Hans Weygoldt had everything on paper. Good money, job security, the family business, the life that looks right from the outside. And he was empty.

He spent ten years trying to leave. Every time he sat down to build the plan, his mind went blank. As he puts it, the more he thought about it, the more self-doubt showed up, so the planning itself was digging the hole deeper.

When he finally went, it took about a second. Something changed at work, he said that's it, and gave notice with no plan B at all. He didn't even tell his wife until days later, halfway to Maine on a camping trip. She was shocked, then she smiled.

His only regret is that he waited so long.

Getting to that point went through some hard ground. A decade of substance abuse while managing in the corporate world, driven by a void he couldn't name. A trip to Peru that broke the addiction but left the guilt behind. And eventually breathwork, which is now what he does for other people.

Two ideas in here I haven't been able to put down.

The first is his split on pressure. External pressure eventually crushes you. Pressure you build from the inside is something you can expand through. He spent a career trying to meet expectations other people set for him. Now he sets them himself, and sets them higher than anyone else ever did.

The second is from a mentor of his, and it's the best thing said in this episode: it takes a lot of curiosity to find out who you are, and then a lot of courage to be that way.

This one pairs with the Geoff Curtis conversation from earlier this week more than I expected. Two guys, completely different paths, both landing on the same thing: the planning is usually the avoidance.

In this episode:

• Golden handcuffs, and the beliefs underneath them
• The decade of substance abuse nobody at work knew about
• Peru, and what broke the pattern
• What actually happens in a breathwork session
• Why the planning kept him stuck for ten years
• External expectations versus the ones you set yourself
• Trust as a practice, not a feeling
• Why he never told his wife until after he'd quit
• Skydiving, piano, and a master's degree at this stage of life

ABOUT THE GUEST

Hans Weygoldt is a breathwork facilitator and emergence coach. He spent years in a family business before leaving with no plan, and now works with people on breaking the patterns underneath addiction, emotional suppression, and self-sabotage. He runs in-person group sessions and one-on-one sessions online, and is pursuing a master's in consciousness-based leadership and coaching.

• LinkedIn: https://www.linkedin.com/in/hans-andreas-weygoldt-151777356/
• Facebook: Hans Weygoldt

THE IDEAS WORTH KEEPING

The plan B was the trap. Ten years of trying to engineer an exit produced nothing but more self-doubt. He left without one and figured it out after.

External pressure crushes, internal pressure expands. The same force, two completely different outcomes depending on who's applying it.

Trying to be strong made him weak. The mask cost more than it protected.

Trust is the first principle. In a session and out of it. He says breathwork reflects life, and learning to trust the process on a mat taught him to trust it everywhere else.

Curiosity first, then courage. Finding out who you are is the curious part. Being that person in public is the hard part.

What you think of me is none of my business. Not original to him, but it's the line that got him on camera after a lifetime of avoiding it.

TIMESTAMPS

Estimated from the transcript. Spot-check and shift for cold open and sting.

• 00:00 — Welcome, and how Hans describes what he does now
• 02:07 — The family business, the money, and the empty feeling
• 03:34 — Golden handcuffs, and the beliefs formed in childhood
• 05:28 — Peru, and how he found breathwork
• 06:13 — First session in 2018, out of the job a year later
• 06:59 — Questioning everything he believed about himself
• 08:41 — Awareness as an ongoing practice, not a destination
• 10:44 — The decade of substance abuse while managing in corporate
• 11:09 — The void he was trying to fill
• 12:46 — The first session: "I cannot keep this up any longer"
• 13:20 — An hour gone, and no inner dialogue
• 14:42 — What actually happens in a session
• 16:28 — The physiology, in his words
• 17:04 — In person versus online, and which suits who
• 19:40 — Why Gen X never invests in itself
• 20:09 — How many sessions, and why integration matters more
• 21:34 — Fear of judgment, failure, and criticism
• 22:02 — "You'd never have seen me on a podcast"
• 23:11 — External expectations versus internal ones
• 23:40 — External pressure crushes. Internal pressure expands.
• 24:05 — First generation college and the path that gets installed
• 26:16 — The mask, and how trying to be strong made him weak
• 27:47 — Ten years of trying to quit
• 28:30 — Why the plan B was making it worse
• 29:00 — Trust as the first principle of breathwork
• 31:03 — The relief after, and his only regret
• 31:40 — Telling his wife on the road to Maine
• 32:20 — The year he spent with his kids
• 34:42 — Skydiving, piano, and going back for a master's
• 37:37 — Boredom, curiosity, and what lit the fire
• 38:00 — Curiosity to find out who you are, courage to be that way
• 38:23 — Approaching a session with childlike curiosity
• 40:00 — It's the most fulfilling work he's done, and it's hard
• 41:30 — Where to find Hans

