental health and relationships.
• Grogan has developed nine daily habits that help her reduce stress and increase productivity.
• Grogan's methods include cold plunges, meditation, and gratitude lists for better mood.

This as-told-to essay is based on a conversation with Regina Grogan, a Zillennial technology executive, AI founder, and former Google consultant based in Salt Lake City. It's been edited for length and clarity.

I worked in high-stress Silicon Valley for over 10 years, including as a Google consultant, before transitioning to being an associate security engineer at one of the largest banks.

Working in the tech industry is stressful — it has extreme volatility, which has led me to feel anxious and depressed in the past. I've seen tech startups shut down very suddenly with zero discussion. I've also worked in big companies undergoing layoffs and wondered, "Am I next?"

High stress also impacted my relationships. My work took up a lot of my personal time, so I wasn't able to build as many relationships as I wish I had.

Over the years, I've discovered hacks to mitigate stress, boost my mood, and increase productivity. These are my favorites.

1. Cold plunge

I take a 15 to 20-minute ice bath or cold shower every morning. The first five minutes are awful and shocking. Then I acclimate to it, and it actually feels really good.

During the plunge, I feel extremely alert, the world looks brighter, and when I emerge, everything feels like a new beginning.

2. Meditation

I was very addicted to my digital devices until I noticed it was severely affecting my mental clarity and focus. Now I try to stay off my phone as much as possible in the morning, and instead, meditate for 25 minutes.

Ever since I made the switch, my mind has become quieter and I feel reset from the attention obsession that my digital devices create.

3. Increase my bodily awareness

I've realized I have to create balance in life by tuning into my body and intuition for guidance. I now listen more to my instincts.

One time, I was working on a partnership and felt physically uneasy while reviewing the terms. Looking back, I realize I was sensing a subconscious resistance in my body about this partnership, which ended up going south.

4. Take a walk without my phone

I often use my phone as an anxiety and comfort tool. The only way I've had luck mitigating this anxiety is by leaving my phone at home, coming back, and seeing that nothing horrible has happened.

5. Think about what I can and can't control

Let's say a vendor messes up a project, or the intern accidentally gets spam-attacked and is freaked out. Instead of panicking, I use the psychological strategy of the "circle of control," asking myself, "What can I control in this stressful situation?"

If the answer is nothing, I have to let it go.

6. Ask myself, "How can I help others today?"

Doing small acts of kindness helps me take the focus off of myself and redirect my energy toward helping others. This can be helping someone at work, volunteering, or simply letting someone in front of me in traffic.

At the end of the day, I can say, "Today didn't go super well, but I did something in my control to improve things."

7. Make a list of what I'm grateful for

I live a privileged life, and it's easy to forget how hard life is for many other people. In my case, I used to have depression. I've seen bad days, but it's easier to forget when I make a gratitude list.

When I zoom out, I can see how lucky I am and that I have a lot to be thankful for.

8. Epsom salt bath

Every evening, around 9 p.m., I take a hot Epsom salt bath. Epsom salt regulates the nervous system and also staves off loneliness — or so they found in some studies.

I do this as a "day ender" to help me officially close out the day. Otherwise, I'll keep working into the night.

9. Write down my worries and wait to review them

Before I go to sleep at 10 p.m., I write down everything I'm worrying about as a "brain dump." I put it in a box and revisit it a week later to see how many of them came to pass.

Almost none of them do. Over time, I've gained more confidence and calmness.

Ever since I started using these hacks, I've been in a great mood and more productive than ever

My colleagues always talk about my energy and good mood. These hacks allow me to be creative and productive at work, even in a stressful environment.

If you work in Big Tech and have productivity hacks you'd like to share, please email Tess Martinelli at [email protected].

• Susie Moore, a life coach, moved to NYC and landed a tech job by leveraging mutual connections.
• Networking to set yourself up for a future opportunity is especially effective during the holidays.
• She suggests setting intentions, creating ping lists, and attending events to expand your network.

When I was 25, I moved to New York City from Sydney without friends, career prospects, or a college degree. Despite being what some might call unprepared, I knew I would land a job because I excel at connecting with people and taking initiative.

Within two months, I started working for a tech company because I leveraged a mutual connection, an industry peer in Australia whose company had an NYC office. I asked for an introduction to her US team, and she gave me one. A single warm email connection was all it took to get me in the door.

Networking is simply building relationships by being proactive, and it doesn't have to be a cringe-worthy chore. It can be fun, graceful, and extremely rewarding, and the holiday season is the perfect time to do it. There's an undeniable "holiday glow" to people in December.

Now, as a life coach of over 10 years, I encourage my community to expand and nurture their networks no matter their career choices or future goals. If you want to step up your networking game as 2025 fast approaches, here's a checklist to seize the season before the year ends.

1. Set an intention

What do you want your networking efforts to accomplish? Are you seeking a new position in the new year? Do you want to attract new clients to your business? Do you want to kick off a side hustle? Or do you simply want to strengthen your network for the future?

A measurable goal is ideal, but networking is valuable even without a specific goal. A mentor of mine once told me she has a spreadsheet of 50 people she emails casually every quarter for no reason but to say hello and keep the relationship alive. So few people do this!

We let so many relationships go to waste because we make too little effort, so those who keep in touch win because we stand out and are top of mind when opportunities roll around — and they do. My connections have brought me investment opportunities, speaking engagements, and book deals.

2. Get into the holiday spirit

The season of goodwill is a great time to reach out and express gratitude. Most people are reflective and slow down a bit this time of year, so it's the ideal time to send a short gratitude note, text, or DM like this:

"Thanks for your help with X project this year — it meant a lot. Wishing you the best holiday break and start to 2025!"

"I'm lucky to have worked with you this year, and I hope the new job at X is going great! Hi to (spouse name)."

"I just found the coolest candle shop/whisky tasting/tennis memorabilia site (insert picture/link of the thing the person likes). Happy holidays to you!"

Sincere, short, sweet, personal messages go a long way in letting people know how they've encouraged, inspired, or helped you — or even that you're just thinking of them.

3. Create a custom ping list

Success can come down to volume and some experimentation. It's easier to start with people you know, but you can also include some people you'd like to know — for example, I might include 5-10 people I admire with mutual connections.

When I moved to NYC, I looked up connections of my friends on LinkedIn and used that as a way to introduce myself:

"Hi name! You and I are both friends with the lovely (friend's name).

I've just moved to NYC and this city is just beautiful in December. Perhaps we could have a latte if you have 20 minutes free next week? It would be great to share some industry information and connect. I'll gladly come to (part of the city where that person lives/works).

Happy holidays!"

Aim to reach at least 30 people before year-end based on your intention. These can be former coworkers, members of your running or book club, friends of friends, or anyone you'd like to know better.

Not everyone will respond to you, but the right people will. A few Decembers ago, I met up with a fellow entrepreneur who had recently moved to Florida. We've enjoyed more than one business collaboration since, and she's also become a client of mine.

4. Get out there

December is a social season. I've made many connections at apartment lobby parties, holiday celebrations, and New Year's Eve gatherings.

If you're more introverted, be selective about what you attend — just keep returning to your intention (a tech mixer might be worthwhile, for example, but drinks at your next-door neighbor's place may not). Generally, it's worth showing up if you feel on the fence about an invitation. A little face-time goes a long way in nurturing connections.

People are also less busy around the holidays than you think, particularly during the last two weeks of December when schedules slow down. This can be a great time to suggest meeting for coffee, a cocktail, or even a walk. This can also mean a lot to folks in an age of increasing isolation.

