The Corporate Escapee: Sometimes You Gotta Say WTF

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 beforeTIMESTAMPS00:00 — 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 bookQUOTES"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?" — WesABOUT 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/1788464028Wes's site and services https://bio.site/weswhelessWes on LinkedIn — https://www.linkedin.com/in/wwheless/The Collective https://trp-collective.circle.soQuestions or guest ideas? [email protected]

This one's a step back to look at the big picture, because a lot of the Gen Xers I talk to are too busy living life to see it.Three things are colliding at once.Corporate is chaos. It's not your age, it's your expense. Somebody can do half your job for half the price, and that's who gets picked. Getting laid off is one thing. Getting back in is the real problem. Look around your own network if you don't believe me.The savings math. The generation before us had pensions. We got a 401k and a how-to video. Roughly half of Gen X has nothing put away, and the typical household isn't close to what 30 years actually costs.Longevity. This is the good news. If you take care of yourself there's a real chance you're looking at 30 or 40 more years, healthy and active.Put those three together and it doesn't add up.I'm not doing this to scare anybody. It's not a prediction, it's already happening. But there are two ways to react. You can treat it as a sunset and ride it out. Or you can treat it as the start of a second adult lifetime, which is the way I'm choosing to look at it.The back half of this episode is the part that matters: you already have everything you need to generate income on your own. The skills, the experience, the problem solving. What's in the way is unlearning what corporate taught you, and the fact that we make making money way more complicated than it needs to be.In this episode:Why it's your expense, not your 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 everythingTIMESTAMPS00:00 — 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 meLINKS 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.soEverything else https://BrettTrainor.comQuestions or episode ideas? Email me: [email protected] the show's useful to you, hit follow wherever you listen.GenX, laid off over 50, ageism at work, corporate layoffs, retirement math, 401k, longevity, second act, making money outside corporate, career change over 50, side income, Gen X retirement crisis

Corporate quit on me just over six years ago. At the time I thought this was about one thing: replacing my income. Six years, 350 episodes, and a whole lot of experiments later, I've figured out it was never really about the money. This is the first solo episode under the new name, and I wanted to start by sharing the nine things I've learned on this quest so far. Not a playbook. Not a system. Just the stuff that turned out to be true, whether you're still in corporate, recently laid off, or already out and still trying to piece it together. I don't have it all figured out. I'm a lot closer to where I want to be than I was six years ago, and I'm bringing you along for the rest of it. The nine: 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: [email protected] If you're getting something out of the show, hit follow or subscribe wherever you're listening. Still moves the needle. TIMESTAMPS Estimated from the transcript. Spot-check against the final cut, and shift everything by the length of your cold open plus sting. 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 is for Gen Xers who want to get one step closer to living the life they want—on their terms. After six years of building life beyond the default corporate playbook, thousands of conversations with Gen Xers, entrepreneurs, and experts, and features in Fortune, Fast Company, Forbes, Harvard Business Review, and Inc., Brett Trainor is still on the quest to build his ideal life—and he shares what he learns along the way. Part personal journal, part practical guide, and part curious conversation, this is a candid, lightly produced show about stripping away the noise, rejecting unnecessary grind, and seeing more of what is possible. Brett is a deconstructor, explorer, dot connector, and self-admitted high-functioning lazy person. Through solo episodes and unfiltered conversations with Gen Xers, founders, creators, and experts, he explores the decisions, habits, tools, tradeoffs, and ideas that can help you build a life you actually want to live. The conversations span the areas that make life worth living: money, mind and body, purpose, connections, possibility, and fun. There is no singular path. No hustle theater. No permission required. Just better questions, useful ideas, and real examples that help you see what is possible—and ask: Why not me?

You can always make more money. You can't make more time. This is the episode that ties the whole thing together: what a time rich life actually is, and why control of your time, not your income, is the key to the life you want. My first year out of corporate, I chased one thing: replace the paycheck and then some. I did it. And I wasn't much happier. This is the story of what I was actually missing, and the simple framework that fixed it. In this episode: 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/

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

Pro athletes know their career has an expiration date. Corporate never tells you yours has one too. Here's the part nobody says out loud: when corporate moves on from you, it usually isn't because your talent slipped. You just got too expensive. Gen X is the first generation facing this without a pension to catch us, and we're going to outlive the old retirement math by decades. So this episode borrows from the people who have been managing forced career transitions for 50 years: professional athletes. What do they lose when the game ends, and what can we take from their playbook? In this episode: The four things you lose when corporate retires you: identity, community, structure, and money Why "you got too expensive" is not the same as "you're done" The three-part transition: design the life you want, fund it, then live it The four areas to rebuild around: relationships, mind and body, purpose, and fun Separating mission from money so you don't burn out chasing the wrong one Becoming a high-functioning lazy person: funding your life in the fewest hours possible You've got another 30 good years, and 20-plus years of experience the athletes don't have. This is the sunrise, not the sunset. Let's build the plan. 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) → Website → https://timerichproject.life Mentioned in this episode: https://trp-collective.circle.so/checkout/the-time-rich-project-collective Paul Shirley (former pro basketball player and author) — earlier TRP episode Diana Alt — "separate mission from money" (recent TRP guest episode) ABOUT THE SHOW The Time Rich Project is for Gen Xers who paid their dues and are ready to write the next chapter. It's about taking back control of your time and funding the life you want in the fewest hours possible, so the rest of your time is yours. Real stories, real mechanics, no hustle. Hosted by Brett Trainor. CHAPTERS / TIMESTAMPS 00:00 — The parallel nobody talks about: pro athletes and corporate 00:50 — You didn't get worse, you got too expensive 01:30 — The first generation without a pension (and outliving retirement) 02:45 — The four things you lose when corporate retires you 02:55 — 1. Identity: who are you without the title? 03:40 — 2. Community: everyone misses the locker room 04:50 — 3. Structure: owning your calendar, and my time-blocking mistake 06:45 — Why it's called Time Rich 07:30 — 4. Money: funding the lifestyle instead of chasing a paycheck 09:00 — Turn the faucet up or down: your first dollar out 10:00 — Start with what you know, then go wider (UGC, AI, small services) 10:50 — Separate mission from money (thanks, Diana Alt) 11:50 — The pyramid: from C-suite to everyone else 13:40 — What we have that athletes don't: 20+ years of experience 14:30 — Sunset or sunrise: it's your call 16:30 — Designing the life: relationships and the no-asshole policy 18:15 — Mind and body: built to live to 90 18:40 — Purpose: follow the energy 19:40 — Fun: are you getting enough of it? 20:00 — Funding the life you designed 21:00 — Living it: the 80/20 way 22:00 — Design, fund, live: putting it together

"Work should feel good. Not a long, slow march to oblivion." That's Diana Alt, and it's the perfect line to open our first guest episode under The Time Rich Project. Diana is an executive and career coach who came out of tech. She works with people who are still in corporate and quietly wondering if this is it. Her take lines up with where this show is headed: corporate isn't the enemy. It's a client. You get to decide if the deal still works for you. We got into: The four cornerstones of an aligned career (right work, right boss, environment, culture) and how to spot which one is actually broken Why burnout comes more from misalignment than from long hours "The hardest boss to fire is you," and why building a business you hate is easier than you'd think Mission vs. money: don't burn down the thing paying the bills to chase the thing that lights you up Why anyone with 10+ years of experience should have an LLC in their back pocket The only two things you need to make your first dollar on your own: an offer and a way to get paid If corporate has stopped feeling good, this one gives you a way to figure out why, and what to do next. GUEST: DIANA ALT Executive and career coach helping people build work that aligns with who they are, in corporate or on their own. Host of the Work Should Feel Good podcast. * Podcast & site: https://workshouldfeelgood.com * Newsletter: https://dianaalt.com (click the "Let's Connect" button) * LinkedIn: Diana Alt, the No BS Coach: https://www.linkedin.com/in/dianakalt/  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: * Working Genius (Patrick Lencioni) — the six genius types * Time Rich by Steve Glaveski * Grace McCarrick — soft skills coach CHAPTERS / TIMESTAMPS 00:00 — First guest under the new name (and how we found each other) 01:15 — Fountains and drains: choosing who you spend your time on 02:10 — Who Diana is: work should feel good 04:05 — Your company isn't your boss, it's your only client 05:00 — The biggest flex in business: firing what isn't aligned 07:00 — The hardest boss to fire is you 07:30 — The four cornerstones of an aligned career 10:40 — Why burnout is about alignment, not just hours 16:00 — The 50-hour week and how little of it is real work 16:50 — Someone says "I'm done." Now what? Find what's actually broken 20:30 — Agency, victim mode, and the clients Diana won't take 23:00 — Good people who lost confidence in what they're great at 28:30 — Diana flips it: what to build for time freedom 29:00 — Owning your calendar, and the time-blocking experiment that failed 31:40 — The scorecard: relationships, health, purpose, fun 34:00 — Low-friction income and becoming a high-functioning lazy person 35:50 — The car-buying guy doing $300K a month 36:40 — Mission vs. money: don't burn down the day job 39:50 — Everyone should have an LLC in their back pocket 42:40 — You only need two things to start: an offer and a way to get paid 44:10 — Where to find Diana

For six years I thought I was running from corporate. Turns out I was chasing the wrong thing. Welcome to The Time Rich Project. Same host, evolved mission, new name. This is the first episode under it, and I get into why the change and why it matters if corporate has stopped working for you. Here's the shift: I wasn't escaping corporate. The real unlock was taking back control of my time. Once I had that, everything else opened up. In this episode: Why Gen X is at a crossroads (and why it's a bigger opportunity than getting out) Sunrise, not sunset: you could have 30+ good years ahead, so what do you actually want to do with them? The four things that decide your happiness: relationships, health, purpose, and fun Return on hours: how to fund the life you want in the fewest hours possible Why your first dollar outside corporate is easier to make than they told you The time-blocking experiment that failed twice before it worked You don't have to quit corporate to start living better. You do have to get intentional about your time. Corporate isn't the enemy. It's a deal. This show is about going in eyes wide open and deciding for yourself if it's still worth it. Do what you want, when you want, where you want, with who you want. That's the whole thing. Let's go get it. TRP Collective: https://trp-collective.circle.so/checkout/the-time-rich-project-collective  https://stan.store/thecorporateescapee CHAPTERS / TIMESTAMPS 00:00 — Why the name changed (again), and why this one sticks 02:24 — The real unlock: I stopped chasing paychecks and took back my time 04:39 — The Gen X crossroads: career, family, and the retirement myth 06:53 — Sunrise, not sunset: 30+ years to do what you actually want 08:20 — The four things that make you happy: relationships, health, purpose, fun 11:43 — How to check in on the four without turning it into a spreadsheet 13:10 — Return on hours: making the money you need in the fewest hours 16:30 — Make your first dollar outside corporate (easier than they told you) 18:53 — My time-blocking disaster, and what finally worked 21:15 — What you want, when you want, where you want, who with

