You Don’t Need a Jackpot. You Need Time.
Why winning the lottery isn’t the same as financial independence
Winner Winner
There’s a game I play when the lottery gets big enough that it makes national news.
I ask my friends and family two questions:
Would you keep working if you won?
What would you do instead?
The first answer is usually quick.
Occasionally someone says yes, but when they do, it’s usually because their work already gives them something beyond a paycheck. It’s something they chose for reasons other than money.
Most people say no. For them, a job is often just that. Something they do because they need the income, even if it comes with decent pay or flexibility along the way.
But they still see it as just a job. So it's not surprising how quickly most people would walk away from it if that need disappeared.
What Comes Next
The second question is where things can get a little more challenging.
Some people have an answer ready and say it with excitement. They want to start a nonprofit. Open a restaurant. Make music. Do something they’ve clearly thought about before.
But a lot of people don’t have an answer at all.
“I have no idea.”
That was always my answer.
The question wasn’t really about my job. It was about what I’d build my time around if I no longer had to build it around work at all. That’s a different question. And one most people haven’t fully answered.
I have a good job and it treats me well. But the odds of me still reporting to work every day if money no longer mattered were pretty slim. I just didn’t know what I would do instead.
For a while, I assumed I was one of the few who hadn’t figured it out.
But the more I’ve talked with friends and others in similar situations, the more I’ve realized that’s not true.
There’s a group of people who feel the same way. Maybe even a silent majority who just don’t talk about it.
We look around and assume everyone else must have it figured out. That they’re satisfied. That they know what they would do. We stay quiet.
Why Just Winning Isn’t Enough
Winning the lottery doesn’t solve that problem. It removes the need to make money, but it doesn’t replace what money was supporting.
It doesn’t tell you what to do with your time, or what you’ll miss when the structure of work is gone. It won’t give you a signal for what will feel meaningful when you no longer need a paycheck.
It just removes the constraint. Instantly.
When everything changes overnight, you don’t get the chance to figure things out along the way. You’re left with a question you haven’t had time to explore. Only now you’re expected to already have an answer.
What Financial Independence Actually Gives You
Financial independence (FI) works differently. It’s a slow building process.
You’re not just accumulating assets. You start to notice things. What you enjoy. What you don’t. What you wish you had more time for. What actually feels worth your attention.
That awareness develops slowly, and with it comes your ability to adjust:
Try something and realize it’s not what you expected.
Change direction without it needing to be permanent.
Begin to move away from things that don’t matter and toward things that might.
By the time you have the option to step away, you’re not starting from zero. You’ve already been moving in a direction.
You Don’t Figure It Out All at Once
There’s an assumption built into the lottery question. That if money were no longer a factor, you should already know what you would do instead.
It’s just the reality that most of us don’t have that answer.
You don’t discover what matters most in a single decision. This happens gradually, as you pay attention to how you’re actually spending your time, including what you’d choose to avoid if you had the option.
For me, that's become clearer through the decisions I've made and adjusted along the way. Spending time with my wife. Focusing on my health and connections with my family and friends. Writing about financial independence and what drives our decisions, which grew out of wanting to help people and my own personal interest in it.
Just as important has been recognizing what I want less of. Things like spending weekends cleaning the house, or working longer than I actually need to. Even minor ones, like a long drive home from the airport after an already long travel day, have shaped how I think about where we might live someday.
None of this showed up all at once. It came from trying things and noticing what I enjoyed and what I didn’t.
And it’s still evolving. I don’t need to be certain about any of it. I just need to see how these preferences start to influence my decisions.
That's where the FI equation begins to take shape. In how I prioritize things like paying for a cleaning service, choosing where I live, or thinking about whether I'd be open to working part-time in the future as a way to test my readiness for retirement. Decisions that can be adjusted as I learn more.
Nothing is set in stone. The equation changes as my decisions do.
Building toward financial independence gives you the space for that.
Revisit The Questions
The decisions you’re already making, including the ones you keep putting off, are telling you something.
Go back to those two questions. Would you keep working if money wasn’t a factor? And what would you do instead?
Pay attention to what comes up when you sit with those a bit longer than you might have before. What you keep coming back to, what you’ve been putting off, what you’d do more of if the excuse of not having time went away. And if there’s just silence, take note of that too.
That’s not nothing. That’s where the direction starts to take shape.
Winning the lottery removes the need to work. Working toward FI gives you time to figure out what fills the space it leaves. Otherwise retirement just becomes the absence of work, which sounds about as enjoyable as a job that just pays the bills.
— Brad
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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice.