A listener wrote in this week with a problem I hear constantly from successful business owners. He is in his mid-40s, still running his company, and has about $10 million saved. He told me that when he first hit a million, he thought he would feel different. Then it was the paid-off house. Then the next milestone. Now he is at $10 million, and he already knows how it is going to go. He is going to keep moving the goalpost. What mistakes, he asked, do we see people in his position make?
This is one of the most common patterns we, your advisors, see in high net worth clients, and it almost never gets talked about honestly. So let’s talk about it.
Why the Number Stops Being the Answer
The financial industry trains people to chase a number. Once you hit this number, you can retire. Once you hit this number, you are done. Even our clients almost always come in with the same question: what number do I need? For people still building toward true needs, food, shelter, basic security in retirement, that is actually the right question.
But once you cross the threshold where most of your spending is discretionary, the number stops working. The marginal value of every additional dollar gets smaller. That is not a personality flaw. That is just how money works. So if you have already passed that point and you are still chasing a number, you will be disappointed every time you hit one. The next one is already forming in your head.
The Three Mistakes I See Most Often
The first is tying identity to net worth. It never works. Net worth becomes a scoreboard, and scoreboards are never satisfying once the game itself stops being the point.
The second is tying identity to a profession. This one is sneaky, because it feels like a strength. You have built something. You are known for it. But if you ever try to step away, you feel like you are losing who you are. That is a fragile place to be, especially heading into your fifties and sixties.
The third is never defining what “enough” looks like in any way other than a dollar figure. It sounds philosophical, and people resist it, but the question of what you actually want your life to look like has to come first. Otherwise you will keep working backward from a moving target.
Work Backward From the Life, Not Toward the Number
Here is the shift I would encourage. Instead of asking what number gets you free, ask what your life looks like once you have time, energy, and capital to spend on it. House paid off, vacation home, down payments for the kids, charitable goals, time with family, travel, the hobbies you have put off for fifteen years. Build that picture in detail.
Then work backward. What does that picture cost, on an annual basis, for as long as you expect to need it? That is a real number, anchored in your life, not in financial press headlines.
The trap is that even after you do this exercise, you can still talk yourself into moving the goalpost. You hit the number you calculated, and then you say, well, $10 million would feel safer. So this only works if you are honest with yourself about what enough actually means.
When You Just Enjoy the Game
There is another possibility worth taking seriously, especially for entrepreneurs. You may simply enjoy the game. Business owners rarely retire in the traditional sense. The odds are very low that you stop working entirely. You like building. You like the puzzle. You like watching what you have built grow.
If that is you, that is fine. Own it. You do not have to retire because some calculator says you have crossed a threshold. But name it for what it is. You are not accumulating wealth because you need it. You are accumulating wealth because you enjoy playing. That is a much healthier framing than telling yourself you will feel different at $15 million when you did not feel different at $10 million.
Playing for Fun, Not for Score
The shift I would suggest, for anyone who has already crossed the threshold of real financial security, is to stop keeping score and start playing for fun. The score has already been settled. You won the part of the game that matters. Anything you build from here is bonus.
That does not mean stop working, stop investing, or stop pushing your business forward. It means recognize that the next dollar is not doing what the first million did. Spend your effort on the parts of life and work that actually move you. The goalpost only keeps moving as long as you keep watching it.
This post is adapted from a recent episode of the Scholar Wealth Podcast. For more perspective on what to do once you have crossed past your financial number, listen to the full podcast episode here.