Brett Trainor Unplugged

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/ 

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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.

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

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:

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

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.

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:

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 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.