After I left Stoked in 2021, I took some time off to work on a novel I’d been trying to write for years. A good friend who lives in my neighborhood offered up his garage apartment for me to use as an office and I spent the next year sitting up there by myself writing for about six hours a day.
I started to get kind of depressed. Not the “I can’t get out of bed” depressed, but more of a general malaise and lack of enthusiasm.
I went to see a therapist to see if I needed medication. As a means of getting to know her new client, she asked me to share what had been going on in my life for the past few years. I gave her a quick 10 year summary of my personal and professional life and when I was done she said:
Therapist: “So let me get this straight. For the past ten years, you’ve been traveling the world, working with amazing leaders and companies on big projects. You’ve been speaking on stage in front of thousands of people AND teaching at the prestigious d.school at Stanford. Then you abruptly quit the company you’d co-founded after experiencing some burnout, retreated to your friends garage, and have been sitting up there by yourself living in a world of fiction?”
Me: “Ummm, yep.”
Therapist: “Yeah, you’re not depressed and you don’t need medicine. You need to get back to work.”
It seems so obvious when you read it like that but honestly you guys, I never considered my situation like that! To have it mirrored back to me was incredibly powerful and life changing!
This seems like an obvious place to plug my 1:1 coaching, but that’s now what this is about.
So I took her suggestion and decided to divvy up my time by writing fiction in the morning when my brain was freshest, and working in the afternoons.
I wasn’t positive what I wanted to do for work, but my friend and colleague (and sometimes coach) Barbara suggested I give coaching a shot because she thought I’d be naturally good at it.
So this is how it all started: I quickly learned I knew fuck-all about coaching people and enrolled in a coaching school. While I was still taking classes, I started creating content online as means of marketing my new services.
I began posting little YouTube shorts on mindfulness and leadership and entrepreneurship. I’d been writing on Medium for years but moved over to Substack. I also started posting almost daily on LinkedIn and Instagram. It’s all the same content for the most part, just in different locations.
Now, I have never had a post go viral. I get very little engagement on my content. My followers and subscribers grow sloooowly.
However, I regularly get texts, emails and DM’s from people who consume my content with very nice, thoughtful feedback. I guess you could call it “praise” but that word makes me itchy.
I’d started making content because I was trying to advertise my coaching business AND because I genuinely loved writing, recording, editing, etc. The creative process helps me clarify ideas and advance my thinking on those subjects.
But I continue to make content because I actually love making content. And that brings me to a few final points.
- There is often an unexpected, non-linear path to finding work you love. Teaching at Stanford, starting Stoked, coaching, writing, making content. None of these things were on my map 15 years ago. As a matter of fact, I would have never dreamed I’d get to do these things. I found them all through starting and experimenting. Not through thinking.
- Creative work without a big audience still allows me to be creative! And that process still allows me to explore and distill ideas and experiments. Again, get started making and publishing your shit. You won’t ever get there by trying to think your way through it.
- Getting stuck is normal. That therapist helped me see something I couldn’t see and unlocked my next few moves in life. Find someone that can be an objective and supportive mirror in your life. Like me maybe.
All that to say: getting started before I was ready, experimenting early and often, and taking action even when I was scared has helped me to find the work I love.