Brett Trainor Unplugged

The Future of Work Is Changing: Gen X Is the Winner

Join the Escape Collective for Free! I keep hearing the same phrase in my strategy calls, and it's costing people money. Somebody who spent twenty-five years in corporate describes what they can do and says: I'm kind of a Swiss Army knife. I get why. After two or three decades you really can do a lot of things. But to a business owner that doesn't read as expertise, it reads as unfocused. And unfocused doesn't get paid like expertise does. Flip it. You're not a Swiss Army knife. You're special ops. You drop in, you solve the one problem, you get out. Think about how you'd pick a plumber. One says he does tubs, installs, remodels, whatever you need. The other says that exact leak is the thing I fix, I'm in and out in an hour. Who do you call, and who charges more? Here's the part that matters more than the repositioning. This is happening whether you do anything about it or not. A full-time employee is an expensive way to buy expertise. In my last corporate job, a week where I spent more than twenty percent of my time on the actual work I was hired for was a good week. The rest was meetings I didn't need to be in and fire drills. Salary plus benefits, for twenty percent. Companies have been cutting that expense for years and they are not going to stop. Shorter CEO tenures, quarterly targets, the profits over people playbook. My bet on the last shoe to drop is benefits, and we're already watching big employers trim what they cover. Meanwhile small businesses and startups have quietly figured out a better way to buy talent. Look at how a movie gets made or how a house gets built. Nobody employs the whole crew. Specialists come in, do the one thing they're excellent at, and leave. So the question isn't whether the model changes. It's whether you're positioned as the generalist on a salary or the specialist they call. That part is up to you. In this episode: Swiss Army knife versus special ops, and why the words matter What a full-time employee actually costs for the work you get Ocean's Eleven, Hollywood, and the home builder Why fractional is a delivery model, not an identity The only two things a business owner is deciding about you The general contractor role, and why it's the most valuable seat What to actually say to a local business owner this week The two things they're deciding Forget your title. When you talk to a small business owner, they are answering two questions, in this order. Can you solve the problem? You've been doing this on the biggest stage for twenty or thirty years. This one is usually already answered. Can I see myself working with you? Did we connect, or didn't we. Price is third, and it's a long way third. Clear the first two and nine times out of ten you'll find a number that works. What this sounds like out loud You don't need a deck or an offer. You need one conversation with a local business owner. Not a pitch, not a proposal. "I spent twenty-five years in corporate doing X. I'm starting my own thing focused on Y. Does that make sense to you? Is that a problem you run into?" You're not committing to anything. You're building your own confidence and quietly educating a business owner that there's a better way to buy the talent they need. Quotes "You're not a Swiss Army knife. You're special ops. Drop in, solve the problem, get out." "Fractional is a delivery model. It isn't an identity. Attach yourself to a problem, not a title." "A week where I spent more than twenty percent of my time on the job they hired me to do was a pretty good week." Moments: Why the Collective is free now The Swiss Army knife problem The plumber test What a full-time employee really costs Ocean's Eleven and talent density Fractional is a delivery model, not an identity The only two things they care about Hollywood and the home builder The general contractor seat What to say to a business owner this week The Escapee Collective is free now No paywall, no upsell, close to 350 members. Education, connection, and a room full of Gen Xers working on the same thing. TheEscapeeCollective.com

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Gill Keogh: 25 Years at Barclays, Then 4 Months Frozen

If you're a few weeks out and nothing is happening, this is the episode. Gill Keogh spent 25 years at Barclays and left happy, by choice, at 49. Then she sat frozen in front of a laptop for three or four months and couldn't work out why. Her words: I skipped out the door thinking this is it, I'm going to build the dream. And then I was just stuck. Most escapee stories jump from the decision straight to the business. Gill walks you through the dead months in between, which nobody talks about and almost everybody has. She didn't see it coming, because this was a decision she made on purpose, and nobody tells you that the freeze doesn't care whether you chose it. She did CBT, not because anything was broken, and found out how much of her life had been built on safety. The salary, the badge, the building full of people. Fight, flight or freeze, and she's a freezer. Her first move out of it was the one most of us make: go get another qualification. A piece of paper that says you're allowed. She did it, then worked out that 25 years across the UK and offshore is not a thing you can put on a certificate. A year on she runs her own coaching practice, picks who she works with and who she doesn't, has no revenue target for the first time in her life, and is leading the Escapee Collective here in the UK. The line I'm stealing from her, on why networking never worked until it did: it's about connecting, not collecting. In this episode: Bleeding Barclays Blue, and what happens when that stops Leaving a job you liked, which nobody prepares you for either Four months frozen, and why choosing to leave made it worse What CBT turned up about safety The qualification trap, and what to do instead Nobody asks for your credentials. They ask whether they get you. Getting rid of the guilt Connecting, not collecting About Gill Gill Keogh is the founder of Gillian Keogh Coaching, working with senior leaders, business owners and teams on executive coaching, leadership development and change. She spent 25 years in corporate at Barclays, in the UK and offshore, before leaving in October 2025 to build her own practice. Connect with Gill LinkedIn: https://www.linkedin.com/in/gilliankeoghcoaching/ Year one, as it actually went October. Takes the package after 25 years. Leaves happy. Three months off. Gardening leave. Gym at six, volunteering at a dog shelter, a holiday, time in the garden. Her only regret: she did all of it feeling guilty. Then the freeze. Three or four months. Laptop open, nothing moving. CBT, out of curiosity. Surfaces that the freeze was her brain protecting a safe zone that no longer existed. The qualification detour. Useful, and also the thing you reach for when you want permission. January to March. The business actually starts. A year out. Narrow idea gone wide. Says yes to work she didn't plan for. No monetary target. Her own days, without guilt. Quotes "Some people get fight, some people get flight. I clearly get freeze." "Twenty-five years of experience, working in the UK, working offshore. You cannot write that on a bit of paper." "People said, should you really be having a nice holiday when you've just been made redundant? The only person saying that was me."

