Brett Trainor Unplugged

Brett Trainor
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  • Self-Improvement
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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?

  1. 2d ago

    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 statesWhy she doesn't call it burnoutFalling out of favor, and how it's never one big thingThe pension she walked away fromInterviewing for a C-suite role and realizing she didn't want itWhy the SVP math stopped making senseLeaving the industry, not just the jobRebuilding a network from three hundred connections, most of them deadThe post that went semi-viral and brought the first clientYear zero, and the seven or eight offers nobody remembersBuilding a neighborhood instead of chasing an ICPWhy she has no content pillarsDeciding what you don't want to be known forThe 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 — Welcome00:46 — English degree, law school, attorney, caregiving break, seventeen years in corporate01:40 — Joined the Escapee Collective in October 2024, and the deadline she set herself02:56 — Why she wouldn't call it burnout03:00 — The VP opportunity, and what it cost03:30 — Uprooting the family to Arizona during the pandemic04:30 — Sunday scaries, and thinking everyone had them05:09 — Landing in mid-June at a hundred and fifteen degrees05:20 — Finding Brett on LinkedIn, and "corporate gave up on you"05:40 — Falling out of favor, and how it's never one big thing06:00 — The process of elimination: the job, the company, or the work itself06:45 — The pension she left on the table06:56 — Brett on purgatory and the Geoff Curtis episode08:18 — A suit that kinda fits09:02 — A long notice period, and leaving before next year's projects09:30 — Walking away from the industry, not just the company10:00 — Turning fifty. "Too old. Maybe tired is the word."11:36 — Caregiving and what corporate flexibility actually means13:16 — Interviewing for a C-suite job and not wanting it13:53 — The SVP math: a lot more responsibility for a little more money14:40 — Six months of experiments15:00 — Being excellent in corporate doesn't mean you can talk about your work15:22 — A reputation built inside one office16:00 — Three hundred connections, and starting LinkedIn over16:46 — Build quietly, or build somewhere your peers won't look18:57 — The post that went semi-viral20:16 — The first contract and the first inbound client21:00 — Brett on what happened when he got polished21:47 — Solo on purpose, and saying no to an agency22:30 — Sustainable, and where your energy goes24:00 — Not building a light version of your corporate career24:30 — Year zero24:54 — When AI told her the target audience was "marketers who want revenue"26:00 — High functioning lazy, and the world-class lollygagger26:48 — There is no one path27:48 — The neighborhood28:34 — ICP bombardment versus actual neighbors29:19 — LinkedIn's identity crisis29:56 — Control what you can control30:14 — Why she has no content pillars30:24 — The content that worked, and why she dropped it31:08 — Hana asking Brett if he was walking away from the Escapee brand31:31 — Brett on how AI quietly boxed him in32:19 — Nobody remembers your failed offers33:18 — Building in public, intentionally33:51 — Deciding what not to be known for35:42 — Brett on optimizing the next thirty years37:05 — Separate the money from the mission37:36 — Get offline. Chamber of commerce. Actual neighbors.39:20 — The rented land problem39:30 — Why she's investing in her own site40:03 — Locked out of LinkedIn, with no way back in40:30 — The guy who walked into office parks and left with three engagements41:28 — Business owners don't care about your label, they care about the problem42:08 — Where to find Hana LINKS: Questions or guest ideas? bt@bretttrainor.com

  2. Sep 30

    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 anywayFour days in banking and the sweater vest that ended itThe boss who told her at a book signing that she almost made him quitWhy the questions stop after enough years insideFinding the work by accident at a chamber of commerceThe five whys, and why the fifth one is the real answerThree values as the filter for everything you say no toHow to actually build a board, and the words to keep off itWhat she does with people who have four ideas at onceVision 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 from01:35 — The spitball training02:33 — Ten years in anyway, then done03:11 — Four days in banking03:29 — Day two: all the ways you could be killed on the job03:46 — The sweater vest, in the parking lot, at ninety nine degrees04:33 — The old boss who showed up at her book signing04:50 — The four column form nobody could explain05:30 — What happens when you stop asking why06:36 — No plan, and what came next06:48 — The chamber of commerce, and finding the work by accident07:47 — Why lenders squash dreams, and why she wanted a room where they couldn't08:11 — Your life experience qualifies you for more than you think08:46 — The ski instructor is only a few lessons ahead09:26 — Getting past the fear of judgment11:14 — Breaking the rut while you're still in it12:05 — The book, and what's in it15:47 — The five whys16:00 — Three values, and how to get to them16:30 — Using the three to say no18:00 — Asking other people how they see you19:25 — Clearing the old stuff out19:54 — Cutting the negative people, and how easy it turned out to be20:55 — The gossip in the office, and the woman who ended it with one sentence22:34 — Asking for a sign, and the fish sign23:50 — Why she asked for eagles25:35 — How to actually build a board26:43 — Numbers, timelines, and specificity27:00 — The words to keep off your board27:40 — The Buddha, and the trip to China28:00 — Using the business model canvas for a company29:30 — Brett's half marathon, and day eleven of 75 Hard30:20 — 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 like32:29 — Small steps that break the pattern33:27 — Connecting dots across 370 conversations34:07 — Why AI won't connect those dots for you35:22 — Take the free step. The open house. The test drive.36:53 — Four ideas, four boards, and watching which one lights you up38:25 — What happens when you run this inside a company • • 40:49 — Where to find Janet