5. Underthink it — do it now

The reach-out part is fast. Attacking your ping list doesn't require blocking out hours on your calendar. You can act on it in small pockets throughout the day — waiting for an Uber, in line at CVS, when you have five minutes to spare before a meeting. Ditch the social media scroll and do something valuable with these idle minutes.

Doors open for those willing to knock. It's no secret that those who create and maintain sincere relationships experience more opportunities over time. Your network provides a safety net and a steady foundation for information-sharing, mutual support, and fun, so stay connected.

Susie Moore is a former sales director and startup advisor, a life coach and advice columnist, and the host of the Let It Be Easy podcast.

• Stephen Wu transitioned from tech to finance, starting a hedge fund with $10 million.
• Wu's experience at Amazon and Microsoft taught him efficiency and managing technical debt.
• He said trading is more fun and more money than tech.

This as-told-to essay is based on a conversation with Stephen Wu, a 29-year-old hedge fund manager from New York. It's been edited for length and clarity.

If you ask Alexa to play Taylor Swift, my team built the system that recommends similar songs to listen to afterward.

I studied computer science and philosophy at Carnegie Mellon during college and always thought I would work in engineering. I applied to work at Amazon during my senior fall semester in college and started at Amazon Alexa right after graduating. I was hired as a software engineer in Seattle, creating and building the music recommendation system and overseeing a team of three engineers.

It was a good mix of my passion for music and engineering, but eventually, I left Amazon for Microsoft and then left tech to start a hedge fund with about 80 investors.

I raised almost $10 million from friends, family, high-net-worth individuals, influencers, and others in the hedge fund space that first year. I still love engineering, but hedge funds make money, so they're much more fun.

Amazon taught me how to prioritize and be efficient

Working at Amazon, I learned that its ethos differs from other tech companies.

Google and Meta are more engineering-focused. Microsoft aims to build the best tool for the customer, even if it takes extra time. Amazon, on the other hand, seeks to make things fast.

Instead of building it right the first time, Amazon allowed me to create the minimum viable product usable to meet the deadline. While working there, I learned a lot about prioritization and efficiency.

Still, after about three years, I wanted to explore new roles. A Microsoft recruiter reached out to me via LinkedIn. I took the call and was intrigued by their offer of an engineering-heavy business role. I would work directly with engineers to build and plan the machine translation system used by Microsoft Azure.

I liked the opportunity to combine my strengths in engineering and business for this role, so I accepted it in 2020.

I learned a lot in tech and used it to launch my hedge fund career

I loved working at Microsoft and worked there for about three years. In my free time, I dabbled in hedge funds, which are any fund using a non-traditional investment style.

One crucial learning takeaway that helped me in my future endeavors was technical debt — if you build something too quickly and take shortcuts, you may spend twice the time just fixing the bugs.

I can tell if a product wasn't built right or if it might incur additional unforeseen costs that other hedge fund managers may not know about. Also, because I built statistical models and AI algorithms recommending songs to users at Amazon Alexa Music, I understand the statistical behavior of price movements. This allows me to take a more data-driven, probabilistic approach to trading, while most fund managers focus on financials.

After 6 years, I left Big Tech for the finance industry

I specifically invest in options trading after volatile events. I always loved it, but I never thought I could do it full-time.

Along the way, I discovered a very lucrative strategy for trading in a specific niche in the options market. I did this for fun with my portfolio through 2020 and 2022. It was during the pandemic in 2022 that I realized that NASDAQ was down 33%. That year, I proved my strategy in a bear market and felt confident enough to pursue this as a serious career.

For years, my friends and family asked to invest with me, and I was finally comfortable trading with their money. I left Microsoft in April 2023 to work on the hedge fund full-time. I worked extremely hard during my first year of fundraising and trading simultaneously and was very stressed.

Fundraising was difficult initially, but I allowed investors to try with a small amount first and see the returns for themselves. The minimum amount to invest is $100,000.

I love trading and plan to do it forever

Since our trades are weekly, I allowed them to withdraw any week if the performance was poor. This was highly unusual and risky for hedge funds because they could withdraw any week, and my fund would die. However, I was confident I could perform. After several months of good performance, many of my investors doubled or tripled their investments.

And now, more folks continue to invest through word-of-mouth.

I aim to grow this to a $100 to $200 million fund in the next few years. It's just me, so it's a lot of work, although I have part-time analysts helping. Once reaching $100 million, I can hire more analysts and expand the strategy.

I love trading. It's fascinating because it's like solving a puzzle every single day. As an engineer, I was making a solid six figures a year. It depends on how much profit I generate this year, but if my fund is $15 million and I achieve the 30% yearly profit target, I'll make $1.2 million.

I enjoyed solving complex engineering challenges, but trading offers a more dynamic, fast-paced environment and I plan to do this for the rest of my life.

If you left Big Tech for another industry and would like to tell your story, please email Manseen Logan at [email protected].

• Rebecca Vijay, an online entrepreneur, faces isolation and challenges due to time zone differences.
• She works in publishing through the night and sleeps during the day while her family is away.
• Global connections through coaching groups have helped her overcome isolation and find support.

I'm an online business owner who provides book writing and publishing services. My focus is on women's empowerment through faith, entrepreneurship, and financial literacy.

As a child growing up in New Delhi, every day was an adventure with friends and weekends were busy with church, youth events, and programs. Coming from a carefree youth setting to stepping into the workforce and adjusting to a 9-5 schedule took some time.

Now, as I run my business from home alone, I feel even more isolated.

I worked a few corporate jobs before starting my business

After working in different organizations at the start of my career, I settled at Oxford University Press for almost eight years, heading a commissioning team that published management books.

I got married in 2008, found we were expecting twins, and lost my firstborn twin son on the third day of his life. I raised my preemie daughter with my husband's support.

Infant loss can be a taboo subject, and most people around me chose to ignore it. Stifling my thoughts and emotions forced me into my shell.

I had another son, and when he was a few months old and my daughter was in kindergarten, I decided that money can always be made but spending time with my kids during their formative years was more important. I left corporate life in 2014. Not many people in my life understood this decision.

I became an author and struggled to feel understood by my community even further

I started blogging, and in 2017, I wrote my first book, "My Angel in Heaven," about my son's death and finding comfort in God, which helped many bereaved parents and became a bestseller on Amazon.

Though people around me congratulated me, I didn't feel like they understood what it took out of me to bring the book to life. I went on to have two more books published that year, and the response was the same, as they hit bestseller lists, too. It made me feel even more disconnected from the people around me.

I then faced new challenges when I became an online entrepreneur

I started my company, Fount of Grace Creatives, in 2018, providing publishing services to local authors and expanded it into an international publishing house in 2021.

I created a concept for an anthology featuring inspiring stories of global women changemakers, trailblazers, and visionaries. Arranging coaching or networking calls is difficult; when for some, it's midnight, for others, it's early morning.

As I work mostly with US clients now, I tend to work during the evenings, leading to late nights. Sometimes, I'm even up until 4 a.m. or 5 a.m. or maybe not sleeping at all, as I need to be up by 6 a.m. to get my kids up for school.

Once my kids and my husband are out for their day, I try to get a few hours of sleep. It's extremely difficult as our maid will come, trash will need to be picked up, some courier will come, etc.

I generally put my phone on silent as otherwise it will keep ringing and disturb my irregular sleep. On top of that, I get migraines, which get triggered by lack of or interrupted sleep.

