What If It Never Feels Like Enough?
On money, identity, and what your life actually costs
I was invited to speak to a group of guys about financial literacy.
Not just a random group. This is a group of men who meet regularly to work out together, to push themselves physically, to take care of their bodies, and just as intentionally, to take care of each other.
There’s a steadiness to them. Beards. Boots. Carhartt. Plaid shirts and many wearing the kind of t-shirts that fit tightly in all the places that suggest discipline… and that, if I put one on, would look less “fitted” and more like I borrowed my dad’s pajamas.
Before we talked about money, we did five minutes of breathing work.
Arms up. Right elbow to left knee. Twist. Exhale. Back up. Switch. Repeat.
And to be clear, this wasn’t “exercise.” This looked a whole lot like yoga.
At one point, during a long collective exhale, it felt like a room full of pirates trying to collectively blow out a birthday cake that was very, very far away. At another point, with knees up and elbows down, it looked like a bunch of frozen Heisman Trophy poses. Add Halloween costumes and you’ve got a full Hall of Heroes exhibit.
Everyone locked in. Strong. Intentional.
And it would be easy to write this off as “a bunch of guys getting together.”
But it’s not that.
This isn’t bro culture.
There was a level of honesty in that room that you don’t see often. Guys talking about reconnecting with a parent after years of silence. Celebrating an adoption that finally looks like it’s going to happen. Admitting that certain kinds of debt feel… soul crushing.
Not as a performance.
Just… real.
Then we sat down and talked about money.
I shared my story — how my partner and I, as teachers, didn’t make huge salaries but still built toward financial freedom. How we’ve reached a point where work is optional.
Not as a flex. Just context. Because they invited me there for this exact conversation.
We talked about buffers and not crashing your financial car. We talked about thinking of money as priorities, passions, play, and problems. (links to past Cadence of Cash posts on those topics)
Both of those landed.
But the moment I keep coming back to was a question.
One of the guys said he understood how to spend less. But it felt easier to make more money than to cut back. And even when more money comes in, it seems to go just as quickly.
This wasn’t someone reckless. This was someone who saves, invests, lives relatively modestly, and is trying to do things right. And still feels like meaningful change is just out of reach.
He didn’t say this exactly, but what I heard underneath it was:
What if this just… doesn’t change?
That’s not a math question.
That’s a life question.
And it’s one worth sitting with.
Because a lot of people are living that exact pattern:
Make more. Spend more. Still feel behind.
Not because they’re careless. Not because they’re greedy. Just because life expands, quietly.
Better versions of things. More convenience. More “this will make life easier.”
And suddenly the life that once felt like progress just becomes normal.
Then insufficient.
The question underneath all of this — the one nobody really wants to ask out loud — is:
Where is enough? (I deal with this more in depth here)
I don’t think that question needs a perfect answer.
I think it needs to be taken seriously.
Because there is a way through it, and it starts with something more concrete:
What does your life actually cost?
Not what you make.
What you need.
Maybe you make $100,000, and maybe your life really does cost $100,000. That’s possible.
But maybe it costs $80,000.
And maybe that $20,000 gap is the thing that changes everything.
Start there. Take an honest audit.
What are your true necessities, your priorities? Then your passions — not ten of them, not even five. Three. The things you actually care about enough to build your life around.
Then look at what’s left and ask yourself one hard question:
Do you value those things more than you value your own financial freedom?
That’s not a condemnation. It’s not a finger point.
It’s a question to wrestle with.
Because only you know what you need. Only you know what you want. And if that’s not clear yet, that’s the work.
There is also a numerical truth worth knowing.
A dollar you don’t spend does double work. It gets invested, and it lowers the amount you need to live on. Every new dollar you earn gets taxed before it’s ever yours.
So mathematically, subtraction often beats addition.
But the more powerful shift isn’t really about cutting.
It’s about identity.
The people who find their way through this tend to stop identifying with their full income. They pretend they make less.
If you make $100,000, you decide your life runs on $80,000 before the money ever has a chance to become lifestyle.
It’s a psychological game. But it works.
Because in the same way you can imagine life with more, you can practice life with less.
And if your life genuinely costs what it costs — if there really isn’t room to subtract — that’s worth knowing too.
That’s what points you toward earning more, or toward somewhere your money goes further.
But you have to find the baseline first.
Otherwise every decision that comes after it is just noise.
What struck me, sitting in that room, is that these guys already understand something most people don’t.
They know it takes reps. They know it takes intention. They know it takes doing hard things consistently, even when you don’t feel like it.
They’ve already figured out how to take care of their bodies and show up for each other.
Money is just the place where that same mindset hasn’t fully transferred yet.
But it will.
Because they already know how to do the hardest part.
They just have to keep showing up.
Because that’s what the practice is.
Money isn’t a destination you arrive at.
It’s a practice — one that, done consistently, protects the thing that matters most:
Your time.