Most people assume the dangerous thing to do with money is something reckless. You’ll get chastised for betting on a sports event or pouring your savings into a stock only because your feed couldn’t stop talking about it. Putting a big trip on a credit card or checking out the hottest restaurant in town when your emergency savings account couldn’t cover a few months’ expenses will earn you the label of “irresponsible”. These are the type of decisions that get all the attention and are lightning rods for derisive feedback.
What isn’t talked about enough is that the most damaging move is rarely doing something impulsive or reckless. It’s avoidance. It shows up as the auto insurance renewal paperwork that you never question or the lease that’s gone up $500 in the past 2 years that you renewed because moving would be exhausting. It’s the raise you never asked for because the conversation would feel awkward or the plan to deal with your mounting debt once life “settles down.” None of these things feel like decisions but all of them are.
Many people avoid thinking about their finances because it’s a source of depression and anxiety. When money is tight, being reminded of your bank balance can be soul crushing. But some people exhibit avoidance behavior for a different reason. They’ve looked at the game of life and decided that no matter what they do they can’t win.
I’ve been writing about this concept for a while and coined the phrase “when p(win)=0”. Once someone concludes that the probability of winning a game is zero, they stop playing by the established rules. They make moves that shock friends and family, but to them, doing something irrational is better than doing something rational knowing that it won’t work.
And the p(win)=0 feeling isn’t crazy because the game is harder than it used to be. The version of the American Dream your parents described to you isn’t true anymore. It costs between five and six million dollars to live your life and earn enough to retire, and the median college graduate won’t earn half of that in salary alone. Savings and investments need to close the gap, but socking away money is incredibly hard because incomes haven’t kept up with rising costs. Housing is now out of reach for most young families, one batch of medical bills can erase years of savings, and inflation keeps reducing your purchasing power while the official numbers insist everything is fine. If the math feels like it stopped working, it’s because it has.
So the instinct to step away and stop trying can be strong. It’s also the one response that guarantees things won’t get better. Waiting for structural fixes that are in the hands of politicians runs on a clock you don’t control. You can be right about every unfair thing in the economy and spend your whole life miserably waiting for fixes that might not come. The only question that really matters is: “What are you going to do to improve your financial situation tomorrow?”
It’s hardest if you did everything right
This lands hardest on the people who followed the rules. You went to school, worked hard, got the degree and the job, and ran the playbook you were told works: Do A then B then C and life will be great. The result was watching the milestones your parents hit on a predictable schedule float out of reach.
It feels like betrayal because it is one. The playbook didn’t fail because you ran it wrong. It failed because the prices it assumed roughly tripled while wages didn’t keep pace. Many people stare at today’s reality and conclude that the people who have already won have rigged the game against them. Maybe they’re right.
The one player you control
In any game, exactly one character moves when you tell it to: You. You can’t reset the price of a house, or fix what healthcare costs, or make a dollar buy what it did for your parents. But where you live, what you study, who you build a household with, and where every dollar goes are still your choices. What you can control defines a bigger surface than it might feel, but objectively it’s large enough to change how your life is lived. It’s also chock full of decisions that aren’t made with enough care.
Drift is a decision
Avoidance never feels like a choice. It feels like keeping your options open by always waiting for a better moment. Meanwhile inertia makes choices for you.
Stack five, ten or twenty years of those non-choices on top of each other and you wake up with fewer options and certainty that the game is rigged. The person who avoids thinking about the seven or eight big decisions that are responsible for 80-90% of their financial life has set their own p(win) to zero and placed the blame on a broken system. It’s hard to watch because failure is almost guaranteed.
You can’t have it all, and that’s just the way it is
Winning has to start by internalizing that the game of life shouldn’t be measured using someone else’s scoreboard. The measuring stick you were handed by your parents was built for a world that stopped existing. And because of social media, it’s easy to fall into the trap of comparing yourself to everyone’s highly filtered highlight reel. The real traps are believing you’re owed what other people have or grieving a future you were promised.
Today’s world requires a different mindset and a different way of navigating life. In a world this expensive, winning requires defining the set of tradeoffs you can live with and then doing what matters most to you without guilt. Winning is about building a life with enough room for your priorities because you got the scaffolding right. That’s it.
And the tradeoffs that work for you might horrify your parents or be a lightning rod for judgmental comments in your social feed. Who cares? You shouldn’t!
Graduating on time might be difficult, but adding an extra year of school might cost you the equivalent of a vacation every single year of your twenties or a down payment on a house. Don’t think of this as the system being unfair. It’s just the price being made visible. The only tragedy that matters is refusing to choose, because in today’s world you can’t have everything, and pretending you can is how you end up broke and anxious. Pick what matters most and structure everything else around it. The people who are happy aren’t always the ones with the most “stuff”. They’re the ones who decided what they wanted and stopped apologizing for the rest.
The big stuff is where the leverage is
So if you’re going to make trade-offs, make them where they move the needle. If you skip every $28 salad and cancel every subscription for a year, you might claw back a couple thousand dollars. It’s real money but it’s a decision worth almost nothing next to the big decisions in your life. The big stuff dwarfs the small stuff, but most people pour their energy into the small stuff because it’s more comfortable to stare at and it’s what your apps know how to measure.
But something profound happens if you get the big stuff roughly right. Suddenly you can buy the new running shoes or cover dinner for a friend or go to the concert and none of it trips an alarm. This is the freedom that comes from getting the structure underneath your life right. Policing how many ingredients you add to your salad is never going to do it. Sorry Dave Ramsey. Sorry Kevin O’Leary. Sorry budgeting app. You’re just wrong.
Blame won’t pay the rent
I know this sounds like I’m telling people to swallow a mess they didn’t make. I’m not. The mess is real, and most of the blame is earned by bad policy, an economy that’s not rewarding the typical worker and people who climbed the ladder and are busy pulling it up behind them. If housing and healthcare and the slow leak in your paycheck make you furious, good. Stay furious.
But don’t confuse being right with being powerless. Anger doesn’t pay the rent. You still have to live in the system as it stands while the bigger fights grind on. Waiting for the rules to change is just hopium and not a real plan. Going from p(win)=0 to p(win)=1 rarely happens by accident. It takes work aimed at the handful of things that you control.
Why I’m optimistic anyway
You might not believe me, but I’m actually quite optimistic about today’s upcoming generation being able to win the game of life. I believe that most people are capable of making difficult choices once they understand them. Some make the hard call at twenty-eight and some at forty-eight. Not everyone is on the same timeline. But the resilience in our society is real. It just refuses to show up without a little prodding.
I’ve started calling the whole posture being fintentional. It’s about making the big calls on purpose instead of letting them get made for you. It’s the opposite of drift, and it’s the theory behind what I’m building. It’s not a promise that the game will be easy, but it’s a map and a flashlight, a price tag on the choices you’ve been making blind, and a hand on your shoulder while you make the calls only you can make.
If this is a cause you’re interested in or have thoughts about, let’s talk!



Frank, I really look up to you. I've been fintentional my entire life (with the exception of biting off more crypto than I should have). Growing up, my mom would drop my two brothers and me off at the local arcade during summer work days. She would hand each of us $5-10 each time. My older brother could make his last a couple hours or more playing sports games. My little brother blew it immediately to use his tickets on candy. I saved 90-100% of mine every time. Just one example.
What advice would you give someone who has the desire, willingness, and dedication to build but does not have a clear vision or mission or problem which he wants to solve. It's about finding a problem and providing a solution. Refine. Repeat. Finding the problem that one finds passion in the solution for is the trick.