The Expert's Privilege: Wes Wheless on Leaving Corporate and Going Solo

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:

You've built real, transferable expertise over your decades in corporate.That expertise has been inefficiently deployed inside the corporate machine.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 backClient zero, and why hourly was the wrong modelGetting pigeonholed as "a writer" and the pricing that comes with itThe coach question that triggered his pivot: do you actually like doing this work?Writing daily for two years before there was a bookWhy he deliberately left AI out of the bookThe Expert's Privilege, definedIntellectual headshots, and how asking former clients one question reshaped his businessInvesting in yourself when corporate always paid for it before

TIMESTAMPS00:00 — Intro01:43 — Two layoffs, and why he didn't want another corporate role03:26 — Why almost nobody who gets out wants to go back04:32 — He didn't know solo consulting was even an option06:43 — What the work actually was: executive ghostwriting and content strategy08:22 — Client zero, and the first lesson about hourly rates09:18 — Project fees, and putting guardrails on your availability10:44 — Getting pigeonholed as "a writer" before the conversation starts1