Brett Trainor Unplugged

Almost everything written about Gen X and corporate right now is negative, and some of it is fair. Ageism is real. The profit over people playbook is accelerating. CEO tenures keep getting shorter, which means the pressure for a short-term number keeps getting higher.

This episode is the other side of that.

Five reasons I'm optimistic, and I mean actually optimistic, not the motivational poster kind. Save this one. Pull it up on a Sunday night when the week ahead looks long.

One. You get to design the life instead of fitting a...

Almost every escapee story on this show starts with corporate going bad. This one doesn't.

Jim Barke spent nearly twelve years at a company he genuinely liked, with what he calls the best team he's ever worked with, and six weeks of PTO. Nobody pushed him out. He wasn't burned out. He hired a career coach because he knew he was at a crossroad, and on their second or third meeting she told him he should quit his job.

He laughed at her. He was divorced, single income, with his oldest headed to college.

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Most people stay stuck in corporate because they think there are only two options: find another job, or start a business that eats five years of your life before it pays you.

There's a lot of room between those.

This one is about how you actually make money after corporate, and the first thing to get straight is what you're aiming at. Replacing your salary and funding your life are two different targets. One is a number somebody else set for you. The...

Hana Kim did almost everything you're not supposed to do.

She spent seventeen years in corporate, all of it in insurance, and made VP. Then she took a bigger VP role that required moving her whole family from Southern California to Arizona during the pandemic. House to sell, house to buy, a dog, and her mom, who lives with them. She landed in mid-June when it was a hundred and fifteen degrees.

The job was great, until it wasn't.

She describes the feeling the way a lot of us would recognize. Not burnout...

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Episode Overview:

Janet Tanguay got spitballed by her own colleagues in a corporate training for going off script. She lasted four days in her next job. Now she helps people build the life they actually want, and she has the most practical approach to it I've come across.

Janet Tanguay is a serial entrepreneur who has run a record label and an art business, and now runs Hammock Way of Life, helping people and companies get clear on what they actually want through vision boarding. She's...

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Hans Weygoldt had everything on paper. Good money, job security, the family business, the life that looks right from the outside. And he was empty.

He spent ten years trying to leave. Every time he sat down to build the plan, his mind went blank. As he puts it, the more he thought about it, the more self-doubt showed up, so the planning itself was digging the hole deeper.

When he finally went, it took about a second. Something changed at wo...

I've had north of a hundred authors on this show. This one stuck with me differently, and it's because of one word: Purgatory.

Geoff Curtis spent nearly thirty years building a career in healthcare communications. Title, expertise, platform, the whole thing. Then the company was acquired, his role went redundant, and all of it disappeared at once. What followed wasn't a reinvention arc. It was the discovery that he'd spent his adult life using work to avoid feeling anything.

He picked purgatory on purpose. As he puts it, words like transition imply progress, and he...

Megan Collier's first appearance is still one of my most downloaded episodes, so she's back.

Quick version if you missed it. UGC is user generated content. Brands pay you to make short videos, and instead of posting them yourself, they use the footage in their own ads. No followers required. No production setup. Megan's been doing it four years and has taught more than 16,000 Gen X and Boomers how to do it, including her mom.

Her origin story is the part I keep thinking about. She was on a call trying to sell a footwear...

Shelley McIntyre is back on the show, and her first appearance is still one of the most downloaded episodes I've done.

She was a grief counselor before she was a coach, which is why she talks about layoffs differently than anyone else I know. We opened on the Oracle news, because the math on it is ugly. Twenty years in, fifty or sixty hour weeks, and what shows up is an automated email at 6 a.m. that doesn't say thank you.

Her point stuck with me: you spend a career radiating loyalty outward, and at...

Somebody commented on one of my TikToks. He'd started his own solo business a couple years back, it's working, he's happy. Then he said "but it's not for everyone."

I'd been repeating that exact line for years and never once dug into it.

So this episode is two things. Why people still say entrepreneurship isn't for everyone, and why I think it's true about something almost nobody is actually doing.

When people hear "entrepreneur" they picture the same movie. Raise money, hire a team, sign a lease, bet the house. That version is...

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...

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...

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...

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...

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 abou...

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 abou...

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:<...

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:<...

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...

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...

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...

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...

"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...

"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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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 wh...

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 wh...

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.

<...

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.

<...

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 info...

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 info...