It's difficult for friends, family, and acquaintances to understand my schedule

My husband works in logistics and others around me are mostly in IT, teaching, HR, finance, banking, or ministry.

For them, I'm at home and need to be available whenever they call or message. Some feel that the online world where I work is not a "real" job and don't seek to understand it. They also don't understand why I've invested in mentors, online programs, and courses.

I work on business development, sales and marketing, social media, and fulfillment. This is very different from more traditional jobs, and I'm all the more isolated as I can't share about my work or what it entails.

The pandemic came and made everything worse

We were imprisoned within our own four walls. I lost my mom and some close friends.

Before I could even make sense of that, cancer stole two of my favorite and most inspiring authors whose stories I published.

All this left me spinning out of control and alone.

I started to make friends online

I've connected with others through global coaching groups to learn strategy and skills for my business. These women have helped me break boundaries in my mind and figure out how to cater to international audiences and charge in USD, as they've had to break their own barriers and obstacles to gain success.

These women have become friends and helped me feel less alone. We have similar struggles, share our success stories or tips, and speak the same jargon.

Investing in myself, following through on my vision even when others didn't understand or see it, and focusing on my mission have helped me develop these deeper virtual personal relationships.

The struggles are worth it

Life as an online entrepreneur from a different time zone than most of my clients has been difficult and lonely, but when I look back at the lives I've touched through publishing their inspiring stories, the sacrifices have been worth it.

I plan to go on to train corporations and educational institutes in personal development and women's leadership and continue to encourage my kids and women across the world to dream big, not be limited to a 9-5 job, and consider working online as a way to gain time and financial freedom.

Do you have an isolating job and want to share your story? Email Lauryn Haas at [email protected]

• A group of early 2000s PayPal employees and founders came to be known as the "PayPal Mafia."
• The members have all gone on to impact Silicon Valley by founding and developing major companies.
• The group includes Elon Musk, Peter Thiel, Reid Hoffman, and the founders of both YouTube and Yelp.

What do the founders of YouTube, Yelp, Tesla, and LinkedIn have in common?

Apart from creating some of the biggest companies in tech, they all share a common résumé line item: they've all worked at PayPal.

Many of PayPal's early employees went on to become major names in tech and the venture capital world, founding, funding, and otherwise developing successful companies. This elite group came to be known as the "PayPal Mafia," a nickname that gained popularity after Fortune used the term in a 2007 piece alongside a photo of some of the members dressed in gangster attire.

Members of the group include Elon Musk, Peter Thiel, Reid Hoffman, and over a dozen others. Here's a rundown of the most prominent members of this exclusive group and what they're up to over two decades later.

Peter Thiel: PayPal's founder and the so-called "don" of the PayPal Mafia

Peter Thiel cofounded the company that would become Paypal — called Confinity — in 1999 alongside Max Levchin and Luke Nosek. Confinity was launched as a developer of security software for hand-held devices like the PalmPilot, but it later pivoted toward digital money transfers. 

Thiel served as CEO of PayPal until October 2002, when eBay acquired the company for $1.5 billion. Thiel's 3.7% stake was worth a $55 million, according to SEC filings.

Thiel went on to cofound Founders Fund, a venture capital firm that has helped launch companies like SpaceX and Airbnb.

Thiel, now a billionaire with a net worth of $15.9 billion, according to Bloomberg, cofounded the big data analysis firm Palantir in 2003. He was the first major outside investor in Facebook and contributed early funding to Yelp and LinkedIn, along with a number of other ventures launched by his PayPal peers. Thiel's also a partner of Founders Fund, a venture capital fund based in San Francisco.

Thiel has also drawn criticism in recent years for his support of President Donald Trump and for secretly funding Hulk Hogan's lawsuit against Gawker Media, which resulted in the company shutting down Gawker and selling the company's assets.

After facilitating talks between Trump and now Sen. JD Vance, Thiel gave a record-breaking $15 million to Vance's campaign, the largest donation ever given to a single senate candidate. 

Thiel later told The Atlantic he was taking a break from politics. Business Insider later reported that he served as an FBI informant.

While his and Trump's relationship has reportedly soured, Trump's recent announcement of Vance as his vice president pick has put Thiel back to playing kingmaker.

Max Levchin: PayPal cofounder and Chief Technology Officer.

Max Levchin is sometimes called the "consigliere" of the PayPal Mafia — in "The Godfather," a consigliere is an advisor to the boss.

Levchin made significant contributions to PayPal's anti-fraud efforts. Together with PayPal technical architect David Gausebeck, he helped create the Gausebeck-Levchin test, an early version of a CAPTCHA for commercial applications.

Levchin now serves as the CEO of Affirm.

After PayPal was bought by eBay, Levchin founded a media-sharing service called Slide that was later bought by Google. He was also an early investor in Yelp — at one point he was the company's largest shareholder — and he served as chairman of Yelp from its founding in 2004 until July 2015.

He founded fintech company Affirm, which allows consumers to finance online purchases at the point of sale and pay for them over time. Affirm went public in 2021, raising $1.2 billion in its IPO. Levchin is also the chairman of Glow, a fertility-tracking app that helps users improve their odds of conceiving.

Ken Howery: PayPal cofounder and CFO from 1998 to 2002.

After eBay bought PayPal, Howery stayed on as eBay's director of corporate development until 2003. After PayPal's acquisition, he served as cofounder and partner of Founders Fund alongside Peter Thiel.

Howery recently served as US ambassador to Sweden.

He was appointed by former President Trump in January 2019 and confirmed in September of that year. He also donated $1 million earlier this year to America PAC, a pro-Trump super PAC created by fellow PayPal mafia member Elon Musk.

Howery is active in several nonprofits and serves as a founding advisor to Kiva, an organization that facilitates loans to low-income entrepreneurs. Kiva was founded in part by Premal Shah, PayPal's former product manager.

Howery is reportedly still good friends with Elon Musk. 

Elon Musk: founder of (the other) X.com, which merged with Thiel's Confinity to become PayPal

In 1999, Elon Musk founded a payments company called X.com, which merged with Thiel's Confinity in 2000. He briefly served as CEO of PayPal before he was ousted by the board in September 2000 and replaced with Thiel. But as the company's largest shareholder, he still walked away from the PayPal sale to eBay with a cool $165 million.

Musk is currently the world's richest person.

Perhaps the best-known of all the members of the PayPal mafia now, Musk's estimated net worth is $362 billion.

Since his PayPal days, Musk has moved on to oversee companies like Tesla, SpaceX, the Boring Company, and Neuralink. He also bought Twitter and renamed it X, after buying back the X.com domain name from PayPal. 

Musk, who has been a vocal supporter of Trump's 2024 presidential campaign and donated more than $200 million to Republican election efforts, will also co-lead the newly created Department of Government Efficiency alongside former Republican presidential candidate Vivek Ramaswamy, Trump announced after winning the election.

Luke Nosek: PayPal cofounder and vice president of marketing and strategy.

Nosek was also reportedly the person who clued in Peter Thiel to cryogenic preservation, which Thiel has since invested in heavily.

Nosek explored angel investing.

In 2005, Nosek joined Thiel and Howery as a partner at Founders Fund. In 2017, Nosek left Founders Fund to launch investment firm Gigafund, which helped raise money for SpaceX.

Nosek was also the first institutional investor in SpaceX and is a board member. He also joined the board of ResearchGate, a platform where scientists and researchers can ask questions, follow topics, and review one another's papers.

