Brett Trainor Unplugged

Bradley Richardson has been writing about Gen X since we were the young ones.

He published one of the very first business books aimed at this generation back in the nineties, then five more on everything from being a dad to starting over. These days he runs Advanced Adulting, which he describes as helping grown adults navigate midlife and beyond. Not the nostalgia version. Not the shuffle dance and testosterone check version. The real stuff: your career, your parents, your kids, your money, and figuring out who you actually are now that nobody's telling you.

He just turned 60, which he calls joining the freshman class of old people.

A few things in here I haven't stopped thinking about.

Reinvention is the wrong word. Everybody sells it like you have to become someone new. His version is remodeling. You strip the house to the studs, and the bones are good. What you're looking for isn't a new person, it's the person you were before the world and your job and everyone's expectations sanded you down.

His take on ageism is not the take you've heard. It isn't going away, it's been happening since the dawn of time, and we did it too when we were the young ones complaining about the fifty year olds in our way. That doesn't mean you have no value. It means you have to create your own market now.

He's done with the gurus, and he says he used to be one. His words: there are a lot of Gen X midlife bullshit artists out there and I've been one, so I can call it. Everybody's got a three step plan and a blueprint. He stopped doing that, because he's still figuring it out himself every day.

He also has the best math on criticism I've heard. A third of people will decide they don't like you for no reason at all. A third are situational. A third are your people. That last third is the only one that gets a vote.

We also get into the part nobody plans for: the two twenty-five year friendships he lost, not in a blowup but by slow drain, and his rule about it. You don't have to like what I do, you don't have to agree with it, you don't even have to understand it. But you do have to support it.

Oh, and the video that got ten million views. "I'm fifty-eight and I'll never get hired again."

In this episode:

• Thirty years of chronicling the same generation
• Why forward beats nostalgia
• Life in thirds, and what the next thirty actually looks like
• Ageism, and the uncomfortable part nobody says
• How Gen X got issued labels and Gen Z didn't
• Losing a company in 2000 and having to go get a job
• Choosing a school, a major, a job, a spouse on somebody else's expectations
• Remodeling instead of reinventing
• The friendships that don't survive, and the ones that do
• Worth is what somebody will pay today, not what you used to make
• Why he'd go blue collar if he were starting over
• The baseball rule, and why corporate makes you hit .900
• Sixty by sixty, and what he's building next

TIMESTAMPS

• 00:01 — Welcome
• 00:28 — Advanced Adulting, and what it isn't
• 00:50 — Thirty years of writing about Gen X, starting in the nineties
• 01:45 — Why he looks forward instead of back
• 02:17 — No pensions, uncertain 401ks, and thirty more years to fund
• 02:40 — Just turned sixty, and why he won't call it midlife
• 03:30 — Life in thirds
• 04:37 — Look back to learn, then stop looking
• 05:30 — Too young to be old, too old to be young
• 06:06 — "You don't know technology." We invented it.
• 06:47 — The ageism take: it isn't going away, and we did it too
• 07:25 — The pro athlete analogy, and the corporate equivalent
• 08:23 — Labels, and what Gen Z does better than we do
• 09:00 — The cocktail party question
• 09:23 — Losing the company in 2000, and having to go get a job
• 10:24 — Identity tied to title, industry, and employer
• 10:57 — Wall Street, Secret of My Success, and buying in
• 11:38 — Expectations, and choosing a life somebody else picked
• 13:23 — You get to choose you now
• 14:13 — Chasing energy
• 15:05 — Who's actually in your corner
• 15:24 — The two twenty-five year friendships he lost
• 16:19 — The four people whose opinion counts
• 17:36 — What's changed in thirty years of watching this generation
• 18:40 — Remodeling, not reinventing
• 20:08 — Stripping away the character corporate made you play
• 20:45 — Two years without an alarm clock
• 21:30 — "What kind of music do you like?" and not knowing the answer
• 22:30 — The Gen X midlife bullshit artists, and admitting he was one
• 23:07 — Life keeps handing you things you weren't prepared for
• 24:00 — Why he changed what he does
• 25:00 — The people who shout loudest
• 26:04 — The nine figure founder and the Walmart test
• 27:28 — Caregiving as the great equalizer
• 28:13 — The divorce cluster in Brett's last corporate job
• 28:54 — Married too young, and the no-quitter problem
• 30:14 — Divorced at forty-four, and bringing the same mistakes along
• 30:47 — "You're choosing the same damn thing" in careers too
• 32:36 — History doesn't mean you have a connection
• 32:51 — The "we're family" lie
• 33:05 — Work besties, and how fast that goes
• 35:00 — "I'm fifty-eight and I'll never get hired again," and ten million views
• 36:10 — The trolls, and why it isn't about being lazy
• 36:42 — Why he'd go blue collar if he were starting over
• 38:00 — What something is actually worth
• 39:24 — The Comfort Crisis, and the podcast that took Brett two months to start
• 40:31 — You're not going to be an expert, and you're going to screw it up
• 41:37 — The tennis points stat
• 42:14 — Why corporate makes you hit .900
• 43:09 — How he handles the comments now
• 44:00 — The thirds rule for people
• 45:32 — Where to find him
• 46:01 — Sixty by sixty, and the next thirty

ABOUT THE GUEST

Bradley Richardson is the creator of Advanced Adulting, a platform about navigating midlife and whatever comes after it. He's the author of six books, starting with one of the first business books written for Gen X in the 1990s, covering careers, fatherhood, and starting over. A former headhunter and a Division I tennis player at Oklahoma, he's been writing about this generation for roughly thirty years. He turned sixty in 2026.