LINKS

Connect with Hans — LinkedIn or Facebook, both under Hans Weygoldt

Mentioned: The Ultimate Journey: The Mystery of Life and Death by Stanislav Grof, and Grof's work on holotropic breathwork

Get the letters — Letters from a Corporate Escapee:https://bretttrainor.substack.com/

The Escapee Collective: https://theescapeecollective.com/

Questions or guest ideas? [email protected]

HASHTAGS / KEYWORDS

breathwork, emergence coaching, golden handcuffs, leaving corporate, patterns, emotional suppression, self sabotage, GenX transition, personal development, holotropic breathwork, consciousness

I've had north of a hundred authors on this show. This one stuck with me differently, and it's because of one word: Purgatory.

Geoff Curtis spent nearly thirty years building a career in healthcare communications. Title, expertise, platform, the whole thing. Then the company was acquired, his role went redundant, and all of it disappeared at once. What followed wasn't a reinvention arc. It was the discovery that he'd spent his adult life using work to avoid feeling anything.

He picked purgatory on purpose. As he puts it, words like transition imply progress, and he wasn't making any.

The other choice that makes this book different: most people write about this from the far side, after they've figured it out. Geoff is writing from inside it. Three years out and still working through it. There's no five step plan in here, and some readers are frustrated by that. I think it's the reason the book works.

The idea I keep coming back to is his separation of three things we tend to mash together. Livelihood, identity, and self-worth. Livelihood puts food on the table. That's all it has to be. The trouble starts when livelihood quietly becomes identity, and identity becomes self-worth. Then losing the job isn't a financial event, it's an existential one.

We also got into something that isn't in the book. Four weeks before we talked, Geoff did the Hoffman Process. Eight days, completely unplugged, thirty nine strangers, fifteen hours of prep work and days running 7:15 in the morning to 9:30 at night, all aimed at understanding which of your behavior patterns you inherited from your parents. He says he wishes he'd written the book afterward.

Fair warning, this one is heavier than most. Depression, grief, his father's death, and a lot of honesty about patterns neither of us is done with.

In this episode:

• Why he chose purgatory over transition
• Livelihood versus identity versus self-worth
• Thirty years of running on external validation
• Running as emotional suppression, and how to tell it from progress
• New metrics for happiness, and why the old ones keep coming back
• Investing in yourself, therapy, and the Hoffman Process
• Why people doubt themselves inside corporate, not just outside it
• The imposter syndrome nobody on his team ever mentioned to each other
• Everything is a choice, and why we only price the downside

ABOUT THE GUEST

Geoff Curtis spent nearly thirty years in healthcare communications before an acquisition made his role redundant. He's the author of Embracing Your Own Purgatory, written from inside the transition rather than after it, and he now runs a nonprofit he built with his wife that works with college students.

LINKS

The book: Embracing Your Own Purgatory — Amazon, Barnes & Noble, and anywhere books are sold

Author site: https://geoffreycurtis.com/)

LinkedIn: https://www.linkedin.com/in/geoffreycurtis/

THE IDEAS WORTH KEEPING

Livelihood is not identity is not self-worth. Three things, and we let them fuse. "Livelihood puts food on the table. If you don't make the livelihood the identity, then you're good."

