Happy New Year! I hope your holidays were restful, that you got quality time with family, and that you’re heading into 2026 recharged and ready.
And hopefully, by most conventional measures, 2025 was a great year for you financially. Income up. Bonus bigger. 401(k) and brokerage accounts climbing. Net worth increasing. Maybe you even exited a business or hit some other major milestone.
If all those things happened, congratulations. The scoreboard says you’re winning.
But as we start a fresh new year, I think it’s worth asking: Are you winning at the game you actually want to be winning?
Or are you just getting really good at a game that won't get you where you actually want to go?
Two Different Games
To use another analogy, imagine spending your entire life climbing a ladder, only to reach the top and realize it was leaning against the wrong building.
You’re at the top. You made it. You “won.” But you’re nowhere near where you thought you’d be.
This is the tension between the accumulation game and the freedom game. They may look similar – but they have completely different rules, different strategies, and most importantly, different outcomes.
The accumulation game is what mainstream financial media obsesses over. Grow your investment balances. Watch your 401(k) climb. See net worth increase. It’s easy to measure and track, and it feels good seeing those numbers go up.
But the freedom (or cash flow) game asks a different question entirely: What percentage of my life can I fund without working?
That’s not necessarily about how big the number on your screen is. It’s about reducing how much you rely on actively trading time for money, whether that’s a W-2 job or working in your own business.
The Part Nobody Talks About
Most high earners don’t realize that it’s entirely possible to dominate the scoreboard of one game while making zero progress on the other.
You can have your best accumulation year ever and still be just as tied to your paycheck as you were 12 months ago.
I like to call this “number go up” investing. The balance increases. You feel wealthier. But can you actually use any of it without selling assets or waiting decades?
Nothing changes about your freedom. Nothing changes about your choices. The number got bigger, but your life stays exactly the same.
As I’ve written many times before: you can’t eat equity.
The numbers on the screen getting bigger doesn’t change anything in your everyday life. It doesn’t give you more options or reduce your need to show up to work Monday morning.
Playing Both Games
Now, I don’t want to suggest you completely abandon accumulation. Especially if you’re earlier in your journey, you need to be building that base.
But at the very least, you probably need to be playing both games.
And as you progress, you should be tilting more and more toward freedom. Toward assets that:
- Pay you to own them
- Put cash in your pocket today
- Reduce how much you need to work
The accumulation game compounds your wealth, no doubt. And while that’s not bad, it’s probably not your end goal when you really sit down and think about it.
The freedom game compounds your choices. And more choices is the whole point.
The Question for 2026
2025 might have been your best financial year ever. But if accumulation was the only game you played, nothing changed about your freedom. Nothing changed about your choices.
So as you head into the new year, maybe the best question isn’t “Can I have another winning year?”
The better question could be: Am I playing the right game?
Just because the scoreboard says you’re winning doesn’t mean you're keeping score of what actually matters.