Janice Porter has been on LinkedIn since 2004, hosts the Relationships Rule podcast (368+ episodes), and has spent almost two decades teaching solo operators the part of business most of us got wrong in corporate: the relationship part. In this conversation, Janice walks Brett through her REAL Connection System, a four-part framework for solo escapees who'd rather build a business through referrals than spend their week shouting into the LinkedIn algorithm. It's a refreshingly old-school playbook for a world that's getting more synthetic by the month. They dig into why direct mail to strangers gets a 1% open rate while cards in envelopes hit 99.5%, the story of the CMO who sent $5,000 in chocolates and closed $12 million in deals, and why the rental company owner who shifted from "send to get" to "send to give" went from zero replies to a full pipeline. If you've been treating networking like a phase to get through instead of the actual work, this episode is the reset. For most solo escapees, 95% of their business will come from referrals. This is the playbook for earning them. What you'll learn 🎯 The REAL Connection System (Refresh, Engage, Appreciate, Leverage) explained step by step 🎯 Why Googling yourself in an incognito window is the first thing every escapee should do this week 🎯 The 5-comments-a-day move that beats posting (and where to actually leave them) 🎯 The "send to give, not to get" mindset shift that turns cold outreach into real relationships 🎯 How to leverage your first-degree connections for warm intros without being weird about it 🎯 Why "human-to-human" is the move in an AI-augmented world Quotable moments "Don't send to get. Send to give." "95% of solo business comes from referrals." "Direct mail to strangers: 1% open rate. A card in an envelope: 99.5%." "How you do anything is how you do everything." "Don't be attached to the outcome. Just keep moving." Resources mentioned 📋 Janice's REAL Connection System (free ebook): janiceporter.com 🎙️ Relationships Rule Podcast: [LINK] 💼 Connect with Janice on LinkedIn: Janice Porter (mention you heard her on TCE) 📬 Send Out Cards: sendoutcards.com Connect with Brett 📰 The newsletter (10K+ GenXers building life-first futures): [NEWSLETTER LINK] 🐬 The Escapee Collective. First month $1: theescapeecollective.com

Episode Description Megan Collier (@megan_ugc, 300K+ on TikTok) is back on The Corporate Escapee for a Round 2 conversation, and the market has shifted under our feet. UGC, user-generated content, is now a real path to $2K to $15K a month for people who've never been in front of a camera. And the demographic brands are scrambling to find isn't 25-year-old influencers. It's GenX. Megan walks through what she's calling the "trust recession." Polished ads are losing. Real faces, messy houses, lived experience are winning. New state laws are fining companies for undisclosed AI-generated content. The result: human creators just got more valuable, not less. Brett and Megan dig into the cat litter brand story (where Megan got rejected, then called back asking for her 65-year-old mom instead), why GenX experience is the unfair advantage brands need right now, and the four-step play to land your first UGC deal this month using products you already own. If you've been waiting for the "what would I actually do" piece of escaping corporate, this is one of the cleanest entry plays going. What you'll learn 🎯 Why "we're in a trust recession" and what it means for anyone making content 🎯 The four-step outreach play (notes app, Instagram ad audit, Loom video, brands you already use) 🎯 Why your age is the asset brands are paying double for right now 🎯 How to land your first deal even if you've never been on camera before 🎯 The Loom pitch script that converts way better than cold email Quotable moments "We are in a trust recession." "The ageism you felt in corporate is the exact thing brands are paying for in marketing." "Just figure out how to make that first dollar outside of corporate. I don't care if it's 25 bucks." "You don't need followers to do this. You need to be a real human in a world full of AI." "The skill that got you fired is the skill that's about to get you paid." Resources mentioned 📋 Megan's free UGC checklist: [STAN STORE LINK] 🎓 Megan's UGC course ($87, lifetime access): [COURSE LINK] 📱 Follow Megan on TikTok and Instagram: @megan_ugc

Episode description: GenX is elite at overcomplicating making money. A Millennial gets a side hustle idea and is live by Sunday. A Gen Z is already filming the TikTok. A GenXer opens a Google Doc, then a spreadsheet, then researches LLC structure, then goes to bed. Brett admits he's been part of the problem. For years he's preached solo consulting and fractional work as THE path out of corporate. It's a real path. He still believes in it. But it's not the only one, and it's not the fastest one. In this episode, Brett walks through 8 service businesses a GenXer could start running this weekend. None of them require corporate experience. All of them work on the same model: find a known, friction-heavy problem, solve it for $500-$1,000, and stack the deals. He breaks down the proof points (Tommy at Delivrd doing 300 car negotiations per month at $1K each, plus a friend billing $15K/month on credit card points optimization), walks through the filter for what makes a good escapee service, and runs through the full list from subscription audits to federal subcontracting to the Escapee Starter Pack. If you're still trying to figure out your "big idea," this episode is the reframe. 🎯 What you'll learn: 🎯 Why solo consulting isn't the only path out of corporate  🎯 The $500-$1,000 "stack the deals" model and why it works  🎯 The 6-point filter for a good escapee service business  🎯 8 specific service businesses you could start this weekend  🎯 Tommy's $300K/month service business and what it reveals about every other category  🎯 The federal subcontracting sleeper play (full episode coming) Resources mentioned: 🐬 Join the Escapee Collective for $1 your first month: theescapeecollective.com  🎧 Subscribe to The Corporate Escapee Podcast wherever you listen  Quotable moments: "GenX is elite at overcomplicating making money." "You don't have to be light years ahead of somebody to teach them or offer a service. You just have to be slightly ahead of where they are." "Find a known, friction-heavy problem. Solve it for $500 to $1,000. Stack the deals. That's the whole game." "Tommy didn't invent anything. He just found a friction-heavy problem and charged people to make it go away." "When I was in corporate, I paid somebody to do my expense reports for me every month. Was I capable? Yes. Did I want to? No. That's the whole secret."

No one is coming to save you. Not your company. Not HR. Not the next reorg, promotion, or administration. That's not doom and gloom. That's actually the good news. Because once you accept it, you stop waiting. You stop hoping. And you start doing something about it. In this solo episode, Brett walks through the single mindset shift that changes everything for corporate professionals, whether you're planning your escape or staying right where you are. You're not an employee. You never were. You're the owner of a one-person business, and your employer is just your first and only client. Same job. Same paycheck. Completely different relationship to it. Then Brett walks you through the One Client Audit, the exact framework he uses with escapees inside the Collective. Six questions. Thirty points. By the end you'll know whether the client you're working for is worth keeping, worth renegotiating, or worth firing. This episode is for the still-in-corporate crowd, the recently laid off, and anyone who's tired of living a completely reactionary work life.   👉 Run the audit yourself. Grab 3 free frameworks to take control of your work and your life: the One Client Audit, the What Do You Really Want Worksheet, and the 5Fs Scorecard. → https://stan.store/thecorporateescapee   What you'll learn: 🎯 Why "nobody is coming to save you" is the best news you'll get this year 🎯 The mindset shift that takes you from reactionary to in charge (whether you stay in corporate or leave) 🎯 The six-question One Client Audit you can run on your employer tonight 🎯 The three owner's moves: renew, renegotiate, or fire 🎯 How the hidden cost of your job is bigger than your paycheck 🎯 Why running your corporate career like a business is the prep work for running an actual one 🎯 Plus: grab the One Client Audit, the 5Fs Scorecard, and the What Do You Really Want Worksheet free in the show notes Quotable moments: "No one is coming to save you. Not your company, not HR, not your manager, not the economy, not the next reorg." "You are not an employee. You never were. You're the owner of a one-person business. Your employer is your first and only client." "Same job. Same paycheck. Completely different relationship to it." "Trying to keep a corporate career is going to be harder than starting your own business, especially if you start running your career in corporate like it is a business." "You've already done everything you'd have to do if you went solo. Landing a corporate job is harder than landing a client." Resources mentioned: 📋 Download 3 free frameworks (One Client Audit, What Do You Really Want Worksheet, 5Fs Scorecard): https://stan.store/thecorporateescapee 📬 Join 10,000+ readers of The Escapee Insider newsletter: escapeeinsider.beehiiv.com 🐬 The Escapee Collective (first month $1): theescapeecollective.com Connect with Brett: 🎙️ Subscribe to The Corporate Escapee Podcast wherever you listen 📬 Newsletter: escapeeinsider.beehiiv.com 🔗

The Setup Six-plus years ago, when corporate quit on Brett, the goal was simple: make more money than corporate was paying him. That was it. Money, money, money. It took two years to realize money was never the real prize. What he was actually chasing was control. Freedom. The ability to design a life where work fit into it, instead of 25 years of life fitting around the job. Most of us spend a lot of time thinking about the escape — the transition, the layoff, the leap. Not enough time thinking about what life actually looks like on the other side. And here's the thing: you can't build a future you can't picture. Most of us have never been given permission to picture one. That's what this episode is for. What You'll Get In This Episode A definition of a Life First Future, the contrast with the corporate-first life most of us have been living, and a four-step exercise to help you actually see your own. Grab a notebook before you press play — you're going to use it. Key Concepts The shift Brett didn't expect. It wasn't more money that changed everything after corporate. It was realizing he was getting more done by noon working for himself than he used to get done in full days inside the system. Strip out the unnecessary meetings, the fire drills, the commute, the reorgs — and the time you've been giving away comes back. Corporate-time vs. Life-time. Corporate trained us to think in fiscal years and 2-to-4-year promotion cycles. The Life First Future requires thinking in 5-, 15-, and 30-year horizons. That's not a small reframe. It's the entire game. Why "energy" beats "purpose" or "passion." Most people get stuck looking for the One Thing that lights them up. Brett spent six years monetizing his corporate experience eight different ways before landing on The Corporate Escapee. The signal that kept him moving wasn't passion — it was energy. Each move gave him more energy than the last. That's the real compass. You're not designing a fantasy. You're using 25 years of evidence. This isn't a 25-year-old's exercise. We have something better than time — we have data. We've lived enough to know what energizes us, what drains us, and what corporate actually delivers (and doesn't). The 4-Step Ideal Life Framework Step 1 — Map Four Milestones Today. 5 years. 15 years. 30 years. For each, answer four questions: Where am I living? Who am I with? What am I working on (if anything)? How do I feel each morning? This is a living document — Brett's been doing it for years and it still evolves. Step 2 — Find Your North Star Look across the four milestones for what stays the same. The patterns are your non-negotiables. Don't get hung up on finding your "passion" — chase the things that give you energy, and follow them as they evolve. Step 3 — Connect Today to Tomorrow Every decision becomes a filter: does this move me toward my North Star or away from it? (Brett goes deeper on this in Episode 2.) Step 4 — Write Your Vision Statement One guiding sentence. Revisit quarterly. Brett does this with his wife as a quarterly business review — a session that fundamentally changed how he runs the post-corporate life. Brett's Real-World Life First Schedule (mentioned in the episode): 6–8 AM: Deep work, client work, strategy 8 AM: Gym (six days a week, non-negotiable, no meetings before 10) Friday afternoons: Golf Granddaughter time, family dinners, vacations on his schedule Result: more done by noon than he used to do in full corporate days The Bottom Line A Life First Future is one where your time, energy, and decisions are organized around the life you actually want — and your work fits into that, not the other way around. Define it first. Build toward it second. Episode 2 covers the how. If this episode hit, the best way to help is to subscribe wherever you listen — Apple, Spotify, Overcast, Pocket Casts — and share it with one who needs to hear it. Get Busy Living