• Instagram, TikTok and Facebook: @iambradleyrichardson
• YouTube: @AdvancedAdulting

Tania gave her team six weeks’ notice that she’d miss a meeting to close on her house. Four months later, she got blasted for it in her performance review. That was the moment she was done.

Today she’s a CFP who helps Gen X leaders quit corporate without wrecking the 30 years of financial security they’ve built, or having to run back before they want to.

We get into what the first year really looks like, why so many people head back around month nine, and the blind spots she sees in almost every plan.

What we cover:

• Who’s quitting now, and why it’s changing
• The first year: detox, first clients, the month-nine panic, and month-twelve reality
• Why niching too soon can box you in
• What are you running to? Why bitterness creates blindness to opportunity
• Why you should talk to real self-employed people, not social media
• Pollyanna budgeting: planning for the best version of yourself
• Benefits blindness: how much your employer quietly pays for
• Why open enrollment is your Black Friday if you’re thinking about leaving
• The insurance tip nobody uses: ask your provider’s billing office
• The business black hole: why a write-off isn’t a reimbursement
• Pricing for poverty, and the bunny hops between leaping and staying

Chapters (times are approximate, so confirm them after the cold open and music are added)

00:00 Cold open

00:40 Welcome Tania

01:35 Helping people quit

04:10 Who’s quitting now has changed

05:40 Death by a thousand corporate cuts

06:35 The house closing review

09:10 Seeing the blind spots from inside corporate

11:00 The emotional side nobody warns you about

14:15 The first year, quarter by quarter

17:25 Not the business she planned

20:15 Niching too soon

26:10 Too many steps ahead

30:00 What are you running to?

31:25 Talk to people who’ve actually done it

33:45 Blind spot: Pollyanna budgeting

35:40 Blind spot: benefits blindness

38:05 Open enrollment is your Black Friday

41:20 Ask your provider’s billing office

42:25 Blind spot: the business black hole

46:00 Pricing for poverty, and bunny hops

47:10 Where to find Tania

Connect with Tania

LinkedIn: Tania P. Brown, CFP

Website: taniapbrown.com

Free Quit Smart Scorecard (nine questions to find your biggest blind spot): taniapbrown.com/scorecard

Come hang out

The Escapee Collective is free. It’s for Gen Xers curious about life outside corporate, whether you’re in, out or just lurking. theescapeecollective.com

Get busy living.

Brett

If I got walked out on a Friday, here’s what I’d do, knowing what I know six years later.

This is the escapee playbook, step by step. It’s not the only way, because there isn’t one way. But it’s how I’d shorten the learning curve and skip a lot of the mistakes I made.

Even if you plan to land another corporate job, learning to make money on your own gives you options. And you might find out you don’t need corporate at all.

What we cover:

• Why the first move is taking two weeks off
• The two questions most of us never answer: what do you want, and what do you really need
• Knowing your monthly number and dialing it up or down
• Belief, Action, Momentum, plus the Shark Tank email that took 10 minutes
• Why singles and doubles beat chasing home runs
• Picking one problem to solve, and making it a need-to-solve, not a nice-to-solve
• The four things every business owner buys: save time, make money, save money, reduce risk
• The LinkedIn job alert move that gets you in front of owners
• Good, better, best: how to pitch a small business without calling their baby ugly
• Coffee with six local business owners
• Low-friction, high-margin ideas: car negotiation, travel points, garage organizing, government subcontracting

Chapters (times are approximate, so confirm them after the cold open and music are added)

00:00 Cold open

00:40 What I’d do if I got laid off tomorrow

02:55 Take two weeks first

05:15 What do you actually want?

07:35 What do you really need? Know your number

10:45 Belief: flip the mindset

12:30 Action: the Shark Tank email

14:25 Momentum: singles and doubles

16:50 Pick one problem

19:35 Need-to-solve vs. nice-to-solve

21:00 The four things business owners buy

22:20 The LinkedIn job alert move

25:55 Good, better, best

28:10 Coffee with local business owners

30:25 Low-friction, high-margin ideas

33:00 Stack a few small deals

35:15 Wrap

Come hang out

The Escapee Collective is free. It’s for Gen Xers curious about life outside corporate, whether you’re in, out or just lurking. Lurkers welcome. theescapeecollective.com

Want to talk through your situation? DM me on LinkedIn for a free 20-minute strategy session.

