A few weeks ago, I was at the Tennessee-Oklahoma game when “All I Do Is Win” started blasting through the stadium speakers.
Great pump-up song. Not exactly true for the 2025 Tennessee Volunteers.
I’ve heard that song a thousand times over the years, but for some reason, a certain line really stuck out to me this time: “Got money on my mind, I can’t never get enough.”
I immediately thought of Morgan Housel’s excellent book The Psychology of Money, which dedicates an entire chapter to a concept most investors completely ignore: the idea of enough.
The Goalpost Problem
If you can’t define what enough looks like for you, you’re setting yourself up for disaster.
I’m not saying you shouldn’t grow. I’m not saying you shouldn’t set aggressive goals.
But there’s a massive difference between thoughtful recalibration and automatic goalpost moving.
Most of us have lived this pattern. You tell yourself, “If I just hit $X in net worth, I’ll be set.” You grind toward that number. You finally hit it. It feels amazing for about two weeks.
Then a new target emerges. Usually 2-3x the first number.
We rationalize the change. “Well, inflation.” “Well, I didn’t account for X.” “Well, I really should have Y.”
And some of this is legitimate, for sure. Targets evolve. Life changes.
But when it becomes reflexive – when you’re changing the target to some arbitrary number because you hit the previous arbitrary number – you’re playing a dangerous game.
The Real Cost of “Never Enough”
Morgan Housel uses Bernie Madoff as his cautionary tale. Bernie had a wildly successful, legitimate market-making business on Wall Street. A business that made him incredibly wealthy by any reasonable definition.
But he couldn’t define enough. That insatiable appetite for more led to the largest Ponzi scheme in history.
And while that’s an extreme example, the inability to define enough creates three very real problems for passive investors:
1. Chasing unnecessary returns
You take on more risk than your situation actually requires. If you stepped back and calculated what you truly need, you’d probably realize half the deals you’re considering are far riskier than necessary.
2. Staying in accumulation mode too long
You may already have enough capital to generate the cash flow you need. But you keep optimizing for growth, accepting volatility and risk you don’t actually need to take on.
3. Wrong portfolio allocation
If you don’t know the finish line, how can you properly build a portfolio to get you where you want to go? You end up with allocations that don’t align with any coherent strategy.
What Changes When You Define It
When you sit down and actually calculate how much passive cash flow you need (and you put real thought behind that number) several things happen.
First, you’re way less likely to randomly move that number just because you hit it. There’s intentionality behind it.
Second, you know when to start transitioning from wealth accumulation to wealth preservation. Too many investors stay in accumulation mode far too long, exposing themselves to unnecessary risk when they should be focused on protecting what they’ve built.
Third, you can evaluate syndication deals within the context of your actual goals, not just based on which one has the highest projected returns.
“Does this deal move me toward my target? Does it fit my current strategy?”
Plus, this makes it way easier to say no to deals that don’t fit, even if the numbers look great on paper. That development deal projecting 25% IRR might be fantastic, but if it doesn’t align with where you are in your wealth journey, you can pass without regret.
Why It Matters
When you define enough, you stop chasing the highest returns and start pursuing returns that actually get you to your goal with the right amount of risk.
You make different decisions. Better ones.
So my question for you: what’s your number?
Not the one you’d blurt out if I asked you right now. The real number. The one you’d arrive at if you actually sat down, worked through your expenses, factored in the lifestyle you want, and built a plan around it.
Because until you truly define that number, the goalposts will keep moving on you.
And if you’re not careful, they’ll keep moving until you either make a mistake that costs you, or wake up at 65 wondering why you’re still grinding.