Sidequest Series: Part 1

Taking the Leap

6/10/20253 min read

I've finally done it: I've left what many would consider a dream company--a unicorn, even.. and I did it without a backup plan. No company waiting for me to render my hours, no business I can dive into as soon as my time frees up. I'm not sure if you can count that as brave or foolish, but the line between the two has always been a very thin one.

I've known I was going to leave for a while. Probably months before I even submitted my resignation. The truth is: no matter how great of a company I work for, if the growth that company prioritizes and rewards doesn't align with the way I want to grow as a creative, then I would be doing myself (and the company, tbh) a disservice if I stay. The longer I stayed, the more I felt like an impostor, and that didn't sit right with me. So finally, one afternoon in late May, I finally got all my ducks in a row and finalized my exit plan. It was a clumsily-made google sheet I called Break Bucketlist.

I called it a break bucketlist because another driving force behind my resignation was the fact that I haven't stopped working since I was 17 years old. I'm now 33 years old, and I didn't even realize how burnt out I actually was. I haven't had a real vacation in years, and I haven't tried pursuing other things I'm passionate about, like coffee or women's sports. "Sometimes I can hear my bones straining under the weight of all the lives I’m not living," I think about that quote a lot. There's so many things I want to do, and I saw this resignation as a rare chance to do a lot of them.

a WIP version of my Break Bucketlist

Letting the Past Be My Guide

Winston Churchill once said, "The farther backward you can look, the farther forward you can see"

Given how sore I felt about where I worked, it was difficult to force myself to take the time to look back before deciding how to move forward. Whatever my next step was going to be, I didn't want to feel the way work made me feel again, and that meant a bit (okay, maybe a lot) of introspection was needed. If I was already in an amazing company, why wasn't I happy? Did I even have to be happy at work? Can't it just be a means to make a living?

For me, needing work to feel fulfillment is giving it too much credit. My life shouldn't be defined by what I do to make a living, but at the very least, I didn't want to dread going to work, and I wanted to be able to see a clear future with it.

The Plan

So here was the plan: I'll figure out how to resign by June, take a long break, try out one of the 'lives' I've been wanting to live in July, upskill and plan all my product releases in August, and finally, go job hunting and launch all my products in September. This meant I had 4 months to rest, quiet my curiosities, upskill, and find a new source of income. Seems doable, but we'll see!

Now it was just a matter of figuring out what 'life' I wanted to try out, and figuring out the most inexpensive way to do it. I've been interested in many things, but I've sampled most of them enough to know which ones I was deeply invested in: coffee, sports, and wood working. I've already tried being a basketball coach, but I quickly figured out it wasn't the type of relationship I wanted to have with the sport. I was most intrigued by woodworking, but it was the most expensive one to try, and I had zero connections in the field. Coffee, however, I knew I had a connection I could possibly tap into.