If this helped, share it with one person who just got the call.

Get busy living.

Brett

Almost everything written about Gen X and corporate right now is negative, and some of it is fair. Ageism is real. The profit over people playbook is accelerating. CEO tenures keep getting shorter, which means the pressure for a short-term number keeps getting higher.

This episode is the other side of that.

Five reasons I'm optimistic, and I mean actually optimistic, not the motivational poster kind. Save this one. Pull it up on a Sunday night when the week ahead looks long.

One. You get to design the life instead of fitting a life around the job. For twenty or thirty years, vacations happened when there was a lull or your boss said yes, and dinners got missed because you were paying dues. The question now is different. How much do you actually need, how much do you want, and why. Then you fund that, instead of trying to replace a salary somebody else set.

Two. We're going to live longer and stay active longer. Which matters more than it sounds. If you free up all this time and then can't enjoy it, what was the point.

Three. You get to reinvent yourself. For decades you were a title, a company, an industry. I'm proof that the thing that lights you up might not even exist yet. Six years ago it would not have occurred to me that TikTok would pay me, that I'd have a podcast, and that writing a newsletter would be the best part of my week.

Four. The future of work is solo businesses. Before the industrial revolution it was blacksmiths and bakers and shop owners, and work and life were the same thing. We're heading back there. Look at how a movie gets made, or how a house gets built. Nobody employs the whole crew. They bring in expertise when they need it and everyone goes their own way after. Small businesses already work like this. Corporate will get there, dragging and screaming.

Five. AI needs Gen X. This is the one nobody says out loud. AI without context is a problem. AI on bad data is a problem. AI in a business where no process is written down is a problem. Those are the exact problems you spent twenty years fixing. You don't need to be an expert. You need to be two steps ahead of the business owner.

In this episode:

• Why the latchkey thing matters now more than it did then
• Funding your life versus replacing your income
• What actually happens to your hours when you go solo
• Why living longer is an opportunity, not a fact
• Energy as a better test than purpose
• Hollywood and the general contractor
• Why corporate will have to buy back the experience it cut
• The three twenty-somethings and the word "bottleneck"
• Why action beats planning every single time

You told people to save this episode. Here it is in a form they can actually save.

1. You can design the life instead of squeezing one in around the job. The question stops being "how do I replace $180K" and becomes "what do I need, what do I want, and what's the fewest hours that funds it."

2. You'll live longer and stay active longer. Which means the runway is longer than you think. Thirty productive years is longer than most careers.

3. You get to reinvent yourself. You were a title for twenty years. The thing that lights you up may not have existed when you picked that title.

4. The future of work is solo. Hollywood and homebuilding already run this way. Corporate is cutting experience for cost right now, and it will have to buy that experience back on a project basis.

5. AI needs Gen X. Context, clean data, documented process, knowing where a business actually breaks. AI has none of that. You have all of it.

And the thing underneath all five: action beats planning. Every time.

• 00:01 — Why this episode exists, and the negativity it's answering
• 00:40 — Ageism, the profit playbook, and shorter CEO tenures
• 01:20 — The latchkey kid argument
• 01:50 — Save this one for a bad day
• 02:17 — The money reality, and running out before you die
• 02:50 — The two old paths: corporate, or a business with employees
• 03:20 — High functioning lazy
• 03:45 — Reason one: design the life you want
• 04:10 — The questions: what you need, what you want, and why
• 04:35 — Funding the life instead of replacing the income
• 05:10 — Seventeen income streams and counting
• 05:30 — How many of your corporate hours go to the job you were hired for
• 06:20 — What AI takes off your plate
• 06:58 — The gym block, and Friday afternoon golf
• 07:20 — Mini experiments, and why corporate trained them out of you
• 07:50 — Reason two: living longer and staying active
• 08:10 — His own slide in the later corporate years
• 08:40 — Reason three: reinvent yourself
• 09:00 — TikTok, the podcast, the newsletter, none of it on the radar six years ago
• 09:17 — Twenty years old with fifty year old experience
• 09:45 — Chasing energy instead of purpose
• 10:30 — No more weekends, and why that's a good thing
• 11:00 — Reason four: the future of work is solo
• 11:10 — Blacksmiths, bakers, and life before the industrial revolution
• 11:50 — Hollywood
• 12:20 — The general contractor
• 12:50 — Why corporate has to buy the experience back
• 13:46 — Recap of one through four
• 14:10 — Reason five: AI needs Gen X
• 14:40 — Bad data, no process, no automation. Same lesson as 2005.
• 15:20 — Doing the work of three people for one salary, and why it ends
• 15:45 — The three twenty-somethings selling bottleneck removal
• 16:30 — Two steps ahead of the business owner is enough
• 17:10 — Why owners want a person, not a handed-off agent
• 18:00 — Internet, then mobile, now this
• 18:25 — AI helps you fail faster on a broken process
• 18:50 — Unapologetic optimist
• 19:20 — Take action. Don't overplan.
• 19:50 — Close

Almost every escapee story on this show starts with corporate going bad. This one doesn't.

