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Rick Foerster writes one of my favourite newsletters on Substack, The Way of Work, so I was thrilled to chat with him about work, meaning, and creativity to kick off Season Two of the podcast.
Rick spent 12 years at a healthcare startup, from early employee to public company exec managing hundreds of people. He left, armed with a war chest and soon after 100+ company ideas of his own ready to go. He was at the starting line of what he thought was his entrepreneurial dream.
Then he stopped.
What was supposed to be a three-month sabbatical turned into two years of what Rick calls "the wilderness phase". No building or “output”. Rick wanted to figure out who he was and what he wanted to do when he wasn't on the hook to actually do anything.
He’s now emerged from the other side of that wilderness writing post-apocalyptic fiction.
We talk about why his executive coach told him to disappear, what led him to writing about his experiences on Substack, the trap of suppressing existential questions with productivity, the "first mountain vs. second mountain", and why following weird creative interests matters more than having a plan.
Highlights from my chat with Rick
1. “You need to sit down in the middle of the road”
When Rick told his coach something felt off, she told him to go dark for six months. Stop networking, stop building, stop producing. Just read, write, disappear, but nothing public. Most people treat transitions like crossing a road: get to the other side as fast as possible and avoid the discomfort. But Rick found his way through by sitting in the middle of traffic and letting himself be fully, uncomfortably lost.
2. Doing can be a form of avoidance
Rick spent three months building 100+ startup ideas after leaving his exec role. He was busy as hell. He was also running away from the real question: why am I doing any of this? Sometimes hustle is just existential angst dressed up as ambition. Staying busy feels productive, but it can be the most effective way to avoid sitting with what’s actually wrong.
3. Don’t grasp for the next permanent identity.
The temptation after leaving something is to grab the next label fast. Founder. Coach. Writer. Whatever stops the discomfort of not knowing who you are or what you want to do. Rick learned to stop searching for “the one thing” that would define him forever. Instead he asked: What interests me today? What am I curious about right now? He’s writing fiction, but he’s not tied to the “writer” identity. If he stops enjoying it in a year, he’ll move on.
4. The best signal might be work you’d pay to do
Everyone wants to “get paid to do what you love.” Rick flips it: the best work is what you’d be willing to lose money doing. If you’re only doing it because it pays well, you’re probably avoiding finding out what you truly want. Money warps your sense of value, even when you have enough. Ask yourself: what would I pay for the privilege to do?
5. Avoid “either/or” thinking
You don’t have to choose between “quit everything and pursue your creative dreams” or “stay in corporate hell forever.” There’s a whole menu of options: side project experiments, sabbaticals, moving somewhere cheaper, working 3 days a week, stair-stepping your way there. Even successful creative people fund their work through something else, often for a long time (or forever).
6. Not having an audience is liberating
There can be a lot of pressure online to “build an audience” before you do anything else. Rick found that having no audience for his fiction work freed him from expectations entirely. He could write his book without worrying about what his followers would think, whether it fit his “brand,” or if it would disappoint people. He could quit the experiment if he wanted to.
7. Avoid the pressure to monetize everything
These days, every hobby gets the same question: “how do you monetize it?” Start a YouTube channel. Launch a course. Build an audience. We’ve been conditioned to ask “what’s the monetary value?” of literally everything. When you reduce creative work to its dollar value, you destroy the intrinsic joy that made it worth doing in the first place.
8. Follow your weird creative inklings
Don’t overthink it. Don’t ask if it’ll make money. If you’re curious about something, be it writing fiction, playing an instrument, or painting, just try it. Don’t worry if it’s permanent. Don’t put a deadline on it. Just see where it takes you. Enjoy it. Most of the good stuff in life comes from following those weird pulls. Get weird with it.
Resources Mentioned
Rick’s Substack: The Way of Work.
Transitions by William Bridges
Rick’s Book recommendations:
Working Identity by Herminia Ibarra
The Second Mountain by David Brooks
Full transcript available here.
