Michael Perry - Self-Employed Writer

For more than 30 years, Michael Perry has built a life around words — from essays and bestselling books to one-man shows and live events. In this conversation, Mike shares how his blue-collar roots shaped his approach to creative work and money, why he still keeps his nursing license “just in case,” and what it really takes to sustain a self-employed creative life. He and Tim talk about saying no to the wrong opportunities (even when Oprah calls), learning business skills on the fly, and how low overhead, multiple income streams, and a willingness to keep “shoveling” have allowed him to keep doing what he loves.

Mike's question for me: Regular IRA, Roth IRA, or SIMPLE IRA?

Key takeaways:

1. Longevity through discipline: Mike has supported himself solely through writing since 1992 — proof that persistence can outlast uncertainty.
2. Money is part of the craft: Understanding taxes, mileage, bookkeeping, and contracts enables creative independence.
3. Multiple income streams matter: Like his farmer father, Mike learned to diversify work to stay sustainable.
4. Integrity over exposure: Turning down a high-profile appearance taught him the value of aligning work with values.
5. Freedom, not fame: For Mike, success means autonomy, stability, and the ability to keep creating on his own terms.

Links:
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Michael Perry's website
His new book Improbable Mentors & Happy Tangents
Population: 485, Mike's breakout memoir about small-town life and volunteer firefighting