  3. Sep 26

    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 themThe decade of substance abuse nobody at work knew aboutPeru, and what broke the patternWhat actually happens in a breathwork sessionWhy the planning kept him stuck for ten yearsExternal expectations versus the ones you set yourselfTrust as a practice, not a feelingWhy he never told his wife until after he'd quitSkydiving, 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 now02:07 — The family business, the money, and the empty feeling03:34 — Golden handcuffs, and the beliefs formed in childhood05:28 — Peru, and how he found breathwork06:13 — First session in 2018, out of the job a year later06:59 — Questioning everything he believed about himself08:41 — Awareness as an ongoing practice, not a destination10:44 — The decade of substance abuse while managing in corporate11:09 — The void he was trying to fill12:46 — The first session: "I cannot keep this up any longer"13:20 — An hour gone, and no inner dialogue14:42 — What actually happens in a session16:28 — The physiology, in his words17:04 — In person versus online, and which suits who19:40 — Why Gen X never invests in itself20:09 — How many sessions, and why integration matters more21:34 — Fear of judgment, failure, and criticism22:02 — "You'd never have seen me on a podcast"23:11 — External expectations versus internal ones23:40 — External pressure crushes. Internal pressure expands.24:05 — First generation college and the path that gets installed26:16 — The mask, and how trying to be strong made him weak27:47 — Ten years of trying to quit28:30 — Why the plan B was making it worse29:00 — Trust as the first principle of breathwork31:03 — The relief after, and his only regret31:40 — Telling his wife on the road to Maine32:20 — The year he spent with his kids34:42 — Skydiving, piano, and going back for a master's37:37 — Boredom, curiosity, and what lit the fire38:00 — Curiosity to find out who you are, courage to be that way38:23 — Approaching a session with childlike curiosity40:00 — It's the most fulfilling work he's done, and it's hard41:30 — 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

  4. Sep 24

    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 transitionLivelihood versus identity versus self-worthThirty years of running on external validationRunning as emotional suppression, and how to tell it from progressNew metrics for happiness, and why the old ones keep coming backInvesting in yourself, therapy, and the Hoffman ProcessWhy people doubt themselves inside corporate, not just outside itThe imposter syndrome nobody on his team ever mentioned to each otherEverything 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 differently01:31 — Why he chose the word purgatory02:46 — Not brave enough to say we're unfinished02:51 — Brett: I think I was in purgatory while still employed03:53 — His wife knew it was going to hit him before he did05:08 — Identity, self-worth, and what work was really providing05:49 — Thirty years of running on external validation06:48 — Why there's no path out in the book, only questions08:30 — Livelihood is not identity is not self-worth09:35 — Separate the money from the mission10:49 — The college senior who wants success and fun12:36 — First generation college, and the expectations that come with it13:49 — Running when things get uncomfortable14:25 — Evaluate the ending, or you'll repeat it15:45 — Running as emotional suppression, and his father16:35 — Love the process and eventually the process loves you17:30 — Three years out, and building new metrics for happiness18:57 — The old metrics never fully stop flashing back20:00 — Brett talked his way back into a full time job because it was comfortable21:18 — Geoff turns it around: how much was external pressure?22:58 — What changes when you finally become value driven24:20 — Following energy as a compass25:17 — Why the nonprofit took two and a half years, and why that was right26:52 — First dollar out versus being methodical29:41 — Why you'd be a better leader now than you were then30:25 — Gen X and the refusal to invest in ourselves31:25 — The Hoffman Process, eight days unplugged33:06 — The patterns you inherited and repeat under stress35:44 — Getting comfortable being uncomfortable36:58 — Doing the uncomfortable thing, and how the podcast started37:41 — The nonprofit as his uncomfortable thing40:17 — People are doubting themselves inside corporate now41:50 — The imposter syndrome nobody admitted to each other43:00 — Everything is a choice, and we only price the downside44:15 — Negativity as an inherited pattern46:15 — The quarterly business review Brett runs with his wife48:11 — 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

