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:

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

• 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 workshop and the parachute metaphor
• 27:44 — Why he left AI out on purpose
• 30:04 — The Expert's Privilege, the three stacked ideas
• 30:53 — A hundred ships and fifty of them tied up in port
• 32:10 — In the corner four months ago, desperate for his brain today
• 34:00 — Most businesses need level one help, not level three
• 36:28 — "I don't know what I know," and why that trap is so common
• 37:34 — Start with the problem, not with yourself
• 38:48 — Need-to-solve versus nice-to-solve
• 39:26 — Brett on chasing energy as the compass
• 40:31 — Intellectual headshots, and the one question that created them
• 42:08 — Saying no, and the add-on that killed Brett's margin
• 43:18 — Investing in yourself when corporate always covered it
• 45:39 — Laid off tomorrow: square one, or a head start?
• 48:05 — You're a business with one client. Is that a good deal?
• 49:28 — Where to find Wes and the book

"I wasn't angry. I just didn't have the energy to attach myself to someone else's mission again, just for it to get taken away in a couple of years." — Wes

"Imagine you had a cruise line with a hundred ships and fifty of them were tied up in port permanently. That's how we are in corporate." — Wes

"I was that person four months ago that was getting put in the corner. And here, in a different context, they're desperate to know what I know." — Wes

"If you're good at something, an hourly rate doesn't do you any favors." — Wes

"Don't think of it as the book. Think of it as a book. Even easier, your first book." — Wes, on the advice that unstuck him

"I don't know what I know. I've done so many things that I feel like I can't do any of them." — Wes, on what he hears constantly

"Think of your current job like you're a small business owner with one client. Is that a good deal for you?" — Brett

"If you were laid off tomorrow, do you want to start from square one, or do you want to feel like you had a head start?" — Wes

Wes Wheless is the author of The Expert's Privilege: A Self-Deployment Guide to Leaving Corporate and Going Solo (July 2026). After two layoffs, including one from the tech education company Reforge, he built an independent practice helping solo consultants pull their expertise out of their heads and turn it into visual frameworks, something he calls intellectual headshots. He now also works with people still inside corporate who want to map and pressure-test a consulting lane before they need one.

The book The Expert's Privilege: A Self-Deployment Guide to Leaving Corporate and Going Solo https://theexpertsprivilege.com/ Amazon: https://www.amazon.com/Experts-Privilege-Self-Deployment-Leaving-Corporate/dp/1788464028

Wes's site and services https://bio.site/weswheless

Wes on LinkedIn — https://www.linkedin.com/in/wwheless/

The Collective https://trp-collective.circle.so

Questions or guest ideas? bt@bretttrainor.com