How to Win at Life in Two Really Hard Steps

(This might seem like an odd place to start, but trust me — it makes sense.)

Almost no one seems to enjoy managing money.

For some folks, it's pure stress. I know too many people who were raised by parents who managed their money poorly, or not at all. When you live in constant fear of bill collectors, it makes a kind of sense to spend whatever you have while you can, before someone else gets their hands on it. But longterm, that strategy just means finances will always be tight, and it will always be a struggle to save for big purchases — and credit cards will always be a trap.

For others, it's feeling adrift, like there's no one they can really trust to give solid advice on how to do... any of it. When everything seems to come with hidden fees and pages of legalese... they've got a point. And credit cards themselves are the biggest lie of all, promising ease and only delivering more payment deadlines and higher interest rates.

Others have been screwed by the system -- or other people who exploited them -- one too many times. There's no good recourse for thefts like opening a credit card in someone else's name, or for using a partner's income to make your business a success at their expense. 

Whatever the background, what it comes down to is this: managing money sounds like torture to far too many of us.

To me, managing money sounds like the key to fulfilling my dreams.

Let me back up. I'm incredibly lucky not to have started with any of those hangups. 

And I went beyond lucky into charmed years ago: I started to enjoy managing money, setting goals, reaching them. For me, managing money well became a reward in itself. 

But maybe lucky isn't the best way to look at it. Luck was present for me, absolutely -- I grew up in a family where we actually talked about managing money, and where we always had enough of it. So those conversations weren't about stress. It felt more like we were talking about a game, and strategies to play it well. 

Calling it luck, though... implies that if you weren't also lucky, that's that. And that's not how I see it at all. Here's what I see.

I wrote about my idea of a luxury month a few years back. The gist is that it can be incredibly liberating to take a month off from buying physical stuff -- clothes, household goods, whatever it is. Instead, everywhere you are, enjoy just looking at all the things around you. You can walk into a store and walk out again with nothing. It may sound counterintuitive, but it's a powerful exercise not only in self-discipline, but in breaking free of the culture that says ownership is necessary for enjoyment. I've never liked being in stores more than when I knew I wouldn't bring anything home with me. No pressure to decide what to buy! I hadn’t even known that pressure was there until it went away.

Indian Garden, Bright Angel Trail in the Grand Canyon. Maybe you’re like me, and the thing that matters most to you is being able to visit incredible, unique places like this. It’s a mystical experience for sure, but unless you’re a more accomplished hitchhiker than I am, managing money is a necessary part of being able to enjoy them. Just another paradox from your wannabe-capitalist system!

Indian Garden, Bright Angel Trail in the Grand Canyon. Maybe you’re like me, and the thing that matters most to you is being able to visit incredible, unique places like this. It’s a mystical experience for sure, but unless you’re a more accomplished hitchhiker than I am, managing money is a necessary part of being able to enjoy them. Just another paradox from your wannabe-capitalist system!

And the idea of money management, I think, is similar. It demands that we reframe our relationship with money. Instead of asking "what can I buy with this money?" it requires asking different questions. Questions like "In a year, what will I wish I had done with this money?" Questions like, "what matters most to me, and how can I use this money to support that?" And questions like "how can I make this money work for me, instead of the other way around?"

For me, that last one is the core question that drives money management. What do I want to accomplish in the world? How can money help me do it? I decided when I was 18 that doing my best to protect our planet was the most important thing to focus on. Because of that decision, I've lived with roommates almost my entire adult life -- the ecological savings are impressive, and with the right people it's great fun. (Not to mention, it makes housing way more affordable!)

We've all been trained to believe that owning more things — houses, cars, businesses, clothes, yachts, companies — is the only way to succeed. That's a load of bullshit right there, and it plays right into the hands of all the companies who count on you to buy their products. The only way to succeed is to first understand what success means to YOU -- your unique, individual, goals in life, the ones that bring you so much fulfillment when you work towards them that very little else matters. And once you've found what those goals are, give them your heart. Works toward them and don't let anything -- including yourself -- stand in their way. 

It may be that you discover your version of success actually IS owning a lot of stuff -- and that's fine! But if you're spending money out of habit, out of routine, out of fear, take this opportunity to stop. Assess what really matters to you in the world, and in your life. And then ask yourself -- how can I manage money to help me achieve my goal, feed my passion, nourish my soul? 

You might be surprised what those questions help you discover, and what you can accomplish. It's not an easy road, but… well, it's the only one that gets to where you want to be. And why would you want to walk on a road that doesn’t go where you want to be?