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? [email protected]

This one's a step back to look at the big picture, because a lot of the Gen Xers I talk to are too busy living life to see it.

Three things are colliding at once.

Corporate is chaos. It's not your age, it's your expense. Somebody can do half your job for half the price, and that's who gets picked. Getting laid off is one thing. Getting back in is the real problem. Look around your own network if you don't believe me.

The savings math. The generation before us had pensions. We got a 401k and a how-to video. Roughly half of Gen X has nothing put away, and the typical household isn't close to what 30 years actually costs.

Longevity. This is the good news. If you take care of yourself there's a real chance you're looking at 30 or 40 more years, healthy and active.

Put those three together and it doesn't add up.

I'm not doing this to scare anybody. It's not a prediction, it's already happening. But there are two ways to react. You can treat it as a sunset and ride it out. Or you can treat it as the start of a second adult lifetime, which is the way I'm choosing to look at it.

The back half of this episode is the part that matters: you already have everything you need to generate income on your own. The skills, the experience, the problem solving. What's in the way is unlearning what corporate taught you, and the fact that we make making money way more complicated than it needs to be.

In this episode:

• Why it's your expense, not your age
• The musical chairs problem, and why the chairs aren't coming back
• Pensions versus the 401k handoff
• What 30 or 40 more years actually costs
• Why gig work is the wrong answer
• Low friction, high margin income, and what that actually looks like
• Why the first dollar outside corporate changes everything

• 00:00 — Welcome, and why I'm zooming out this week
• 01:20 — Naming it: Gen X has a math problem
• 01:42 — Two ways to react: sunset, or jumpstart
• 02:05 — Musical chairs, and why they're pulling five at a time
• 02:25 — Part 1: It's not your age, it's your expense
• 03:40 — Getting laid off isn't the problem. Getting back in is.
• 04:20 — The professional athlete parallel
• 04:46 — Part 2: How prepared are we, really
• 05:05 — They got pensions. We got a how-to video.
• 06:00 — The savings numbers nobody wants to look at
• 07:05 — How few of us actually have a pension
• 07:45 — Part 3: Longevity, and why it's genuinely good news
• 08:45 — Putting all three together
• 09:15 — This isn't a prediction. It's happening now.
• 09:55 — The good news: you already have what you need
• 10:30 — Seventeen income streams, and why I'm not special
• 11:05 — Why it's not Uber and it's not DoorDash
• 11:45 — The real blocker: unlearning corporate
• 12:45 — Low friction, high margin income
• 13:40 — Go sell that first dollar
• 14:05 — Don't bet on another 20 years in corporate
• 14:45 — The opportunity sitting in your own backyard
• 15:05 — Don't replace your job with a worse version of it
• 16:00 — What changed inside the community
• 16:25 — Nobody's judging you (my TikTok debut says hi)
• 17:35 — The better you are, the more at risk you are
• 18:20 — What the 20-somethings figured out that we didn't
• 18:45 — How to reach me

The Collective Now focused entirely on the thing most people are stuck on: making money outside of corporate. A group of Gen Xers figuring it out together. https://trp-collective.circle.so

Everything else https://BrettTrainor.com

Questions or episode ideas? Email me: [email protected]

If the show's useful to you, hit follow wherever you listen.

GenX, laid off over 50, ageism at work, corporate layoffs, retirement math, 401k, longevity, second act, making money outside corporate, career change over 50, side income, Gen X retirement crisis

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:

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.

Brett Trainor Unplugged is for Gen Xers who want to get one step closer to living the life they want—on their terms.

After six years of building life beyond the default corporate playbook, thousands of conversations with Gen Xers, entrepreneurs, and experts, and features in Fortune, Fast Company, Forbes, Harvard Business Review, and Inc., Brett Trainor is still on the quest to build his ideal life—and he shares what he learns along the way.

Part personal journal, part practical guide, and part curious conversation, this is a candid, lightly produced show about stripping away the noise, rejecting unnecessary grind, and seeing more of what is possible.

Brett is a deconstructor, explorer, dot connector, and self-admitted high-functioning lazy person. Through solo episodes and unfiltered conversations with Gen Xers, founders, creators, and experts, he explores the decisions, habits, tools, tradeoffs, and ideas that can help you build a life you actually want to live.

The conversations span the areas that make life worth living: money, mind and body, purpose, connections, possibility, and fun.

