Financial Planning for the Reckless

A bold new approach to your golden years

Welcome back to Geoff Rodkey’s Bad Advice! I’d apologize for the six-month hiatus, but if you’re one of the 97% of readers who haven’t submitted a question, it’s kinda your fault?

A sincere thanks to the other three percent, especially the two of you who wrote in with almost exactly the same question.

Maxed-Out in Milwaukee wants to know: 

“Should I wait until I’m old and broke to retire, or should I call it quits now, escape to the beaches of Southern California, and enjoy my poverty with relative youth and nice weather?”

First things first, Maxed-Out: Southern California is NOT an attractive retirement destination.

It’s a dystopian hellscape camouflaged by palm trees and low humidity. 

I’m not just saying this because I heard it on Joe Rogan. I personally spent the worst year of my life in Los Angeles. Granted, it was thirty years ago, and I was unemployed, clinically depressed, chronically single, and had a drug problem. But I still maintain that was L.A.’s fault, not mine. And only one of us has bounced back since then.

Let’s not get too deep in the weeds with the geography, though. The real question you’re asking isn’t so much where to retire, but when. 

Clueless in Cleveland is also wrestling with this:

“Should my husband and I save up enough now for a comfortable retirement by working very hard and often, or should we have more fun now and hope that Social Security will remain robust and inheritance will be on the high side of our estimates?”

I’m tempted to get bogged down in the specifics of this one, too.

Cleveland, who are you expecting to inherit money from? Are they keeping the principal intact, or pissing it away? If it’s the latter, any chance they could meet with an untimely but not otherwise suspicious accident? 

And does your definition of “robust” extend to getting only three-fourths of what our government promised us? Because the Social Security Administration itself is admitting that’s all we’ll get after the Baby Boomers finish bleeding the trust fund dry.

But you know what? It doesn’t even matter.

Because financial planning isn’t really about numbers. It’s about values.

I’m lying. It’s about numbers. Financial planning is NOTHING but numbers. Which is why most people suck at it. 

Including me, and apparently both of you. 

Except that the question of when to retire can stump even folks who are good at math, because the REALLY key variable—how much time do I have left?—is unknowable. 

Will you be on this earth for another fifty years? Or five?

Either way, here’s my advice:

Start living in the present.

You’re middle aged, right? You’ve got a little money in the bank. You don’t love your job, or you wouldn’t have asked me this question. 

You’re sick and tired of grinding out a decades-long, real-world version of the marshmallow test. And in the back of your mind lurks the creeping dread that one of these days, when the bell rings and the overworked psychology grad student administering the experiment shows up with your next marshmallow, it won’t be a grad student, it’ll be the Angel of Death. 

At which point you’ll realize, WAY TOO LATE, that the truly scarce resource wasn’t marshmallows after all.

It was time.

Did this guy wait too long to cash in his marshmallows?

So set yourself free! Dial back on your work hours. If your boss doesn’t like it, quit.

It’s time to start doing the things you always told yourself you’d do someday. Take up a hobby! Travel the world! Move to the beach!

(Not an L.A. beach, though. Maybe Thailand?)

Make every day count. You’ll be glad you did.

Right up until you run out of money. 

Because you ALSO wouldn’t have asked me this question if you could actually afford to retire without going broke.  

That doesn’t mean you shouldn’t take my advice. It just means that when you DO run out of money in a decade or two, you’ll have to get creative about supporting yourself.

Here’s how you can do that:

Commit a major felony. 

Not just any felony. An art heist.

I know what you’re thinking: “Aren’t art heists incredibly hard to pull off?”

Yes! That’s the whole point. You don’t want to get away with it.

You just want to get sentenced to prison for the rest of your life. Because then feeding, clothing, and sheltering you is the government’s job!

Think of it as a non-traditional way to claim the Social Security benefits that you’ll otherwise be getting screwed out of.

What makes an art heist so perfect is that it’s serious, but non-violent. So when they lock you up, it’ll be minimum security. (Just don’t do anything stupid, like hitting a museum guard with the artwork you’re stealing. Adding aggravated assault to your indictment will screw up the whole thing.)

And make sure you steal something expensive enough that they really throw the book at you. If all you get is a slap on the wrist, in eighteen to twenty-four months you’ll be right back at square one.

I’d suggest a piece that’s high-profile but either has no redeeming cultural value—like one of those Jeff Koons sculptures of horny cartoon characters—or is super-easy to replace if you accidentally drop it. Which you probably will, because you’ll be suffering from osteoporosis.

A Mondrian would be a great choice. There’s almost nothing in Piet Mondrian’s oeuvre that you couldn’t swap out with some construction paper, scissors, and a ruler.

seriously, how hard could this be?

I realize the idea of incarcerating yourself for the final years of your life might not sound appealing. But keep in mind that this is AFTER you’ve spent all the time between now and then living your best life. So you’ll have nothing left to regret. 

And in twenty years, is there really going to be any difference between a retirement home and a prison? They’re already both owned by private equity. It’s only a matter of time before corporate synergy renders them functionally identical.

Sure, you’ll only get an hour a day of outdoor exercise in the prison yard. But when you’re eighty-five, how much more will you even want? 

Good luck! I really like this life plan for both of you. 

And thanks for your interest in my bad advice! Please share it with others, because I deleted my Twitter account, I’m still not sure I’m using Instagram correctly, and TikTok frightens me. So if you want to read more of these, it’s on you to get the word out.

Also: if you’ve read this far and haven’t submitted a question yet, SEND ME ONE! I can’t do this without you.