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Escapee to Shark Tank: The Story Behind Hackees Lacrosse

Four years ago Charlie Patterson was fifteen years into a public relations career in Washington DC. A few weeks ago he was standing in front of the Sharks pitching Hackees Lacrosse (Hackeeslax.com) That's the reason this episode exists. Most of us, when we think about what's on the other side of corporate, we think about consulting. Maybe fractional. Maybe calling a few people in our network and seeing what shakes loose. Almost nobody pictures a national TV pitch for a product they invented in their own backyard. Charlie didn't picture it either. That's the point. He didn't hate his job, which is worth saying out loud. Fifteen years at the same firm, interesting clients, good benefits, solid pay, lunches out in the city. He still sees his old boss. By every outside measure it was working, and in the back of his head the whole time: this isn't what I'm supposed to be doing. Then he was in the backyard with his nephew playing the kind of unpadded pickup lacrosse that always ends with somebody getting cracked, and he took one on the knuckle. Ice pack. Beer. Done for the day. Two weeks later he's on a walk, taking a break from work, and it lands. Take the pads off the player and put them on the stick. That's Hackees. A padded lacrosse stick you can use in the backyard, the basement, the beach, anywhere, the way we all played wiffle ball and street hockey growing up. It's also a real accessibility play. Charlie says it runs six to eight hundred dollars to put a kid in full lacrosse pads, which is a tough sell for a parent weighing that against flag football. What I wanted from this conversation was the staircase. Not the highlight. So he walks all of it. Calling two guys he's known since first grade because he knew he couldn't do it alone. The product they tried before this one that went nowhere. Calling every lacrosse manufacturer in the country. A year of getting the padding wrong. Twelve to fifteen thousand dollars each, which is the entire starting capital. Five hundred boxes landing in his one car garage on a ninety-five degree day with zero sales and a newborn at home. Writing a thank-you note by hand to every single customer. And the thing he says about deciding to leave, which is better than any framework: you've got two gas tanks, and one of them is never going to fill up. Then the part nobody plans for. Three years in, enough traction that it was worth asking for help, six months of due diligence, and three guys who have known each other since first grade standing on that carpet together. None of the rungs on this ladder are exotic. That's what makes it worth your forty minutes. In this episode: The knuckle, the ice pack, and the walk Fifteen years at a job he liked, and the thought that wouldn't leave The app and the restaurant that never happened Calling two childhood friends because he knew he couldn't do it alone The product that failed first, and what it taught them How you actually get a lacrosse stick manufactured Five hundred boxes and a one car garage The gas tank test Why they turned down outside money for three years Six months of due diligence, and what the room is actually like Barbara, and the one sentence that decided it ABOUT THE GUEST Charlie Patterson is a co-founder and the CEO of Hackees Lacrosse, maker of a patented padded lacrosse stick built for backyard and pickup play. He started the company with two childhood friends, Phil Toran and Anthony Phalen, after fifteen years in public relations. He grew up in a Massachusetts lacrosse family and played from fourth grade through high school. LINKS Hackees Lacrosse — hackeeslax.com The Escapee Collective: TheEscapeeCollective.com Questions or guest ideas? bt@bretttrainor.com

Bradley Richardson: You're Not Reinventing, You're Remodeling

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

How to Quit Corporate Without Blowing Up Your Finances, with Tania P. Brown

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

Laid Off Tomorrow? Here’s Exactly What I’d Do

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

Why I'm an Unapologetic Optimist About Gen X

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 THE FIVE, IN ONE PLACE 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. TIMESTAMPS 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

Jim Barke: His First 2 Years Going Solo, Unfiltered & Honest

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 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. 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. 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