This one is personal. Brett flies solo to deliver the one thing he wishes someone had told him when he was still inside corporate grinding it out and telling himself it was the responsible thing to do. You already have permission. Permission to want something different. Permission to design a life where work fits into it instead of the other way around. Permission to stop waiting for corporate to decide your future and start building one on your own terms. Nobody is coming to give it to you. So Brett does. What You'll Learn 1️⃣ Why corporate conditions you to ask for permission for everything — and how that conditioning follows you home long after you leave 2️⃣ The hidden cost of corporate that goes way beyond the paycheck — time, energy, identity, and control 3️⃣ What living life on your own terms actually looks like in practice — the real daily routine not the highlight reel 4️⃣ Why the chaos of going solo is temporary and what comes after it 5️⃣ How Brett went from scheduling every 30 minutes — which was worse than corporate — to finding his actual rhythm 6️⃣ Why the gym at 8am every morning is possible when you own your calendar and impossible when corporate owns it 7️⃣ Why you don't have to wait for corporate to kick you out to start designing something different 8️⃣ The only thing actually standing between you and the life you want Key Quotes "Life is too damn short to follow somebody else's plan." — Brett Trainor "I'd rather be homeless than go back to corporate." — Laine, Escapee Collective Member "The only thing stopping you is you. And it doesn't have to be a perfect plan. Done is better than perfect." — Brett Trainor "Give yourself permission to want something more. Because nobody else is going to give it to you." — Brett Trainor Your Permission Slip You have permission to want more than what you have right now. You have permission to design a life where work supports you instead of consuming you. You have permission to find out what's actually possible when you stop waiting for corporate to decide your future. Connect With Brett Ready to stop waiting and start building? The Escapee Collective is the community for ex-corporates taking control of their future and getting busy living.

Most people leave corporate and immediately chase the familiar paths — consulting, coaching, fractional work. Those are valid. But they take time, runway, and a warm network. In this episode Brett breaks down three unexpected ways GenXers are generating real income right now, using skills they already have, without needing a big audience or startup capital. The backdrop is an AI world that most people are reading completely wrong. AI didn't shrink the opportunity for skilled humans — it exploded it. Because now there's an entire population of people who are aware of their problems, have access to the information, and will still pay someone else to just handle it. WHAT YOU'LL LEARN ✅ Why AI makes YOUR corporate skills more valuable, not less ✅ The "skill flip" model — how to charge for what you already know ✅ What UGC is, why GenX is uniquely positioned for it, and how to start ✅ How to turn what you know into paying clients without building a course empire ✅ Why your first dollar outside corporate changes everything THE 3 PATHS 01 — The skill flip Tomi Mikula spent 10 years on the dealer side of car sales. He now runs Delivrd — charging consumers $1,000 flat to negotiate car deals on their behalf. 300 customers a month. $300K in monthly revenue. His customers could use AI to do what he does. They pay him anyway. Because the problem was never information — it was execution, accountability, and not wanting to deal with it. That's the model. Find a high-stress transaction, one side has information the other side doesn't, and charge to be the expert in the room. HR disputes, salary negotiation, medical billing, contractor bids — it's everywhere. 02 — UGC (User Generated Content) Brands are paying real people — not influencers — to record short videos about products they actually use. No following required. Platforms like Billo and JoinBrands connect brands with creators, paying $150–$500 per video. GenX is ideal for this: authentic, credible, and speaks to a demographic most brands can't reach. Brett just signed two deals in one week for just under $1,000 combined. You don't need an audience. You need a phone, a face, and something real to say. 03 — Teaching what you know Not a course empire — just solving one specific problem for one specific person who's standing exactly where you were. The AI translation angle is huge right now: small business owners know they're falling behind and will pay someone who speaks both business AND AI to help them catch up. And you don't need to be far ahead — you just need to be far enough ahead. The people in Brett's community who are winning fastest are teaching hyper-specific things to people one or two steps behind them on the journey. MEMORABLE QUOTE "The problem was never information. It's about execution, accountability, and people just not wanting to deal with it. Your 20 to 30 years of corporate experience puts you right in the middle of that opportunity."

Kristen Hamborg is six weeks out of a 25-year corporate interior design career — and she's never looked back. In this episode Kristen shares how burnout, a pandemic pivot, and a coaching certification she pursued on the side slowly shifted everything. Unlike most escapees who get pushed out Kristen made the decision herself — and she'll tell you exactly what it took to get there. This one is for anyone still in corporate feeling the slow fade of work that used to light them up. What You'll Learn 🎯 How Kristen recognized the burnout before it broke her — and what finally pushed her to act 🎯 Why she pursued a coaching certification during the pandemic and what it unlocked 🎯 How every single client she has landed came through referrals — no ads, no cold outreach 🎯 The identity shift that happens when you leave a career that defined you for 25 years 🎯 Why creativity isn't just art — and how corporate professionals are more creative than they think 🎯 What it actually feels like in the first six weeks — the excitement, the fear, and the glass case of emotions 🎯 Why you don't have to do this alone — and why the right community changes everything 🎯 How Kristen is already thinking big with her first virtual retreat just months into her solo journey Key Quotes "If your gut is telling you something is off — it is off. Don't sit in it alone." — Kristen Hamborg "We all have this fear of not enoughness. But you have to get there and trust that you can do it." — Kristen Hamborg "Comfortable isn't always good. Getting outside your comfort zone is where the growth happens." — Kristen Hamborg About Kristen Hamborg Kristen Hamborg is a coach and feng shui practitioner helping women navigate major life and career transitions. After 25 years in corporate interior design she made the leap to build something of her own — six weeks in and already building toward her first virtual retreat. LinkedIn: https://www.linkedin.com/in/kristenhamborg/ 📧 [email protected] Connect With Brett If Kristen's story resonated and you're ready to stop watching from the sidelines — The Escapee Collective is the community built for corporate professionals who are done waiting and ready to build something of their own. 👉 Join us at theescapeecollective.com Get Busy Living.

Danielle Burken escaped corporate in September 2023 — but her journey started six years before that. In this episode Danielle shares how she went from a full-time agency job with two kids under two, to building a six-figure solopreneur business in under 90 days by doing one thing most corporate professionals never do: listening to what people were already asking her for and charging for it. She also breaks down human design — what it is, why it works, and how she uses it to help entrepreneurs build businesses that are aligned with how they naturally operate. If you've ever felt like you're forcing something that should feel easier, this episode is for you. What You'll Learn 🎯 Why Danielle tried to escape corporate for six years before it finally clicked 🎯 The exact moment she realized she was sitting on a business nobody told her to build 🎯 How she landed her first clients using a local networking group — no social media, no ads, no cold outreach 🎯 Why overthinking your offer is the #1 thing keeping corporate escapees stuck 🎯 What human design actually is and why it's not as woo as it sounds 🎯 How she built her business during Tuesday nights at Panera while her husband handled bedtime 🎯 Why confidence comes from doing — not from waiting until you feel ready 🎯 The push that finally got her to put in her notice — and why timing matters less than decision Key Quotes "I trusted so deeply that I was going to be caught. And I was." — Danielle Burken "Business gets to be easy and fun. We just weren't taught that in corporate." — Danielle Burken "Anybody exiting corporate has the skills to do it. They're overqualified. They just need to go have the conversation." — Brett Trainor About Danielle Burken Danielle Burken is a human design-based business coach and marketing strategist who helps solopreneurs build sustainable businesses in alignment with how they're naturally wired to operate. She escaped corporate in September 2023 and built a six-figure business in her first year. 🌐 Website: https://www.danielleburken.com/  📱 Instagram: https://www.instagram.com/danielleburken_/  Connect With Brett Ready to stop watching from the sidelines and make your move? The Escapee Collective is the community built for corporate professionals who are done with corporate and ready to build something of their own. 👉 Join the conversation at theescapeecollective.com

Corporate is using AI to eliminate jobs. Escapees get to use it to multiply themselves. In this solo episode Brett pulls back the curtain on exactly how he runs his entire business with AI — the tools, the use cases, and the honest truth about what it can and can’t do. He also covers the single biggest opportunity most escapees are missing right now — helping small and midsize businesses actually leverage AI. Not programming. Not building agents. Bringing the business judgment that 20+ years of corporate experience gives you and marrying it with the right tools. That’s the superpower. And right now, the market is wide open. What You’ll Learn • How Brett uses AI daily — content editing, research, strategy, operations and more • Why AI is a content editor not a content creator — and why that distinction matters • The SMB opportunity — 88% of small business owners know they need AI, only 14% are doing something about it • Why the real value is pairing business judgment with AI — not programming • The EAD framework — Eliminate, Automate, Delegate • Brett’s current AI stack and exactly what each tool is used for • Why he switched from ChatGPT to Claude — and what that decision taught him about auditing your tools Key Timestamps • 00:00 — Intro: Corporate is using AI against you. Here’s how to flip it. • 01:00 — How Brett uses AI in his own business every day • 02:00 — AI as content editor not content creator — keeping your voice • 03:30 — Podcast production: from a full day to under an hour • 05:00 — AI as strategy and thought partner • 07:00 — The SMB opportunity — the 74% gap nobody is filling • 09:00 — Flex staffing + AI — why small businesses don’t need full-time hires • 11:00 — The EAD framework: Eliminate, Automate, Delegate • 14:00 — Brett’s AI stack: Claude, Perplexity, Gemini, Canva, Riverside • 16:30 — Close: The one-person army is here. Are you using it? Brett’s AI Stack • Claude — Primary thinking partner, content editor, strategy, writing, business frameworks • Perplexity — Deep research, stats validation, sourced intel • Gemini — Currently testing; Google ecosystem integration • Riverside.fm — Podcast recording, editing, transcription, show notes • Canva — AI-assisted graphics and visuals • Durable — AI website builder (used for Small Business Hotline landing page) Enjoyed This Episode? If you’re using AI in an interesting way as a solopreneur or escapee Brett would love to hear from you — and potentially have you on the podcast. Drop him a note at [email protected]. Please share this episode with someone who needs to hear it — and subscribe on your favorite podcast platform. The old school way still works.