Transition implies progress. Purgatory doesn't. That's why he picked the harder word.

Running versus progressing. Both are fine, but you have to evaluate the ending. Why did you leave? Bored, burned out, actually moving toward something? Skip that and you rinse and repeat for thirty years.

Closer to right than quick. The nonprofit took two and a half years instead of the five months his old metrics demanded. That gap is where the real work happened.

Realism as a Trojan horse. Geoff's admission that he uses "I'm a realist" to smuggle in negativity is the sharpest self-observation in the episode.

You're not your patterns. The Hoffman framing: you absorb your parents' patterns as a kid to stay close to them, rebel against them as a teenager, then repeat them under stress for the rest of your life until somebody shows you where they came from.

The conversation nobody has. Geoff and a former direct report both had imposter syndrome the whole time and never said a word. "I always thought you had it together, and I wanted to make sure you thought I had it together."

TIMESTAMPS

Estimated from the transcript. Spot-check and shift for cold open and sting.

• 00:00 — Why this book landed differently
• 01:31 — Why he chose the word purgatory
• 02:46 — Not brave enough to say we're unfinished
• 02:51 — Brett: I think I was in purgatory while still employed
• 03:53 — His wife knew it was going to hit him before he did
• 05:08 — Identity, self-worth, and what work was really providing
• 05:49 — Thirty years of running on external validation
• 06:48 — Why there's no path out in the book, only questions
• 08:30 — Livelihood is not identity is not self-worth
• 09:35 — Separate the money from the mission
• 10:49 — The college senior who wants success and fun
• 12:36 — First generation college, and the expectations that come with it
• 13:49 — Running when things get uncomfortable
• 14:25 — Evaluate the ending, or you'll repeat it
• 15:45 — Running as emotional suppression, and his father
• 16:35 — Love the process and eventually the process loves you
• 17:30 — Three years out, and building new metrics for happiness
• 18:57 — The old metrics never fully stop flashing back
• 20:00 — Brett talked his way back into a full time job because it was comfortable
• 21:18 — Geoff turns it around: how much was external pressure?
• 22:58 — What changes when you finally become value driven
• 24:20 — Following energy as a compass
• 25:17 — Why the nonprofit took two and a half years, and why that was right
• 26:52 — First dollar out versus being methodical
• 29:41 — Why you'd be a better leader now than you were then
• 30:25 — Gen X and the refusal to invest in ourselves
• 31:25 — The Hoffman Process, eight days unplugged
• 33:06 — The patterns you inherited and repeat under stress
• 35:44 — Getting comfortable being uncomfortable
• 36:58 — Doing the uncomfortable thing, and how the podcast started
• 37:41 — The nonprofit as his uncomfortable thing
• 40:17 — People are doubting themselves inside corporate now
• 41:50 — The imposter syndrome nobody admitted to each other
• 43:00 — Everything is a choice, and we only price the downside
• 44:15 — Negativity as an inherited pattern
• 46:15 — The quarterly business review Brett runs with his wife
• 48:11 — Why most of the book's feedback is coming from men

QUOTES

"Words like transition mean progress. In purgatory, there's a lot less progress." — Geoff

"We're too focused on being finished, and not brave enough to say that we're unfinished." — Geoff

"Livelihood puts food on the table. If you don't make the livelihood the identity, then you're good." — Geoff

"We're tying how we feel to what somebody else thinks about us. That's an interesting psychological juxtaposition when you sit down to think about it." — Geoff

"Things don't need to be quick anymore. They need to be closer to right than quick." — Geoff

"I use my realism to mask my negativity. It's almost a Trojan horse." — Geoff

"He said, I always thought you had it together, and I wanted to make sure that you thought I had it together." — Geoff, on imposter syndrome with a former direct report

"I convinced them to hire me full time. In hindsight it made no sense. But it was comfortable." — Brett

"You're not being let go because you don't have the skills. Drop you into any situation and you know more than ninety five percent of the people in the room." — Brett

Questions or guest ideas

Megan Collier's first appearance is still one of my most downloaded episodes, so she's back.