Jim Barke spent nearly twelve years at a company he genuinely liked, with what he calls the best team he's ever worked with, and six weeks of PTO. Nobody pushed him out. He wasn't burned out. He hired a career coach because he knew he was at a crossroad, and on their second or third meeting she told him he should quit his job.

He laughed at her. He was divorced, single income, with his oldest headed to college.

Then he came back to the next meeting and said he was going to do it.

What flipped it happened on a walk. He was spinning on how am I going to make money, and realized money isn't actually his top value. Being a present dad is. Being a decent neighbor is. What he wanted was the ability to say yes. And he has the receipts. When a local father went missing and the community put out a call to search, he moved his one meeting and went. During a local emergency he spent about forty hours delivering groceries in a month.

Two years in, this is the most useful kind of guest, because he still remembers the numbers.

He set written goals before he left. Three months to momentum. Six months to a first client. Twelve months to sustainability, which he's careful to say does not mean replacing his corporate income. It means seeing a path.

His first client came from announcing on LinkedIn that he'd left. A guy he used to train for triathlons with had just become chief legal officer at a nonprofit and had a project. His best client over two years came from an email somebody in the Collective sent him about Catalant, a marketplace for consulting work with private equity backed companies. He bid, won it in three days, did good work, and ended up flown to San Francisco to present to the PE firm's leadership. His words: that one email changed the trajectory of my business.

He's also honest about the parts that are hard. The loneliness of a basement office after a team he loved. Three kids in college. Income that moves up and down. And the two hundred thousand dollar question nobody in this space answers well: how do you build enough trust in a networking group to actually refer someone's work when you've never seen their work?

He doesn't know. He says so.

And when I asked whether he'd ever go back to corporate, he didn't give me the usual answer. He said maybe. Under specific conditions. But that he'd be running away rather than running toward, and he doesn't like that feeling.

In this episode:

• Why strategy alone doesn't sell in the mid market, and what AI changed
• Leaving a job he liked, with six weeks of PTO on the table
• The career coach who told him to quit
• The walk where money stopped being the point
• Two months from decision to exit, with no client lined up
• The three written goals he set before he left
• How the first client actually came in
• Catalant, and the email that changed everything
• The loneliness nobody warns you about, and his fix for it
• Why a ten o'clock email feels different now
• The $150,000 in commissions he turned down
• The trust problem in networking that nobody has solved
• Whether he'd go back, and the conditions

THE SCOREBOARD

Jim wrote these down before he left. This is the most transferable thing in the episode.

Month 3 — Momentum. Not revenue. Conversations, calls, referrals, people responding. The test is whether you're moving or staring at a blank screen.

Month 6 — First client. He set it that far out on purpose so it wasn't a pipe dream. His came faster, but he says waiting six months would have been brutal, and he planned for brutal.

Month 12 — Sustainability. Note what this does not mean. It is not replacing your corporate income. It's seeing that people buy what you sell and that there's a path.

Year 2 — The one Brett adds. You stop wondering whether you have to go back. Not because you couldn't, but because you've seen enough cycles that the swings don't rattle you.

HOW THE CLIENTS ACTUALLY CAME IN

1. Announced on LinkedIn that he'd left. A former triathlon training partner, newly a chief legal officer at a large nonprofit, reached out with a project. Flat bid, project based. That one relationship has produced several engagements since, and kept producing after the guy moved on.
2. An email from somebody in the Collective pointing him at Catalant, a marketplace for consultants working with private equity backed companies. He found a fit at a hundred million dollar PE owned healthcare company, bid, and won it in three days. Worth noting he says three days is not typical. He has proposals that have been open for three months.
3. That client compounding. The CFO turned out to be a partner at the PE firm, flew him to San Francisco to present to their leadership, and has been his best account for two years. When work slows down he emails them that he has bandwidth and asks what they've got.