The 4 Real Paths to Replace Your Corporate Income Most corporate escapees think they only have two options: find another job or figure out how to start a business from scratch. But there are actually four legitimate paths to replacing your corporate income — and one of them is seriously underrated. In this solo episode, Brett breaks down all four paths and then goes deep on the one he doesn't talk about nearly enough: franchising. If you've been thinking about leaving corporate but the blank page feels too risky, this episode is for you. The 4 Paths: 🔹 Path 1 — Go Solo: Consulting, fractional, advisory, coaching, content. Monetize what you already know. Lowest barrier to entry, no investment required, and you can start while still in corporate. Brett's lane — and the focus of most of this podcast. 🔹 Path 2 — Start a Business: Build something from scratch. A passion, an idea, an agency. Full ownership but requires capital, time, and infrastructure. Often the natural evolution of going solo. 🔹 Path 3 — Buy a Business: Acquire an existing operation with revenue already in place. Faster path to cash flow but requires serious due diligence, capital, and comfort with complexity. 🔹 Path 4 — Buy a Franchise: Get into a proven system with a built-in playbook, training, support, and brand. A business in a box — and the focus of today's episode. Why Franchising Makes Sense for Corporate Escapees: Most people picture Subway or McDonald's. That's not the conversation. There are thousands of franchise concepts across senior care, home services, B2B services, fitness, wellness, and more — and many of them map directly to the skills you built in corporate. What you're actually buying is a proven playbook: operating systems, customer acquisition, marketing support, training, and a network of franchisees who've already solved the problems you'll face. Brett covers: Why franchising is a business model, not an industry The real pros: faster path to revenue, built-in support, proven model, equity building, franchisee community The real cons: upfront investment, royalty fees, operating within someone else's system Why your corporate skills — P&L, leadership, process thinking, client relationships — transfer directly The ownership reframe: a job pays you, it doesn't build an asset How platforms like Franzy and coaches like Entrepreneurial Source can help you research and find the right fit Key questions to ask yourself before going down this path Connect with Brett & The Corporate Escapee: 🌐 TheEscapeeCollective.com If this episode opened your eyes to a path you hadn't seriously considered — share it with someone still sitting in a corporate job wondering what their options are. That's exactly who this is for. And if you've made it this far — please subscribe. It helps more escapees find the show. Live Life First. 🐬✌️

750 layoffs a day. No, that's not a typo — and it's not slowing down. Brett sits down with Steve Jaffe, marketing veteran and author of The Layoff Journey: From Dismissal to Discovery, to talk about what most career books completely skip: the emotional and psychological toll of losing a job — and why processing that first is the key to what comes next. Steve was laid off four times over a 30-year career. His first layoff took him years to recover from. His last one in 2023? Water off a duck's back. The difference? He finally understood what he was actually experiencing: grief. This one is for anyone who's been laid off, is worried about being laid off, or is watching colleagues get cut and wondering when it's their turn. In this episode: Why January 2026 had the highest single-month layoffs since 2009 — and why the job market isn't bouncing back How layoffs became a business strategy instead of a last resort (and what that means for your career security) The stages of grief that apply to job loss — and why skipping them is costing people months of their job search Why the "myth of meritocracy" is one of the most dangerous things to believe in corporate The identity crisis that hits when your job title is your identity — and how to separate the two What Gen Z is getting right about corporate that older generations sacrificed Steve's pivot from laid-off marketing exec to published author — without a Plan B in place first Why having a side hustle isn't just a trend — it's now a survival strategy About Steve Jaffe Steve spent 30 years in marketing and advertising — from West Coast ad agencies to in-house brand roles, including work on the iconic What Happens in Vegas Stays in Vegas campaign. After being laid off four times, he channeled those 10,000 hours of experience into his book, The Layoff Journey: From Dismissal to Discovery — a practical, grief-informed guide to navigating job loss without losing yourself in the process. Resources mentioned: 📖 The Layoff Journey: From Dismissal to Discovery — available on Amazon and wherever books are sold 🌐 Website & free chapter download: https://thestevejaffe.com/ 💼 Connect on LinkedIn: Steve Jaffe: https://www.linkedin.com/in/jaffesteve/  Connect with Brett & The Corporate Escapee: 🌐 TheEscapeeCollective.com If this episode resonated, share it with someone who's currently in the middle of a layoff — or someone who should probably start building their Plan B now.

There's a Lit song that's been stuck in my head for weeks: "My Own Worst Enemy." And it's the perfect metaphor for my entire solo journey. I've blocked myself at every stage—consulting, fractional leadership, and now with The Escapee Collective. Not intentionally, but by doing what corporate trained me to do: overanalyze, overstructure, and wait for perfection before taking action. In this episode, I walk you through the three times I made the same mistake—and what I'm doing differently now. If you're overthinking, over-structuring, or waiting for the "perfect" website, pitch deck, or system before you start—this one's for you. In This Episode: The consulting mistake: Building the perfect website, pitch deck, and pricing before having a single conversation with a client (and why it led to zero wins) The fractional repeat: Doing the EXACT same thing again—new methodology, new deck, same lack of results The Escapee Collective lesson: How TikTok took off with zero plan, then how I complicated it again with masterminds, classes, and modules—and why I had to simplify Why corporate trains us backwards: Plan first, act second works in corporate—but solo requires the opposite What actually works: Conversations, experimentation, messy wins FIRST—then structure The 79% reality: Why most burned-out corporate workers won't take action (and how to be in the 35% who do) How to catch yourself: Recognizing when you're building systems before you have proof Key Takeaway: Action beats planning. Momentum beats perfection. Get early wins first—THEN build the structure around what's working.

Fractional work is exploding — and it’s still confusing for a lot of corporate escapees. In this Featured Speaker session inside the Escapee Collective, John Arms breaks down Fractional 101 in plain English: what fractional really is, who it’s for, how to get clients (spoiler: it’s not campaigns), and what you can realistically charge. If you’re still in corporate, recently laid off, or already freelancing and want more stability, this is the clearest “how it works” primer you’ll hear. What you’ll learn • The “W2 → 1099 bridge” and why more people are getting pushed across it • Why fractional is mostly a referral-based business (and what to do with that) • The mindset shift: conversations, not campaigns • John’s simple relationship model: the “10-person circle” (fractionals, independents, super-connectors) • What companies actually care about (hint: pain, not the definition of fractional) • Typical pricing and why fractional often lands in the $8K–$10K/month retainer range • Why fractional is proactive leadership, not “wait to be told what to do” • The “project first” entry strategy — and why it usually turns into ongoing leadership • How to reconnect with old contacts without being weird or salesy • The core principle: get involved with other people’s success Notable moments / lines you’ll remember • “You’ll work for the people you get referred to.” • “Referrals come from conversations, not campaigns.” • “Fractional is leadership — solve it and keep it solved.” • “Most barriers are fear and assumptions… it’s hard work, but it’s not complicated.” Resources mentioned • The Go-Giver (Bob Burg) • The NCG Factor (Larry Kaufman — Network, Connect, Give)

Jon the Escapee Collective! What keeps 79% of corporate professionals stuck isn't lack of skills or opportunity—it's something deeper. In this solo episode, Brett shares the story of landing his first client, making good money, and then doing something that still makes him cringe: convincing that company to hire him full-time. Nobody forced him back. He walked himself in. This mistake cost him 18 months and taught him the hard truth: leaving corporate is tactical, but breaking your dependency on it is psychological. Brett breaks down what corporate dependency actually is (hint: it's not just the paycheck), why going solo alone reinforces that dependency, and the two critical milestones that finally sever the tie. If you're still in corporate and thinking about making a move—or you've already left but still feel the pull—this episode will help you understand what you're really up against and how to break free for good. What You'll Learn: Why corporate dependency is psychological, not financial The three things you're actually dependent on (and it's not what you think) Why isolation amplifies doubt and keeps you stuck The two milestones that break corporate reliance How to avoid the mistake that sent Brett back 18 months Why community matters more than tactics when going solo Key Quotes: "I hadn't really thought about why I did it, but it was really my dependence and my reliance on corporate." "What I really broke it down into three areas: I wanted control of my future, control of my money, and control of my time." "When you go alone, you have nothing else except yourself to talk you in or out of what you're doing." "Once you get to the point where you're confident that you can bring in that next deal, you know you're never going back." "I wasn't escaping corporate per se. I didn't have to stay there. I had options." Resources Mentioned: The Escapee Collective: Join Brett's community Subscribe & Connect: If this episode resonated with you, please subscribe to The Corporate Escapee Podcast on your favorite platform. New episodes drop multiple times per week featuring guest interviews and solo deep-dives like this one. Looking to break your corporate dependency? Visit TheEscapeeCollective.com to connect with others on the same journey.

Corporate isn’t stabilizing—and that matters if your income still depends on it. In this solo episode, Brett breaks down three trends shaping the Escapee economy in 2026: a corporate metric that’s quietly driving layoffs, the rapid expansion of revenue streams outside corporate, and why small businesses are moving away from full-time hires in favor of fractional and specialist talent. If you’re still in corporate, this episode helps you see what’s coming. If you’ve already escaped, it explains why demand for your experience is only growing. This episode is for you if: You’re questioning whether corporate is still a safe long-term bet You want practical ways to monetize your experience outside a job You’re curious how small businesses are really hiring and growing now The 3 trends covered in this episode Trend #1: The metric driving modern layoffs — Revenue Per Employee (RPE) Why boards and executives are fixated on RPE, how it incentivizes headcount reduction, and why even “healthy” companies continue cutting roles. Trend #2: The explosion of revenue streams for escapees Fractional leadership, consulting, advisory, UGC, content creation, mentoring, and more—why monetizing what you already know is the fastest, lowest-friction path to income. Trend #3: The small business go-to-market model is changing Why businesses are ditching traditional silos, hiring specialists instead of full-time staff, and how this shift creates long-term opportunity for experienced operators. Key takeaways • Corporate risk is structural, not cyclical • Escapees have more income options than they think • Small businesses want outcomes, not headcount • Your experience is often more valuable outside corporate than inside it If this episode helped you rethink corporate risk or life after it, connect with Brett on LinkedIn or email him at [email protected]. And if there’s a topic you want covered in a future solo episode, let him know.