Quick version if you missed it. UGC is user generated content. Brands pay you to make short videos, and instead of posting them yourself, they use the footage in their own ads. No followers required. No production setup. Megan's been doing it four years and has taught more than 16,000 Gen X and Boomers how to do it, including her mom.

Her origin story is the part I keep thinking about. She was on a call trying to sell a footwear brand on hiring her, mentioned her mom in passing, and the brand got noticeably more excited about her mom than about her. Nobody that age was doing this. So she went and built the thing that didn't exist.

I keep coming back to UGC because I've been hunting low friction, high value income, and this one lands at the top of the list every single time. You're not applying for a job. You're not competing against five hundred other applicants. You already own the equipment.

We got into the money, and Megan gives real numbers instead of vague ones. What a beginner should charge. What the performance-based deals actually pay and why she turns them down. What her students are making, from a few hundred a month up to one who cleared twenty-two thousand last month.

Also worth your time: brands are now writing "no AI content" directly into their creative briefs. Megan's read is that the flood of AI has made real human video more valuable, not less. Her phrase for the moment is a trust recession, and it's the most useful thing said in the whole episode.

In this episode:

• What UGC actually is, and why followers don't matter
• The brand call that accidentally started her business
• Why brands are banning AI content in their briefs
• What to charge when you're brand new
• Performance-based deals and why she passes on them
• What her students actually earn, at every level
• Where the Amazon Influencer program fits, and where it doesn't
• Why she quit TikTok Shop
• Local businesses, and trading content for services
• How to find the right person at a brand

HOW TO ACTUALLY START, ASSEMBLED

Megan walked through this across the conversation. Here it is in order.

1. Go look at UGC videos on TikTok or Instagram so you know what you're making. It isn't for everyone and it's better to find that out in ten minutes than ten weeks.
2. Make three or four videos using products already in your house. Megan's first two were cat treats. Basic editing. Nothing fancy.
3. Put them in a portfolio. Canva works. Any simple site works. Brands need proof you can make content, same as any other business.
4. Pick a lane to get hired. Either join the creator platforms, or pitch brands directly. Megan pitches.
5. Start local or start small. Local service businesses, gyms, spas, a fencing company. Many have real marketing budgets and have never worked with a creator. Gifted or traded work counts here.
6. To reach a bigger brand, DM their customer service account and ask who handles content partnerships. They want a quick answer they can check off, and they'll usually give you the name.
7. Treat pitching as volume. Megan's rule of thumb is that roughly one in fifty says yes, and a no often just means not right now.
8. Then chase repeat clients. That's where the margin is, because you stop relearning a new brand every time.

TIMESTAMPS

Estimated from the transcript. Spot-check and shift for cold open and sting.

• 00:00 — Why Megan's back
• 01:10 — What UGC is, and the 16,000 students
• 02:13 — Why Brett keeps coming back to low friction income
• 03:13 — Why so many people freeze before they start
• 04:24 — She saw it on TikTok while working a corporate job
• 05:00 — Out of that job in fourteen months
• 05:32 — The footwear call where they got excited about her mom
• 06:33 — Nobody that age was doing this
• 07:01 — Why corporate trained us to overthink it
• 08:37 — Who am I to teach this, and why two steps ahead is enough
• 09:26 — A detour into other low friction businesses
• 10:18 — What AI is doing to this market
• 10:37 — Brands writing "no AI content" into the brief
• 11:55 — The trust recession
• 12:32 — Is it too late to start?
• 13:10 — Why it's an ongoing need and not a trend
• 14:18 — What to charge when you're brand new
• 15:00 — Performance based deals, and the math on them
• 16:42 — Why Megan turns those down
• 17:11 — Brett butchering a brand name on camera, and the brand not caring
• 18:24 — The part-timers, and what a summer looks like
• 19:00 — Replacing corporate income
• 19:45 — The student who made $22,000 last month
• 20:48 — Why repeat clients change the economics
• 21:52 — Where the Amazon Influencer program fits
• 23:29 — Income stacking and double dipping
• 24:45 — Why she quit TikTok Shop
• 27:11 — How to start, step one
• 28:39 — Cat treats, and your first videos
• 29:30 — Platforms versus pitching
• 30:27 — Big brands versus local businesses
• 32:00 — Why local wins give you momentum
• 33:13 — What the first fifty dollars does to your head
• 33:20 — Trading content for services
• 34:38 — How to find the right contact at a brand
• 35:30 — Pitching as a volume game
• 36:41 — Getting a fence stained in exchange for content
• 38:30 — The fears that stop people, and why none of them hold
• 40:03 — Belief, action, and the first dollar
• 41:09 — Where to find Megan