  5. Sep 22

    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 matterThe brand call that accidentally started her businessWhy brands are banning AI content in their briefsWhat to charge when you're brand newPerformance-based deals and why she passes on themWhat her students actually earn, at every levelWhere the Amazon Influencer program fits, and where it doesn'tWhy she quit TikTok ShopLocal businesses, and trading content for servicesHow 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 back01:10 — What UGC is, and the 16,000 students02:13 — Why Brett keeps coming back to low friction income03:13 — Why so many people freeze before they start04:24 — She saw it on TikTok while working a corporate job05:00 — Out of that job in fourteen months05:32 — The footwear call where they got excited about her mom06:33 — Nobody that age was doing this07:01 — Why corporate trained us to overthink it08:37 — Who am I to teach this, and why two steps ahead is enough09:26 — A detour into other low friction businesses10:18 — What AI is doing to this market10:37 — Brands writing "no AI content" into the brief11:55 — The trust recession12:32 — Is it too late to start?13:10 — Why it's an ongoing need and not a trend14:18 — What to charge when you're brand new15:00 — Performance based deals, and the math on them16:42 — Why Megan turns those down17:11 — Brett butchering a brand name on camera, and the brand not caring18:24 — The part-timers, and what a summer looks like19:00 — Replacing corporate income19:45 — The student who made $22,000 last month20:48 — Why repeat clients change the economics21:52 — Where the Amazon Influencer program fits23:29 — Income stacking and double dipping24:45 — Why she quit TikTok Shop27:11 — How to start, step one28:39 — Cat treats, and your first videos29:30 — Platforms versus pitching30:27 — Big brands versus local businesses32:00 — Why local wins give you momentum33:13 — What the first fifty dollars does to your head33:20 — Trading content for services34:38 — How to find the right contact at a brand35:30 — Pitching as a volume game36:41 — Getting a fence stained in exchange for content38:30 — The fears that stop people, and why none of them hold40:03 — Belief, action, and the first dollar41:09 — 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

  6. Sep 16

    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 admitIdentity, job titles, and the shorthand you loseThe comfort trap, and why rebuilding the old job is a normal human response, not a failureThe physical toll nobody talks aboutWhy performance reviews are useless for thisHow to ask people who know you what you're like at your bestTurning what comes back into five words, and using them as a filterThe portfolio approach when one opportunity only delivers part of what you needThe guilt of not being busy, and why you were never productive nine hours a day anyway THE EXERCISE, ASSEMBLEDWe 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 GUESTShelley 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 MapSite: https://burnthemapcoaching.comLinkedIn: https://www.linkedin.com/in/shelley-mcintyre/ TIMESTAMPSEstimated from the transcript. Spot-check and shift for cold open and sting. 00:00 — Welcome back, and why her first episode still gets downloads01:00 — The Oracle layoffs, and the severance math02:08 — Getting numb to the coldness of it02:40 — You radiate loyalty your whole career and don't get it back03:41 — The 6 a.m. automated email that doesn't say thank you04:22 — Why identity and job title get intertwined05:08 — "I'm a VP of marketing" as shorthand for who you are06:11 — Title, industry, company. The trifecta.07:18 — The trap: going independent and rebuilding the same role08:16 — "I built the same box I just escaped"09:29 — Brett talked his way back into a full time job and hated it10:26 — We are wired for comfort, and that's not a character flaw11:38 — The losses stack up all at once12:17 — Remembering who you are underneath all of it14:02 — Why skills lists and performance reviews don't work here14:58 — When the doubt spreads to things you were always good at15:50 — The physical toll: illness, accidents, the hospital16:32 — Usefulness, and being told you're not needed17:25 — You're not the most qualified person to say how great you are18:23 — Becoming a detective of your best self19:16 — Why corporate feedback is performative20:00 — What actually happens when you ask21:07 — "Let me tell you a story"23:00 — The surprise birthday party nobody would have predicted24:00 — If you don't believe it, you're calling them liars24:51 — What to do with it: five words26:08 — Using the five as a filter for every opportunity27:00 — But what if nobody has anything good to say?28:19 — The portfolio: when one thing only delivers three of five29:01 — Separate the mission from the money29:55 — "What do you do for fun?" "Fun?"32:15 — What if you could do something you're good at and it's fun33:11 — 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 work35:41 — It nets out the same. You're just doing it on your terms.36:33 — A walk in the park beats a useless meeting40:00 — The former client who'd never go back40:28 — Take a part-time job and watch all your time disappear40:43 — The real hourly math on a hundred thousand dollar salary43:03 — 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