Ashley Evenson returns for her third appearance on The Corporate Escapee Podcast — and this time it’s a real update from the field. Two years into her escape, she breaks down what actually helped her land fractional work, what surprised her, and the biggest mistake most new escapees make once they get busy. This is a practical conversation about network-first business development, creating momentum without feeling “salesy,” and why the long game matters more than the perfect plan. What you’ll learn • How Ashley landed her first fractional roles through her existing network • Why “pick your brain” beats cold outreach for most escapees • The content → connection flywheel: using LinkedIn engagement to reopen relationships • What fractional work can feel like behind the scenes (and why it can get lonely) • How Ashley uses frameworks + a single grounding slide to lead discovery conversations • Why you must keep “breadcrumbing” even when client work gets busy • The reality of income volatility — and how to reduce the “oh crap” moments • Portfolio career thinking: experimenting with speaking, books, and new revenue streams • A fun (and honest) AI/TikTok viral experiment — and what it taught her about unit economics • The mindset truth: escaping requires hustle — but it’s a better “hard” than corporate Key quotes • “You’re in here for the long game.” • “People are sick of being sold to on LinkedIn.” • “Always be top of mind… keep breadcrumbing.” • “Both paths are hard. Choose which hard you want.” Resources & mentions • Connect with Ashley on LinkedIn: https://www.linkedin.com/in/ashleyevenson/  • Ashley’s site: AE Marketing Collective: aemarketingcollective.com • AI slide tool mentioned: Gamma (export to Google Slides / PowerPoint) If this episode hit home… If you’re still in corporate and thinking about an exit strategy: • Start with one conversation this week. • Don’t pitch. Ask for perspective. • Keep one weekly “breadcrumb” habit so you don’t disappear when you get busy. About the guest Ashley is a fractional marketing leader with experience across agency, brand, and consul

Corporate gives you an easy identity: your title, your company, your lane. But once you start building something outside corporate—consulting, fractional, content, a book, a business—that identity disappears fast. And that’s where most people get stuck. In this episode, Brett sits down with Catherine Jelinek, founder of The Skinny Platform, to talk about the shift from being “defined by your role” to being known for your thinking, your story, and the outcomes you create. Catherine shares why so many high-performing corporate pros struggle in the “formless” world outside corporate, how to create structure without recreating corporate, and why the fastest way to clarify your thought leadership is often talking it out—not trying to write it alone. They also get into “skinny books” (short, high-impact nonfiction) and how to use AI and conversation-based drafts to accelerate publishing and content creation. What You’ll Learn • Why corporate identity feels safe—even when corporate is miserable • How to replace “job title identity” with outcome-based positioning • Catherine’s framework for navigating change: Forming → Storming → Norming → Performing • How Brett created structure outside corporate (without turning life into a calendar prison) • Why most people can’t “see” their own differentiators—and how a mirror helps • Why conversation + transcripts can be the fastest path to content (and even a book) • The “skinny book” approach: short, readable, practical nonfiction that people actually finish • How to use AI to generate multiple story arcs and content angles—without losing your voice Key Takeaways • You don’t need to reinvent yourself. You need to reframe yourself. • Progress outside corporate isn’t linear—so you need your own way to measure wins. • If you want thought leadership, stop trying to “perfect-write” it. Talk it out first. • Your story isn’t just for a book. It can power your LinkedIn, website, offers, and messaging. About Catherine Jelinek Catherine is the founder of The Skinny Platform, an alternative to ghostwriting for entrepreneurs and thought leaders. The Skinny Platform helps people clarify their story, shape it into a compelling narrative, and turn it into a short, high-impact book—faster than the traditional publishing process. Connect with Catherine • https://www.linkedin.com/in/cjelinek/ • Email: [email protected] • Websites: theskinnyplatform.com

Post Corporate Life with Brett Trainor & John Arms I recently had the chance to join John Arms on his podcast: Fractional Unfiltered Link: https://open.spotify.com/episode/0z9pQOOMZEVI4T2NvoOiqP?si=uJoycF4LRGyZQNB4MofrtQ John was kind enough to allow me to share this with my audience. Corporate has done a number on people. A bad one. For 30 minutes we bitch about what is and was, and then we spend 30 minutes on how to thrive in the post corporate world. This episode also includes real-time audience coaching around “job hugging,” starting from zero, and how to simplify your entry point so you can land your first client. What you’ll hear in this episode Why corporate feels colder now (profits over people, layoffs as strategy) The “solo employee” mindset: treat your employer like your first customer Why job searches after 45 can feel like PTSD — and how to reframe it How Brett monetized his corporate experience in 10 different ways Why chasing “big deals” first can slow you down (and what to do instead) The good / better / best ladder to get in the door with business owners Why community and relationships beat lone-wolf execution The difference between being capable and being confident (and how corporate crushes confidence) The simplest success ingredients: take action, build relationships, stay curious Live coaching: why “starting from zero” is hard — and how to find your “entry problem” so you can get traction Key frameworks + concepts mentioned Corporate is a transaction (not a family): loyalty is gone, act accordingly Start before you hit the breaking point: build an exit strategy while you still have income Small wins stack: don’t wait for the home run The 3 revenue levers every business cares about: Problem-solving > selling: discovery conversations look a lot like job interviews “Done is better than perfect”: unlearn corporate perfectionism Community as leverage: don’t do this alone Job hugging: holding on until you’re forced out — and why you still need a plan Memorable lines / moments “Layoffs are a business strategy now.” “You are your own company — even if you’re still employed.” “It’s not a tightrope between skyscrapers. If you misstep, you’re six inches off the ground.” Call to action If corporate feels unstable — don’t wait for it to get personal. Start building momentum now: Have one conversation this week Identify one “must-solve” problem you can help with Get your first small win and stack it into the next one

Most people believe the ones who succeed after escaping corporate are the smartest, most experienced, or most credentialed. They’re not. In this solo episode, Brett breaks down a pattern he’s seen across hundreds—if not thousands—of conversations with corporate escapees: success outside corporate has far less to do with talent and far more to do with action. This episode is for anyone still in corporate, recently laid off, or quietly wondering if there’s another path—but feeling stuck, underqualified, or unsure where to start. What You’ll Learn in This Episode • Why the most talented corporate professionals often struggle after leaving • The real traits shared by people who successfully escape—and stay out • Why overthinking your offer is one of the biggest mistakes escapees make • How job interviews and client conversations are essentially the same thing • Why “sales” after corporate is really just problem-solving • How small wins (not big plans) create momentum • Why redefining success becomes inevitable once you regain control of your time • How to safely test a solo path while still in corporate—or during a job search Key Takeaways • You don’t need more experience to get started—you need movement • Confidence comes after action, not before • Business owners care about outcomes, not job titles • Your network is your greatest advantage if you’re willing to use it • The biggest risk isn’t trying—it’s never testing what’s possible If You’re Still in Corporate (or Recently Laid Off) You’re not behind. You’re not underqualified. And you already have skills people will pay for. The fastest way forward isn’t a perfect plan—it’s one conversation. Join the Escapee Collective If you’re tired of figuring this out alone, the Escapee Collective is a community for corporate castaways and escapees at every stage—still in corporate, newly out, or building momentum. Peer groups. Live sessions. Real conversations. Real progress. You can find the link in the show notes or visit TheEscapeeCollective.com to learn more.

Michelle Warner took the “escapee avoidance” route — she planned to do the traditional MBA-to-consulting path… then graduated straight into the Great Recession (the day Lehman fell). That curveball pushed her into entrepreneurship early: a founder-for-hire role turning a multi-billion-dollar foundation asset into a business, followed by a mission-driven tech startup, and eventually her current work helping small business owners design the next iteration of their business. This is a tactical episode about what actually works when you’re leaving corporate: why you should “throw spaghetti at the wall” early, how to stop doing random coffee chats, and how to use relationship marketing and audience borrowing to land clients faster — without turning into a sales robot. What you’ll learn • Why “sequence over strategy” matters more than the perfect plan • The hidden risk of being too strict and narrow early on (and why it creates regret later) • How Michelle built her business through relationship marketing, not content churn • “Audience borrowing” as the fastest way to build trust and pipeline • How to approach connector conversations vs. client conversations • Why your early goal is simple: learn how to make money and stack wins • A practical way to think about packaging: repeatable frameworks, flexible middle Key moments / highlights • Graduating into chaos: the day Lehman fell and what it changed • Founder-for-hire: getting a salary while living the startup founder life • Affordable internet in inner cities — and what customers actually did with it • “Fractional CEO” before fractional was trendy • The rule: don’t build with blinders on for too long • The shift from “networking for jobs” to networking as a long-term business asset • The line that matters: say something that people can’t “unsee” after the call Michelle’s core concepts (worth stealing) • Sequence over strategy: the order of moves beats the elegance of the plan • Throw spaghetti first: test offers, clients, and problems before you commit • Connection avatar: define who’s worth meeting so networking doesn’t waste your life • Trust transfer: get introduced through people/places your audience already trusts • Audience borrowing: build relationships with people who “own the room” your clients are in Best quote energy • “Learn all the rules so you can go break them.” • “It’s more important the order you do things than how good you are at it.” • “I’m totally unemployable.” (Escapee anthem) Connect with Michelle • Website: themichellewarner.com • Podcast: Sequence Over Strategy (short, practical episodes; curated playlists on her site) Connect with Brett / The Escapee ecosystem • If corporate is broken and you’re looking at an exit strategy, this is your sign. • Join the community: TheEscapeeCollective.com

