Before I worked in technology, I worked in everything else.

Grocery store. T-Mobile. UPS overnights. All while going to community college. There was no schedule. There was just filling every available hour with work or class, sleeping when I could, and doing it again the next day.

I didn't have a trust fund. I didn't have connections. My mom was my role model. She worked hard, and I watched her do it. I knew if I kept going, I could make it somewhere. I didn't know where yet. I just knew I wasn't going to stop.

There's a version of this story where I tell you it was character-building and I'm grateful for every minute of it. That's not the whole truth. It was exhausting. There were stretches where I was running on four hours of sleep between shifts, sitting in a lecture hall trying to stay awake, then clocking in again. The question wasn't "what do I want to do with my life." The question was "how do I get through this week."

But that time taught me things no classroom or certification ever could.

When you're juggling three jobs and school, you learn which problems need attention right now and which can wait. Triage. I still use that instinct every day. When a client's network is down, their email is broken, and their printer stopped working at the same time, I don't panic. I prioritize. I learned that at the grocery store, at T-Mobile, at UPS. Not in a textbook.

Dealing with frustrated people is the same skill at T-Mobile as it is in IT. A customer who can't get their phone working and a CEO whose office is offline before a board meeting are feeling the same thing. They need someone calm who can figure it out. I got good at that early.

And the biggest lesson: when you're working three jobs, there's no backup plan walking through the door. You solve the problem in front of you or it stays broken. That mindset never left me. It's why I build my own tools, run my own infrastructure, and don't sit around waiting for someone else to figure things out.

Then the fork in the road showed up.

I had a chance to become a UPS truck driver. Full-time, stable, good pay. Or I could take a job at the Microsoft Store. Less money, less security, but it was technology. It was the thing I'd been pulled toward my entire life.

I picked Microsoft.

I don't romanticize the three-job years. I don't regret them either. Every difficult client call, every midnight outage, every moment where the pressure is on and the answer isn't obvious. I've been in harder rooms.

- Roger