  7. Sep 8

    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 planYou need a website, a brand, an LLC, a logoYou need to be a salespersonIt'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 thingThe four myths, one at a timeWhy corporate politics skills don't transfer, and why that's good newsYour job is one customer with one hundred percent concentrationThe interview and the discovery call are the same conversationGood, better, best, and pricing your first engagementOwning your own calendar, which took me longer than I want to admit TIMESTAMPS 00:00 — The LinkedIn article, and what this episode adds to it01:30 — The TikTok comment that started it01:55 — I'd been saying the same line for years02:20 — Hundreds worked with, thousands talked to, and almost none were prototypical entrepreneurs03:00 — Where the stereotype came from03:45 — 117,000 one-person businesses over a million in revenue04:10 — Stop thinking customers. Think micro jobs.04:25 — Myth 1: you need a business plan04:41 — Myth 2: you need a website, a brand, an LLC05:15 — Myth 3: you need to be a salesperson05:50 — Why corporate politics skills don't help you out here06:20 — Myth 4: it's risky07:15 — Your corporate job is your one customer08:00 — What a diversified solo practice actually looks like08:30 — If it takes six months to find your next customer, you're running it wrong08:50 — Put a tenth of your job hunt effort into finding clients09:55 — Finding clients looks a lot like looking for a job10:25 — Seven of my eight roles came from referrals. None from a posting.11:00 — Think of it as mini job applications11:36 — The interview process, walked through step by step12:15 — Same conversation, but with a business owner12:45 — Good, better, best13:35 — They take the middle option nine times out of ten14:20 — Nobody's judging you14:55 — You'll probably underprice the first one. It doesn't matter.15:30 — You'll work fewer hours than you do now15:50 — Owning your own calendar, and why it took me so long16:11 — Don't feel guilty when you're not busy16:40 — The few who go back, and why they go back with a plan17:20 — Reallocate some of those job hunting hours17:45 — It's relationships, not postings18:15 — Don't chase shiny objects. Pick one or two.18:30 — Maybe the word itself is the problem19:00 — 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

  8. Sep 2

    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 backClient zero, and why hourly was the wrong modelGetting pigeonholed as "a writer" and the pricing that comes with itThe coach question that triggered his pivot: do you actually like doing this work?Writing daily for two years before there was a bookWhy he deliberately left AI out of the bookThe Expert's Privilege, definedIntellectual headshots, and how asking former clients one question reshaped his businessInvesting in yourself when corporate always paid for it before TIMESTAMPS00:00 — Intro01:43 — Two layoffs, and why he didn't want another corporate role03:26 — Why almost nobody who gets out wants to go back04:32 — He didn't know solo consulting was even an option06:43 — What the work actually was: executive ghostwriting and content strategy08:22 — Client zero, and the first lesson about hourly rates09:18 — Project fees, and putting guardrails on your availability10:44 — Getting pigeonholed as "a writer" before the conversation starts12:14 — When the business model started breaking13:11 — The coach's question: do you actually like doing this work?13:41 — The pivot to serving independent consultants14:59 — Brett's own winding path out of corporate15:53 — The three-tier offer, and why clients almost always pick the middle16:50 — Helping people map their lane while they're still employed17:47 — "I never gave serious thought that I could take the reins myself"20:18 — Building authority from zero, and writing daily for two years21:44 — You turn around and there's a library there22:34 — The self-doubt going into the book23:10 — Not the book. A book. Your first book.26:11 — Brett's stuck manuscript problem26:33 — The North Star workshop and the parachute metaphor27:44 — Why he left AI out on purpose30:04 — The Expert's Privilege, the three stacked ideas30:53 — A hundred ships and fifty of them tied up in port32:10 — In the corner four months ago, desperate for his brain today34:00 — Most businesses need level one help, not level three36:28 — "I don't know what I know," and why that trap is so common37:34 — Start with the problem, not with yourself38:48 — Need-to-solve versus nice-to-solve39:26 — Brett on chasing energy as the compass40:31 — Intellectual headshots, and the one question that created them42:08 — Saying no, and the add-on that killed Brett's margin43:18 — Investing in yourself when corporate always covered it45:39 — Laid off tomorrow: square one, or a head start?48:05 — You're a business with one client. Is that a good deal?49:28 — Where to find Wes and the 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 GUESTWes Wheless is the author of The Expert's Privilege: A Self-Deployment Guide to Leaving Corporate and Going Solo (July 2026). After two layoffs, including one from the tech education company Reforge, he built an independent practice helping solo consultants pull their expertise out of their heads and turn it into visual frameworks, something he calls intellectual headshots. He now also works with people still inside corporate who want to map and pressure-test a consulting lane before they need one. LINKSThe book The Expert's Privilege: A Self-Deployment Guide to Leaving Corporate and Going Solo https://theexpertsprivilege.com/ Amazon: https://www.amazon.com/Experts-Privilege-Self-Deployment-Leaving-Corporate/dp/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

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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?

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  • Creator
    Brett Trainor
  • Years Active
    2019 - 2026
  • Episodes
    350
  • Rating
    Clean
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    © 2026 2019 B.T. LLC
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    Brett Trainor Unplugged

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