The Corporate Escapee

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 successNotable 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 financialThe three things you're actually dependent on (and it's not what you think)Why isolation amplifies doubt and keeps you stuckThe two milestones that break corporate relianceHow to avoid the mistake that sent Brett back 18 monthsWhy community matters more than tactics when going soloKey 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 betYou want practical ways to monetize your experience outside a jobYou’re curious how small businesses are really hiring and growing nowThe 3 trends covered in this episodeTrend #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 escapeesFractional 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 changingWhy 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 itIf 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 corporateKey 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 guestAshley 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 voiceKey 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 JelinekCatherine 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 ArmsI recently had the chance to join John Arms on his podcast: Fractional Unfiltered Link: https://open.spotify.com/episode/0z9pQOOMZEVI4T2NvoOiqP?si=uJoycF4LRGyZQNB4MofrtQJohn 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 episodeWhy corporate feels colder now (profits over people, layoffs as strategy)The “solo employee” mindset: treat your employer like your first customerWhy job searches after 45 can feel like PTSD — and how to reframe itHow Brett monetized his corporate experience in 10 different waysWhy 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 ownersWhy community and relationships beat lone-wolf executionThe difference between being capable and being confident (and how corporate crushes confidence)The simplest success ingredients: take action, build relationships, stay curiousLive coaching: why “starting from zero” is hard — and how to find your “entry problem” so you can get tractionKey frameworks + concepts mentionedCorporate is a transaction (not a family): loyalty is gone, act accordinglyStart before you hit the breaking point: build an exit strategy while you still have incomeSmall wins stack: don’t wait for the home runThe 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 perfectionismCommunity as leverage: don’t do this aloneJob hugging: holding on until you’re forced out — and why you still need a planMemorable 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 actionIf corporate feels unstable — don’t wait for it to get personal. Start building momentum now:Have one conversation this weekIdentify one “must-solve” problem you can help withGet 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 searchKey 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 possibleIf 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 CollectiveIf 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 middleKey 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 callMichelle’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 inBest 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 equityKey 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 careerBig 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 stereotypesResources + 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 marketsKey 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.Join the Escapee Collective!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 timeKey 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 creepResources from Pia • Scale Solo Playbook: NoBSMastery.com/playbook • Price to Freedom CalculatorConnect 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 commonKey TakeawayGoing 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 aloneMomentum 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 nextKey TakeawayYou 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 shareIf 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 searchesKey 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 HereIf 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 LearnWhy most people stay stuck—even when they’re miserableHow to reframe yourself from “employee” to “business owner”The 5-factor scorecard to measure your real happinessWhy you’re already a solopreneur with one bad clientHow to inventory your skills without thinking in job titlesA simple way to calculate your real market valueHow to design a future that integrates work into your life—not the other way aroundThe 7 Steps Covered in This EpisodeReframe Your Reality – You don’t need new skills or a new degreeEstablish Your Happiness Baseline – Money isn’t the whole storySee Yourself as a Solopreneur – You already have one client (corporate)Define What You Really Want and Need – Financially, personally, realisticallyTake Inventory of Your Skills and Energy – Focus on problems you like solvingCalculate Your Value – A simple formula to find your hourly baselineDesign Your Ideal Future – Work backward from the life you wantKey TakeawaysIt’s easier to find your first customer than your next jobSmall wins build confidence faster than big, risky betsYou don’t need permission to start testing a new pathDone is better than perfectControl comes from action, not planningFinal ThoughtYou 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 learnThe real first question for escapees: build a business vs replace a paycheckWhy “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 ideasResources Mentioned:Lettuce.co: https://hubs.ly/Q03Yz8KX0Tax Calc: https://hubs.ly/Q03Yz8Rf0Tax Prep: https://hubs.ly/Q03Yz8JY0GuestsDiane KennedyCPA 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 KitJoin the CollectiveIn this episode, you’ll learn:Why the gap is so big between people who know corporate is broken and those who actually take actionHow to think like a “prepper” (without going full doomsday): planning so you don’t have to plan in the middle of chaosStep 1 – Define what you actually wantStep 2 – Get clear on your financial realityStep 3 – Take inventory of your skills and energyStep 4 – Shift from job title to problem-solvingStep 5 – Reframe your current employer as just one clientAlso: • 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 boardsWho this episode is forYou’re still in corporate, you know the system isn’t built for you, but you don’t see a clear path outYou 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 recklessYou 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 inevitableWe 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 LLCRegistered everything needed to operatePosted on LinkedIn that she was going out on her ownListened to what the market actually wantedAnd replaced her former salary by the end of the weekIs 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 ForThis one is for you if:Corporate has stopped making senseEvery job application feels like it goes into a black holeYou’re burned out but can’t “just quit”You want control over your time, income, and healthYou don’t think you have “enough” experience to go out on your ownYou just need one real example of someone who actually did itConnect with ClaireMaven Course: How to Layoff-Proof Your Career by Becoming a Solopreneur: https://maven.com/clair-sullivan-associates/launch-your-solopreneur-business?promoCode=ESCAPELinkedIn: 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” timeConnect with Michael & ClymWebsite: https://clym.ioMore From BrettEscapee 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 youMy path from 25 years in corporate → consulting → fractional → building 10+ income streamsHow TikTok unexpectedly became the platform that changed everythingWhy 80% of my 76K TikTok followers are over 40The moment one video brought in 300+ strategy call requests in 48 hoursThe three stages of an escapee: Curious, Motivated, and LiberatedWhy your path out of corporate isn’t a leap — it’s a shiftThe reality of layoffs, RTO mandates, and the “profits over people” eraWhy authenticity beats production quality every timeThe mindset shift corporate doesn’t prepare you forWhy this conversation mattersA 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 CatherineCheck out Catherine Jelinek’s podcast:👉 Breaking Through the NoiseAvailable 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 LearnNeil’s escape path: agency burnout → COVID pivots → higher-ed → soloThe “Root Thread” deep testimonial approach and why it delivers strategic customer insightHow to productize what you already do without boxing yourself inWhy referrals and local networks are enough for a one-person businessHow Neil priced his offer and why undercharging early is part of the processThe 4 levers every offer should hit: save time, save money, make money, reduce riskWhy betting on yourself beats betting on corporate stabilityKey TakeawaysYour corporate title doesn’t matter—your ability to solve problems doesProductized services make selling and delivery easierCustomer conversations reveal the real value you offerSolopreneurs don’t need 100 clients—you need a few right-fit onesYou can always go back to corporate… but very few people want to once they leaveAbout Neil K. CarrollNeil 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. CarrollWebsite: vidwheel.com

Download the FREE Escapee Starter KitEpisode SummaryAfter 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 CloseKey takeawaysPlan 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.GuestEd 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-GiverNote 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 LearnWho 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.Timestamps00:00 Welcome & why healthcare keeps people stuck02:00 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 premiums15:00 Getting a quote in minutes; three plan designs; preventive care at 100%18:45 Networks (MultiPlan/PHCS), open access, prior auth for big bills21:00 White-glove support & Trustpilot traction22:45 Who it’s not for (questionnaire fails; ACA may be better)24:30 Simplicity: deductible = out-of-pocket; families cap at 2x deductible25:40 Future: biomarkers program, better health → better rates30:30 Policy watch: portable benefits & association health plans34:30 Final advice: know all your options; compare total cost & designAbout Our GuestTom 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.DisclaimerThis 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 happinessIf 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 SolopreneurConnect with Brett Trainor🎧 Subscribe to The Corporate Escapee Podcast📩 Download the FREE Escapee Starter Kit