Roelof Botha: PayPal's director of corporate development, vice-president of finance, CFO

Botha went to school to be an actuary. He said he never planned to get into tech, but when he saw the opportunity in Silicon Valley, his intuition told him it was where he needed to be.

He started as PayPal's director of corporate development, went on to become vice-president of finance, and later served as CFO.

Botha is now a partner at venture capital firm Sequoia Capital

Botha is now considered one of the top tech investors in the world.

Sequoia Capital has funded tech giants like Apple, Google, YouTube, and Instagram. 

Botha as served on the board at more than a dozen companies, including Square, EventBrite, Weebly, Tumblr, Instagram, YouTube, as well as 23andMe, which he resigned alongside the rest of the board in September over CEO Anne Wojcicki's proposal to take the company private.

Reid Hoffman: board of directors at PayPal, COO

LinkedIn cofounder Reid Hoffman served on the board of directors when PayPal was founded.

He eventually joined the company full-time as PayPal's COO. In a New York Times interview, Peter Thiel referred to Hoffman as PayPal's "firefighter in chief," noting that there were many fires that needed putting out in the company's early days.

When PayPal was acquired by eBay, Hoffman was the company's executive vice president.

Hoffman cofounded LinkedIn and is one of Silicon Valley's most prolific angel investors.

Hoffman was an early investor in Facebook, Flickr, Care.com, and many more. In 2017 he joined the board of Microsoft.

Hoffman has coauthored several books on startups and professional development. He hosts the "Masters of Scale" podcast, on which he interviews founders about how they launched and scaled their companies, and is a partner at VC firm Greylock Partners. He was an early investor in OpenAI and used to serve on its board, and cofounded Inflection AI.

Hoffman has also recently criticized business leaders, including his fellow PayPal mafia members, for supporting Trump.

 

David Sacks: PayPal COO

Like Hoffman, Sacks also served as COO at PayPal. Previously a management consultant for McKinsey & Company, David Sacks joined PayPal in 1999.

After PayPal was bought by eBay, Sacks produced and financed the box office hit "Thank You For Smoking," which would go on to be nominated for two Golden Globes. In 2006 he founded Geni.com, an online tool for building family trees.

 

Sacks founded several companies, became an angel investor, and was named Trump's AI and crypto 'czar'

In 2016, Sacks was briefly interim CEO at Zenefits, an HR software firm that was plagued by scandal, including allowing unlicensed brokers to sell insurance to its customers. In 2017, Sacks cofounded the early-stage investment firm Craft Ventures. 

Sacks is a serial entrepreneur and investor, with angel investments in Airbnb, Postmates, Slack, and many more. 

He's also a member of Elon Musk's inner circle and, like the Tesla CEO, is an avid Trump supporter, hosting a fundraiser for the president-elect at his home. Sacks reportedly urged Trump personally to choose Vance as his running mate, whom he was introduced to by fellow Paypal mafia member Thiel.

Trump said in December that he is appointing Sacks as his White House AI and crypto czar.

 

 

 

Jawed Karim, Chad Hurley, and Steve Chen met at PayPal during its early days.

Karim and Chen were engineers, while Hurley was a web designer.

In 2005, the trio launched the video-sharing platform YouTube. Karim uploaded the platform's very first video, "Me at the zoo," an 18-second clip of Karim in front of the San Diego Zoo's elephant exhibit. It's been viewed over 292 million times.

Today, Karim, Hurley, and Chen remain active entrepreneurs and investors with a hand in projects from finance to music.

Karim launched venture fund YVentures in 2008, through which he invested in Palantir, Reddit, Eventbrite, and Airbnb.

Hurley stepped down as CEO of YouTube in 2010. Since then, he's backed education startup Uptime and invested in several sports teams.

Chen invested in actor Joseph Gordon-Levitt's musical collaboration platform HitRecord, which in February secured $6.4 million in Series A funding.

Andrew McCormack: assistant to Peter Thiel at PayPal

McCormack joined PayPal in 2001, working as an assistant to Peter Thiel as the company prepared for its IPO.

In 2003, McCormack started a restaurant group in San Francisco. In 2008, he joined Thiel Capital and worked there for 5 years.

McCormack went on to launch VC firm Valar Ventures

McCormack partnered up with Thiel again in 2010 to found Valar Ventures, a venture capital fund.

Valar Ventures has invested in technology startups well beyond Silicon Valley, including some in Europe and Canada. In August, Crunchbase reported the firm had closed on a $150 million funding round for a new venture capital fund, Valar Fund V.

McCormack continues to serve as a managing partner of the firm.

 

Keith Rabois: PayPal's executive vice president

Entrepreneur Keith Rabois served as PayPal's executive vice president from 2000 to 2002.

He would go on to join his PayPal colleague Reid Hoffman at LinkedIn as its vice president for business and corporate development from 2005 to 2007. He was an early investor in startups like Square, where he spent two-and-a-half years as COO. 

Rabois joined Thiel, Howery, and Nosek as a partner at Founders Fund.

Rabois is the CEO of OpenStore and has served on the board of directors for Yelp, Xoom, and Reddit.

He was a general partner at Founder's Fund, where he cofounded OpenStore, before returning to Khosla Ventures in early 2024.

Russel Simmons and Jeremy Stoppelman: worked on technology at PayPal.

Simmons was an engineer and Stoppelman was the vice president of technology after joining PayPal from X.com.

In 2004, the pair came up with the idea for a platform where users could leave recommendations about businesses in their area. They pitched the idea to Levchin, who provided an early investment of $1 million, and Yelp was born.

Simmons left his official role at Yelp in 2010, while Stoppelman continues to serve as Yelp's CEO.

Simmons served as CTO at Yelp from 2004 until he left the role in 2010. Stoppelman is still CEO of Yelp, and has publicly spoken out in support of political issues like women's reproductive rights.

Jack Selby: PayPal's vice president of corporate and international development.

After leaving PayPal, Selby partnered with Thiel to start Clarium Capital Management.

In 2017, Selby was revealed to be the generous tipper behind "Tips for Jesus."

Selby later helped manage Thiel Capital, the Thiel's family office, and started his own venture capital fund, AZ-VC, where he serves as managing partner. He still serves as managing director at Thiel Capital.

Starting in 2013, Selby began anonymously leaving tips for unsuspecting waitstaff, ranging into the thousands, and signing them "Tips for Jesus." His identity was confirmed by a New York City bartender who served him prior to receiving a $5,000 tip.

Dave McClure: PayPal's director of marketing

McClure served PayPal's director of marketing as for four years beginning in 2001.

According to McClure's LinkedIn, he began a program called the PayPal Developer Network, which consisted of about 300,000 developers that were using PayPal. 

McClure left PayPal in 2004.

He had a brief stint at Founders Fund before launching 500 Startups, an early stage venture fund. McClure stayed at 500 Startups until June 2017, when he was accused of "inappropriate behavior with women" in a New York Times report and stepped down from his role at the firm, writing an apology post titled "I'm a creep. I'm sorry."

He's since become an investor and owner in a professional sports league for ultimate frisbee and cofounded Practical Venture Capital, according to his LinkedIn.

 

Several more former PayPal employees went on to have careers both in and out of tech.