There is no singular path. No hustle theater. No permission required. Just better questions, useful ideas, and real examples that help you see what is possible—and ask:

Why not 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:

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:

Listen / subscribe:

Making money outside corporate is easier than landing your next corporate job. After a thousand-plus conversations with people leaving corporate, the blocker is almost never skill or experience. It's that we overcomplicate it.

This one is all mechanics. If you're 45+ and trying to make your first dollar outside corporate, or just want to stop betting everything on one paycheck, this is the playbook.

In this episode:

Watch the version with slides on YouTube, or grab the deck from the resources below.

Money is solvable. Time is the thing you can't get back. Stop trading so much of it.

THE 15 WAYS (quick reference)

Higher-effort income (monetize your corporate experience — great cornerstone accounts, but more hours):

Audience-based (helps to have a following): 8. Sponsored posts 9. Paid community 10. Speaking 11. Paid content / brand sponsorships

Low-friction income (anyone can start, small audience or none): 12. Paid workshops 13. Coaching (business, career, or a hobby — you just have to be a step ahead) 14. Facilitating webinars 15. User-generated content (UGC)

Bonus area to dig into: AI services for business owners.

THE FILTER (score each idea 1–10)

LINKS & RESOURCES

Watch this episode with the slides on YouTube → https://youtu.be/p5rxv-f1M7k

Download the deck (the 15 ways + the filter) → https://stan.store/thecorporateescapee

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) → [COMMUNITY LINK — drop in]

Website → https://timerichproject.life

Mentioned in this episode:

CHAPTERS / TIMESTAMPS

00:00 — Making money outside corporate at 45+ 01:00 — The real blocker: we overcomplicate it 02:20 — The five things this episode covers 02:50 — 1. Stop thinking salary, start thinking cash flow 04:00 — No pension, and becoming a high-functioning lazy person 05:00 — 2. Why one boss is the riskiest bet 06:45 — 3. Separate mission from money (thanks, Diana Alt) 07:50 — 4. The 15 ways I've made money (deck on YouTube) 08:30 — What low-friction income actually means 09:00 — Higher-effort: fractional, consulting, advisory, reselling 11:20 — For the record: I've spent $0 on marketing 11:40 — Audience-based: sponsored posts, community, speaking 12:20 — Low-friction anyone can start: workshops and coaching 15:00 — UGC: my favorite way to start 15:40 — The solo-business boom (WSJ) 16:10 — Solve one simple problem, not all of them 16:40 — AI services for business owners 18:30 — Example 1: Tommy negotiates car deals 20:30 — Example 2: the wedding-dress business I built in 4 hours 24:30 — Example 3: the Amazon Influencer Program 26:30 — The filter: pay, demand, ease, repeatability 27:50 — Don't chase shiny objects 28:40 — Money is solvable

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:

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

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

"Work should feel good. Not a long, slow march to oblivion."

That's Diana Alt, and it's the perfect line to open our first guest episode under The Time Rich Project.

Diana is an executive and career coach who came out of tech. She works with people who are still in corporate and quietly wondering if this is it. Her take lines up with where this show is headed: corporate isn't the enemy. It's a client. You get to decide if the deal still works for you.

We got into:

If corporate has stopped feeling good, this one gives you a way to figure out why, and what to do next.

GUEST: DIANA ALT

Executive and career coach helping people build work that aligns with who they are, in corporate or on their own. Host of the Work Should Feel Good podcast.

* Podcast & site: https://workshouldfeelgood.com

* Newsletter: https://dianaalt.com (click the "Let's Connect" button)

* LinkedIn: Diana Alt, the No BS Coach: https://www.linkedin.com/in/dianakalt/ 

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:

