“If money didn’t matter, what would I do?”
A few ideas came to mind:
- Electrical engineer
- Storm chaser (because… why not?)
- Programmer
These were the thoughts I kept turning over as I spun in my comfortable office chair, working at a luxury hotel in Boston.
The industry had been good to me. I worked in various roles, met people from all walks of life, and developed strong social skills that broadened my perspective. I spent about eight years in hospitality, and on paper, everything looked solid—I had stability, experience, and a clear path forward.
But something was missing. I couldn’t see myself doing it for the rest of my life.
Which brought me back to that question:
“If money didn’t matter, what would I do?”
Looking back, falling out of love with hospitality wasn’t the only reason. In the early to mid-2010s, people like Elon Musk and Neil deGrasse Tyson made STEM feel exciting—almost magnetic. They made building things, exploring the unknown, and solving complex problems feel meaningful… and cool.
Turning a Question Into a Decision
So I had to turn that abstract question into a practical one:
Since money does matter… which path is actually viable?
Going back to school for electrical engineering wasn’t realistic. I was already dealing with significant student loan debt, and adding more felt overwhelming.
Storm chasing? As fun as it sounded, money is still a factor—and I wasn’t going to risk my life with no guarantee of financial stability.
Programming stood out for one simple reason: it was accessible. I didn’t need another degree or more debt. Free resources like freeCodeCamp, Khan Academy, and W3Schools meant I could start immediately.
At the same time, the world was buzzing about tech—how great the offices were and how lucrative it could be to become a programmer.
So I made a decision that felt both exciting and terrifying—I quit my job.
To support myself, I took on odd jobs—de-icing planes overnight, taking contract work as a hospital software trainer—anything that gave me the flexibility to keep learning and building my skills.
As I was teaching myself to code, I realized I needed guidance. I reached out to my network, and through my college career advisor, I was connected with a tech professional who would eventually become my mentor.
She was smart, experienced, and honest. At the time, she had her own company but wasn’t in a position to hire me. It was disappointing—but when she told me my work ethic and ambition stood out, it gave me something I hadn’t felt in a while: validation, hope, and direction.
So I kept going.
Learning the Hard Way
I started freelancing, and she guided me through the realities of entrepreneurship—how to price my work, value my time, and manage the emotional ups and downs of working with clients.
Some of my favorite clients were startups. It felt like we were in the trenches together. At the same time, I had to learn how to balance being friendly with being professional.
I also learned that doing business doesn’t have to feel transactional. It’s not about getting the most while giving the least—most clients just want to feel heard, understood, and informed.
But growth came at a cost.
There were long, grueling hours. In software, there are countless ways to solve a problem—and just as many ways things can go wrong. Systems depend on each other, and fixing one issue can easily create another somewhere else.
Many times, I absorbed that cost myself. I treated it as part of the learning process rather than passing it on to my clients.
During that phase, I met other developers who helped me put a name to what I was feeling: imposter syndrome. No matter how confident or social you are, there will always be moments that challenge your self-perception.
So how did I get through it?
Grit.
I told myself that the discomfort was temporary, and that nothing great comes easy.
I also found perspective outside of work. Hiking through the mountains of New Hampshire, standing at the peaks and taking in the landscape, I was reminded of how big and beautiful the world really is. From that vantage point, everything shifts.
Standing there, I was reminded how small I am—and how connected everything is. The macro and the micro depend on each other. My struggles didn’t disappear, but they felt smaller. More manageable. Just one part of a much bigger picture.
Looking back, I don’t think my mentor intended it this way—but it felt like a test.
Because over a year later, she brought me on.
Through her, I met some of the most talented developers I’ve ever worked with—people who challenged me, supported me, and helped shape me into the engineer I am today. I still keep in touch with many of them.
I got to work on enterprise sites for universities and museums, attend DrupalCon for the first time, and—finally—feel like I could be a professional without wearing a “penguin suit.”
That chapter eventually came to an end when the company shut down. But by then, something had changed.
I had built real skills, real confidence, and real experience. Those foundations opened new doors, eventually leading me to where I am today—working at Harvard University.
Final Thoughts
Looking back, that simple question led me to something deeper.
The reason hospitality no longer worked for me wasn’t just about the job—it was about what I needed.
I needed something that kept me curious, challenged me, and made me feel like I was building a life—not just maintaining one.
In the end, financial success has its place.
But it’s measured against something important:
How you spend your time.
And who you become along the way.