From “Success” to Starting Over: Why I Left My Comfortable Tech Job to Try Entrepreneurship

September 22, 2024
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Lessons learned

From the outside, my career has been more than I could have hoped for. Growing up as a blue-collar kid in Western Colorado, I never imagined I'd reach the professional success I have. By mid-career, I’d worked at some of the world’s most respected companies, built new skills, and increased my pay along the way.

It seemed like the (professional) dream:

  • A steady rise in my career, taking on new roles when I felt inspired or restless.
  • Wonderful colleagues I not only admired but counted as friends.
  • A comfortable lifestyle and the sweet sweet perks.
  • Literally traveling the world.
  • Calling an exciting city home (just like TV!).

But the reality was different. I was a Product Manager at Alphabet (Google’s parent company), leading AI and data science products. That sounds impressive, right? It should’ve been.

Let me take you to a pivotal but pretty normal moment from earlier this year. I was in yet another heated meeting with our legal team, debating whether a chatbot I was working on could launch. This was our 17th meeting on the same topic, after 145 emails and hundreds of hours arguing over the safety and compliance of... what?

A chatbot. Not an innovative AI tool, but an outdated, rigid Q&A bot from like 15 years ago. And it was destined for a landing page that might get a few hundred visitors—if we were lucky. As for the chatbot itself? Maybe 10 users total.

That’s when it hit me: I was spending my life fighting for pixels on a screen that wouldn’t make a meaningful impact on anyone. I was mired in corporate bureaucracy, and this was my everyday reality. What was I doing with my life?

It was terrifying, but I knew I needed a change. So, after countless bike rides, coffee chats, and soul-searching with friends and mentors, I made the leap. This year, I left my cushy tech job.

The decision came down to four things:

  1. I didn’t want to look back on my life and feel like I’d wasted my time.
  2. I still wanted to make a positive impact—even if just a small one.
  3. I needed to make a living, of course.
  4. I wanted to enjoy my day-to-day work and accomplish something real.

Now what? I’m diving headfirst into entrepreneurship—but I’m taking an unconventional route. Over the coming posts, I’ll share more about:

  • How I built a software business from scratch in just a few months (without being an engineer).
  • The tools I discovered and how I learned them quickly.
  • The lessons I’ve learned, including how to prototype and find product market fit on a tight budget.
  • The product we’re about to launch—and how it’s all coming together.
  • And the results—because this is a fast-paced, fast-to-revenue business. We’ll know soon whether it’s working.

Many of my friends and colleagues are in the same place I was: mid-career, wondering, “What am I really doing here?” If you’re curious about entrepreneurship but unsure where to start, this series is for you. I’ll share my journey, the highs and lows, and help you see that you’re more capable of building something than you think.