TIMESTAMPS

• 00:01 — Welcome, and the different kind of escapee story
• 00:42 — Who Jim is and what sourcing and procurement actually means
• 01:23 — Getting out of bad contracts, and why relationships are the product
• 02:30 — Mid market wants strategy and execution, not just strategy
• 03:13 — How he uses AI on contracts, and where twenty years of judgment comes in
• 04:19 — Two years out almost to the day
• 04:26 — Brett on the two year mark
• 05:02 — Twelve years at one company, and why that was unusual for him
• 05:30 — Six weeks of PTO, and leaving anyway
• 05:50 — The career coach who told him to quit
• 06:10 — Divorced, single income, oldest headed to college
• 07:07 — The walk, and the moment money stopped being the driver
• 07:40 — The search for a missing father, and what saying yes looks like
• 08:20 — Forty hours delivering groceries during a local emergency
• 09:15 — Two months from decision to exit
• 09:30 — Why he couldn't build anything before he left
• 09:44 — Brett on finding your first dollar outside corporate
• 10:43 — What he actually sells, and why he still sells it
• 11:00 — The part nobody tells you: you get to dream
• 12:00 — The first week, and the Ron Burgundy glass case of emotion
• 12:22 — Two years later the swings are monthly, not daily
• 13:27 — The honest part: three kids in college
• 14:10 — Loneliness, and the team he misses
• 14:50 — Out of the basement once a week
• 15:02 — Brett on not telling anyone he'd gone solo
• 15:40 — The circle of ten, and why Brett started with five
• 17:07 — Corporate isn't the enemy, it's the trade-off
• 17:55 — Answering email at ten at night and why it feels different
• 19:43 — Clients only send you the high value stuff
• 20:17 — Six hours of Zoom you were invited to
• 21:35 — The walk as work time, and getting over the guilt
• 22:00 — What he thinks of expensive consultants now that he is one
• 23:18 — The 20 to 30 percent rule
• 24:29 — The ninety pound coworker
• 25:00 — Executives who block time to think
• 25:44 — Walking notes, voice memos, and the folder of things you can't decipher later
• 26:56 — Podcasts and silence, fifty fifty
• 27:18 — Rediscovering the joy of learning
• 28:25 — The three written goals
• 29:30 — The first client, and the triathlon connection
• 30:22 — The Collective email, and Catalant
• 31:19 — San Francisco, and the client that's carried two years
• 32:18 — Why the second and third clients are the hard ones
• 33:28 — The trust problem in networking
• 34:48 — How Brett handles a referral when he doesn't know the work
• 36:12 — From chasing six figure deals to the four to six week roadmap project
• 37:27 — His dad, two jobs, seven days a week, and what it taught him
• 38:35 — The commissions he's turned down, and the 25% offer
• 39:33 — Where that revenue stream is legitimate for other people
• 40:54 — Would you go back to corporate?
• 41:07 — The conditions, and why it would be running away
• 44:26 — The nurse line, and 30% of calls that didn't need a nurse
• 47:09 — Where to find Jim

Join the Escapee Collective: A Free Community for Gen X

Most people stay stuck in corporate because they think there are only two options: find another job, or start a business that eats five years of your life before it pays you.

There's a lot of room between those.

This one is about how you actually make money after corporate, and the first thing to get straight is what you're aiming at. Replacing your salary and funding your life are two different targets. One is a number somebody else set for you. The other is the number you need, plus the life you want, with a dial you control.

I go through the three stories that keep people from ever starting:

Entrepreneurship sounds as bad as corporate. True for the traditional version. Not true for solo done right, which is fewer hours, no employees, and a lot less complexity.

I don't have the skills. You already ran a solo business. It had one client, you went through a five-round sales process to land it, and you traded a lot of hours for the contract. We called it a job.

I can't sell. Selling is problem solving. When I ran sales ops, I studied our best reps across every segment to find the common trait. It was simple. The customer believed that person understood their problem and could fix it. That's it.

Then the five paths: gig work, starting a traditional business, buying a business, buying a franchise, and building a solo business. I spend most of the time on the last one, because that's where I see escapees actually winning.

Inside solo there are two roads. Monetize what corporate taught you, which is consulting, fractional and advisory work, and makes a good cornerstone. Or build low friction, high margin income streams, which is the part most people have never considered.

Nine real examples in here, including the guy who makes three hundred thousand a month negotiating car deals, the guy who gets paid to turn business owners' unused credit card points into trips, and the woman charging eight hundred dollars to organize a garage in a couple of hours.

Stack three or four of those and you're at ten thousand a month on a handful of hours a week.

In this episode:

• Funding your life versus replacing your income
• The three stories that keep people in corporate
• Why your corporate job was already a solo business with one client
• What I learned studying our best salespeople across every segment
• The five paths, and who each one is actually for
• Why buying a business is the most underrated option right now
• The two roads inside going solo
• Nine low friction, high margin examples
• Must solve versus nice to solve
• The only four things anybody pays for

THE NINE EXAMPLES, ORGANIZED

They come out of the episode in sequence. Here they are grouped, so a listener can find the one that fits.

Things that use something you already know

1. UGC for brands. Record short videos for brands that want Gen X and boomer faces. Around $500 for a couple of hours. People are doing $10K a month once a brand keeps re-upping.
2. Credit card points optimization. Small business owners run everything through one Amex or Chase card and sit on piles of points they never use. Learn the redemption game, plan the trip, charge about a thousand dollars.
3. Car purchase negotiation. A decade inside a dealership finance office turned into a flat $1,000 fee per deal, three hundred deals a month.

