You can spend without regret

There is no such thing as a single spending decision.

About 15 years ago, I became obsessed with a blue Osprey backpack with black mesh and hip strap pockets.

I had been dealing with neuropathy and a pain condition in my arms and neck that had forced me to stop working for a while. It made life a lot more difficult, and I was searching for a way to carry things around New York City without hurting myself any further.

I didn’t really have a job and I constantly worried about money, but that didn’t stop me from pouring countless hours into the search for the perfect backpack! I learned more than I ever thought I’d know about seam construction, carrying capacity, and ventilation systems (back sweat being one of the great under-diagnosed problems of our time.)

What I could not figure out was one fairly important question: how much was I willing and able to spend on this backpack?

I generally felt panicked about money, but what’s a couple hundred dollars for a bag when you’ve got thousands in your checking account?

Except, I knew that every month, the initially plump account balance I shared with my wife would slowly drain until we were shuffling money around to avoid an overdraft. So on one hand, I knew our finances weren’t good. But on the other hand… didn’t I deserve a good bag?

Without a clear sense of where all that money was going, I had no context for this spending decision. When every purchase exists in a vacuum, one of two things occurs:

1. You either wave any concerns away, promising you’ll figure it out later (”What’s a couple hundred dollars?”) or

2. You spiral, and simple spending decisions become torturous: Should I buy lunch today? Is it responsible? Am I responsible?!

I’ll share a happy update: I don’t really think this way about spending money anymore. Because I’m rich! I use YNAB. Here’s why:

There is no such thing as a single spending decision.

Every purchase exists inside a web of trade-offs, and the YNAB method makes those trade-offs visible, which really helps when you’re trying to figure out if you can spend a couple hundred dollars on a backpack.

When I glance at the app in the morning, I see that I’m making progress on funding a tennis weekend with my brother-in-law in the Catskills. I see I’m almost done saving for my daughter’s birthday party. That brief check-in means I can go through the day knowing where I want my money to go (and where I don’t.)

Which brings me back to the backpack. Hauling myself around those Manhattan outdoor stores, I was looking for more than the perfect bag.

Sometimes we buy things hoping we’ll become someone else in the process: healthy, active, organized. But that puts too much pressure on a single purchase.

The backpack wouldn’t make me into a different person, but it could help me carry things without pain. And as it turned out, that was enough — it was one of the smartest things I ever spent money on. I just couldn’t see that clearly at the time, because I didn’t understand how it fit into the context of all my other spending.

Without knowing what else my money was doing, every spending decision felt equally loaded and uncertain.

Buying the world’s “best” backpack might have meant one less Yankees game with my dad, or one fewer acupuncture session. Those were real trade-offs worth knowing about.

When you can see your trade-offs clearly, some purchases get an easy yes, some get a clear no, and you stop exhausting yourself over the difference. You make the best decision with the information you have and move on, because time is also finite and I wouldn’t want to spend too much of it browsing for backpacks on a beautiful day

I’d love to hear from you:

What’s a purchase you agonized over that turned out to be completely worth it?

Until next time,

Dan