* Working Genius (Patrick Lencioni) — the six genius types

* Time Rich by Steve Glaveski

* Grace McCarrick — soft skills coach

CHAPTERS / TIMESTAMPS

00:00 — First guest under the new name (and how we found each other) 01:15 — Fountains and drains: choosing who you spend your time on 02:10 — Who Diana is: work should feel good 04:05 — Your company isn't your boss, it's your only client 05:00 — The biggest flex in business: firing what isn't aligned 07:00 — The hardest boss to fire is you 07:30 — The four cornerstones of an aligned career 10:40 — Why burnout is about alignment, not just hours 16:00 — The 50-hour week and how little of it is real work 16:50 — Someone says "I'm done." Now what? Find what's actually broken 20:30 — Agency, victim mode, and the clients Diana won't take 23:00 — Good people who lost confidence in what they're great at 28:30 — Diana flips it: what to build for time freedom 29:00 — Owning your calendar, and the time-blocking experiment that failed 31:40 — The scorecard: relationships, health, purpose, fun 34:00 — Low-friction income and becoming a high-functioning lazy person 35:50 — The car-buying guy doing $300K a month 36:40 — Mission vs. money: don't burn down the day job 39:50 — Everyone should have an LLC in their back pocket 42:40 — You only need two things to start: an offer and a way to get paid 44:10 — Where to find Diana

For six years I thought I was running from corporate. Turns out I was chasing the wrong thing.

Welcome to The Time Rich Project. Same host, evolved mission, new name. This is the first episode under it, and I get into why the change and why it matters if corporate has stopped working for you.

Here's the shift: I wasn't escaping corporate. The real unlock was taking back control of my time. Once I had that, everything else opened up.

In this episode:

You don't have to quit corporate to start living better. You do have to get intentional about your time. Corporate isn't the enemy. It's a deal. This show is about going in eyes wide open and deciding for yourself if it's still worth it.

Do what you want, when you want, where you want, with who you want. That's the whole thing. Let's go get it.

TRP Collective: https://trp-collective.circle.so/checkout/the-time-rich-project-collective 

https://stan.store/thecorporateescapee

CHAPTERS / TIMESTAMPS

00:00 — Why the name changed (again), and why this one sticks 02:24 — The real unlock: I stopped chasing paychecks and took back my time 04:39 — The Gen X crossroads: career, family, and the retirement myth 06:53 — Sunrise, not sunset: 30+ years to do what you actually want 08:20 — The four things that make you happy: relationships, health, purpose, fun 11:43 — How to check in on the four without turning it into a spreadsheet 13:10 — Return on hours: making the money you need in the fewest hours 16:30 — Make your first dollar outside corporate (easier than they told you) 18:53 — My time-blocking disaster, and what finally worked 21:15 — What you want, when you want, where you want, who with

Janice Porter has been on LinkedIn since 2004, hosts the Relationships Rule podcast (368+ episodes), and has spent almost two decades teaching solo operators the part of business most of us got wrong in corporate: the relationship part.

In this conversation, Janice walks Brett through her REAL Connection System, a four-part framework for solo escapees who'd rather build a business through referrals than spend their week shouting into the LinkedIn algorithm. It's a refreshingly old-school playbook for a world that's getting more synthetic by the month.

They dig into why direct mail to strangers gets a 1% open rate while cards in envelopes hit 99.5%, the story of the CMO who sent $5,000 in chocolates and closed $12 million in deals, and why the rental company owner who shifted from "send to get" to "send to give" went from zero replies to a full pipeline.

If you've been treating networking like a phase to get through instead of the actual work, this episode is the reset. For most solo escapees, 95% of their business will come from referrals. This is the playbook for earning them.

What you'll learn

🎯 The REAL Connection System (Refresh, Engage, Appreciate, Leverage) explained step by step

🎯 Why Googling yourself in an incognito window is the first thing every escapee should do this week

🎯 The 5-comments-a-day move that beats posting (and where to actually leave them)

🎯 The "send to give, not to get" mindset shift that turns cold outreach into real relationships

🎯 How to leverage your first-degree connections for warm intros without being weird about it

🎯 Why "human-to-human" is the move in an AI-augmented world

Quotable moments

"Don't send to get. Send to give."

"95% of solo business comes from referrals."

"Direct mail to strangers: 1% open rate. A card in an envelope: 99.5%."

"How you do anything is how you do everything."

"Don't be attached to the outcome. Just keep moving."

Resources mentioned

📋 Janice's REAL Connection System (free ebook): janiceporter.com

🎙️ Relationships Rule Podcast: [LINK]

💼 Connect with Janice on LinkedIn: Janice Porter (mention you heard her on TCE)

📬 Send Out Cards: sendoutcards.com

Connect with Brett

📰 The newsletter (10K+ GenXers building life-first futures): [NEWSLETTER LINK]

🐬 The Escapee Collective. First month $1: theescapeecollective.com