Just one more year.

Over the last five years, I've probably received thousands of emails from people who have built successful businesses, make great money, and have accomplished nearly everything they originally set out to do as an entrepreneur. But I'm always surprised when those same emails say some version of this:

"Justin, I'm making great money, but I hate what I do."

As I’ve started thinking about this a bit more, I realize how people end up in this situation. You find products or services that folks are willing to pay you for, get exceptionally good at delivering them, and build a successful business over the years. Happy customers come back, tell more customers, your popularity and reputation skyrocket, and eventually you become the guy or gal known for whatever it is that you do.

But something else is often happening in the background at the same time. You're growing as a person, your interests are changing, and the urge to start wandering away from your core business might become pretty hard to ignore.

If I’m being honest, this has happened multiple times in my little "portfolio" career. Back in 2019, when I left my startup executive role, all I wanted to do was advise healthcare tech companies. I loved it! But after a year or two, I became obsessed with social media attention and building digital products that could sell without me being on a call. So I stopped consulting and started focusing nearly all of my time and attention on that.

That led to a reputation as some sort of “LinkedIn Guy.” People from all over the world were coming to me to learn how to grow their audiences, write social media content, and turn that attention into income. To be clear, that part of my career was super rewarding. But after years of talking about LinkedIn and social media, I stopped caring about that and started becoming interested in the intersection of good work and great living. Naturally, that meant I wanted to stop talking about LinkedIn and X and hooks and CTAs and all of that other stuff.

The trickiest part of each pivot is that I wanted to make them at a time when the current thing was working exceptionally well and making a lot of money. And, it turns out, the better you become at something, the more money people will pay you to keep doing it. Even if you don't want to.

Imagine that you’re making a good amount of money from a business you no longer have any interest in running. If you've done it long enough, you might have enough financial security to be able to try something new. But walking away means you could be giving up a huge amount of money for the foreseeable future. That's a very tough pill to swallow, especially when you've spent years ascending to that level of success.

So you convince yourself to grind away for another year. Hell, the money's great, your customers are thrilled, and you're taking care of your family. You've got a pretty darn good thing going! Why would you mess with that? I've watched people have this argument with themselves for years after they've stopped enjoying their work. Sometimes for decades.

The real advantage of working for yourself is having the ability to change your mind, even when doing so costs you money.

That doesn't mean that you should change your mind tomorrow if you don’t like your work. Any big change to your life should be done responsibly. You probably have a family to support, bills to pay, and obligations that make giving up your predictable income a really bad idea. There are plenty of scenarios where continuing to do work you don't like is a perfectly rational decision.

But if you've got some financial flexibility, ask yourself this question:

Would you rather make the same money you make today running the business you have now, or half of what you make building something you're genuinely excited about?

If you'd choose the second option, that doesn't mean you have to shut everything down either. You could decide to charge more and take fewer clients, or stop selling a service you don't love delivering, or experiment with a new business in your spare time. Or maybe even take a small sabbatical. You could make those changes gradually, see how they turn out, and then decide what direction makes the most sense for you.

What an awesome choice to even have.

Whenever I get an email from a reader who doesn't like their business, I get the sense that they're almost embarrassed to admit they're bored or miserable in a situation other people might kill for. They're worried about leaving money on the table or making some big decision they'll regret six months from now. I get it.

But I also wonder how many of them will send me the exact same email five or ten years down the road. Maybe they'll have made millions more, grown their businesses even bigger, and become even better at work they hate doing.

All because they keep deciding to give it just “one more year”…five, ten, or fifteen times over.