Finding Your Ski House (or not)

Why smart lawyers can’t save, and how a daydream could fix that

Ask me where I see myself in thirty years—hopefully sooner—and I’ll give you a very specific answer: in a large leather recliner, next to a roaring fire in an enormous stone fireplace, in my ski-in, ski-out house. With too many tempting options, the exact town is the one part I haven’t pinned down. But I’ve got finalists. Maybe Sun Valley, Idaho. Or Taos, New Mexico, which I loved visiting. For sheer scenery, it has to be Telluride or Jackson Hole. Either way, I clearly picture myself in that recliner, surrounded by family, friends, and good books, with a full day of skiing behind me. This isn’t a new thought; I’ve been running this short film on loop in my head since my twenties.

As a suburban, minivan-driving forty-year-old, I’m aware that precious little about me is interesting these days. I don’t expect my retirement daydream to thrill you or change that. But I share it because you need to know that comfy leather recliner I picture myself in has done more for my finances than any budget I ever wrote. And I’ve come to believe that the absence of a similarly vivid, specific, and personal motivator is a big reason so many capable professionals, lawyers very much included, struggle with money.

Lawyers, you bill your life in six-minute increments. You also went to seven extra years of school. If you’re having problems saving, the problem isn’t discipline or intelligence. It’s that the human mind is terrible at decades. It is superb at the imminent, and you—master of the deal closing Friday that you only learned about on Wednesday—could teach a graduate-level seminar on the topic.

After years under the tyranny of the imminent, at work and at home, asking your brain to care about a hypothetical version of yourself in the 2050s or 60s is asking too much. A nebulous idea like “retirement security” cannot contend with the email notification ding that sends you into a Pavlovian sweat. Or your infant child who may be simultaneously crying, blowing out a diaper, and vomiting as you read this. The right recliner can. Amidst ferociously competing demands, the mind will not save for an abstraction—even with an array of the best budgeting apps and tools helping out. But, I’ve found, it will save for the vivid heat of a crackling fireplace and the comfort of soft leather.

Why a recliner beats a spreadsheet

A spreadsheet (or a similar tool) can provide you with information, but it can’t make you act on that information. On the other hand, time and again, the superfluous ski house of my dreams has powerfully compelled me to act zealously in its pursuit.

Ski-in, ski-out property is not a modest ambition. In the marquee towns it starts in the middle seven figures and climbs to nosebleed heights; in the smaller, scrappier ones, you might sneak in for a million or two. Let’s say that, on the low end, I’m in the market for something around $3 million in today’s dollars. Reaching that goal in thirty years, assuming markets deliver something like their long-run 7-or-so percent, takes a bit under $2,500 a month. Every month. For thirty years. And that’s before inflation renegotiates the price upward while you save.

So far, this is ordinary spreadsheet work. Inputs and outputs. Excel does the math; you get a number. It seems cut and dried, but you and I both know that the twenty-fifth of the month—when all your money is already spoken for—is where good financial plans go to die. That’s precisely when the car won’t start, your kid breaks their arm, or work is just so brutal that some retail therapy seems not just desirable but necessary to continue. Even if you have leftover funds, the idea of transferring them to Schwab or Fidelity for some abstract purpose thirty years from now is about as exciting as flossing (which, of course, like saving money, is also virtuous and easy to neglect). And nothing immediately bad happens if you skip it just this once, so you do.

It’s here where the recliner has always saved my financial life in ways no spreadsheet or tool could. When that $2,500 staying in my checking account is the only thing between me and the big leather chair, the fire, and two weeks every Christmas with everyone I love under one roof, the missed transfer stops being an abstraction and starts being personally offensive. The empty Schwab account is the antagonist standing between me and the future I can picture so clearly. That, I’ve found, is powerful motivation.

It’s not magic

I’m slightly embarrassed by my unsophisticated methodology. There’s no magic app; it requires no spreadsheet discipline; and there’s no budgeting system beyond automation and paying myself first. All I have is a picture clear enough to defend zealously, and I fight like hell against everything and everyone that stands between it and me. Somehow, it’s been more than enough.

So, next time you’re tempted to spring for the latest and greatest app, or you find yourself budgeting every month down to the penny yet saving only meager amounts, try finding the picture you’ve been running on loop since your twenties. If you can put a dollar value on it and it’s personal enough to defend, you may have just found a new financial north star. Then, on the twenty-fifth of the month, when it feels like your money is already spoken for and the transfer feels easy to skip, remember there’s something big on the other side of it. Not making the deposit is letting the wrong future steal your spot in the leather chair by the fire.

For now, my chair is empty. But I know exactly where I’ll be sitting. The remaining question that matters is whether you’ve found yours yet.