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What Would You Do If You Had All The Money In The World?

There is a question they ask in self-help groups that drives me crazy.

The question is: “What would you do with your time if you had $10 million in cash?”

The first problem with this question is it assumes the people who struggle with what they’re doing in their lives don’t have $10 million in cash, which is wrong. The second problem is it assumes that $10 million is enough to free you of your financial burdens – which is also wrong. Because financial burdens (after a certain point) are psychological burdens. And there is no amount of money that can rid you of psychological burdens. (You have to actually do the work.)

The third problem is: Is this $10 million pre or post-tax?

And, lastly, this question sucks because the answer is not helpful.

Assuming you can get your mind to a place where you can entertain not-having-a-financial-burden, then the question triggers the paradox of choice problem. Which is basically that we collapse under the weight of limitless possibility. TL;DR: More is ​not​ better when it comes to decision making.

[Read: Paradox of Choice by Barry Schwartz]

The question is ​supposed​ to help you identify your *true* desire. Like, “If I had all the money in the world, I’d paint every day!” So it uncovers your not-so-secret desire to paint and then you can reverse engineer your life to include more painting​ time. Or something.

Most humans, however, don’t have a clear cut passion like “painting.” We’re a bit more complicated (and interesting). And this question is a bit too simplistic. BUT MOREOVER.

The answer confuses (or rather ​equates) “enjoyment” and “fulfillment.” Which are not the same. I ​enjoy​ a full-bodied earthy cabernet, but it doesn’t fulfill me. Writing fulfills me and I almost never enjoy it. (that’s not entirely true, but like I’d hardly call this “fun.” I’d call it hard fucking work that I wouldn’t trade for the world.)


A recent interaction has me reevaluating my stance on this aforementioned garbage question. (Contrary to what cancel culture will have you think, we humans can, in fact, change our minds.)

Ok that was a little snarky: what I mean to say is that the gift of being human is changing your mind, expanding your worldview, and updating your opinions based on new evidence or information.

Which is what happened to me when I met Kal.

Kal is a friend who I got to know shortly after he’d gotten laid off and became a default-stay-at-home-dad. Kal cowered in shame as he told me that he’d recently realized that if he had all the money in the world, he’d drink beer, watch reality TV, and spend time with his kids.

He was embarrassed. He was embarrassed because, he believed, his “true desires” revealed that he was an unambitious sack of shit.

He’d even started going to therapy to try and understand what was wrong with him. Why wasn’t he ambitious? Why didn’t he try harder? Why was he such a lazy sack of shit?

I started asking Kal some questions and what I discovered was pretty mundane which is going to be annoying for you as the reader wondering where this story is going. He was a regular dude who enjoyed his life. That’s it. That was what the world told him was a problem.


We = his friends, family, me, probably you, even his therapist entertained this for a bit (bad therapist, bad. No treats for you.).

His “problem” was he wasn’t striving for anything. He was (wait for it) content. He was happy. He loved time with his kids, even when he was exhausted and annoyed. He liked being a dad. He enjoyed beer and reading books and watching TV and going out with friends. He simply enjoyed his life. And while he agreed more money would be nice, he wasn’t feeling like his life or his kids’ lives were wanting.

This. blew. my. mind.

I didn’t know anyone like Kal. 

The people I knew who lived like Kal got there by “settling,” aka submitting to circumstances they were ​deeply unhappy with. Marriages they hated, children they resented, jobs they felt bitter about. Lest we forget, ALSO, an addiction to the acquisition of stuff. I thought Kal was one of those. I thought he was a settler who had a secret ambition to do MORE with his life when he first shared this with me. I agreed with what the world told him: TRY HARDER. HUSTLE. BE MORE!!!

But he was actually a pioneer. In feeling fulfilled.

The things most of us are chasing we can’t find outside of ourselves. Which yes, eye-roll, it’s a nice bumper sticker, but it isn’t gonna pay for your kid’s college. I get it, trust me. Living in a world that rewards your sense of “not enough-ness” is why we have an epidemic of internalized shame in this country.

We live in a world where the most subversive thing you can do is be satisfied with who you are and what you want.


What would you do if you had all the money in the world?

Same thing you should do now:

Love and accept yourself.

I dare you to believe you are enough.


– Margo


PS: One of the links I put above is from Contrapoints and if you haven’t heard of Contrapoints I AM SO JEALOUS OF WHAT’S IN STORE FOR YOU. Contrapoints did a video on Cancel Culture that I believe should be recommended viewing (or reading) for any and everyone who wants to participate in public or private debate. ever. in life.

Along with this playlist on logical fallacies (why we don’t troll the entire internet with these I WILL NEVER KNOW).

Anyway. If you’re not familiar with cancel culture, this will get you all caught up.