Brett Trainor Unplugged

Brett Trainor
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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. 12h ago

    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

  2. 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

  3. 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

  4. Aug 28

    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 ageThe musical chairs problem, and why the chairs aren't coming backPensions versus the 401k handoffWhat 30 or 40 more years actually costsWhy gig work is the wrong answerLow friction, high margin income, and what that actually looks likeWhy the first dollar outside corporate changes everything TIMESTAMPS00:00 — Welcome, and why I'm zooming out this week01:20 — Naming it: Gen X has a math problem01:42 — Two ways to react: sunset, or jumpstart02:05 — Musical chairs, and why they're pulling five at a time02:25 — Part 1: It's not your age, it's your expense03:40 — Getting laid off isn't the problem. Getting back in is.04:20 — The professional athlete parallel04:46 — Part 2: How prepared are we, really05:05 — They got pensions. We got a how-to video.06:00 — The savings numbers nobody wants to look at07:05 — How few of us actually have a pension07:45 — Part 3: Longevity, and why it's genuinely good news08:45 — Putting all three together09:15 — This isn't a prediction. It's happening now.09:55 — The good news: you already have what you need10:30 — Seventeen income streams, and why I'm not special11:05 — Why it's not Uber and it's not DoorDash11:45 — The real blocker: unlearning corporate12:45 — Low friction, high margin income13:40 — Go sell that first dollar14:05 — Don't bet on another 20 years in corporate14:45 — The opportunity sitting in your own backyard15:05 — Don't replace your job with a worse version of it16:00 — What changed inside the community16:25 — Nobody's judging you (my TikTok debut says hi)17:35 — The better you are, the more at risk you are18:20 — What the 20-somethings figured out that we didn't18:45 — How to reach me LINKS AND CTAThe 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

  5. Aug 22

    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

    9 Things I Learned in 6 Years Out of Corporate

  6. Aug 20

    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?

    Brett Trainor Unplugged

  7. Aug 12

    You Can Always Make More Money. You Can't Make More Time

    You can always make more money. You can't make more time. This is the episode that ties the whole thing together: what a time rich life actually is, and why control of your time, not your income, is the key to the life you want. My first year out of corporate, I chased one thing: replace the paycheck and then some. I did it. And I wasn't much happier. This is the story of what I was actually missing, and the simple framework that fixed it. In this episode: What a time rich life really is, and why money isn't part of it The four areas that actually move your happiness: connections, health, purpose, fun The "50 hours back" question that reframes everything The calendar mistake I made that was worse than corporate Define, Fund, Live: the three moves to get there Low-friction income: funding your life in the fewest hours If corporate has you trading every hour for a paycheck, this is your blueprint for taking the hours back. CHAPTERS / TIMESTAMPS 00:00 — What this episode answers, and why it matters 02:18 — Kicked out: I chased the money and wasn't happier 03:30 — What a time rich life actually is 04:44 — The "50 hours back" question 05:30 — The four areas: Connections and Health 07:07 — Purpose, and why "escape" was the wrong word 08:20 — Fun, and my two non-negotiable time blocks 09:24 — What control actually looks like (golf Friday, granddaughter over) 10:49 — Why it all comes down to time 12:00 — We overcomplicate making money 13:16 — The calendar problem, and losing the guilt 14:30 — Time blocking, and the 30-minute disaster (thanks Glaveski + Shirley) 15:38 — Learning to say no 17:52 — The four areas as your monthly barometer 19:20 — Money is a tool, not the goal (thanks Diana Alt) 20:03 — The framework: Define it, Fund it, Live it 22:24 — Funding the life: from fractional to low-friction income 25:00 — Two things you can do today LINKS & RESOURCES Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes The Time Rich Collective (connect with Gen Xers on the same path) → https://trp-collective.circle.so/checkout/the-time-rich-project-collective Website → https://timerichproject.life Mentioned in this episode: Steve Glaveski, author of Time Rich — earlier TRP episode Paul Shirley, The Art of Focused Work — earlier TRP episode Diana Alt on separating mission from money — recent TRP guest episode The "15 ways I've made money outside corporate" episode → https://youtu.be/p5rxv-f1M7k Listen / subscribe: Spotify → https://open.spotify.com/show/5UQSv8iKydo8E2cevuIAB5 Apple Podcasts → https://podcasts.apple.com/us/podcast/the-time-rich-project-formerly-the-corporate-escapee/id1469405998 Newsletter → https://trpnewsletter.beehiiv.com/