Things any competent adult can do well

1. Websites for local businesses. In my town of about forty thousand, I found forty one local non-franchise businesses. Half had no website at all.
2. Google Business Profile cleanup. Fill out the profile, build a process for responding to every review, and ask for new ones. Reviews matter more now that AI is reading them.
3. Garage cleaning and organizing. $800 to $1,000, a couple of hours. People will happily pay not to do it themselves.

Things that are arbitrage or access

1. Marketplace arbitrage. One guy buys VCRs cheap on Facebook Marketplace and sells them at a premium on eBay. Not for me. Real money for him.
2. Government subcontracting. Primes are encouraged to subcontract and don't have time to go find capable small businesses. Be the connector.
3. ADA website advisory. Accessibility is a live legal risk for businesses with public-facing sites. See the note at the bottom before you build an offer here.

THE TWO FILTERS

Is it a need to solve problem? Must solve and need to solve close. Nice to solve drags. If it's something the owner would like done but isn't a priority, you'll work twice as hard for the same fee.

Does it do one of four things? Everything anybody pays for comes down to:

• Save them time
• Save them money
• Make them money
• Reduce their risk

Hit a need to solve problem that checks two or three of those and you can start generating income fast. You don't need a website. You need conversations.

TIMESTAMPS

• 00:01 — Why income is the thing that keeps people stuck
• 00:40 — Two million Americans between 45 and 64, and what most of them are doing about it
• 01:30 — The 83% only looking for another corporate job
• 02:00 — The entrepreneur stereotype, and why it's half right
• 02:50 — Hundreds of ways to make money, and why experience expands your options
• 03:20 — Funding your life versus replacing your income
• 04:00 — Cash flow thinking instead of paycheck thinking
• 04:42 — It's hard work either way. The difference is who keeps the upside.
• 05:30 — 17 ways and counting, and why that's not a flex
• 06:50 — Story one: entrepreneurship sounds as bad as corporate
• 07:30 — Story two: I don't have the skills. Your job was a solo business with one client.
• 08:40 — You can go solo without burning the boats
• 09:00 — Story three: I can't sell
• 09:20 — What the best reps in every segment had in common
• 10:20 — The Microsoft story
• 11:40 — The five paths
• 11:50 — Path one: gig work
• 12:50 — Path two: start a traditional business
• 13:20 — Path three: buy a business, and why it's underrated
• 14:01 — Path four: buy a franchise
• 15:00 — Path five: build a solo business
• 15:40 — Road one: monetize what corporate taught you
• 16:16 — Why small businesses need foundational help, not level three work
• 17:20 — Road two: low friction, high margin
• 18:00 — Why the $5K engagement beat chasing six figures
• 19:00 — UGC
• 20:00 — The credit card points guy
• 21:00 — Tommy, and $300K a month negotiating car deals
• 22:20 — Websites in a town of forty thousand
• 23:16 — Google profiles, reviews, and ADA
• 24:20 — VCR arbitrage
• 24:50 — Garages at $300 to $400 an hour
• 25:00 — Government subcontracting
• 25:24 — Stack three or four and you're at 10K a month
• 26:00 — High functioning lazy
• 26:40 — Must solve versus nice to solve
• 27:00 — The only four things people pay for
• 27:39 — You don't need a website. You need conversations.
• 28:30 — Why this isn't like a job interview
• 29:00 — The AI episode coming next
• 29:30 — Close

LINKS

Got something working? Drop a note, and if it's replicable let's get you on the show. [email protected]

Hana Kim did almost everything you're not supposed to do.

She spent seventeen years in corporate, all of it in insurance, and made VP. Then she took a bigger VP role that required moving her whole family from Southern California to Arizona during the pandemic. House to sell, house to buy, a dog, and her mom, who lives with them. She landed in mid-June when it was a hundred and fifteen degrees.

The job was great, until it wasn't.

She describes the feeling the way a lot of us would recognize. Not burnout exactly. More like wearing a suit that kinda fits. Day by day you notice the fit is off, and then one day you have to take it off or lose your mind.

She joined the Escapee Collective in October of 2024, gave herself until the end of 2025 to decide, gave notice in July, and walked out in December. Two or three months before her pension vested. On paper, a terrible decision. She'll tell you she had no choice.

Then she made it harder. Insurance is a small world, and the easy path out is referrals and consulting gigs inside the industry you came from. She left the industry too. Which meant starting over with about three hundred LinkedIn connections, more than half of them in a business she was never going back to.

What she says about that period is the part I keep thinking about. Being excellent in corporate doesn't mean you know how to talk about your work. Her reputation was built inside the walls of one office and one industry, and none of it came with her.

The back half is her actual craft, and it's good. Her idea of building a neighborhood instead of an audience is the best framing I've heard on LinkedIn, and I'm stealing it. Not finding your ICP and bombarding them. Building a street where some people hire you, some people refer you, and some people are just people you talk to.

