Million-Dollar Decisions vs. Million-Dollar Mistakes.
I was speaking with a doctor who was sitting on close to eight figures, outside his retirement accounts.
This accumulation had come at a cost.
“I would be thrilled to never touch another tooth again.”
Then, in the same breath, he told me why he couldn't walk away.
“I need to get what my practice is worth.”
I understood. I've felt that.
But, he explained, the only buyer who could afford full price for his practice was private equity, and private equity wanted him to sign a five year contract.
So I asked him the question nobody had asked yet.
“What are those five years actually worth to you?”
He didn't have an immediate answer. That's tough to put a price tag on.
Time Spent vs Future Time – Which Has More Value?
If I offered you the chance to buy back a decade — ten years in your prime to live again — for one million dollars, would you take it?
Many folks my age would say yes. In a heartbeat.
Which tells you something: we'll pay almost anything to buy back time we've already spent, but we rarely price it that high while we still have it ahead of us.
Decisions are costly.
The cost is often hidden.
The older you get, the more you value time over money.
Repricing Decisions
The real cost of decisions rarely comes itemized as money. It comes as:
- The associate hire that didn't work out the way you hoped
- The marriage you let go quiet while you were “just getting through” a hard season
- The health you took for granted while chasing other goals
- The decade of optionality you gave up without ever deciding to
Losing track of a marriage while heads-down building a business has cost many an unwitting founder half of everything they worked so hard to build.
That's a million-dollar mistake with a wedding ring attached to it. Nobody plans for it. It accumulates, one missed dinner at a time, until the bill arrives all at once.
You are living million dollar decisions every day.
Million Dollar Decision Frameworks
- Use decision filters. My favorite is the Freedom Filter: “does this move me toward a freer life, or away from one?” Pick your filter: “Does this give me more ______?”. You get to decide.
- Ask who, not what. Often our instinct is to figure it out alone. But people who are able to challenge your view and give you perspective are million dollar mistake insurance.
- Turn big decisions into smaller ones: Before you sign the five-year deal, ask what the smaller version looks like — a pilot, a trial, something with an exit built in.
- At some point, stop analyzing and act. The filters and the outside counsel earn their keep right up until this moment, and then they're done. The fork isn't waiting for certainty. Great decision makers embrace uncertainty. The answer you're looking for might be waiting on the other side of action.
The Question Worth Asking This Week
You're standing at a fork right now. Maybe it's obvious. Maybe it's quiet, the kind that doesn't feel like a decision because you've been putting it off so long it just feels like life.
Either way, it's pricing itself as we speak.
Which pathway leads to more Freedom?