You Don't Need to Replace Your Salary. You Need to Fund Your Life- Here’s How

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 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. 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. 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 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. 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. 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 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. Government subcontracting. Primes are encouraged to subcontract and don't have time to go find capable small businesses. Be the connector. 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. bt@bretttrainor.com

Hana Kim: I Left 3 Months Before My Pension Vested

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? bt@bretttrainor.com

Janet Tanguay: Spitballs, Sweater Vests, & 4 Days in Banking

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? bt@bretttrainor.com 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

Ten Years of Planning. Then He Quit in a Day

Join Brett’s Substack: Letters from an Escapee: :https://bretttrainor.substack.com/ 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? bt@bretttrainor.com HASHTAGS / KEYWORDS breathwork, emergence coaching, golden handcuffs, leaving corporate, patterns, emotional suppression, self sabotage, GenX transition, personal development, holotropic breathwork, consciousness

Geoff Curtis: You're Not Burned Out, You're in Purgatory

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: You Don't Need Followers to Get Paid (UGC)

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. 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. Make three or four videos using products already in your house. Megan's first two were cat treats. Basic editing. Nothing fancy. Put them in a portfolio. Canva works. Any simple site works. Brands need proof you can make content, same as any other business. Pick a lane to get hired. Either join the creator platforms, or pitch brands directly. Megan pitches. 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. 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. 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. 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? bt@bretttrainor.com 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: Who Are You Without the Title?

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 THE EXERCISE, ASSEMBLED We covered this across the conversation but never laid it out in one piece. Here it is. 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. Ask one question: "Can you describe what I'm like when I'm operating at my best?" 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. Read all of it together. If you find yourself doubting it, notice what that means. You'd be calling people who love you liars. Synthesize it down to five words that describe how you show up at your best. 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. ABOUT THE GUEST 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/ TIMESTAMPS 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 KEY QUOTES "You're radiating this love and loyalty out throughout your career, and then you don't get it back. At the very end, when it matters the absolute most, you don't get it back." — Shelley "I have built the same box for myself that I just escaped. And how is it that I'm back inside of it?" — Shelley "You're not actually the most qualified person to talk about how great you are. Because you're in a world of doubt." — Shelley "If you don't believe that, then you're calling these people liars and you're out of integrity." — Shelley "You can't rest and be busy at the same time. It doesn't work." — Shelley "You might have been in the chair for nine hours a day, but you did not do productive work for nine hours a day. So why are we beating ourselves up when we're being equally productive? We're just doing it on our terms." — Shelley "Instead of going to a useless meeting, what if you could go for a walk in the park?" — Shelley "I had a good contract gig. Instead of building off of that, I convinced the company to bring me back full time, because it was the title and it was more comfortable. I was absolutely miserable." — Brett

Myth Buster: Entrepreneurship Isn't for Everyone

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: You need a business plan You need a website, a brand, an LLC, a logo You need to be a salesperson 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? bt@bretttrainor.com

The Expert's Privilege: Wes Wheless on Leaving Corporate and Going Solo

Wes Wheless got laid off twice inside a few years. COVID, then the tech downturn. He wasn't angry about the second one. He just didn't have the energy to go attach himself to somebody else's mission again and wait for it to get taken away. He didn't have a plan. He took a couple months, picked up some contract work to hold him over, and then a light bulb went off: if he could find enough of these, he might never need a full-time job again. Four years later he's got a practice serving independent consultants and a book, The Expert's Privilege, that I told him he should have written before I left corporate. The core idea is three stacked pieces: You've built real, transferable expertise over your decades in corporate. That expertise has been inefficiently deployed inside the corporate machine. You can deploy it far better on your own. His metaphor for point two is the one that stuck with me. Imagine running a cruise line with a hundred ships and fifty of them permanently tied up in port. That's what corporate does with what you know. We also get into the stuff nobody tells you. Why hourly pricing punishes you for being good. What happens when a client pigeonholes you before you open your mouth. How he figured out which part of his own service people actually valued, and then sold only that. And the thing I keep running into with Gen Xers: deeply experienced people who sit down, look at twenty-five years of work, and say "I don't know what I know." In this episode: Two layoffs, and the one that changed his mind about going 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 TIMESTAMPS 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 QUOTES "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 ABOUT THE GUEST 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. LINKS The book The Expert's Privilege: A Self-Deployment Guide to Leaving Corporate and Going Solo https://theexpertsprivilege.com/ Amazon: https://www.amazon.com/Experts-Privilege-Self-Deployment-Leaving-Corporate/dp/1788464028 Wes's site and services https://bio.site/weswheless Wes on LinkedIn — https://www.linkedin.com/in/wwheless/ The Collective https://trp-collective.circle.so Questions or guest ideas? bt@bretttrainor.com

Gen X Has a Math Problem

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 TIMESTAMPS 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 LINKS AND CTA 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: bt@bretttrainor.com 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

9 Things I Learned in 6 Years Out of Corporate

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

Brett Trainor Unplugged

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?