ABOUT THE GUEST

Hana Kim is a personal brand strategist who works with solopreneurs and founders. Before going solo in December 2025, she spent seventeen years in B2B marketing in the insurance industry, finishing as a VP. She started out as a freelance writer and editor, went to law school, and practiced as an attorney before moving into corporate. She is intentionally a solo operator and has no plans to build an agency.

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

She also has no content pillars, on purpose, and she'll explain why.

In this episode:

• Seventeen years in one industry, and the VP job that required moving states
• Why she doesn't call it burnout
• Falling out of favor, and how it's never one big thing
• The pension she walked away from
• Interviewing for a C-suite role and realizing she didn't want it
• Why the SVP math stopped making sense
• Leaving the industry, not just the job
• Rebuilding a network from three hundred connections, most of them dead
• The post that went semi-viral and brought the first client
• Year zero, and the seven or eight offers nobody remembers
• Building a neighborhood instead of chasing an ICP
• Why she has no content pillars
• Deciding what you don't want to be known for
• The rented land problem, and why she's planning her exit from social

THE NEIGHBORHOOD, ASSEMBLED

Hana's core idea, pulled into one place.

The wrong model: find your ICP, connect with your ICP, bombard your ICP with information until they like you enough to hire you.

The right model: a neighborhood. Not everyone on your street is a customer. Some are people you chat with. Some will refer you to the person who needs what you do. The value of the street isn't that everybody on it buys from you.

What that changes in practice:

• You talk to people who will never hire you, on purpose.
• You stop optimizing every post for conversion.
• You control what you can control, which is how you show up, because the algorithm is not yours.
• You decide what you want people to say about you when you're not in the room, and then you stay on brand even in the throwaway posts.
• You pick what you don't want to be known for, and you walk away from content that works but points the wrong direction.

And the one that takes the pressure off: nobody remembers your early offers, and nobody remembers your failed ones. Hana tested seven or eight in her first year and can't recall what was in most of them.

TIMESTAMPS

Taken from the raw transcript. Shift for cold open and sting.

• 00:01 — Welcome
• 00:46 — English degree, law school, attorney, caregiving break, seventeen years in corporate
• 01:40 — Joined the Escapee Collective in October 2024, and the deadline she set herself
• 02:56 — Why she wouldn't call it burnout
• 03:00 — The VP opportunity, and what it cost
• 03:30 — Uprooting the family to Arizona during the pandemic
• 04:30 — Sunday scaries, and thinking everyone had them
• 05:09 — Landing in mid-June at a hundred and fifteen degrees
• 05:20 — Finding Brett on LinkedIn, and "corporate gave up on you"
• 05:40 — Falling out of favor, and how it's never one big thing
• 06:00 — The process of elimination: the job, the company, or the work itself
• 06:45 — The pension she left on the table
• 06:56 — Brett on purgatory and the Geoff Curtis episode
• 08:18 — A suit that kinda fits
• 09:02 — A long notice period, and leaving before next year's projects
• 09:30 — Walking away from the industry, not just the company
• 10:00 — Turning fifty. "Too old. Maybe tired is the word."
• 11:36 — Caregiving and what corporate flexibility actually means
• 13:16 — Interviewing for a C-suite job and not wanting it
• 13:53 — The SVP math: a lot more responsibility for a little more money
• 14:40 — Six months of experiments
• 15:00 — Being excellent in corporate doesn't mean you can talk about your work
• 15:22 — A reputation built inside one office
• 16:00 — Three hundred connections, and starting LinkedIn over
• 16:46 — Build quietly, or build somewhere your peers won't look
• 18:57 — The post that went semi-viral
• 20:16 — The first contract and the first inbound client
• 21:00 — Brett on what happened when he got polished
• 21:47 — Solo on purpose, and saying no to an agency
• 22:30 — Sustainable, and where your energy goes
• 24:00 — Not building a light version of your corporate career
• 24:30 — Year zero
• 24:54 — When AI told her the target audience was "marketers who want revenue"
• 26:00 — High functioning lazy, and the world-class lollygagger
• 26:48 — There is no one path
• 27:48 — The neighborhood
• 28:34 — ICP bombardment versus actual neighbors
• 29:19 — LinkedIn's identity crisis
• 29:56 — Control what you can control
• 30:14 — Why she has no content pillars
• 30:24 — The content that worked, and why she dropped it
• 31:08 — Hana asking Brett if he was walking away from the Escapee brand
• 31:31 — Brett on how AI quietly boxed him in
• 32:19 — Nobody remembers your failed offers
• 33:18 — Building in public, intentionally
• 33:51 — Deciding what not to be known for
• 35:42 — Brett on optimizing the next thirty years
• 37:05 — Separate the money from the mission
• 37:36 — Get offline. Chamber of commerce. Actual neighbors.
• 39:20 — The rented land problem
• 39:30 — Why she's investing in her own site
• 40:03 — Locked out of LinkedIn, with no way back in
• 40:30 — The guy who walked into office parks and left with three engagements
• 41:28 — Business owners don't care about your label, they care about the problem
• 42:08 — Where to find Hana

LINKS:

Questions or guest ideas? [email protected]

Join my Substack: https://bretttrainor.substack.com/

Episode Overview:

Janet Tanguay got spitballed by her own colleagues in a corporate training for going off script. She lasted four days in her next job. Now she helps people build the life they actually want, and she has the most practical approach to it I've come across.