• Yishan Wong was an engineering manager who later served as CEO of Reddit from 2011 to 2014. He then founded the reforestation company Terraformation in 2020, where he now serves as CEO.
• Jason Portnoy worked in finance at PayPal, and went on to work at Clarium Capital and Palantir. He's now a partner at VC firm Oakhouse Partners. 
• Premal Shah was a product manager at PayPal beginning in 2000, then went on to work at technology nonprofit Kiva. He's now president at financial-services startup Branch. 
• David Gausebeck was a technical architect at PayPal. Now, he serves as chief scientist at 3D modeling company Matterport. He cofounded 3D modeling company Matterport, where he now serves as chief scientist.
• Joe Lonsdale started his career as a finance intern at PayPal before moving into venture capital — he's worked at VC firms Clarium Capital, Formation 8, and 8VC. Lonsdale also cofounded Palantir, and has reportedly contributed to a Trump PAC.
• Eric Jackson was director of marketing at PayPal and went on to write a book about the company called "The PayPal Wars." He's currently the CEO of CapLinked. 

• Ethan Evans, a former Amazon VP, led a failed project in 2011 that interrupted Jeff Bezos' launch plans.
• The failure involved a critical design flaw in the Amazon Appstore's "Test Drive" feature.
• It taught Evans to communicate in a crisis, take ownership of a problem, and rebuild trust slowly.

I worked at Amazon for 15 years, starting in 2005 as a senior manager. When I left in 2020, I was a vice president.

My biggest launch failure was in 2011 on a project Jeff Bezos personally cared about. The failure interrupted Bezos' plan to present the feature publicly, causing me to miss my promotion and almost leave the company. However, I went on to be promoted from director to VP and have a long and happy career.

I learned a lot about dealing with a crisis and rebuilding trust as well as a lot about Bezos as a leader. He taught me the importance of maintaining high standards while being willing to forgive and move on.

Here's the story of my biggest failure

When I started at Amazon, I was assigned to Prime Video and had periodic direct exposure to Bezos.

When I was promoted to director, I continued working with Bezos on creating Amazon Studios. Throughout my first six years at the company, I met with him at least once a quarter about one of my projects.

In 2010, I started working on the Amazon Appstore. We planned a new feature called "Test Drive," which allowed you to simulate an app on your phone before buying it.

Bezos was excited about this feature and planned to make it the focus of his launch announcement. At the time, when Amazon launched something new, the company would replace the normal homepage with a personal letter from him explaining the new offering.

Our launch's "Jeff Letter" focused on the "Test Drive" feature. The night before the launch, our team launched the new store.

Everything except the "Test Drive" feature was working well

We worked through the night to debug the intermittent failures, but as morning came and the announcement was supposed to go out, the feature wasn't working. At 6 a.m., I got an email from Bezos asking why his letter was not on the homepage.

I replied that we were working on some problems, hoping he would get in the shower, go on the treadmill, or do anything else to buy us more time. Within a few minutes, he responded and asked, what problems?

All hell broke loose.

The VP and SVP above me both woke up and started asking questions, and more and more leaders were CC'ed into the email thread. We quickly realized that our feature had some critical design flaws and wouldn't be a quick or easy fix.

The first three lessons I learned were during the crisis, and the next three were learned after.

Mid-crisis

Lesson one: Communicate clearly and predictably

I began sending hourly updates to Bezos and the other leaders, working to slowly re-establish trust. Each message briefly explained where we stood and what we would be doing in the next hour, and they each promised a further update in the next hour.

Lesson two: Accept help

Other leaders who had experienced similar problems reached out and offered help from their teams, so within a couple of hours, several very senior engineers were working with my team.

They quickly figured out the problems and announced that we had a design flaw that needed to be re-written. The temporary solution was to work around it with extra hardware. Without this workaround, it could've been days before the feature was up and running.

Lesson three: No all-night launches

Planning an early morning launch that required us to work all night became an obvious flaw. I needed to be sharp to manage the crisis, and my team needed to be able to help with the fixes. We started rotating people home to sleep in shifts, and we learned never to accept a launch schedule that would put us in this position again.

As my team and I became increasingly exhausted, Bezos became increasingly frustrated. He wanted a fix that day. This led to the other leaders ramping up the pressure, and the weight on us kept getting heavier.

We were finally saved when the CTO, Werner Vogels, intervened and said the team could not fix this problem in one day. Bezos fell silent on the email threads.

Over the next few days, we patched the design problem and rewrote the code to eliminate the issue, but as the technical obstacles were removed, the management problems only increased.

The "Jeff Letter" never went live on the website. By the time we had everything fixed and tested, the news cycle had moved on, and Bezos' moment to tell his customers about the exciting new feature was gone.

After the crisis

Lesson four: Own the problem

My direct report volunteered to take the fall. The engineer who wrote some of the code did the same. My manager also sought to take overall responsibility. Ultimately, Bezos knew it was my team and code, meaning I had to own the problem.

Amazon has a process called COE (Correction of Errors), which involves a written investigation of a problem's root causes and a plan to prevent similar problems in the future. I wrote this report and was asked to share it with all my peers in the organization. Publicly sharing an analysis of our mistakes was embarrassing, but doing a good job of it helped me re-establish trust in my leadership ability.

The week after the launch, I was scheduled to attend a meeting with Bezos about another project. I considered skipping it, but I decided that if I couldn't face Bezos, I should probably pack my desk and find a new place to work.

I went to the meeting.

Bezos always sat in the same chair in his conference room. I went early and chose a chair right next to where he would sit. He came in, sat next to me, and ran the meeting. As the meeting ended, he asked me how I was doing because it must've been a tough week.

Bezos showed empathy for my experience and concern for my well-being. He could've just as easily asked for a status report or taken me to task for the problems; instead, he chose to focus on me as a person rather than on any frustration or curiosity about the project.

Lesson five: Face your leaders

Don't hide. I understand the temptation to avoid those who might criticize you, but facing Bezos reassured me that he was over his initial frustration and was willing to give me the time to rebuild trust.

In short, going to the meeting allowed me to stay at the company. I knew my job was on the line, and a single word from Bezos would've sent me packing.

Lesson six: Patiently rebuild trust

I'd been close to a promotion to VP, but now I had to re-establish that I could operate a key business carefully and consistently. I was eventually promoted, but it took two more years.

I learned that trust can be rebuilt but that it takes time.

Bezos taught me how important it is to hold your teams to high standards but also be willing to forgive and move on. He chose to be kind, empathize, and offer encouragement to me, which inspired me to spend the rest of my corporate career with Amazon.

I left in 2020, less than a year before Bezos stepped down, to focus on teaching leadership lessons to the next generation.

An Amazon representative didn't comment on this story when contacted by Business Insider.

Ethan Evans is a retired Amazon vice president with over 23 years of experience as a business executive.

• Jamie Lynch, an operations manager, has noticed key differences in her employees of different ages.
• Gen Z values work-life balance, unlike older generations who prioritize job commitment.
• COVID-19 influenced Gen Z's approach to work, emphasizing health over climbing the ladder.

This as-told-to essay is based on a conversation with Jamie Lynch, a 34-year-old operations manager and content creator in Ontario, Canada. It has been edited for length and clarity.

I've been an operations manager for eight years at various companies, including my latest role at a real-estate media company.

I now also run Simply Jamie, where I create content focused on conversations with my Gen Z employees on social media.

As a manager who has worked with people of all ages, I've noticed differences between employees of different generations.

They aren't necessarily bad, but they're eye-opening differences in how we work. Here are four of the biggest ones I've noticed.

1. To call out or not to call out

For the most part, boomers won't call off work. Instead, they might come to work and say, "My car broke down. I had to borrow my neighbor's car to arrive on time," — but they still made it in.

Millennials can be that way, too. When I worked at a restaurant in high school, my manager still expected me to come to work if I was sick — there wasn't an option or a second thought about not working.

