I’ve had 2 inflection points in my life - moments where the wheels were spinning in the mud, the train was off it’s track, I didn’t feel satisfied with the life I was living, and it took extended periods of deep introspection to get back on course.
The first occurred nearly a decade ago on a ski lift in Breckenridge, Colorado (I know, how can you be unhappy in that paradise?). At this point I was a college junior at the University of Michigan, and my entire world was politics. I studied political science. I volunteered and worked on campaigns. I even worked my way into a Campaign Manager position for a state house incumbent at just 18 years old, still the youngest I’ve ever heard of to do that. I thought my entire life was going to be lived in 2-4 year election cycles — and yet, I fucking hated politics.
With graduation impending and very little time until I reached the real world, I had to figure out:
On that ski lift, I came to a realization that was months in the making: what I loved about politics had nothing to do with politics at all.
I loved grassroots organizations of hard-working, motivated people working toward a common goal or objective. And even more so, I LOVED being their leader. It’s not difficult to see how this led to a career in small to medium sized business.
After graduation, I worked for 3 different companies in a span of 4 years. I also started 2 companies, one of which failed.
At the start, I took a shitty job selling software and consulting services to small to medium-sized tax & accounting firms at Thomson Reuters. I lasted less than a year, but I’m grateful for that experience. I got to spend time with literally hundreds of SMB entrepreneurs who’d been doing this thing for decades. I spent so much time learning about them and and their businesses that I’d often forget to sell them anything. Woof. No sales = no money in my pocket. By the end, I was working harder at getting out of there than anything else.
And I did. I got out, and I got in to