    You Can Always Make More Money. You Can't Make More Time

  8. Aug 1

    15 Ways I've Made Money Since Leaving Corporate

    Making money outside corporate is easier than landing your next corporate job. After a thousand-plus conversations with people leaving corporate, the blocker is almost never skill or experience. It's that we overcomplicate it. This one is all mechanics. If you're 45+ and trying to make your first dollar outside corporate, or just want to stop betting everything on one paycheck, this is the playbook. In this episode: Your real number: why you think in cash flow now, not salary, and why it's lower than you'd guess Why one boss is the riskiest bet you can make Separating mission from money so you fund the life without burning out 15 ways I've actually made money since leaving corporate, from higher-effort work to low-friction income anyone can start Three live examples with real numbers: the guy negotiating car deals, a wedding-dress business I built in 4 hours for $10, and the Amazon Influencer Program A simple four-part filter to score any idea: pay, demand, ease, repeatability Watch the version with slides on YouTube, or grab the deck from the resources below. Money is solvable. Time is the thing you can't get back. Stop trading so much of it. THE 15 WAYS (quick reference) Higher-effort income (monetize your corporate experience — great cornerstone accounts, but more hours): Fractional leadership Consulting (project-based) Solo consulting Advisory Business development (setting meetings for brands in your network) Reselling services for smaller brands Affiliate sales Audience-based (helps to have a following): 8. Sponsored posts 9. Paid community 10. Speaking 11. Paid content / brand sponsorships Low-friction income (anyone can start, small audience or none): 12. Paid workshops 13. Coaching (business, career, or a hobby — you just have to be a step ahead) 14. Facilitating webinars 15. User-generated content (UGC) Bonus area to dig into: AI services for business owners. THE FILTER (score each idea 1–10) Pay — how much per hour? Demand — is this a need-to-solve problem, not a nice-to-solve one? Ease — how fast and simple to deliver? Repeatability — can you do it again and again? LINKS & RESOURCES Watch this episode with the slides on YouTube → https://youtu.be/p5rxv-f1M7k Download the deck (the 15 ways + the filter) → https://stan.store/thecorporateescapee Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes The Time Rich Collective (connect with Gen Xers on the same path) → [COMMUNITY LINK — drop in] Website → https://timerichproject.life Mentioned in this episode: Unveiled + Unboxed (the wedding-dress project) → https://unveiledunboxed.com Megan's UGC course for Gen X and Boomers → https://stan.store/affiliates/bd030aba-a9a1-4f50-9073-45cc67b073f1 Tommy / Deliver (car-buying negotiation service) Wall Street Journal, "The Rise of Million-Dollar Companies With Just One Employee" → https://www.wsj.com/tech/ai/the-rise-of-million-dollar-companies-with-just-one-employee-f36a77c1 Amazon Influencer Program CHAPTERS / TIMESTAMPS 00:00 — Making money outside corporate at 45+ 01:00 — The real blocker: we overcomplicate it 02:20 — The five things this episode covers 02:50 — 1. Stop thinking salary, start thinking cash flow 04:00 — No pension, and becoming a high-functioning lazy person 05:00 — 2. Why one boss is the riskiest bet 06:45 — 3. Separate mission from money (thanks, Diana Alt) 07:50 — 4. The 15 ways I've made money (deck on YouTube) 08:30 — What low-friction income actually means 09:00 — Higher-effort: fractional, consulting, advisory, reselling 11:20 — For the record: I've spent $0 on marketing 11:40 — Audience-based: sponsored posts, community, speaking 12:20 — Low-friction anyone can start: workshops and coaching 15:00 — UGC: my favorite way to start 15:40 — The solo-business boom (WSJ) 16:10 — Solve one simple problem, not all of them 16:40 — AI services for business owners 18:30 — Example 1: Tommy negotiates car deals 20:30 — Example 2: the wedding-dress business I built in 4 hours 24:30 — Example 3: the Amazon Influencer Program 26:30 — The filter: pay, demand, ease, repeatability 27:50 — Don't chase shiny objects 28:40 — Money is solvable

    15 Ways I've Made Money Since Leaving Corporate
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About

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?

Information

  • Creator
    Brett Trainor
  • Years Active
    2019 - 2026
  • Episodes
    345
  • Rating
    Clean
  • Copyright
    © 2026 2019 B.T. LLC
  • Show Website
    Brett Trainor Unplugged

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