If you’ve been thinking about leaving corporate but the risk feels too big, this episode gives you a smarter way to look at it. Brett sits down with Alex Smereczniak, a former EY consultant who left corporate early, built a high-growth business in the laundry space, and later launched Franzy—a platform designed to make franchising easier to research and navigate. This conversation covers the mindset shift that helps people stop overestimating the risk of leaving, plus why franchising can be an underrated “business with guardrails” path for escapees who want ownership without building from scratch. What we cover • Alex’s escape story: college entrepreneurship → EY → leaving after a year and change • The moment that validated his decision: an EY partner’s biggest career regret • Why fear is often self-created—and how to get past it • A practical worst-case scenario exercise to reset your risk tolerance • Why franchising is a business model, not an industry • Franzy’s concept: “Zillow for buying and selling franchise businesses” • How AI + coaching can narrow thousands of franchise options into a realistic short list • Underrated franchise categories and trends (senior care, home services, turf, and more) • The “corporate is one customer” reframe—and why ownership builds equity Key timestamps (approx.) • 00:00–03:30 – Alex’s corporate stint + why he left fast • 03:30–08:30 – The EY exit interview story: “It wasn’t my ladder” • 08:30–12:30 – Why making money outside corporate is more possible than people think • 12:30–20:30 – The worst-case scenario exercise (the fear-killer) • 20:30–28:30 – Alex’s journey building a scaled laundry business + why franchising clicked • 28:30–33:30 – What franchising actually is (and what most people misunderstand) • 33:30–40:30 – Franchise categories you probably haven’t considered • 40:30–46:30 – Equity, control, and why “owning” beats “leasing” your career Big takeaways • Most people overestimate the risk of leaving corporate. The real risk is staying dependent on one employer. • You don’t need a perfect plan. You need small wins and momentum—then you adjust. • Franchising can be a fast path to ownership because you start with a proven playbook, support, and guardrails. • Ownership builds equity. A job pays you, but it doesn’t typically create an asset you can sell. Who this episode is for • Corporate pros who want out but feel stuck because of risk, family, or finances • Escapees who want a “business with guardrails” instead of starting from scratch • Anyone curious about franchising beyond the usual fast-food stereotypes Resources + links • Franzy https://franzy.com/ • Alex on LinkedIn: https://www.linkedin.com/in/alex-smereczniak-40310329/

Tom Mirabella left corporate at 30 and never looked back. Seventeen years later, he’s built Wingman into a 25-person business by doing what corporate rarely rewards: solving problems fast, betting on relationships, and staying obsessively close to customers. In this conversation, Tom breaks down his escape story, why “local + in-person” is making a comeback, and how Wingman’s franchise model flips the typical franchise script — where the franchisee focuses on relationships and sales while the central team handles fulfillment and delivery. If you’re stuck in corporate and can’t see a path out, this episode gives you a practical look at what “building your own lane” can really look like — without pretending it’s easy. Join the Escapee Collective: TheEscapeeCollective.com What You’ll Learn • Why Tom left corporate early (and what corporate policies taught him about ceilings) • The side-hustle-to-business path: how one small project turned into real clients • How to think about risk when leaving: your monthly “number” vs. replacing a salary • Why entrepreneurship can swing from best day to worst day in 30 minutes — and how to handle it • The “digital mayor” concept: becoming the trusted local hub in your town • Why Tom believes physical locations + community presence still win in a digital world • A modern franchise approach: franchisee sells + builds relationships, HQ team delivers • Why customer service and trust are the real differentiators in crowded markets Key Quotes • “The problem’s now. Two weeks from now, it’s worse.” • “As an entrepreneur, you can have the best and worst day within a half hour.” • “I want you to be the digital mayor of your town.” • “If you do what you love, the money follows.” Mentioned in This Episode • COBRA and how Tom thought about early-stage risk • Networking groups, chambers, community events, and “planting seeds” • Using a podcast as a lead generator (and why it worked) Connect with Tom • Email: Tom at wingmanplanning.com • Website: WingmanPlanning.com • Social: Instagram / Facebook / TikTok / LinkedIn (search “Wingman Planning”)

What if scaling your business didn’t require hiring, hustling harder, or stacking endless clients? In this episode, Brett sits down with Pia Silva (No BS Mastery) to break down a simple model for building a highly profitable solo (or two-person) business — built around intensives, clear boundaries, and pricing for outcomes (not hours). Pia shares how she and her husband went from $40K in debt to $500K in revenue by shifting from long, drawn-out projects to a focused, high-value intensive model. Then she explains her signature framework — the 50-25-25 Rule — and how to reverse-engineer your pricing based on the life you actually want. If you’re a corporate escapee (or future one) trying to make real money without recreating the corporate grind… this is the blueprint. What you’ll learn • Why most “big ticket” projects are often the least profitable • Pia’s 50-25-25 Rule for profit + freedom (and how to use it to price your offers) • How to design offers so you make your monthly revenue in 50% of your client hours • The two levers to grow profit without working more: • Increase value (real + perceived) • Decrease time (intensify delivery) • A smarter version of “good / better / best” packaging (without selling deliverables) • How to use a Lead Product (paid) instead of free proposals to build trust fast • Why warm networks beat websites and content in the early stages • How to build boundaries that prevent scope creep (without sounding rigid) • The mindset shift escapees must make: sell outcomes, not time Key frameworks + concepts mentioned • The Intensives Model: Focused delivery in a compressed timeframe vs. dragging projects out for months • 50-25-25 Rule: Make your total revenue in 50% (or less) of your client-working hours so you have time for life • Lead Product Method: A paid diagnostic/strategy step that replaces proposals and tees up an easy upsell • Boundaries via Process: Clear steps + expectations reduce pushback and scope creep Resources from Pia • Scale Solo Playbook: NoBSMastery.com/playbook • Price to Freedom Calculator Connect with Pia • Instagram: @pialovesyourbiz • LinkedIn: Pia Silva

Why do so many people leave corporate… only to end up going back? In this solo episode, Brett breaks down the two core reasons most corporate escapees fail—and more importantly, how to avoid them. Failure here doesn’t mean experimenting and choosing corporate again. It means wanting out, trying to go solo, and giving up before momentum ever takes hold. If you’re thinking about leaving corporate—or you’ve already made the leap—this episode will help you understand what really trips people up and how to build a path that actually sticks. Resources Mentioned  The Escapee Collective – A milestone-based community designed to help corporate escapees get out and stay out: Link: https://escapee-collective.circle.so/checkout/the-escapee-collective What You’ll Learn in This Episode • Why not getting an early win is the fastest way to lose confidence • How long gaps without income create doubt, panic, and backtracking • Why most escapees don’t lack skills—they lack momentum • The hidden cost of isolation and loneliness when you go solo • Why “doing it alone” dramatically increases emotional swings • How peer support and feedback shorten the learning curve • Why community works better when people are at similar stages • The difference between education, theory, and applied learning • What successful long-term escapees all have in common Key Takeaway Going solo doesn’t fail because you’re not smart enough or experienced enough. It fails when: • You don’t get a win early • You try to figure everything out alone Momentum and connection matter more than perfection. Resources Mentioned  The Escapee Collective – A milestone-based community designed to help corporate escapees get out and stay out: Link: https://escapee-collective.circle.so/checkout/the-escapee-collective You can also reach out directly to Brett on LinkedIn with questions about the community or your escape path.

What if podcasting wasn’t just content—but a bridge out of corporate? In this episode, Brett sits down with Mark Hayward, former PwC and KPMG consultant turned podcast host and podcast guesting entrepreneur, to break down his escape from corporate—and how podcasting quietly became one of his most powerful tools. Mark shares how he started a podcast while still in corporate, not to make money, but to build confidence, find his voice, and explore what life outside the corporate box could look like. That passion project eventually opened doors to consulting, coaching, real estate experimentation—and ultimately a business built around helping others grow through podcast guesting. This is a real, honest conversation about experimentation, false starts, energy, and why podcasting works differently than most people expect. What We Cover • Leaving PwC and KPMG after a 14-year corporate career • Why Mark started a podcast before leaving corporate • The role experimentation plays in finding your escape path • Why not every revenue stream is worth keeping • Coaching vs. consulting vs. creative work (and the energy test) • Podcast hosting vs. podcast guesting — and how each actually works • Why guests often get more business than hosts • How podcasting builds confidence, clarity, and opportunity • Practical advice for corporate professionals who know they want out—but don’t know what’s next Key Takeaway You don’t need a perfect plan to escape corporate. You need momentum, experimentation, and a way to get into conversations that open doors. Podcasting can be one of those doors. Connect with Mark • Website: podcastintroduction.com • Podcast: Business Growth Talks • LinkedIn: https://www.linkedin.com/in/mark-hayward-163721a0/  Listen, subscribe, and share If corporate feels off—but you can’t see the exit yet—this episode will help you think differently about your options.

If you know corporate isn’t for you but you can’t see a clean exit, this episode is your roadmap. Brett sits down with Sam Lee (Indie Collective) to break down how experienced professionals can build a “portfolio career” — consulting, coaching, fractional work, and productized services — without quitting their full-time job first. Sam shares the simple frameworks that helped him build $1M+ in annual revenue through independent work for over a decade, and he explains why most people get stuck trading time for money. You’ll walk away with a practical way to tell your story, activate your network, and design an exit strategy with less risk. In this episode, you’ll learn: • Why the “side hustle first” approach builds confidence and reduces risk • The simple sales story that unlocks referrals: Client → Problem → Outcome • How to activate your network without sounding awkward or salesy • Why “fractional” isn’t always the fastest path to revenue — and what is • The real goal: stop trading time for money and start selling outcomes • Sam’s 3-part productization path: 1. Niche down to best-fit clients 2. Solve painkiller problems (not vitamins) 3. Build a portfolio of offers, including productized work • The two killers of the independent path: no early wins + isolation • Why productizing your expertise helps both client work and job searches Key quotes / soundbites: • “The most pernicious trade independent builders make is trading time for money.” • “Your sales story is three things: who you serve, their problem, and the outcome.” • “Nobody is hiring a generalist right now. They want been-there-done-that experts.” • “Trial and error at this stage of your career is expensive.” Resources mentioned: • Indie Collective: IndieCollective.co

Get the New Escapee Starter Kit Here If you know corporate is broken—but you’re not ready to quit—this episode is for you. In this year-end solo episode, Brett walks through 7 practical steps to help you rethink your relationship with work, assess how happy you actually are, and explore whether there’s a path outside corporate—without making a risky leap. This isn’t about quitting your job. It’s about getting prepared, taking back control, and testing what’s possible using the experience you already have. Whether you’re 25 or 65, this episode helps you stop being reactionary and start designing what comes next. What You’ll Learn Why most people stay stuck—even when they’re miserable How to reframe yourself from “employee” to “business owner” The 5-factor scorecard to measure your real happiness Why you’re already a solopreneur with one bad client How to inventory your skills without thinking in job titles A simple way to calculate your real market value How to design a future that integrates work into your life—not the other way around The 7 Steps Covered in This Episode Reframe Your Reality – You don’t need new skills or a new degree Establish Your Happiness Baseline – Money isn’t the whole story See Yourself as a Solopreneur – You already have one client (corporate) Define What You Really Want and Need – Financially, personally, realistically Take Inventory of Your Skills and Energy – Focus on problems you like solving Calculate Your Value – A simple formula to find your hourly baseline Design Your Ideal Future – Work backward from the life you want Key Takeaways It’s easier to find your first customer than your next job Small wins build confidence faster than big, risky bets You don’t need permission to start testing a new path Done is better than perfect Control comes from action, not planning Final Thought You don’t have to leave corporate to take back control. But if you don’t start preparing, another year will pass—and you’ll be having the same conversation again. If you’re still in corporate… good luck. And if you’re ready to take the first step—this is it.