Gen Z, on the other hand, might say, "Well, my car is broken," or "I'm sick, so I can't come in." They don't feel an overwhelming guilt about calling in sick when needed.

I think some of this feeling stems from the COVID-19 pandemic. For three years, we told everyone not to leave their houses if they felt sick, and the younger generation has carried that message into the workplace.

I know some employees in the older generation dislike the younger generation for it, but I respect them, and I wish I had a bit more of their work-life balance.

2. To make small talk or to just not

Boomers and millennials are more known for 'water cooler' talk — or small talk conversations in the office. Before technology took over, that's what everyone did. You'd talk about the weather; we weren't all holding phones to entertain us.

Now, Gen Z doesn't feel the need to have those awkward conversations at work. They've grown up with a new form of distraction that previous generations did not have.

COVID-19 also occurred at a critical juncture in the lives of many members of the younger generation, causing them to miss experiences like proms and face the challenge of attending college from home because they had nothing else. Due to this, they keep to themselves.

I don't blame Gen Z, but older generations judge younger ones for being less social.

3. What they know and what they don't

Gen Z is tech-savvy. I consider myself low-tech and often ask my younger employees for help with my phone. They can also grasp new things quickly.

I've noticed that Gen Z sometimes doesn't know how to do other important things, like writing a check, driving without a GPS, or mailing a letter — that's a big one. To be fair, why would they? It's rare for people to send letters anymore.

Boomers can do these things as they grew up doing them, but technology is often new and harder for them since they spent most of their lives without it. Learning how to sign in and out of apps, for instance, can be a bit more difficult.

4. What they care about

The older generations seem to be more worried about job security. They believe in working hard because that's what you're supposed to do: you go to work and you work.

They're also more willing to deal with difficult bosses. I remember my mom would say, "You just can't let people get to you. All your bosses are going to suck," and that was the widely held belief.

Gen Z, however, has a different mindset. They're not as focused on getting promoted or constantly moving up. They need money and want a job, but they're not necessarily aiming to climb the ladder.

Gen Z also sets stronger boundaries around things like criticism. I don't think it's bad — if your job isn't your whole life and personality, why should you worry about losing it?

Gen Z does seem to care about social issues, like saving the planet. For example, reusable cups are important to them.

Every generation brings something different to the workplace, a whole new set of strengths and weaknesses. Understanding and using them as advantages is the key to harmoniously working together.

• Aprajita Anand has been a life coach for children of the ultrawealthy for more than a decade.
• Anand says most clients come to her after failing to find success with traditional therapy.
• She emphasizes the importance of taking action, shifting motivations, and contributing to others.

This as-told-to essay is based on a conversation with Aprajita Anand, 41, a life coach in New York City. It's been edited for length and clarity.

I've been a life coach for children of the ultrawealthy for 12 years. I started on this career path very organically. I was working as a tutor in New York City, largely supporting wealthy students, and I found them to be emotionally struggling in profound ways.

Society often dismisses them as spoiled rich kids who are perhaps unworthy of sympathy, though I think this assumption makes them a strangely underserved population.

Therefore, I pivoted into life coaching and dedicated my career to helping my students —teens and young adults — navigate the core issues their wealth brings.

Most of my clients have the same story

Problems typically arise when the child encounters rejection, failure, or a struggle that cannot be solved with money.

Many of these problems are social in nature, such as a breakup or excommunication from a friend group or even more systemic issues like racism.

This shock response is commonly followed up by a withdrawal from academic, social, or family life in which they numb themselves with social media, video games, drugs, online shopping, or another behavior of choice.

The parents' first response is often to send their child to a therapist or psychiatrist. I'm a huge believer in therapy, but in some cases, these children end up feeling even more lost and despondent because they're sitting in their feelings and don't know what to do with them. They may wonder how they have every advantage in the world yet are still unable to escape from difficult emotions, which can cause them to sink deeper into their numbing behaviors.

This is often the point when parents bring their children to me.

3 steps to overcoming the 3 biggest issues

In my experience, much of traditional talk therapy is about processing feelings and breaking down thinking patterns. I use some of those elements as a life coach, but I emphasize taking action. I've developed a curriculum to guide young people through three core problems with three core actions.

1. Shift to an internal point of control

Many of my clients fall into a victim mindset, believing they are at the mercy of an unkind world. I empower them to understand they can choose how they respond to any situation.

I had a student who didn't get into her first-choice college, which was difficult for her because it was possibly her first major rejection.

She begrudgingly went to her second choice but refused to engage in freshman orientation or socialize with her peers, and locked herself in her room, numbing herself with social media and Netflix. She was causing unnecessary suffering by sitting in a victim mindset.

When we began working together, I focused on helping her take back her locus of control by taking action, any action. The action she wanted to take was to mount a transfer application to her first-choice school. I agreed to support her if she engaged in a mindset shift, which is step number two.

2. Find internal motivation

Our culture generally equates success with relatively superficial trappings like grades, prestigious colleges, flashy jobs, and lots of money.

However, I assumed someone raised in a wealthy environment would feel unburdened by money and free to live a life of indulgence, free from expectation. To my surprise, my students feel the opposite. They live in an environment that reinforces the idea that money and status are their source of worth.

So, in my client's case, going to a very good school instead of a great school was a complete failure.

While she waited to hear back about her transfer applications, I encouraged her to tap into positive things in her current environment and engage in things that brought her joy. She reluctantly started attending an interest-based club and started going to her professor's office hours just to talk about big ideas on her mind. Slowly, she began to feel like a member of the campus community.

At the end of that year, she got accepted into her first-choice college and ultimately rejected the offer. She had changed her motivation from external to internal and decided the personal reward was greater than the status.

3. Contribute to someone else's well-being

Many of my clients have never had to work, clean, or think about anyone other than themselves. But the amount of time they spend thinking about themselves can be exhausting.

I advise my students to find a way to contribute to someone else's life, such as volunteering with a professional organization or simply helping with chores around the house.

In the case of the student, she took a leadership position in her sorority and ended up loving her role of helping recruits settle into the community.

Contributing to something greater is a positive, healthy way to put down personal problems and find joy in helping someone else. I make sure they understand it's not to pad their résumé or check off a box; it's necessary for building a meaningful life.

If you work with children of the ultrawealthy and would like to share your expertise, please email Tess Martinelli at [email protected].

• A poor performance review at work led to significant stress and weight loss for the author.
• The review was unexpected, with unclear feedback from a new manager causing confusion.
• The experience taught the author valuable lessons in self-advocacy and career management.

During one particularly difficult fall, in the span of three months, I lost 15 pounds, and people around me quickly noticed. Some friends in passing exclaimed that I looked incredible (I was startlingly underweight). Others expressed concern, asking, as discreetly as possible, if something was wrong.

I'm certain my friends and family would've found it oddly comforting to diagnose this sudden and dramatic shift — maybe it was a devastating break-up or financial stress. How could I tell them that I was unwell because I was just really stressed out? Like, really, really stressed out, all because of a bad performance review.

My first poor performance review

After years of working in tech, I received my first poor performance review. I was deeply anxious about how that would affect my career trajectory and struggled to understand how I "didn't meet expectations" without knowing it.

I interpreted my hitting key milestones, conversations with my manager, and the feedback I received from my peers as positive signals — green lights to continue working as I always had, not red lights that obstructed my career growth.

I was exhausted and discouraged, and the poor performance review only increased my mental fatigue. I saw no escape route.

