When I was 19, I moved to Colorado Springs with dreams of becoming a professional rock climber. Unfortunately, I was very average and honestly I think I liked the idea of being pro, but wasn’t willing to put in the effort.
Instead, I found myself working two jobs that unknowingly gave me the blueprint for my ideal work life. As it turns out, I was temperamentally more blue collar than I was climbing bum.
My first job Colorado Springs was as a line cook at Wooglin’s Deli, a little sandwich and coffee spot on the edge of the Colorado College campus (it has since moved to some suburb). Over time, I became close with the owners Dan and Amy. They were not much older than me which seemed remarkable. I was young and poor earning minimum wage and couldn’t fathom how these two had managed to open up a fully functioning restaurant that served actual food to actual people . That seemed so advanced to me at the time.
The other thing I found attractive about Dan and Amy is that the deli wasn’t their only business. Amy made jewelry and Dan sold real estate. Most of the time that I knew them they were also rehabbing an old house in Manitou Springs and doing much of the work themselves. They had several irons in the fire.
Sidenote: Dan helped me start my very first business endeavor which was a (pre-Starbucks) mail-order coffee business for our local roaster.
I clearly remember thinking that I wanted my life to look like theirs. As a line cook I was in the kitchen all day (and night sometimes). My whole working world was a few hundred square feet. In previous jobs I’d had as a teenager, the same was true. I was in one place doing the same thing over and over and I knew at a young age that wouldn’t work for me. I needed to move around and do lots of different things in order to stay focused, motivated, and interested.
My second job in Colorado Springs was with Dave Vanderwhite. Dave has been my career hero since I was 20 years old and I still want my life to look like his on most days. Dave was a customer at the deli and over time I introduced myself and got to know him a little. Dave was an electrician by trade, but that wasn’t what he loved doing most.
As my time at Wooglin’s drew to a close (long story) I asked Dave for a job. I told him that I was interested in learning something about building trades because I had this vague notion that I wanted to buy and restore old houses (this was well before the term “flipping” entered the cultural lexicon). Dave said he’d take me on as a helper and that changed my life forever.
Dave enjoyed, and made most of his money, in real estate and antiques. I’m not sure how or when he bought his first house, but Dave owned three or four little multi-unit houses close to the CC campus and rented to students. As his helper, I would run around to these houses trying to keep everything working. Occasionally there would be bigger projects, but mostly I learned how to replace lights, switches, sinks, toilets, doors, windows, etc. I learned how to paint and learned the basics of commercial and residential electrical work.
When it was too cold or snowy to do electrical work outside, we’d meet at Dave’s house and spend the day in his workshop where he had scores of old antique lamps, lights, and fixtures that we would disassemble, clean, polish, rewire, and sell at local antique shops. That work was fun and I continued to refurbish antiques for several years after I left Dave’s employ.
Here I am thirty years later and my life looks a lot more like theirs than it used to. I got sidetracked for several years as an IT guy. I was in my early thirties and I guess I was craving more stability and less poverty.
Then I spent another decade running a design consultancy with my partner Anna and that was super fun, but again, the scope of what I was doing on a day to day basis became stifling.
Today, I get to:
- Coach entrepreneurs, executives, and people in recovery
- Write here on Substack AND am seeking publishing for my first novel
- Earn a 1/5 of my income from real estate investments
- Create online courses on entrepreneurship with my buddy Jacob
- Teach at the d.school at Stanford
- Take on 2-4 consulting/teaching projects each year
None of these things make me particularly wealthy in the traditional sense. But combined, they provide a comfortable living. I have more than some and less than others. More importantly, I have been able to design a work life that I find interesting and fulfilling. I get to scratch the many itches that I have like helping people, being creative, teaching, collaboration, solo work, etc.
I’m not suggesting you should have multiple streams of income or several different roles. Everybody has a different working style. Some people thrive on a laptop in Zoom meetings all day. Some people do well in an office environment or huddled in a cubicle free from distractions. I tend to do well with lots of irons in the fire.
If you feel like you want your work life to have a little more diversity, I’d encourage you to find that one small thing you can start quickly and rapidly learn whether or not it’s your cup of tea.
Another Sidenote: I want to be explicit about something here. This idea is often called a side hustle and is most commonly talked about as a vehicle to either a) earn extra income or b) experiment with a business idea you love enough to grow into your main hustle. And I applaud both of these motivations if they sounds interesting to you. But this is not what I’m doing.
I crave variety. I enjoy lots of different inputs and working styles. I enjoy different working spaces and mobility. As much as I daydream about being the kind of novelist that sits at the same desk every morning from 8-12 and cranks out manuscript after manuscript, I think I’d go nuts. So while earning additional revenue or exploring new jobs are great reasons so have side hustles, I just enjoy having several side hustles. I guess I’m more of a buffet guy than a main course guy.
What I hope to dispel here is this old story that we have have one job at a time. That there is only enough time or energy to do one thing at any given point in your life. For some, that may be appropriate, but if you have read this and want your life to look more like Dan or Amy’s, or Dave Vanderwhite’s, or mine, then feel free to let go of that old story.
Unearth that old dream you have about restoring vintage wrist watches or opening a pop-up florist, or doing some graphic design work on the side. Dust that dream off and give it a shot. I mean, why not add a few irons to your own fire?