This episode is a live mini-workshop recorded with members of the Escapee Collective (and released here because it was too useful to keep inside the community). My guest Diane Kennedy (CPA) breaks down what most new escapees get wrong about taxes and business structure — and why the real first question isn’t “LLC or S-Corp?” It’s: Are you building a business… or replacing a paycheck? From there, we get into the most common setup for solopreneurs (LLC + S-Corp election), how to think about deductions without getting cute, and why “keeping it small and keeping it all” is the solopreneur cheat code. We also bring in Lisa Dini from Lettuce, who explains how they help solos run the S-Corp model without turning you into an accountant. Heads up: This is educational, not legal/tax advice. Talk to your pro for your situation. What you’ll learn The real first question for escapees: build a business vs replace a paycheck Why “LLC vs S-Corp” is usually the wrong framing (and what Diane recommends instead) Why Diane believes you should set up an LLC early (asset protection + flexibility) The 3 “buckets” of income for solopreneurs: Earned, Leveraged, & Passive (the holy grail) A simple way to think about deductions: ordinary + necessary (and how to find write-offs you already have) How S-Corps can help you keep more of what you earn (salary vs distributions, plus other benefits discussed) Real-world Q&A on: partners, joint ventures, and multi-state setups, California “special rules” , Schedule C vs S-Corp timing, Solo 401(k) and related retirement ideas Resources Mentioned: Lettuce.co: https://hubs.ly/Q03Yz8KX0 Tax Calc: https://hubs.ly/Q03Yz8Rf0 Tax Prep: https://hubs.ly/Q03Yz8JY0 Guests Diane Kennedy CPA and long-time solopreneur. Diane helps business owners structure their business and income in smarter ways so they can keep more of what they earn and operate like a real business. Lisa Dini (Lettuce) Lettuce helps solopreneurs run an S-Corp model efficiently, without drowning in admin and accounting work.

If you know corporate is broken but jumping straight into solopreneur life feels like too big a leap, this episode is for you. Brett breaks down how to treat your “escape plan” like an insurance policy—not a dramatic leap off a cliff. You don’t have to quit your job tomorrow. But you do owe it to yourself to be prepared for the moment corporate quits on you… or you finally hit your breaking point. Instead of trying to convince you to go all-in on a solo business, this episode walks you through how to build a plan you can keep in your back pocket—so you’re not starting from zero if things go sideways. Download the FREE Starter Kit Join the Collective In this episode, you’ll learn: Why the gap is so big between people who know corporate is broken and those who actually take action How to think like a “prepper” (without going full doomsday): planning so you don’t have to plan in the middle of chaos Step 1 – Define what you actually want Step 2 – Get clear on your financial reality Step 3 – Take inventory of your skills and energy Step 4 – Shift from job title to problem-solving Step 5 – Reframe your current employer as just one client Also: • A simple formula to value your time • Annual salary × 1.25, then drop three zeros → a shockingly accurate baseline hourly rate •. Why many escapees replace their corporate income in ~20–25 hours per week • Why you don’t need 100 customers • How 2–5 good clients can replace (or exceed) your corporate pay • Why most of those opportunities will come from networking and referrals, not job boards Who this episode is for You’re still in corporate, you know the system isn’t built for you, but you don’t see a clear path out You feel stuck between “I hate this” and “I don’t know what else I’d do” You’re curious about going solo, but the idea of just quitting and “figuring it out” feels reckless You want a practical, low-risk way to prepare now, so you’re not scrambling later

If you’ve ever walked out of a meeting thinking, “Why didn’t that land?” Or if you’ve ever felt invisible in corporate… Or if you’re building a life outside of corporate and wondering why some conversations connect and others fall flat… This episode will hit you hard. Today, Brett welcomes back Jake Stahl — author of the brand-new book Own the Room and creator of the STRATA framework, a system for reading people, decoding signals, and communicating with true presence instead of performance. Twelve years ago, Jake lost everything to opioid addiction — his marriage, his home, his reputation, and the identity he’d spent decades building. But his path back didn’t begin with a new job or a second chance. It began with learning how to read people. Jake realized that most communication has nothing to do with the words being spoken. It’s the signals beneath them — the micro-expressions, the posture shifts, the emotional triggers — that determine whether someone trusts you, connects with you, or shuts down entirely. Today, Jake breaks down STRATA, the six-part framework you can use to own every room you enter: • Signal: What you broadcast before you say a word • Trigger: The moment resistance appears • Reframe: How you shift someone’s lens without force • Anchor: Making the insight stick • Transfer: Turning your idea into their idea • Action: Where the next step becomes inevitable We talk about how STRATA applies to sales, relationships, leadership, marriage, friendships — and most importantly, the escapee journey. Because leaving corporate and building your own path requires one core skill: 👉 You must connect with people in a way that feels real. This episode gives you the playbook. Connect with Jake Stahl • LinkedIn: https://www.linkedin.com/in/jakestahl/ • TikTok: @JakeTheMindMechanic • Podcast: https://thejakestahl.com/podcast/  • Book: Own the Room: https://thejakestahl.com/books/

What happens when corporate stress gets so bad you literally can’t swallow solid food? That’s where Claire Sullivan found herself. On December 1st, 2023, corporate quit on her — and she took what most people would call the riskiest step possible: She built a business… the same day. Filed an LLC Registered everything needed to operate Posted on LinkedIn that she was going out on her own Listened to what the market actually wanted And replaced her former salary by the end of the week Is that typical? No. Is it possible? Absolutely. And more importantly — the steps she took are repeatable for anyone stuck in a corporate job that no longer works for them. This is one of the most real and honest conversations we’ve had on what it actually looks like to escape corporate — emotionally, financially, mentally, and practically. Who This Episode Is For This one is for you if: Corporate has stopped making sense Every job application feels like it goes into a black hole You’re burned out but can’t “just quit” You want control over your time, income, and health You don’t think you have “enough” experience to go out on your own You just need one real example of someone who actually did it Connect with Claire Maven Course: How to Layoff-Proof Your Career by Becoming a Solopreneur: https://maven.com/clair-sullivan-associates/launch-your-solopreneur-business?promoCode=ESCAPE LinkedIn: https://www.linkedin.com/in/dr-clair-sullivan/

Freebie from Michael: 20% off: https://www.clym.io/p/bretttrainor Most solo businesses are focused on getting clients—but ignore the compliance risks that can quietly wreck everything. Former tax attorney and CFO Michael Williams joins Brett to break down the ADA, privacy, and regulatory issues small businesses face—and how a $100K GDPR mistake pushed him to finally build Clym.io, an all-in-one website compliance platform. Michael also shares the remarkable story of raising a seven-figure VC round… then paying it back to regain control and stay true to his vision. In This Episode: • The hidden ADA & privacy risks solopreneurs overlook • Why most accessibility lawsuits hit small businesses • How AI-powered scans fuel compliance lawsuits • How Clym.io uses one snippet to manage 150+ regulations • Why Michael left a cushy CFO role at 38 • The identity shift from employee → builder • What it’s really like to take VC money—then give it back • Why taking action beats waiting for the “right” time Connect with Michael & Clym Website: https://clym.io More From Brett Escapee Starter Kit, resources & links → https://linktr.ee/bretttrainor

This episode is a little different. I was a guest on Catherine Jelinek’s podcast, Breaking Through the Noise — and she generously allowed me to share the full conversation with you. We talk about leaving corporate, taking action, finding traction on TikTok, and the honest story behind building the Corporate Escapee movement. If you’re stuck, burned out, or thinking about going solo, this one will hit home. In this episode, we cover: Why taking action is the #1 skill corporate trains out of you My path from 25 years in corporate → consulting → fractional → building 10+ income streams How TikTok unexpectedly became the platform that changed everything Why 80% of my 76K TikTok followers are over 40 The moment one video brought in 300+ strategy call requests in 48 hours The three stages of an escapee: Curious, Motivated, and Liberated Why your path out of corporate isn’t a leap — it’s a shift The reality of layoffs, RTO mandates, and the “profits over people” era Why authenticity beats production quality every time The mindset shift corporate doesn’t prepare you for Why this conversation matters A lot of people want out of corporate, but they overthink the first step. This episode breaks down what actually works — and why you already have more than enough experience to start. Connect With Catherine Check out Catherine Jelinek’s podcast: 👉 Breaking Through the Noise Available on Apple, Spotify, and YouTube. Follow and support her work — she’s having the conversations corporate workers need to hear.

Today I’m joined by Neil K. Carroll, founder of vidwheel, who took the long way out of corporate: video agency → higher-ed job → rebuilding as a lean solo business. Neil shares how a simple testimonial project for a startup turned into something much bigger—a repeatable, productized service that helps founders uncover the stories and insights hidden inside their customer relationships. If you’re stuck in corporate and wondering what you would even sell, this episode will help you see the path: start with what you already know, listen for the real problem, and bet on yourself. What You’ll Learn Neil’s escape path: agency burnout → COVID pivots → higher-ed → solo The “Root Thread” deep testimonial approach and why it delivers strategic customer insight How to productize what you already do without boxing yourself in Why referrals and local networks are enough for a one-person business How Neil priced his offer and why undercharging early is part of the process The 4 levers every offer should hit: save time, save money, make money, reduce risk Why betting on yourself beats betting on corporate stability Key Takeaways Your corporate title doesn’t matter—your ability to solve problems does Productized services make selling and delivery easier Customer conversations reveal the real value you offer Solopreneurs don’t need 100 clients—you need a few right-fit ones You can always go back to corporate… but very few people want to once they leave About Neil K. Carroll Neil is the founder of vidwheel, helping startups and small businesses capture deep customer stories through Root Thread testimonial interviews and his hardware-enabled Mini Studio (VidKit 3). He combines interviewing skill, remote production, and AI-assisted analysis to help companies extract messaging, proof, and product insight directly from their customers. Connect with Neil: LinkedIn: Neil K. Carroll Website: vidwheel.com

Download the FREE Escapee Starter Kit Episode Summary After nearly 30 years in corporate communications, Ed Patterson didn’t just leave corporate—he left the country. He and his partner planned their move to Portugal, secured residency, and designed a new life where work no longer sits at the center. We cover what it really takes to prepare (financial, legal, lifestyle), what he’d do sooner, how he reframed success to “quality of my day,” and practical advice for anyone considering a similar shift—whether you move abroad or simply want more control at home. Chapter markers • 00:00 Intro: Why Ed left corporate and the U.S. • 00:45 Ed’s background: PR/Comms, crisis, agency + in-house • 03:00 The Portugal plan: residency, D7 visa, timelines, consultants • 05:35 How they prepared: roles, finances, finish lines, advisor sign-off • 10:50 Healthcare and costs: private insurance, day-to-day expenses • 14:40 Redefining happiness: “quality of my day,” health, sleep, energy • 20:13 Advice to 30- and 40-somethings: plan for when you want to—and when you have to • 26:14 Do an inventory: skills, network, gaps, use corporate to upskill • 30:11 Action over waiting: fractional, contracts, bridge income • 33:06 The “adventure years” mindset and inviting questions • 35:23 Close Key takeaways Plan with intent: set a finish line, pressure-test with a financial advisor, and define roles at home. Consider geo-arbitrage: lower costs can pull your finish line forward by years. Optimize your day: sleep, movement, and mental space beat title-chasing. Treat corporate like your one client: extract skills, network, and education while you’re there. Build optionality: fractional work and short contracts can bridge income during transitions. Do the inventory: skills, network, marketable experiences, and gaps to close before you jump. Prepare for both scenarios: when you choose to leave—and if corporate chooses for you. Health matters: design a life you can actually enjoy. Guest Ed Patterson: LinkedIn: https://www.linkedin.com/in/edpatterson1/ Instagram: https://www.instagram.com/twoguysinportugal Callout quotes “We hit our finish line sooner because our costs dropped by a third to a half.” “I sleep better, eat better, and feel more creative. That was impossible when work ran my day.” “Plan for your choice—and for the day you may not have one.”

