The Corporate Escapee: Get Busy Living with Brett Trainor

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 beforeTIMESTAMPS00:00 — 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 starts12:14 — When the business model started breaking13:11 — The coach's question: do you actually like doing this work?13:41 — The pivot to serving independent consultants14:59 — Brett's own winding path out of corporate15:53 — The three-tier offer, and why clients almost always pick the middle16:50 — Helping people map their lane while they're still employed17:47 — "I never gave serious thought that I could take the reins myself"20:18 — Building authority from zero, and writing daily for two years21:44 — You turn around and there's a library there22:34 — The self-doubt going into the book23:10 — Not the book. A book. Your first book.26:11 — Brett's stuck manuscript problem26:33 — The North Star workshop and the parachute metaphor27:44 — Why he left AI out on purpose30:04 — The Expert's Privilege, the three stacked ideas30:53 — A hundred ships and fifty of them tied up in port32:10 — In the corner four months ago, desperate for his brain today34:00 — Most businesses need level one help, not level three36:28 — "I don't know what I know," and why that trap is so common37:34 — Start with the problem, not with yourself38:48 — Need-to-solve versus nice-to-solve39:26 — Brett on chasing energy as the compass40:31 — Intellectual headshots, and the one question that created them42:08 — Saying no, and the add-on that killed Brett's margin43:18 — Investing in yourself when corporate always covered it45:39 — 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 bookQUOTES"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?" — WesABOUT THE GUESTWes 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.LINKSThe 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/1788464028Wes's site and services https://bio.site/weswhelessWes on LinkedIn — https://www.linkedin.com/in/wwheless/The Collective https://trp-collective.circle.soQuestions or guest ideas? [email protected]

Corporate quit on me just over six years ago. At the time I thought this was about one thing: replacing my income. Six years, 350 episodes, and a whole lot of experiments later, I've figured out it was never really about the money. This is the first solo episode under the new name, and I wanted to start by sharing the nine things I've learned on this quest so far. Not a playbook. Not a system. Just the stuff that turned out to be true, whether you're still in corporate, recently laid off, or already out and still trying to piece it together. I don't have it all figured out. I'm a lot closer to where I want to be than I was six years ago, and I'm bringing you along for the rest of it. The nine: I wasn't running from corporate. I was running toward control. Time is the currency. Grinding is just rationalizing giving it away. Without your health, none of the time means much. We overcomplicate everything. Especially making money. Stop building your life around a job. Fund the life you want instead. Stop asking permission. Nobody's coming. Action beats planning. Every time. Doing less is the whole skill. It comes down to four buckets: relationships, health, purpose, and fun. The Collective Now focused on the thing most people are actually stuck on: making money outside of corporate. https://trp-collective.circle.so/checkout/the-time-rich-project-collective Got a question, or know a Gen Xer doing something interesting? Email me: [email protected] If you're getting something out of the show, hit follow or subscribe wherever you're listening. Still moves the needle. TIMESTAMPS Estimated from the transcript. Spot-check against the final cut, and shift everything by the length of your cold open plus sting. 00:00 — Six years in, and why I'm doing this podcast with more intention 01:55 — #1: I wasn't running from corporate, I was running toward control 03:00 — #2: Time is the currency (and the 90-minute commute that broke me) 05:05 — #3: Prioritize your health now, not later 06:00 — #4: We overcomplicate everything, especially making money 07:30 — #5: Stop building your life around work, fund the life instead 09:10 — #6: Stop asking for permission 10:25 — #7: Action beats planning, every single time 11:30 — #8: Doing less is the whole skill 13:55 — #9: The four buckets (relationships, health, purpose, fun) 17:50 — Quick recap of all nine 19:20 — There is no one path. Don't follow somebody else's plan. 20:05 — What's changed inside The Collective 21:05 — How to reach me

