Wes Wheless got laid off twice inside a few years. COVID, then the tech downturn. He wasn't angry about the second one. He just didn't have the energy to go attach himself to somebody else's mission again and wait for it to get taken away.

He didn't have a plan. He took a couple months, picked up some contract work to hold him over, and then a light bulb went off: if he could find enough of these, he might never need a full-time job again.

Four years later he's got a practice serving independent consultants and a book, The Expert's Privilege, that I told him he should have written before I left corporate.

The core idea is three stacked pieces:

1. You've built real, transferable expertise over your decades in corporate.
2. That expertise has been inefficiently deployed inside the corporate machine.
3. You can deploy it far better on your own.

His metaphor for point two is the one that stuck with me. Imagine running a cruise line with a hundred ships and fifty of them permanently tied up in port. That's what corporate does with what you know.

We also get into the stuff nobody tells you. Why hourly pricing punishes you for being good. What happens when a client pigeonholes you before you open your mouth. How he figured out which part of his own service people actually valued, and then sold only that. And the thing I keep running into with Gen Xers: deeply experienced people who sit down, look at twenty-five years of work, and say "I don't know what I know."

In this episode:

• Two layoffs, and the one that changed his mind about going back
• Client zero, and why hourly was the wrong model
• Getting pigeonholed as "a writer" and the pricing that comes with it
• The coach question that triggered his pivot: do you actually like doing this work?
• Writing daily for two years before there was a book
• Why he deliberately left AI out of the book
• The Expert's Privilege, defined
• Intellectual headshots, and how asking former clients one question reshaped his business
• Investing in yourself when corporate always paid for it before

TIMESTAMPS

• 00:00 — Intro
• 01:43 — Two layoffs, and why he didn't want another corporate role
• 03:26 — Why almost nobody who gets out wants to go back
• 04:32 — He didn't know solo consulting was even an option
• 06:43 — What the work actually was: executive ghostwriting and content strategy
• 08:22 — Client zero, and the first lesson about hourly rates
• 09:18 — Project fees, and putting guardrails on your availability
• 10:44 — Getting pigeonholed as "a writer" before the conversation starts
• 12:14 — When the business model started breaking
• 13:11 — The coach's question: do you actually like doing this work?
• 13:41 — The pivot to serving independent consultants
• 14:59 — Brett's own winding path out of corporate
• 15:53 — The three-tier offer, and why clients almost always pick the middle
• 16:50 — Helping people map their lane while they're still employed
• 17:47 — "I never gave serious thought that I could take the reins myself"
• 20:18 — Building authority from zero, and writing daily for two years
• 21:44 — You turn around and there's a library there
• 22:34 — The self-doubt going into the book
• 23:10 — Not the book. A book. Your first book.
• 26:11 — Brett's stuck manuscript problem
• 26:33 — The North Star work