QUOTES

"I happened to mention my mom, and they got way more excited about my mom than me." — Megan

"We're all in a trust recession. We don't know what's real and we don't know what's fake. So the more real and raw, the better." — Megan

"Brands are literally writing no AI content into the brief. I've seen it several times just in the past couple of weeks." — Megan

"She's in her fifties, functional medicine, lab coat. She made twenty-two thousand dollars last month." — Megan

"A brand paid me fifty bucks. I'm now a content creator. That carries through everything else." — Megan

"It's a volume game. For every fifty that say no, one's probably going to say yes." — Megan

"We're not saving lives here. This is not brain surgery. Don't take it so seriously." — Megan

"You probably spend a lot of time on social media consuming content, when you could be creating it and getting paid." — Megan

"You're not applying for a job. You're not competing against five hundred other people." — Brett

LINKS

Megan Collier TikTok, Instagram, and YouTube: @megan_ugc Instagram DM is the best place for a specific question.

Megan's UGC course — https://stan.store/affiliates/bd030aba-a9a1-4f50-9073-45cc67b073f1

Mentioned in the episode Creator platforms Megan named: Insense, Billo, Cohley, and others. Confirm exact spellings with Megan before publishing, the audio is unclear on a couple. Email lookup: hunter.io AI pitching service she mentioned: confirm the name with Megan.

Questions or episode ideas? [email protected]

UGC, user generated content, side income, GenX side hustle, content creation, brand deals, making money outside corporate, no followers needed, creator economy, low friction income

Shelley McIntyre is back on the show, and her first appearance is still one of the most downloaded episodes I've done.

She was a grief counselor before she was a coach, which is why she talks about layoffs differently than anyone else I know. We opened on the Oracle news, because the math on it is ugly. Twenty years in, fifty or sixty hour weeks, and what shows up is an automated email at 6 a.m. that doesn't say thank you.

Her point stuck with me: you spend a career radiating loyalty outward, and at the very end, when it matters most, you don't get any of it back.

Then we get into the trap almost nobody sees coming. You leave, you go independent, and because you're wired for comfort and you just absorbed six losses at once, you rebuild the exact role you escaped. Director of sales, but fractional. Same work, same frustrations, now with no benefits. As Shelley put it, you built the same box you just got out of, and you can't figure out how you ended up back inside it.

I did a version of this myself. I had a good contract gig that paid well doing work I liked. Instead of building on it, I talked the company into hiring me full time, because the title felt safer. I was miserable within months.

The back half is her method for getting unstuck, and it's the opposite of what most people do. You don't sit down and list your skills. You don't mine your performance reviews. When you've just been laid off, you are the least qualified person in your own life to describe how good you are, because you're operating from doubt.

So you go gather evidence instead.

In this episode:

• Why the coldness of a modern layoff lands harder than people admit
• Identity, job titles, and the shorthand you lose
• The comfort trap, and why rebuilding the old job is a normal human response, not a failure
• The physical toll nobody talks about
• Why performance reviews are useless for this
• How to ask people who know you what you're like at your best
• Turning what comes back into five words, and using them as a filter
• The portfolio approach when one opportunity only delivers part of what you need
• The guilt of not being busy, and why you were never productive nine hours a day anyway

We covered this across the conversation but never laid it out in one piece. Here it is.