You can always make more money. You can't make more time. This is the episode that ties the whole thing together: what a time rich life actually is, and why control of your time, not your income, is the key to the life you want. My first year out of corporate, I chased one thing: replace the paycheck and then some. I did it. And I wasn't much happier. This is the story of what I was actually missing, and the simple framework that fixed it. In this episode: What a time rich life really is, and why money isn't part of it The four areas that actually move your happiness: connections, health, purpose, fun The "50 hours back" question that reframes everything The calendar mistake I made that was worse than corporate Define, Fund, Live: the three moves to get there Low-friction income: funding your life in the fewest hours If corporate has you trading every hour for a paycheck, this is your blueprint for taking the hours back. CHAPTERS / TIMESTAMPS 00:00 — What this episode answers, and why it matters 02:18 — Kicked out: I chased the money and wasn't happier 03:30 — What a time rich life actually is 04:44 — The "50 hours back" question 05:30 — The four areas: Connections and Health 07:07 — Purpose, and why "escape" was the wrong word 08:20 — Fun, and my two non-negotiable time blocks 09:24 — What control actually looks like (golf Friday, granddaughter over) 10:49 — Why it all comes down to time 12:00 — We overcomplicate making money 13:16 — The calendar problem, and losing the guilt 14:30 — Time blocking, and the 30-minute disaster (thanks Glaveski + Shirley) 15:38 — Learning to say no 17:52 — The four areas as your monthly barometer 19:20 — Money is a tool, not the goal (thanks Diana Alt) 20:03 — The framework: Define it, Fund it, Live it 22:24 — Funding the life: from fractional to low-friction income 25:00 — Two things you can do today LINKS & RESOURCES Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes The Time Rich Collective (connect with Gen Xers on the same path) → https://trp-collective.circle.so/checkout/the-time-rich-project-collective Website → https://timerichproject.life Mentioned in this episode: Steve Glaveski, author of Time Rich — earlier TRP episode Paul Shirley, The Art of Focused Work — earlier TRP episode Diana Alt on separating mission from money — recent TRP guest episode The "15 ways I've made money outside corporate" episode → https://youtu.be/p5rxv-f1M7k Listen / subscribe: Spotify → https://open.spotify.com/show/5UQSv8iKydo8E2cevuIAB5 Apple Podcasts → https://podcasts.apple.com/us/podcast/the-time-rich-project-formerly-the-corporate-escapee/id1469405998 Newsletter → https://trpnewsletter.beehiiv.com/

Pro athletes know their career has an expiration date. Corporate never tells you yours has one too. Here's the part nobody says out loud: when corporate moves on from you, it usually isn't because your talent slipped. You just got too expensive. Gen X is the first generation facing this without a pension to catch us, and we're going to outlive the old retirement math by decades. So this episode borrows from the people who have been managing forced career transitions for 50 years: professional athletes. What do they lose when the game ends, and what can we take from their playbook? In this episode: The four things you lose when corporate retires you: identity, community, structure, and money Why "you got too expensive" is not the same as "you're done" The three-part transition: design the life you want, fund it, then live it The four areas to rebuild around: relationships, mind and body, purpose, and fun Separating mission from money so you don't burn out chasing the wrong one Becoming a high-functioning lazy person: funding your life in the fewest hours possible You've got another 30 good years, and 20-plus years of experience the athletes don't have. This is the sunrise, not the sunset. Let's build the plan. LINKS & RESOURCES Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes The Time Rich Collective (connect with Gen Xers on the same path) → Website → https://timerichproject.life Mentioned in this episode: https://trp-collective.circle.so/checkout/the-time-rich-project-collective Paul Shirley (former pro basketball player and author) — earlier TRP episode Diana Alt — "separate mission from money" (recent TRP guest episode) ABOUT THE SHOW The Time Rich Project is for Gen Xers who paid their dues and are ready to write the next chapter. It's about taking back control of your time and funding the life you want in the fewest hours possible, so the rest of your time is yours. Real stories, real mechanics, no hustle. Hosted by Brett Trainor. CHAPTERS / TIMESTAMPS 00:00 — The parallel nobody talks about: pro athletes and corporate 00:50 — You didn't get worse, you got too expensive 01:30 — The first generation without a pension (and outliving retirement) 02:45 — The four things you lose when corporate retires you 02:55 — 1. Identity: who are you without the title? 03:40 — 2. Community: everyone misses the locker room 04:50 — 3. Structure: owning your calendar, and my time-blocking mistake 06:45 — Why it's called Time Rich 07:30 — 4. Money: funding the lifestyle instead of chasing a paycheck 09:00 — Turn the faucet up or down: your first dollar out 10:00 — Start with what you know, then go wider (UGC, AI, small services) 10:50 — Separate mission from money (thanks, Diana Alt) 11:50 — The pyramid: from C-suite to everyone else 13:40 — What we have that athletes don't: 20+ years of experience 14:30 — Sunset or sunrise: it's your call 16:30 — Designing the life: relationships and the no-asshole policy 18:15 — Mind and body: built to live to 90 18:40 — Purpose: follow the energy 19:40 — Fun: are you getting enough of it? 20:00 — Funding the life you designed 21:00 — Living it: the 80/20 way 22:00 — Design, fund, live: putting it together