The Reverse Lottery Test: What a Billion Dollars Wouldn’t Fix

If money solved everything, we’d all be fine. But the problems that keep us up at night rarely have a price tag.

Years ago, I created something I called the Reverse Lottery Test. The idea was simple: use it to evaluate the activities on your calendar—your routines, obligations, chores, social commitments—and ask a surprisingly clarifying question:

If I won a billion dollars tomorrow, would I still do any of this?

It sounds almost playful, but it’s a powerful exercise. Pull up your calendar from last week or last month. Go line by line. Would you still go to those meetings? Would you show up to your job? Would you clean your house, mow your lawn, attend that committee meeting, or say yes to that favor you didn’t want to do?

Some things would stay exactly the same. You would still show up for the people you love. You’d still play pickleball, show up to book club, volunteer at the shelter, or binge-watch the same shows. These are the parts of life that align with who we are, not how much money we have. The Reverse Lottery Test helps us see the difference between what we do out of obligation and what we do out of identity, joy, purpose, and connection.

For years, I used the test this way and filter out the noise and focus on what mattered.

But lately, I’ve been thinking about it differently.

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What if we applied the Reverse Lottery Test to our problems?

We all carry around stress: worries about money, work, health, family, aging parents, debt, bills, burnout.

So here’s another question:

If you won a billion dollars tomorrow, which of your problems would disappear? And which would still be there?

At first glance, it feels like the answer is: All of them! Every single problem!

Who wouldn’t feel relief if they could quit the job they hate, pay the medical bills, or help their parents through retirement?

And yes—money absolutely solves money problems. There’s no mystery there.

But keep going. Look deeper.

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The problems money doesn’t touch

We spend huge portions of our lives worrying about our kids—whether they’ll be happy, whether they’ll find someone to love, whether they’ll be fulfilled or even safe. A billion dollars doesn’t magically fix that. Children still grow up, make mistakes, fall in love with the wrong people, struggle, celebrate, and learn on their own terms. Money can’t protect them from the world or from themselves.

The same is true of our relationships. Money might make life easier, but it doesn’t guarantee a happy marriage or lifelong friendships. A billionaire can still feel lonely, misunderstood, or disconnected. Even with endless resources, the right people can still drift away.

And then there are the deeper questions, the ones we don’t say out loud. Will I ever write the book I dream about? Will I build something meaningful? Will my life matter? Money can buy time, but it cannot supply courage, creativity, or purpose. Those things come from within, not from a bank account.

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Why financial independence feels disappointing for some people

This is where the Reverse Lottery Test becomes uncomfortable. So many people in the financial independence world assume that once the money arrives, everything else—stress, insecurity, boredom, identity—will fall into place. They chase a number, reach it, retire early…and then feel lost. The anxiety doesn’t vanish. The depression doesn’t disappear. The free time that once sounded luxurious can suddenly feel overwhelming.

Some even return to work, not because they need a paycheck, but because they need a sense of direction. Others become afraid to spend, because saving and scrappiness were the only structures they knew. After ten or twenty years of chasing a FIRE number, loosening that grip can feel like stepping off a cliff.

And this is the realization many eventually reach: the job wasn’t the real problem. The money wasn’t the problem. Life itself was still there, unchanged, waiting. Because money was never the thing that needed fixing.

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The mirage of “when”

We all fall for the same story:

“When I finally have enough money, everything will be better.”

It’s a mirage. Something far away that keeps shifting as we approach it.

But most of the big human struggles are not financial problems:

• Anxiety

• Loneliness

• Purpose

• Self-worth

• Love

• Regret

• Identity

Money doesn’t solve these. You can’t bribe your way into happiness. You can’t buy self-esteem. You can’t pay someone to heal your grief. You can’t swipe your credit card and suddenly feel worthy of love.

There is no amount of financial independence that replaces emotional independence.

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So what does money buy?

The same thing it has always bought:

Safety. Security. The ability to breathe.

Money buys heat in winter, food on the table, medical care, and a sense of stability.

It removes fear at the bottom of Maslow’s hierarchy.

But at the top—belonging, esteem, self-actualization—money’s influence fades quickly.

A billionaire can still feel like a failure.

A millionaire can still feel lonely.

A financially independent person can still feel purposeless.

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Why the Reverse Lottery Test matters

When you run this test on your activities, you discover what belongs in your life.

When you run it on your problems, you discover what deserves your attention.

If a problem disappears with a billion dollars, it’s a logistics problem. You can plan for that. Save for it. Work through it.

But if a problem would still exist—

• your marriage

• your friendships

• your health

• your art

• your identity

• the way you speak to yourself when you’re alone

—that’s the real work.

Those are the problems that matter.

Those are the ones worth facing, no matter how uncomfortable.

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The truth most people learn too late

A lot of us use money to avoid facing the things we’re scared to look at. Money makes it easy to stay distracted. It gives us a sense of control, even when everything else feels uncertain.

But when you strip that illusion away, you’re left with something real:

Most of our problems are human problems, not financial problems.

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Try the test

Take a quiet moment and ask yourself:

If I won a billion dollars tomorrow, what problems would stay?

Those are the places worth investing your time, attention, emotion, and courage.

Those are the investments that pay off.

Because a billion dollars might change your lifestyle—but fixing the parts of your life that are hurting?

That will change you.

And that’s worth more than any lottery you could ever win.

Did you catch this week’s episode of Earn & Invest (Click to listen)?

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