1. Pick five to ten people who know you well and who you genuinely trust. Mix of personal and professional. The trust part matters more than the title.
2. Ask one question: "Can you describe what I'm like when I'm operating at my best?"
3. Let them go long. Most people won't give you adjectives, they'll tell you a story about a specific time you showed up. Those stories are the useful part.
4. Read all of it together. If you find yourself doubting it, notice what that means. You'd be calling people who love you liars.
5. Synthesize it down to five words that describe how you show up at your best.
6. Use the five as a filter. For any opportunity, job or client or project, ask whether it not only allows but requires you to show up that way. If it only hits three, go find the other two somewhere else in your life.

Shelley McIntyre is a coach for Gen X professionals in transition, and a former grief counselor, which is where a lot of her perspective on identity loss comes from. She hosts Burn the Map, a podcast built around short episodes, and works with clients on figuring out who they are outside a job title.

• Podcast: Burn the Map
• Site: https://burnthemapcoaching.com
• LinkedIn: https://www.linkedin.com/in/shelley-mcintyre/

Estimated from the transcript. Spot-check and shift for cold open and sting.

• 00:00 — Welcome back, and why her first episode still gets downloads
• 01:00 — The Oracle layoffs, and the severance math
• 02:08 — Getting numb to the coldness of it
• 02:40 — You radiate loyalty your whole career and don't get it back
• 03:41 — The 6 a.m. automated email that doesn't say thank you
• 04:22 — Why identity and job title get intertwined
• 05:08 — "I'm a VP of marketing" as shorthand for who you are
• 06:11 — Title, industry, company. The trifecta.
• 07:18 — The trap: going independent and rebuilding the same role
• 08:16 — "I built the same box I just escaped"
• 09:29 — Brett talked his way back into a full time job and hated it
• 10:26 — We are wired for comfort, and that's not a character flaw
• 11:38 — The losses stack up all at once
• 12:17 — Remembering who you are underneath all of it
• 14:02 — Why skills lists and performance reviews don't work here
• 14:58 — When the doubt spreads to things you were always good at
• 15:50 — The physical toll: illness, accidents, the hospital
• 16:32 — Usefulness, and being told you're not needed
• 17:25 — You're not the most qualified person to say how great you are
• 18:23 — Becoming a detective of your best self
• 19:16 — Why corporate feedback is performative
• 20:00 — What actually happens when you ask
• 21:07 — "Let me tell you a story"
• 23:00 — The surprise birthday party nobody would have predicted
• 24:00 — If you don't believe it, you're calling them liars
• 24:51 — What to do with it: five words
• 26:08 — Using the five as a filter for every opportunity
• 27:00 — But what if nobody has anything good to say?
• 28:19 — The portfolio: when one thing only delivers three of five
• 29:01 — Separate the mission from the money
• 29:55 — "What do you do for fun?" "Fun?"
• 32:15 — What if you could do something you're good at and it's fun
• 33:11 — Ideas need space. You can't rest and be busy at the same time.
• 34:38 — Nine hours in the chair, maybe four of real work
• 35:41 — It nets out the same. You're just doing it on your terms.
• 36:33 — A walk in the park beats a useless meeting
• 40:00 — The former client who'd never go back
• 40:28 — Take a part-time job and watch all your time disappear
• 40:43 — The real hourly math on a hundred thousand dollar salary
• 43:03 — Burn the Map, and where to find Shelley

Somebody commented on one of my TikToks. He'd started his own solo business a couple years back, it's working, he's happy. Then he said "but it's not for everyone."

I'd been repeating that exact line for years and never once dug into it.

So this episode is two things. Why people still say entrepreneurship isn't for everyone, and why I think it's true about something almost nobody is actually doing.

