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.

• 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]