Build a Life You Don't Want to Escape From

Good vibes aside, I learned so much talking with Jari Roomer today on the Gentle Discipline Podcast. Jari is the co-founder of Write Build Scale, a business development program built for writers growing on Substack, which is how the two of us met. One call in, I recognized we shared many of the same beliefs about discipline, entrepreneurship, and (most importantly) personal freedom.

Twelve years ago, Jari figured out he was unemployable.

He was good at the jobs he had, and the tech startup he worked for had great people and a culture he loved. He still found himself calling in sick on days he wasn’t sick, because he couldn’t leave the office fifteen minutes early without producing a reason for it to his boss. This year he is celebrating a decade of entrepreneurship.

The first eighteen months of that decade produced no revenue at all. He covered rent by delivering cars across the Netherlands and used the driving hours to run podcasts and audio courses through the speakers. He grew up in social housing, where the family advice was to save whatever you could, and years later he caught himself nixing offers that were already selling because the identity of a profitable entrepreneur hadn’t arrived yet.

What I keep coming back to (and the quality I appreciate most in intelligent people worth listening to) is the humility. Jari has built a real thing and he still talks about his own work like a man taking notes. He doesn’t make five-year plans because a long horizon installs a ceiling and he’d rather leave the roof open. He works in ninety-day cycles and treats every season of struggle as a filter that most people quit inside of. The last thing he said in the conversation is the thing I named this episode after.

• Ten years of entrepreneurship this year, and the twelve years since he figured out he was unemployable

• The tech startup with great people and a culture he loved, and the fifteen minutes he couldn’t leave early without a reason

• Calling in sick on days he wasn’t sick, and why he reads a bad day as a call to action

• Rich on five years in the Army and the mental health crisis that ballooned the moment they put him behind a desk

• Tim Ferriss, The 4-Hour Workweek, and finding five or ten people who already have the outcome you want

• Why the first business was a productivity newsletter, and the single instruction every role model gave him

• Medium as the front door, and the path from readers to subscribers to digital products, courses, and coaching

• A year and a half before the first dollar, and the shiny object syndrome that stretched it out

• Delivering cars across the Netherlands at nineteen with podcasts and audio courses running the whole drive

• What he tells someone with a mortgage and kids: the financial buffer, the part-time question, and using your 5 to 9

• The woman on his Substack Live who had been publishing for two weeks and was frustrated nobody was reading

• Frustration as a season, success as a season, and the exact questions where people drop off

• Overconfidence at nineteen, then imposter syndrome the moment the newsletter blew up and got profitable

• Growing up in social housing, the advice to save, and the savings that never accumulated

• The self-sabotage he only saw in hindsight: scrapping offers that were already selling to go build something new

• Systems that hold regardless of how you feel, and the Ironman he trained for by following a plan he didn’t understand

• Rich on the Ranger Assessment psychiatrist who called him out for preferring to improvise, and the Phoenix gym that ran on force of personality until it broke

• Automate, delegate, eliminate, batch, and spending every freed hour on the unscalable

• A half-hour walk with the dog, the whole article spoken into a voice memo, and AI brought in afterward as the ghostwriter

• The line he draws around his own work: is the idea mine, are the insights mine, is the experience truly mine

• The axe and the chainsaw, and whether either one counts as cheating

• Hundreds of Medium articles loaded in as context, and the year and a half it took him to stop blaming the tool

• Why AI agrees with everything you say, and how to prompt your way out of it

• Twenty minutes a day, and the lead outreach automation he built with Claude by asking whether it was even possible

• Standing out with dog photos: the profile picture, the DMs from other dog owners, and the twenty-minute conversation about dogs that ends in a sale

• Why asking how to translate who you are is already a form of filtering yourself

• Rich on the noisy ego, a conversation with a mentor, and being over doing

• The 90-day year, a three-year goal as a ceiling, and what ninety days looks like with a baby due any day and a business that has to run without him

• The compound effect running in both directions, and the life you don’t need an escape from