From Startup to Scale-Up

Changing careers is terrifying. You leave the comfort of what you know for the chaos of the unknown. For me, that leap took me from coding bootcamp to building software at scale—and it’s been the wildest ride of my life.

Healthcare Download

My first stop as a software engineer was at a company called Healthcare Download, a team that took a chance on a kid fresh out of bootcamp.

There, I learned the fundamentals—building small features, deploying code, testing, and shipping changes into production. The ecosystem was simple: a few repos, a few junior devs, and straightforward processes. I felt like I was thriving.

After a year, I left with the confidence that I could jump into any environment and immediately be useful. Or so I thought.

Strongmind

Next, I joined Strongmind, an edtech company filled with brilliant engineers. My first day delivered the biggest case of imposter syndrome I’d ever felt.

I was greeted with a diagram of the company’s entire ecosystem, which included:

• Ruby on Rails repos
• Python repos
• C# and .NET repos
• Event-driven architecture
• AWS and Azure
• Adapters everywhere
• Microservices
• CI/CD pipelines
• DLQs
• And arrows crisscrossing everything like a spiderweb

It was beautiful. And it was terrifying. I knew I was in for a ride.

Trial by Fire

On one hand, I could feel this place was going to force me to grow in ways I hadn’t imagined. On the other hand, my confidence had just hit a new low.

That first month, I leaned hard on my teammates, asked countless questions, and put in long nights. Slowly, I started to feel more comfortable with Rails—setting up controller actions, working with views, and getting familiar with the framework itself.

But even as my Rails skills grew, my understanding of our overall systems was still painfully lacking. The repos, the integrations, the moving parts—it all felt like a massive puzzle I had only just begun to piece together.

At the same time, I was learning more than just code—I was learning processes, standups, planning, communication, team dynamics, and even how to hold my own during lunch conversations. The learning curve was brutal, but I refused to let it beat me.

Fast Forward

Eight months later, I had my full-circle moment: I was asked to explain the user flow through our ecosystem to the entire engineering team.

If you’d told me on my first day that this would happen, I would’ve laughed in your face.

Looking Back

The leap from startup to scale-up has been the hardest and most rewarding experience of my career so far.

If you’re standing on the edge of a career change, nervous about what’s on the other side—take the leap. You’ll be amazed at what you’re capable of.