Janet Tanguay is a serial entrepreneur who has run a record label and an art business, and now runs Hammock Way of Life, helping people and companies get clear on what they actually want through vision boarding. She's the author of Hammock Way of Life: Leaping Toward Joy, part memoir and part business book, available in print and audio.

GUEST LINKS

https://www.linkedin.com/in/jazzyjan/

https://hammockwayoflife.com/

In this episode:

• The spitball training, and the ten years she stayed anyway
• Four days in banking and the sweater vest that ended it
• The boss who told her at a book signing that she almost made him quit
• Why the questions stop after enough years inside
• Finding the work by accident at a chamber of commerce
• The five whys, and why the fifth one is the real answer
• Three values as the filter for everything you say no to
• How to actually build a board, and the words to keep off it
• What she does with people who have four ideas at once
• Vision boarding inside companies, and what it turns up

THE METHOD, ASSEMBLED

Janet laid this out across the whole conversation. Here it is in one place.

1. Run the five whys. Start with one question. "Why do I want to leave?" Answer it, then ask why again, five times. The fifth answer is usually the real one.

2. Pick three values. Start with a list of ten, cut to five, then three. These become your North Star. When something lands in front of you, you check it against the three, and that's how you say no to things that look good but aren't yours.

3. Build the board around one center. Put the single most important thing in the middle. Cluster everything else around it. If you scatter it, your dreams come out scattered.

4. Get specific. Numbers, timelines, how many people, how much money. "I want to be rich" isn't a goal, it's a mood.

5. Watch your words. Nothing with a double meaning. Janet's examples: "nailed it," "crushed it," "a family affair." These things manifest in ways you didn't intend. She put a Buddha in the center of a board because she wanted more yoga and more stillness, and ended up sent to China to the largest Buddha temple in the country.

6. If you have four ideas, make four boards. Then talk through each one out loud with somebody. The one where your eyes light up is the one. Janet says it happens every time.

7. Take the free step. Not the big step. The free one. Go to the open house. Test drive the car. Send one email. She almost didn't test drive a car because she assumed she couldn't afford it, then drove it off the lot.

8. For a business, use the business model canvas as the board. Revenue streams, resources, partners, value proposition. Same exercise, different frame.

Questions or guest ideas? [email protected]

TIMESTAMPS

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

• 00:00 — Welcome, and where the company name came from
• 01:35 — The spitball training
• 02:33 — Ten years in anyway, then done
• 03:11 — Four days in banking
• 03:29 — Day two: all the ways you could be killed on the job
• 03:46 — The sweater vest, in the parking lot, at ninety nine degrees
• 04:33 — The old boss who showed up at her book signing
• 04:50 — The four column form nobody could explain
• 05:30 — What happens when you stop asking why
• 06:36 — No plan, and what came next
• 06:48 — The chamber of commerce, and finding the work by accident
• 07:47 — Why lenders squash dreams, and why she wanted a room where they couldn't
• 08:11 — Your life experience qualifies you for more than you think
• 08:46 — The ski instructor is only a few lessons ahead
• 09:26 — Getting past the fear of judgment
• 11:14 — Breaking the rut while you're still in it
• 12:05 — The book, and what's in it
• 15:47 — The five whys
• 16:00 — Three values, and how to get to them
• 16:30 — Using the three to say no
• 18:00 — Asking other people how they see you
• 19:25 — Clearing the old stuff out
• 19:54 — Cutting the negative people, and how easy it turned out to be
• 20:55 — The gossip in the office, and the woman who ended it with one sentence
• 22:34 — Asking for a sign, and the fish sign
• 23:50 — Why she asked for eagles
• 25:35 — How to actually build a board
• 26:43 — Numbers, timelines, and specificity
• 27:00 — The words to keep off your board
• 27:40 — The Buddha, and the trip to China
• 28:00 — Using the business model canvas for a company
• 29:30 — Brett's half marathon, and day eleven of 75 Hard
• 30:20 — It isn't about thinking anymore. It's about feeling.
• 30:45 — "That's coming to me now"
• 31:31 — What does joy actually feel like
• 32:29 — Small steps that break the pattern
• 33:27 — Connecting dots across 370 conversations
• 34:07 — Why AI won't connect those dots for you
• 35:22 — Take the free step. The open house. The test drive.
• 36:53 — Four ideas, four boards, and watching which one lights you up
• 38:25 — What happens when you run this inside a company

• • 40:49 — Where to find Janet

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