When people hear "entrepreneur" they picture the same movie. Raise money, hire a team, sign a lease, bet the house. That version is brutal and it isn't for most people, me included. But in 2023 roughly 117,000 one-person businesses cleared a million dollars in revenue. No employees. No payroll. Nobody to manage.

The four myths I go after:

1. You need a business plan
2. You need a website, a brand, an LLC, a logo
3. You need to be a salesperson
4. It's risky

That last one is backwards. Your corporate job is one customer providing one hundred percent of your income, and they can end it for reasons that have nothing to do with how good you are. Attach a W-2 to it and we call it stability.

The second half is the part I didn't get into in the LinkedIn article: finding clients is closer to a job search than to building a company. I've had seven or eight corporate roles and seven of them came from a referral or somebody in my network. Not one came from a blind posting. That's the same channel that brings in solo work.

I also walk through how I'd structure a first offer. Good, better, best, and why people almost always take the middle one.

In this episode:

• Where the stereotype came from, and why it was true about a different thing
• The four myths, one at a time
• Why corporate politics skills don't transfer, and why that's good news
• Your job is one customer with one hundred percent concentration
• The interview and the discovery call are the same conversation
• Good, better, best, and pricing your first engagement
• Owning your own calendar, which took me longer than I want to admit

TIMESTAMPS

• 00:00 — The LinkedIn article, and what this episode adds to it
• 01:30 — The TikTok comment that started it
• 01:55 — I'd been saying the same line for years
• 02:20 — Hundreds worked with, thousands talked to, and almost none were prototypical entrepreneurs
• 03:00 — Where the stereotype came from
• 03:45 — 117,000 one-person businesses over a million in revenue
• 04:10 — Stop thinking customers. Think micro jobs.
• 04:25 — Myth 1: you need a business plan
• 04:41 — Myth 2: you need a website, a brand, an LLC
• 05:15 — Myth 3: you need to be a salesperson
• 05:50 — Why corporate politics skills don't help you out here
• 06:20 — Myth 4: it's risky
• 07:15 — Your corporate job is your one customer
• 08:00 — What a diversified solo practice actually looks like
• 08:30 — If it takes six months to find your next customer, you're running it wrong
• 08:50 — Put a tenth of your job hunt effort into finding clients
• 09:55 — Finding clients looks a lot like looking for a job
• 10:25 — Seven of my eight roles came from referrals. None from a posting.
• 11:00 — Think of it as mini job applications
• 11:36 — The interview process, walked through step by step
• 12:15 — Same conversation, but with a business owner
• 12:45 — Good, better, best
• 13:35 — They take the middle option nine times out of ten
• 14:20 — Nobody's judging you
• 14:55 — You'll probably underprice the first one. It doesn't matter.
• 15:30 — You'll work fewer hours than you do now
• 15:50 — Owning your own calendar, and why it took me so long
• 16:11 — Don't feel guilty when you're not busy
• 16:40 — The few who go back, and why they go back with a plan
• 17:20 — Reallocate some of those job hunting hours
• 17:45 — It's relationships, not postings
• 18:15 — Don't chase shiny objects. Pick one or two.
• 18:30 — Maybe the word itself is the problem
• 19:00 — Corporate ends either way. Take control.

Key Quotes

"Seven of my eight corporate roles came from a referral or somebody in my network. I honestly can't think of a single job I got from a blind posting."

"Your corporate job is one customer. One revenue stream. If that customer goes away, you've got nothing."

"One bad quarter, or even a good one with a new VP, and you're gone."

"If it takes you six months to find your next customer, you're not running that business very well."

"Put a tenth of the effort you put into a job hunt into finding problems to solve, and you'd have more customers than you'd know what to do with."

"The people who got ahead in corporate because they knew how to play the games, that doesn't work out here. These people just want their problem solved."

"Nobody's judging you except you."

"Corporate's going to end whether you choose it or not. You might as well take control."

LINKS

Questions, or an episode idea? [email protected]

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

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