What Skiing Every Month Has Taught Me About Investing

It was a Thursday night in October, and my wife Kelli and I were standing on the edge of the Beartooth Plateau with our headlamps on, staring at a field of rocks where our snow was supposed to be.

US 212, "The Beartooth Highway" was set for an early seasonal closure the next afternoon, and we'd been counting on a reliable little patch near the road's summit to find our October turns. Seven minutes into what should have been a five minute walk, the realization hit: The snow had melted out completely. So we did what we've learned to do over the years: we shouldered our skis and switched to plan B, this time a mile-long walk across the plateau in the dark at 10:30pm to a perennial snowfield that's almost always there. Thankfully, it was. We clicked in, made our turns by headlamp, walked back to the truck, and rushed home to Bozeman with my 96th month booked.

If you're wondering what "month 96" means, Kelli and I ski every single month of the year, January through December, and we have for a long time.

Skiing in October on the Beartooth Highway

"Cave Couloir" - Grand Teton National Park skiing in September

My streak is at eight years without a miss. Kelli's is at 143 months, so I'm still chasing her, and I suspect I always will be.

A month before that night on the plateau, we were on the Grand Teton to tag our skiing for September. Our alarms went off at 3 a.m. so we could beat the trailhead crowds and the late-summer heat, and we climbed more than 4,000 feet to a skinny ribbon of snow called Cave Couloir. By the time we got there, the sun had softened it into really fun, carvable snow, and the skiing was genuinely great. It's also one of the more serious places to ski in the summer, because the couloir ends precariously above a field of scree, and a slip at the bottom would almost certainly mean an injury.

I never set out to learn anything about money from chasing snow every month. But the longer the streak goes, the more I notice that the habits keeping it alive are the same ones that make investing work.

Here are five habits that pay off whether you’re a year-round skier or a long-term investor:

1. Start Early

Nobody loves a 3 a.m. alarm, and I'm no exception. But starting early on the Teton bought us cooler temperatures, better snow, and a margin for error in case anything went sideways, and by the time other groups were starting up, we were already on our way down.

Investing rewards the same habit, and time is the one ingredient you can't buy more of later. A dollar you invest in your twenties or thirties will have decades more to compound than dollars you invest in your fifties, so you don't need to start big; you just need to start before it feels convenient.

2. Know Your Runout

Standing at the top of Cave Couloir, the snow looked perfect, and that's exactly what made it a little dangerous. The best skiing sat right above the worst consequence, so before we dropped in, we talked through what would happen if one of us caught an edge near the bottom.

I ask that same question about every investment a client and I consider. It's easy to fall in love with the upside, but what matters more is whether a bad outcome is something you could recover from, because avoiding the one loss you can't come back from is worth far more than squeezing out a little extra return.

3. Always Have A Plan B

When our patch on the Beartooths turned out to be a field of rocks, we didn't panic, and we didn't write off the month. We already knew where the backup was, because after eight years you learn that the snow you're counting on isn't always going to be there.

A good financial plan works the same way. Plan B might be an emergency fund, a few years of retirement withdrawals set aside in cash, a well-thought income plan, or a portfolio that isn't counting on one outcome, and its whole job is to make sure that when something melts out, you're never forced into a bad decision.

4. Don't Gamble The Streak On Timing

Here's the part of the story that still makes me laugh. Not long after our night on the plateau, a storm rolled in, the pass closed earlier than planned, and Bozeman got more than a foot of snow. We could have skied our own driveway, not to mention some quality turns at Bridger Bowl.

Of course, we had no way of knowing that. Fall is the trickiest stretch of the streak, because if you wait long enough it might snow in town (it has happened before), but if you wait too long you end up scrambling to fly somewhere, slogging through the soggy weather that tends to roll in at the end of October, or chasing a far-off snow patch like the one in the Tetons. With our schedules, betting on a maybe wasn't worth risking the whole streak, so we prioritized the sure thing while we could get it.

That's really the whole case against trying to time the market. Waiting for the perfect moment sometimes looks brilliant in hindsight, but the cost of guessing wrong is missing the days that matter most, and some of the market's best days have historically arrived right after its worst ones. Missing even a handful of them can take a noticeable bite out of long-term returns.

5. The Hard Months Count The Most

Hardly anyone brags about a few turns on wet, gray September snow or a headlamp lap on an old snowfield in October, but a streak is built on exactly those days. We’ve had our share of close calls over the years, but we haven’t missed a month yet.

Compounding works the same quiet way. From month to month you hardly notice it, and then one day you look back and realize it has become the biggest number in your plan. That's why I spend so much time on what you keep after taxes, since every dollar lost to unnecessary tax is a dollar that stops compounding for you. It's the idea behind Why Net Worth Starts With the Word Net.

Month 97 And Beyond

November's turns are up next - winter sure makes skiing year-round easier. In February, we'll keep the streak going on our honeymoon in Japan. I'll share the continued streak in my newsletter, Clearing The Net, where every issue starts on the mountain before it gets to the money, and you can subscribe here.

And if you'd like a plan that's built to last through every season, I'd love to hear from you.

Past performance is not indicative of future results. This is for informational purposes only and is not investment advice.

Björn Borg, CFP®  |  Net Worth Financial Planning    www.networthfp.com  |  © 2026