Self-Employment in a Groundless Economy (An Interview)

Every once in a while, someone is lucky or smart enough to enter a career field at the exact right time. For instance, hand sanitizer production in 2020. Or, in the case of Stephen Warley, teaching people how to work for themselves in an uncertain economy.

Stephen has been a serial solopreneur since 2000 and has extensively researched alternative ways of working, both in his and in his forthcoming book, . He founded Life Skills That Matter in 2016. I interviewed Stephen recently because I believe, essentially, we are teaching similar skills: how to work with uncertainty, and how to preserve one’s humanity amidst stress and confusion. The full video interview (about 25 minutes) is here (Stephen and I are both sporting the “self-employment” haircut).

Here are some of the conversation highlights:

Stephen is a true ‘digital nomad. ‘ In the last year, he has lived in Australia, Bali, Boise, the Amazon rainforest, the Catskills, Arkansas, Aruba, and — not to be left out — Cleveland.

The ideal candidate for Stephen’s training programs and self-assessments is someone who wants to work about 30 hours a week and make $75,000 a year doing something they enjoy.

What he’s learned: It generally takes people about two years from when they start thinking about self-employment to when they make the shift.

What’s the most common pitfall in trying to work for yourself? Not enough outreach. “If you’re not doing outreach, you don’t have a business — you have a hobby.”

What skill do all entrepreneurs need to cultivate? Self-awareness. Stephen believes that the economy and workforce is entering “a permanent state of accelerated change.” As a result, “The more and faster that things change, we need to jump back and pause, be still, and hear our inner voice. What’s really bothering us? What do we really want?”

Full interview here.

Stephen’s next 30-day Accelerator begins on October 22. (Confession: I took a 30-day Accelerator with Stephen a few years ago and it transformed the way I think about working for myself, organizing my time, and setting my goals).

AND… He is hosting two workshops coming right up.

9/12 — Find and Validate the Right Business Idea for You

9/16 — Effortless Self-Management for Side-Hustlers, Freelancers and Remote-Workers

In health (and self-employment),


PS — Monday night events (a.k.a. Focus & Relax) will begin on Monday, September 21. More details to follow.

Originally published at on September 11, 2020.

Meditation + Alexander Technique teacher. Author of “Don’t Get Better,” forthcoming guide to sanity, humor, and wisdom during illness.

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