• I chose to be a teacher to connect with and help children — the job wasn't what I expected.
• As a teacher I valued student relationships, but job evaluations focused on other metrics.
• After six years, I quit. Here's what I wish I had known before I chose this career.

I had a lot of good reasons behind deciding to become a teacher, which included job security and setting a good example for my son. But after six years of teaching junior high and high school English, I'm leaving the profession for good. It's not because I think I'm a bad teacher, but because it has taken me some time to accept that teaching just isn't right for me.

Here's what I wish I had known before choosing this career.

The part of teaching that mattered most to me was not valued

What I found most rewarding about teaching was building relationships with students, particularly the difficult ones that other people had given up on. I became a teacher to connect with those kids, because I had been one of them.

My personal barometer for success was when I realized that those difficult students were suddenly giving me a hug or coming by between classes just to see me. I knew I had gotten through to them and could help them build their confidence and see their own value in the world.

The problem with me viewing that as success was that it was not what mattered most to my supervisors. As a teacher, I was evaluated on skills like classroom management, curriculum pacing, and testing scores. While I always put the impact I knew I was making with my students' self-worth first, that was not what my job performance was evaluated on.

Teaching proved to have a poor return on investment

A few years in, I began to realize that a large part of what kept me hanging on to teaching was the sunk-cost fallacy. I had spent so much time becoming a teacher and learning how to be a good one, and I didn't want that effort to have been for nothing.

Even though teaching was taking from me more than what it was giving back, I didn't want to give up on it because of how much I had spent becoming one.

You shouldn't plan your life around your job

Not only had I spent so much of my past on teaching, but many of my future plans depended on being a teacher, too.

When my son finally makes it to middle school, I wanted to have the privilege of teaching at his school so that I could keep a watchful eye on him. Middle school is a pivotal time for a young person, and I wanted to be able to steer him in the right direction if I saw him veering down the wrong path.

When I left the profession, I was only one school year away from getting to teach at the same school that my son.

The breaks were nice on paper, but I was too burnt out to enjoy them

A major part of why I became a teacher was because I wanted to have the same schedule as my son. I also didn't want to have the added expense and stress of having to find childcare during school breaks.

I liked the idea of having secured time off throughout the year that I wouldn't even have to ask for. The problem became that I was so burnt out from a day of teaching, I felt like I could barely show up for my family at home most days. And when those breaks finally did arrive, all I wanted to do was rest, not travel.

The job made me sick — literally

Ever since my first day of teaching six years ago, I've dealt with health issues that I believe were caused by the stress that comes with teaching middle school.

The healthiest I've felt during the last six years was when we had to shut down for six months due to the pandemic. Initially, I thought I would adjust to teaching, thinking that the job would become easier in time and that I would find ways to better manage the stress. But after throwing out my back one too many times, I came to accept that the job was literally breaking my back. I felt that my body was begging me to take care of myself and make some changes.

I'm excited for my future

While my next career move is uncertain, my health is already improving.

I had always wanted a job where I could help others, and I knew I was doing that with my students. But the worse I felt teaching, the more I realized that I couldn't even help myself anymore.

Someone asked me what I would tell my son if he were in my situation, and the answer was obvious. I would have told him to quit. While it was extremely rewarding to help my students, I finally saw that I wasn't showing up for my family in the way I wanted to because the job was taking everything I had to give, including my own well-being.

It wasn't easy walking away from what I thought was going to be my life's career, but my body is already thanking me for it. No matter how scary it is that I have to start over again career-wise, I know I've made the right decision.

• After teaching for 8 years, I quit so I could spend more time with my children.
• I began freelance writing and soon started earning more money than I did as a teacher.
• I found following five strategies helped me become — and stay — successful.

In 2019, I had been a middle and high school English teacher for eight years. I also had two young children. Even though I truly loved my job, I wanted to be a stay-at-home mom, so at the end of the school year, I quit my teaching job in order to stay home full-time.

I knew that I still wanted to be able to contribute financially while spending the majority of my day with my kids, and frankly, I had no idea how to do it. So, I went back to the thing that I've been doing my entire life — writing. I started freelance writing in the spring of 2019, and by the end of 2022, I had replaced my teaching salary with my freelance earnings. It was a big moment.

Fast forward to 2024, and I make more than I did as a teacher and get to write about a range of topics that include home improvement tips, product reviews, design-inspired pieces, personal finance, and more. My clients have included Real Simple, Popular Mechanics, Apartment Therapy, and US News & World Report.

As I look back on the early years and the years that followed, there are a number of things that contributed to that success and that I will continue to do to reach future goals.

I started where I was with what I had

If you wait for conditions to be perfect before starting something, it may never happen. I started my freelance writing business with a school-issued laptop and an hour in the mornings. It wasn't ideal, but it was what I had.

When I quit my job, I bought a $175 laptop and often worked from my bed with a baby sleeping next to me (or on me). Now, six years later, I have a little office nook and a computer with two monitors, but this never would have happened if I hadn't started when I did.

I also had no idea how to find clients, so I made an Upwork account, which at the time allowed you to connect with clients for free. I started sending proposals to any assignment that looked interesting or I had a passing knowledge of and got a few clients. I wrote for an affiliate beekeeping website (we had bees at the time), a property finder in Spain, and a luxury countertop brand.