I didn't know what I did wrong

When I asked why I received a rating for not meeting expectations, which colloquially translates to "not doing your job," I was repeatedly given opaque answers. I continued to ask for supporting evidence for the poor performance review but never received a digestible answer. I struggled to understand my review rating and, as such, struggled to understand how to change it.

At many companies, a performance review is made distinctively by one single person (your manager), and even with the feedback of colleagues and peers, managers decide the final rating.

A bad performance review, which can obstruct impending promotions and team transfers at best and be job-threatening at worst, is often not standardized. Each manager can have a different process and subjective evaluation of employee work. In my case, this was problematic because I had such difficulty understanding how my work translated to the review I received.

A standardized performance process and clear communication would have significantly reduced my mental fatigue and increased my productivity in that specific role, which would've, in the long term, benefited my team and company.

Not understanding the reason for my bad review caused more stress than the bad review itself

To me, it felt like the sentiment from my manager was that this poor review was "just one quarter."

I teared up at how cavalier this seemed. It felt like my job security was being torn apart at the seams. I panicked at the thought of losing my salary, my progress in my career ladder, and my reputation in my role at the time. I often thought about how it must have been only a passing thought to my manager.

The worst part is that I had no idea how I arrived at this point in my career or how to fix it.

My judgment felt clouded, and I had difficulty separating fact from fiction. I didn't and couldn't understand why and how my performance was not meeting the expectations outlined for my role.

I was so poorly equipped to navigate this ambiguous terrain and so stressed at the thought of losing my job that, over the following weeks, eating and sleeping felt like impossible hurdles.

Shortly after, two friends shared their own experiences about damaging work environments, managers, and performance ratings. The surprise of these stories, in conjunction with my own, made me reconsider everything I knew about performance reviews.

The entire experience taught me a powerful lesson

I always avoided asking about my performance at work. I lived with a preconceived idea that my work should and would always speak for itself. If I didn't apply pressure to my performance trajectory — if I didn't ask, engage, or insist on understanding my work evaluation before it was delivered — I avoided what I then considered painfully awkward questions. I now consider those conversations necessary interactions for self-advocacy.

This experience taught me to directly ask the following questions before reviews:

• Do you have any feedback for me?
• What are areas in which my work can improve?
• Is there anything I should be aware of before my next performance review is delivered?
• Where do I stand?

One bad performance review doesn't need to signal the loss of a career. It can be a compelling signal that something isn't functioning as it should — an opportunity to repurpose your current approach to work, a nudge to take agency of your career trajectory (like in my case), or even to recognize that maybe it's time to move on from your current role or company.

The lessons I've learned in self-advocacy are more consequential than any exceeding expectations review could have ever given me. I've learned to speak up, disagree, and champion myself all because of one bad review.

I'm forever grateful for those lessons and where they've led me — to a job I love, a renewed self-confidence in myself and my work, and the excitement to share my story.

Sandra Milosevic works in engineering, product, and design enablement. She has been in the tech space for over eight years and is a former Uber and Snap employee passionate about people, learning, and development processes.

• Amy Zhang has faced five core struggles since quiet quitting her corporate job to start a business.
• Zhang says navigating the current economy and finding the right clients were among the roadblocks.
• Zhang says entrepreneurship involves making mistakes, but it has redefined her idea of success.

This as-told-to essay is based on a conversation with Amy Zhang, a 31-year-old founder based in New York City. It's been edited for length and clarity.

I spent eight months "quiet quitting" my corporate job, which started in June 2022. I then launched a company focused on growing small businesses. I've developed an appreciation for all the ways people can become successful.

But my learning hasn't come without issues. These are the five biggest struggles I've experienced since actually quitting and starting my own business, and what to keep in mind if you're considering it.

1. You have to be able to work alone for days on end

The transition from working with a team to being completely independent has been isolating. The socialization that used to be guaranteed is now a task that falls completely on me, and sometimes I don't leave my house for days.

Being an entrepreneur requires hustle and struggle, which makes it tough for me to put my computer down and stop working.

I make sure to maintain my routine at my gym, where I have a group of people I talk to. I also try to say "yes" to invitations from friends even if it's easier to say no and keep working.

2. You must be prepared for stress, mistakes, and ambiguity

When I started my venture, I realized I was the only one to blame for poor decision-making. The pressure to not make any mistakes plagued me in the beginning, so I've been learning to forgive myself.

One of the biggest mistakes I made was figuring out what tools and technology systems to spend money on and when to make the purchase. I purchased based on referrals and quickly learned that buying tech solutions too soon and solely based on recommendations can be a waste of money.

I also made the mistake of subscribing to annual contracts for discounts. Looking back, I realize the flexibility to cancel month-to-month contracts would've been more financially responsible.

Despite these mistakes, I know that having patience with myself is important for not burning out and giving up.

3. The economy is different now than five years ago

I've noticed that those who started their business five years ago relied heavily on networks and word of mouth to jump-start their companies.

In my experience, right now, I feel like prospective clients need more convincing, touchpoints, and trust to go into business with someone. I've been able to show my commitment through time spent, being active and responsive, and through action — putting my money where my mouth is.

4. Clients might want more time

I thought working as a consultant would benefit companies — it's cheaper for them to hire me with part-time pay, the ability to cancel at any time, and no health insurance. However, many businesses hesitated to work with me because they wanted full ownership of my time.

Don't get me wrong — the clients I work with now are awesome and completely get it. They like having the flexibility and quality of work at a fraction of the cost of a full-time hire.

There's just something about having full control over an employee that I think some businesses still latch onto.

5. Others will try to rank you by title

There's a social bubble — especially in the corporate world — that defines success by titles, promotions, and company prestige.

Even in social circles at events and parties, when I was introduced to someone, the default second question after asking my name was, "So what do you do for a living?" That question used to feel like a way to rank myself among my peers.

Since quitting and starting my own business, I've realized there isn't just one way to be successful, happy, or make money.

If you've "quiet quit" your corporate job and would like to share your story, please email Tess Martinelli at [email protected].

• Adam Knorr left a lucrative finance career to pursue writing in Hawaii in 2022.
• Despite a growing salary and the opportunity for a big promotion, Knorr felt unfulfilled in finance.
• Knorr now freelances as a copywriter and ghostwriter and has no regrets about leaving finance.

I walked away from life-changing money in finance to chase my dream of becoming a writer. I had no experience, clients, or idea where to start.

I moved from Nashville to Hawaii to figure it out.

I graduated with a journalism degree, but my brother worked in finance in Nashville. He told me he could get me an interview at his company. I interviewed, got the job, ditched my dreams, and chased a paycheck for six years.

I never liked working in finance, but the money made it hard to leave

I started working in 2016 and made about $50,000 as a 22-year-old. I felt rich, and the number kept climbing.

By 2021, I was making nearly $150,000 a year. Halfway through my last year, I was on pace to make $205,000. I was also interviewing for new roles in the $250,000 range.

Every day I worked in finance, I knew it wasn't right for me. I wanted to quit and be a writer, but the money was too good.

Finally, in May 2022, when I was up for a promotion, the dam burst. I remember going home one night after a final interview, and I could feel it in my gut. I knew I didn't want to get the job; it would trap me, and I'd regret pursuing it.

I printed off my two-week notice that night and quit the next day. My boss and coworkers were in disbelief when they found out, but for the most part, I had tremendous support from the people in my life.

After quitting my job, I moved to Hawaii in June 2022

I heard about a work-stay program at a coffee farm on the Big Island of Hawaii through my brother and sister-in-law, who had visited Hawaii. You can live on the farm in exchange for 28 hours of work a week. That sounded like a pretty good deal since my income dropped from six figures to $0 overnight.

