266. What Game Are You Going to Win in 2027?

Hey, Family Brand community! I'm flying solo on this episode after an incredible weekend with our team and clients at PSBLTY.

We just wrapped up the UpMarket Experience, where we had around 100 of our clients together for two days. At PSBLTY, we help financial advisors move upmarket in their businesses—but to me, "upmarket" has always meant more than simply working with higher-net-worth clients. It's also a philosophy. How do we move upmarket in our mindset, our beliefs, our relationships, our health, our leadership, and the areas of life that matter most to us?

One of the things we worked on during the event was creating a 2027 Growth Plan, and as I was preparing to teach it, I had a realization that changed a framework I've used for years.

I've often taught that there are three ways to play the game of life. You can play not to lose, where you're mostly trying to avoid failure. You can play to play, where you put in some effort and see what happens. Or you can play to win, where you're committed, intentional, and giving it your best shot.

But I realized there's actually a fourth option:

You just decide to win.

Playing to win still leaves a little room for, I'm going to try really hard, but this may not work out. What happens if instead you decide, No. I'm going to find a way to win this game?

And when I say "whatever it takes," I'm not talking about sacrificing your family, your health, your integrity, or the things that matter most. I'm talking about becoming incredibly clear about what you want and making a real commitment to creating it.

The first step is making sure you've created a winnable game.

"I want to have a great year" isn't really a winnable game. Neither is "I want my business to do better." How would you know if you won?

Maybe winning for you looks like buying your first home. Maybe it's paying off a specific amount of debt, rebuilding your marriage, strengthening your relationship with one of your kids, starting a business, changing careers, going back to school, or hitting a specific health goal.

The point is to create something specific enough that, at the end of the year, you can look at it and know: I won that game.

And you don't have to win every game at once. I have to remind myself of this too. When we try to completely transform our health, finances, marriage, parenting, business, and everything else simultaneously, we can end up making very little meaningful progress anywhere.

Pick a game. Win it. Then move on to the next one.

There's one more part of this that I think matters just as much: you have to believe it's possible—or at least be willing to believe that it could be.

Maybe there's something in your life you've secretly wondered about for a long time.

Is it possible to save my marriage?

Is it possible to become financially free?

Is it possible to rebuild my relationship with my kids?

Is it possible to finally go after the thing I've always wanted to do?

I'm telling you: it is possible.

And if you don't fully believe that yet, that's okay. One of my favorite examples in scripture is the father who tells Jesus, "I believe; help my unbelief." Sometimes faith isn't having absolute confidence that something will happen. Sometimes faith is saying, I don't completely believe this yet, but I want to.

That's enough to begin.

So here's what I want you to do after this episode:

Decide what game you're going to win.

Make it specific. Decide that you're going to find a way. You don't need to know exactly how yet. You don't need to know when every piece will come together.

Get clear. Have the courage to say what you really want. Decide to win. And choose