• 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].