Guest: Bob Burg, co-author of The Go-Giver Note from Brett: This Greatest Hits episode is one of the most shared conversations we’ve ever had — and for good reason. If you’re trying to land your first clients or grow your solo business, Bob’s Go-Giver principles are a masterclass in creating value, building trust, and turning relationships into revenue. I wanted to bring this one back for our thousands of new listeners. There is so much value to be learned from Bob and a core to solopreneur success. Listen for three big takeaways: 👉 How to define value vs. price and articulate your worth. 👉 How to make referrals your #1 growth engine. 👉 Why receiving is just as important as giving. What You’ll Learn: The difference between price and value — and why focusing on value creates loyal clients. The Law of Compensation: your income equals how many people you serve × how well you serve them. Why authenticity and consistency inspire trust. How to stay open to receiving so opportunities can flow back your way. Simple frameworks for building a referral flywheel that compounds over time.

Healthcare is the #1 concern from wannabe escapees DM Brett about. Today, benefits veteran and fellow escapee Tom Morrissey breaks down a solo-friendly health plan designed for one-person companies: Solo Health Collective. We cover who qualifies, how underwriting your business (not you as an individual) changes the game, pricing logic, networks, what’s covered, what’s not, and where this is all headed (biomarkers, portable benefits, and association plans). If you’ve ever said “I’d leave corporate, but… benefits,” this is your episode. Links: Solo Health Collective: https://hbgsolo.com/ Tom Morrissey LinkedIn: https://www.linkedin.com/in/tommorrisseyhbg/ What You’ll Learn Who qualifies & how it works: EIN required, brief medical history, plan in your business’s name (self-insured structure for solos). How it’s different: Not ACA and not a sharing ministry; three high-deductible options ($2.5K / $5K / $10K) with 100% coverage after the deductible and no annual/lifetime max. Network & Rx: Open network with MultiPlan/PHCS PPO; pharmacy via Pharos Rx; prior auth for big procedures. Costs & fit: Age-rated pricing—often competitive vs. ACA when you compare total cost + design—but not for everyone (medical questionnaire matters). Service that doesn’t stink: Human, concierge-style support (aka you can talk to a person). The road ahead: Optional “Solo-Plus” wellness track (full lab panels 2x/year) to drive better health and better underwriting; watch items like portable benefits and association health plans that could expand options for independents. Timestamps 00:00 Welcome & why healthcare keeps people stuck 02:00 What Solo Health Collective is (and isn’t) 04:00 Tom’s background (Cigna → self-insured solutions for small employers → solos) 07:30 Why underwrite the business of one (EIN) 10:30 The cost problem (everywhere) & what drives premiums 15:00 Getting a quote in minutes; three plan designs; preventive care at 100% 18:45 Networks (MultiPlan/PHCS), open access, prior auth for big bills 21:00 White-glove support & Trustpilot traction 22:45 Who it’s not for (questionnaire fails; ACA may be better) 24:30 Simplicity: deductible = out-of-pocket; families cap at 2x deductible 25:40 Future: biomarkers program, better health → better rates 30:30 Policy watch: portable benefits & association health plans 34:30 Final advice: know all your options; compare total cost & design About Our Guest Tom Morrissey is a benefits industry veteran (40+ years) and co-builder of Solo Health Collective, a national health plan purpose-built for self-employed business owners with no W-2 employees. Previously with Cigna serving mid-market and national accounts, Tom now focuses on accessible, concierge-level benefits for one-person companies. Disclaimer This episode is for educational purposes only and is not insurance, legal, or financial advice. Compare options (ACA, off-exchange, group, and Solo Health Collective) and choose what fits your situation.

What happens after you escape corporate? How do you make your solo business work long-term—without burning out or losing the freedom you left for? In this episode, Brett sits down with Jenni Gritters, author of The Sustainable Solopreneur and coach to creatives, consultants, and coaches who want to build profitable, flexible, and fulfilling solo businesses. Jenni shares her journey from The New York Times to building a six-figure business working just 25 hours a week. Together, Brett and Jenni unpack what sustainability really means—financially, mentally, and emotionally—for Gen Xers who’ve left corporate (or are ready to). They dive into: ✅ The “three-to-four-year wall” most solopreneurs hit—and how to move past it ✅ Building multiple revenue streams without chaos ✅ Shifting from survival mode to intentional growth ✅ Why sharing your numbers builds trust (and confidence) ✅ How to measure success beyond money—using purpose, time, and happiness If you’ve escaped corporate or are thinking about it, this conversation is your roadmap for building a business—and a life—you actually want to sustain. Connect with Jenni Gritters 📘 The Sustainable Solopreneur  🌐 jennigritters.com 💌 Newsletter: The Sustainable Solopreneur Connect with Brett Trainor 🎧 Subscribe to The Corporate Escapee Podcast 📩 Download the FREE Escapee Starter Kit

GenX built the systems everyone’s now trying to automate — and that’s exactly why we’re built for what’s next. In this episode, I’m joined by Michael Himmelfarb, one of the original corporate escapees, to talk about why the real opportunity with AI isn’t automation…it’s augmentation. Michael shares how he rebuilt his consulting business by combining AI efficiency with human judgment, creativity, and experience — proving that the GenX advantage lies in knowing how to apply wisdom to new tools. You’ll learn: How to blend AI with your experience to create faster, smarter offers Why augmentation beats automation for consultants, advisors, and fractionals How to sell outcomes, not titles — and why buyers care more about value than ever Why your corporate scars, empathy, and critical thinking are your new superpowers If you’re a GenX pro still in corporate (or newly escaped), this conversation will show you how to use AI to amplify your expertise — not replace it. Guest Michael Himmelfarb — Pricing & product marketing strategist helping companies modernize pricing/packaging with AI-augmented consulting. Connect on LinkedIn and mention this episode for his 48-hour sprint details. LinkedIn: https://www.linkedin.com/in/michaelhimmelfarb/ Resources mentioned • Anthropic’s “automation vs. augmentation” idea (discussion) • Shout-out: Naveen Aggarwal (technical enablement/automation support) For GenX Escapees Grab the Escapee Starter Kit: https://stan.store/thecorporateescapee  Join Escapee Collective Plus: https://escapee-collective.circle.so/checkout/escapee-plus-subscriptions  Chapters • 00:00 Welcome back, OG Escapee + today’s focus • 01:29 From fractional CMO to pricing & packaging specialization • 03:53 The buyer shift: clarity, speed, and specific problems • 04:22 The 20/80 idea: what humans do that AI can’t • 07:40 Automation vs. augmentation (and why it matters) • 10:33 Hybrid delivery: standardized outputs + human judgment • 12:25 Human superpowers: creativity, prediction, empathy • 14:09 Beyond pricing: applying the model across functions • 15:45 Productized sprints → recurring revenue possibilities • 17:23 Big-firm disruption and the GenX advantage • 19:33 Learning curves, iteration, and avoiding “prompt pack” hype • 26:13 Focus, trade-offs, and building a simple offer • 30:28 Shout-outs & resources + workshop idea • 31:30 Michael’s ask + how to connect If this episode hit home Share it with a fellow GenX pro, leave a quick review, and DM Brett if you want the link to the free Starter Kit PDF or details on Michael’s sprint.

About this episode In this solo “CliffsNotes” episode, Brett breaks down how to actually make money from your corporate experience — not theory, not startup fantasy — just 17 real ways GenXers are doing it (plus 2 bonus options if you’ve got some capital to invest). Whether you’re still in corporate wondering if there’s a way out, or already on the outside trying to replace your income, this episode is the playbook. From fractional and advisory work to user-generated content, workshops, and buying a small business — Brett shares what’s working, what he’s tried himself, and what might fit your life right now. You’ll hear: • Why your experience is more valuable outside of corporate than inside • 17 proven ways (and 2 bonus paths) to monetize what you already know • How GenXers are replacing their corporate income in ~25 hours a week • The difference between consulting, fractional, advisory, and coaching • Why “monthly service packages” might be the fastest on-ramp for freedom • Real examples from Brett’s own journey — what worked and what didn’t • How to future-proof your income before corporate “quits” on you This one’s packed with ideas you can start exploring right now — no fancy website, no new degree, and definitely no corporate BS. Mentioned paths include: Solo Consulting • Fractional Leadership • Interim Roles • Advisory • Coaching • Business Development & Affiliate Deals • Services / Subscriptions • Paid Communities • Sponsorships • Influencer & Content Partnerships • Workshops • Speaking • User-Generated Content (UGC) • E-Commerce • Tech-Enabled Services • Plus: Buying a Business & Franchises (the two “bonus” options) If this hit home, follow the show so you don’t miss the next “CliffsNotes” drop. 👉 Want help figuring out your best path out of corporate? Join the Escapee Collective for $20/month (locked for life if you join before December) and connect with other GenXers building freedom on their own terms. 🔗 Links in the notes: Download the free Escapee Starter Kit – https://stan.store/thecorporateescapee Join the Escapee Collective ($20/mo for life before Dec): https://escapee-collective.circle.so/checkout/escapee-plus-subscriptions  Connect with Brett on LinkedIn: https://www.linkedin.com/in/bretttrainor/ Email: [email protected]