You Probably Shouldn't Leave Corporate

Here's how to tell whether you're the exception.

I spend my time helping people leave corporate to build or buy a business. So take it seriously when I tell you most people shouldn't.

You have a solid corporate job with a steady paycheck and a 401K that's benefited from the stock market gravy train of the past four years. Maybe you have a side hustle too (if you belong to the third of the labor market that takes part in the side hustle economy). So from an income perspective, you're doing fine. Maybe better than fine.

So why would you be even remotely interested in leaving all of that to launch or buy your own business?

I mean, your personal financial statement looks decent, right? Maybe there's $100K in your 401K, maybe $1M, depending on where you are in your career. Equity in your home. A paycheck that covers the life you've built, and then some. Maybe a rental and brokerage account on the side. So why on earth would you consider walking away from all of that, maybe risking some of it, to start your own?

Because I'm not talking about getting to comfortable. Whether your net worth is $300K or $3M, with a good share of it tied up in your home, you're already on a path corporate can deliver. Don't get me wrong, that's real progress. Around $660K puts a household in the top quarter of the U.S., and $3M puts you around the top 7%. But to me, leaving corporate isn't only about finances. It's about two fundamental things. First, building something of your own that you believe in. Second, a desire to build generational wealth, the kind that can sustain at least your next generation through an asset that compounds beyond a paycheck.

For most people in corporate, the only way to get there is business ownership. For me, 13 years in well-paying corporate roles simply couldn't replace a burning desire to build something of my own. A desire that couldn't be extinguished with a larger paycheck or a bigger role. I was in shackles, and I needed to break away and build my own business. My own way of solving problems. My own principles. My own culture. My own team.

And yes, I'll admit it was very important to me to break into the top 1%. That meant crossing the $12M net worth threshold. That level of financial security mattered to me.

That's what I meant at the top. Without both of those things, the burning need to build and the desire for wealth well beyond comfortable, I would tell you: don't do it.

You need both

Each one on its own has a predictable ending.

If you have the need to build but you'd be happy with comfortable, you'll probably build a business that stays the size of you. You, a laptop, a handful of clients. It pays something close to what you were making, without the 401K match, the benefits or the paid time off, and with more hours. Nobody will ever buy it, because the business is you. You've rebuilt your job with fewer protections.

If you want the wealth but don't have the need to build, you'll probably go back. The first hard stretch arrives, and nothing is pulling you through it except a number. Corporate offers a surer route to a good number, and sooner or later you take it. You close the shop, update the résumé, and explain the gap in interviews.

Neither of those is a disaster. But neither is what you left for, and both cost you years you don't get back.

Comfortable is the competition

Your business isn't really competing against failure. It's competing against comfortable.

And corporate is very good at comfortable. Predictable raises. A matched 401K. Health insurance someone else negotiates. A paycheck that shows up whether the quarter was good or not. If comfortable is the goal, corporate is the better deal, and it isn't close.

An owned business only beats that deal at the far end, when it becomes an asset that compounds without you, one you can sell or pass on. That's the outcome a paycheck can't produce, and it's the only one that justifies giving up comfortable to chase it.

Which is why the two conditions travel together. The need to build is what gets you through the years before the asset exists. The desire for generational wealth is what keeps you going once the business pays you as well as your old job did. That's the moment it's most tempting to stop.

I tested comfortable

After I sold my first company, I went back into corporate executive roles for a few years, doing well again. By the argument I'm making here, that should've settled it. I'd built something, sold it, and landed somewhere comfortable with an exit behind me.

It didn't settle anything. Those few years clarified both conditions.

The pull to build didn't fade. It was just as strong after the exit as it had been before. Solving problems my way, building my own culture, my own team. A good role and a good paycheck didn't touch any of it.

And the wealth goal sharpened. Before my first company, my goal was to become “wealthy”, whatever that means. That's a goal you can never quite miss, because it never says what it means. After the exit, it became a number: the top 1% I mentioned earlier. Something I could measure myself against, and something the paycheck I was earning wasn't going to reach.

So I left again, this time to buy a company with every dollar of liquidity I had.

I'd had comfortable, and it wasn't enough. An exit, a good role, a good paycheck, and both drives were still there. If comfortable would be enough for you, find that out before you leave, not after.

Two questions before you go

If a bigger role and a bigger paycheck had shown up next quarter, would the itch have gone away?

If your business made you comfortable, paid you what you make now and never grew past that, would you count it as a win?

If the answer to either is yes, stay. That's not a failure of nerve. It's an accurate read of what you want, and corporate is the better place to get it.

If the answer to both is no, you're who this is for.

Corporate and ownership are both good trades. The leap is for the people who can't make the first one.

Until next time,

George