I put my stuff in storage, packed a carry-on and a backpack, and flew to Hawaii, trading in my Nashville high-rise apartment and rooftop pool parties for a one-floor communal living house with six college kids.

I worked as a tour guide on the farm a few days a week. The rest of the time, I tried to figure out how to make a living as a writer.

I had never been to Hawaii before I moved

Visiting and living in a place are different experiences. Hawaii is a rock in the middle of the ocean — sometimes, it feels like it, but for any of the cons, there are more pros.

It was nice to get a break from city life and a good reminder that the world outside your immediate circle is full of people who live life at a different pace.

I had to get creative to land my first client

I wanted to become a freelance copywriter, but the industry is saturated. Many people are attracted to the opportunity to work for themselves, travel the world, and make money by pressing a few keys on a keyboard.

I spent day after day locked in my bedroom in Hawaii — just me and the geckos — sending cold emails and LinkedIn messages. I got a few nibbles but no bites.

I decided I wanted a car to explore the island. I contacted a local car rental service and noticed the owner's website needed serious copywriting work, so we struck a deal. I'd write his entire website for $500 and an extra month of my rented Dodge Challenger. I had my first client.

I started freelancing with an agency thanks to a cold email I sent. Then, I started posting on LinkedIn and picked a couple of clients up that way. Today, I'm a full-time freelance copywriter and ghostwriter.

I started writing a book in Hawaii before moving to Michigan

While in the work-stay program, I wrote some email copy for the farm. The emails did well, and one day, I sat down with the farm's CEO.

He envisioned writing a book about the history of a local church and using it to raise money to restore some of the murals that had deteriorated over the last 125 years. He asked me if I'd be up for writing the book. I agreed and started splitting my time between leading farm tours and researching for the book.

All roads lead home. I moved to Michigan in March 2023 to be closer to my family.

Quitting finance was worth it, but it's more nuanced than that

In my first full year of freelancing, I made $85,500. Through November 2024, I've made $110,000. I'm grateful to be doing as well as I am, but I can't pretend like I don't think about the money I would've made by staying in finance.

Gratitude and perspective are more important than the number on your tax returns, but it's also ignorant to pretend like money doesn't matter. I wonder sometimes if I was dumb for leaving that money behind — it's impossible not to.

But was it worth it? Am I happier? Would I do it again? Yes, 10 times out of 10.

I had to know if there was something more out there for me

When deciding whether to quit my job to pursue this dream, I heard Tim Ferriss on a podcast recommending playing out the worst-case scenario of a decision in your head. How catastrophic is it? How permanent is the impact? How bad would it really be?

Worst-case scenario 1: If I stay in finance, I'll always regret not discovering what I could've made of myself.

Worst-case scenario 2: I try to write, fail, and get another finance job.

For me, the fear of regret was greater than failure.

Now, I never have to wonder, "What if?" or think about what I could've done with my life. I know the answer.

• C-suite executive Michaella Solar-March's husband became a stay-at-home dad in 2017.
• The couple found it financially smarter for him to stay home than to hire a nanny.
• Solar-March balances career and family and feels the pressure as the sole financial provider.

This as-told-to essay is based on a conversation with Michaella Solar-March, a 40-year-old C-suite executive in New York City. The following has been edited for length and clarity.

When my husband and I met in 2011, we were in love with our careers. I worked as a marketing director in the music industry, and he was a bartender and vegetable farmer. We both worked late but always made time to see each other.

We discussed getting married and having kids but never discussed the logistics of starting a family with our work schedules. We got married in 2012, and in 2015, I got pregnant with our first child.

Now, as a family of four, I work full time, and my husband stays home to watch the kids.

We both used to work full-time jobs with nontraditional hours

My husband worked in hospitality and often got called in on nights and weekends to cover shifts. I worked at Soho House in a global role and traveled internationally for two to three weeks every month.

We hired a full-time nanny so we could both continue to work. After nine months, we realized it felt like our nanny was raising our child. While we loved our nanny, we weren't comfortable taking such a backseat role in our son, Townes', life.

My husband loved his career but found that being a present father meant more to him. He didn't grow up with his father around — his parents divorced when he was three, and a single mom raised him. He wanted to be a present and constant support for Townes.

We decided in 2017 that my husband would be a stay-at-home dad, and I'd continue to work as the family's breadwinner.

It was less expensive for my husband to stay home with our child than to have a nanny

We realized my husband's salary was slightly more than what we paid our nanny. It seemed like a financially smart decision for him to leave his job. It also helped us both erase any anxiety about Townes and his care.

When we had our second child, Roma, in 2020, I was the global CMO for a commercial real estate business. Alex returned to work in 2019 as the general manager of a hospitality brand, and we thought we would hire another nanny for our daughter. Then the pandemic started.

We started interviewing nannies remotely and couldn't get comfortable with the idea, so again, Alex quit his job and resumed full-time childcare responsibilities.

The identity shift was hard to understand

When we first started dating, our identities were wrapped up in our careers. When my husband first became a stay-at-home dad and I became the breadwinner, I struggled with our new identities. I felt grateful that I could continue my career but guilty that he had to pause his.

I was also proud of his work and enjoyed the nightlife culture that came with his industry, so leaving that behind was a lifestyle shift for both of us.

My husband never felt bad about this shift. He poured everything into being the best dad, managing the household (cooking, cleaning, and handling the groceries), and constantly reassured me that he was more than OK with taking on this role.

I feel a lot of pressure to provide financially for my family

Neither my husband nor I are independently wealthy, so the long-term stability of our family and creating financial security for our kids are solely my responsibility.

I feel a lot of pressure. I'm naturally ambitious and self-motivated, and I take pride in being good at my work. Yet, I inevitably feel I have to overdeliver and drive value for my employers to ensure job security.

While I'm lucky enough to have an incredible boss and team, that pressure is always an undercurrent. If I'm not working, we can't pay our bills.

Being a C-suite executive and a mother requires compromise

I'm now the chief marketing officer for a Brooklyn-based real estate developer and management company. I'm fully committed at work and home but always feel I'm letting someone down.

I often miss dinner time with the family because of work commitments. Townes made a rule that I'm only allowed to be on my phone at home if I'm dealing with something for work. As my kids have become more aware and emotionally mature, they notice when I'm distracted.

I also feel societal pressure. There's an unspoken expectation that you must be an exceptional employee, mother, friend, community member, and over-performer in every area of life. Those titles are often in conflict with one another.

I have to compromise. I'm no less committed to an area of my life, but I acknowledge that sometimes I can't do it all and must make a choice.

I'm showing my kids a different type of family dynamic, and I'm proud of that

I had a stay-at-home mom who worked from home but was hands-on in the house. This allowed my dad to go out and work long hours every day. My family is now inverted.

I'm proud that my children see me go to work daily, knowing I come home every night after doing work I love and excel at. I hope this shows them they can pursue their professional passions with commitment and ambition.

Sometimes, Roma asks, "Why can't you stay home with Dad? Why do you go to the office every day?" But I know that in 10 years, I will have shown her what a working mother looks like. I also know that when I'm with her, I focus on giving her the attention and support she needs.

While our family setup might be unusual, it works for us, and I'm not sure it would work this well if we did it any other way. Eventually, my husband wants to go back to work, but not in a full-time capacity.

Want to share your story as a female breadwinner? Email Lauryn Haas at [email protected].