I determined when I work best

All of my kids are in school now, so my days are much more flexible as far as work is concerned. But when I had the kids at home with me, the only time that I truly had to work was when they were sleeping. For me, this worked out ok because I'm naturally a morning person, but some days I was waking up at 3:30 or 4:00 am to get my writing done. I did what I had to do to get the hours in and my assignments completed.

While I definitely don't think that everyone has to get up early to be successful, it really paid off (literally) for me to zero in on the fact that I work best in the morning. That knowledge was even more solidified when all of the kids started school this year. Even though I have the option to work at other times, I still get up before 5:00 because that's when I'm the most focused.

I kept pushing forward

In 2019, I chose "relentless" as my word of the year, and I've chosen a word every year since. I really did feel relentless that year and in the years that followed. Every time I wanted to sleep in a little later or I was feeling discouraged about the progress (or lack of) that I was making, I reminded myself that I needed to be relentless. Often, that was the push I needed to reach out to one more person to pitch a potential story or get up and finish an assignment.

I learned to pivot when necessary

I focused on writing about building materials and real estate during COVID when the housing market was exploding. When that started to cool off, I moved into more home improvement topics. Being able to pivot when necessary, while not always easy, keeps your foot in the door even as it revolves. When I lose clients, my immediate thought after I get over the disappointment is to look towards the next thing and evaluate if I should continue doing what I'm doing or pivot to something that can lead me down a new path. Now, I'm also focused on writing "The Simple Freelancer," my Substack newsletter that offers simple tips for freelance success.

I set up systems

I read James Clear's "Atomic Habits," in 2022, and it shifted the way I did a lot of things in my life and business. In it, Clear talks about the importance of systems and routines. Once I started to set up systems for different facets of my business, like my morning routine and how I track assignments, things really started to take off. A lot of times, it seems really difficult to reach a goal, whether it's to replace your current income at a new job or something else entirely, but the systems that can help you get there are much more manageable.

• After 10 years in elementary education, I decided I no longer wanted to be a teacher.
• I wanted a more flexible job that allowed me to stay at home with my kids.
• When time allows, I'm able to make more money than I did as a teacher and have a better work-life balance.

When I went into education, I did so with the best intentions. Being a male elementary school teacher was sort of like being a unicorn. It is extremely rare for a man to be teaching early elementary. There were plenty of single-mom families in the area where I lived, and I knew many students didn't have a male role model at home to inspire them, so I thought I could fill this void. I took the responsibility seriously.

But after ten years in the field, I had to tap out for a few reasons. None of the reasons really had to do with the students themselves. The pay wasn't great (after 10 years of teaching I was still taking home just around $3,000 a month) and I didn't enjoy the politics of teaching. But, the most important reason was probably that my wife and I were ready to start a family. She often works long hours and I didn't want someone else to raise my children. I thought I could find a way to contribute financially and still be home with the children.

Becoming a freelance writer

Before I went into education, I had been a journalist for a few years. It wasn't something I really enjoyed at the time and I didn't see myself wanting to cover mundane board meetings forever. If you ever suffer from insomnia, just drop in on these meetings occasionally. It's like an instant sleeping pill.

Still, I thought I was a decent writer. I've certainly read worse over the years from people who made their living as professional writers. So while I was still teaching, I joined Upwork, a website that connects freelancers with those looking to hire contract workers. Upwork allows people or companies to search for a specific type of writer they are looking for to complete their project at hand. You are competing against other writers who are also applying, but Upwork is a great tool to use when you are first attempting a freelance career.

To begin, I set my fees low to get my foot in the door. Then it wasn't long before I had clients who were asking me to write for them on either a weekly or monthly basis. As an unexpected bonus, most of the topics I covered genuinely interested me. Health and fitness, education, and even ghostwriting children's books were all things I enjoyed writing — and I was getting paid to do it.

Fast forward four months

As I was wrapping up my last weeks in the classroom before the school year ended, I realized I could go give my notice that I would not be coming back to teach the following August.

I had just made $6,000 in one month from freelancing — and that was while I was still teaching. I would definitely miss my students and all the friends I had made, but being able to set my own schedule, work from home, and raise my kids was something I could not pass up. My wife and I were having children later on in life, and the math showed me I would probably not get the chance to spend as much time with my kids as other fathers, so I switched careers.

My plan is mostly working well

I'll admit, I underestimated how much time I would have to write while taking care of two babies at home. I've really had to narrow down my client list over the last five years, picking the ones that are truly worthwhile. Now I only accept writing assignments I can get excited about.

Though I only have about 15 hours of free time at home a week where I can focus on writing, I have made the most of it. In fact, you can find my two children's books "Ellie and Jack: Third Grade Ghost Hunters," and "Ellie and Jack: Third Grade Vampire Hunters," on Amazon and other sites. I always wanted to write children's books, and after helping thousands of children become better readers over the years, I think I have a pretty good idea on the types of stories they love to read. Weaving my teaching past into my current career has been a joy.

With one child getting ready for kindergarten and the other just a couple of years away, it won't be long before I will have more time to write once again.

• 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].