Every four years, the Winter Olympics deliver a concentrated look at excellence under pressure. We remember the iconic victories: the 1980 U.S. hockey team, the Jamaican bobsledders, Shaun White’s gold-medal runs. But the Games also show us something else. Missed turns. Hard falls. Favorites who don’t finish. Years of preparation undone in seconds. Elite athletes crash. They underperform. They lose events they were expected to win. And then, in some cases, they come back.
That cycle—effort, setback, recalibration, persistence—has more in common with long-term financial planning than it might seem at first glance.
1. Success isn’t about getting it right immediately. It’s about getting it right eventually.
In 1988, speedskater Dan Jansen arrived at the Calgary Olympics as the clear favorite in the 500 meters. He had trained for this moment for years. The gold medal felt almost inevitable. Then, just hours before his race, he received devastating news: his sister had died. He skated anyway. On the first turn of the race, his blade lost its grip. He fell hard and slid across the ice, his medal hopes gone in an instant. Days later, in another event, he fell again.
Four years passed. In 1992, he returned to the Olympics—older, more experienced, still chasing the gold that had slipped away. He left without it.
In 1994, at age twenty-nine and likely in his final Olympic appearance, Jansen lined up once more—this time in the 1,000 meters, not his strongest event. It was his last realistic chance. He skated the race of his life and won gold. He carried his young daughter—named after his late sister—during the medal ceremony.
Real progress rarely follows a straight line. Careers stall. Markets decline. Plans need revision. The first attempt doesn’t always work—and sometimes the second doesn’t either. But long-term success is built by continuing to show up, even after disappointment.
2. Setbacks often look worse in the moment than they are over time.
At the 1998 Winter Olympics in Nagano, Austrian skier Hermann Maier launched out of the starting gate in the downhill event as one of the strongest contenders. Midway through the course, at nearly 70 miles per hour, he lost control. He became airborne, flew off the slope, and cartwheeled violently through two layers of safety netting. The crash was replayed worldwide. It looked career-ending. Amazingly, Maier stood up and walked away. Even more remarkably, just days later, he returned to competition—and won gold in the Super-G. Then he won another gold in the giant slalom.
In the moment, setbacks can feel catastrophic. A market correction. A business slowdown. An unexpected expense that forces difficult choices. But history shows that temporary declines are not permanent conditions. Markets recover. Portfolios rebuild. Disciplined plans adapt. What looks like the end of the story often isn’t.
3. A setback is only wasted if nothing is learned.
In 2018, figure skater Nathan Chen entered the Olympics in South Korea as the favorite. He was known for landing quadruple jumps that few others could attempt. Expectations were sky-high. Then, in his first routine, he faltered. He missed jump after jump. Each mistake compounded the pressure. He finished fifth—far from the podium many had already reserved for him. Later, Chen acknowledged that the pressure consumed him. He focused on outcomes he couldn’t control and allowed small mistakes to snowball.
Four years later, at the 2022 Games, he returned. This time, he skated with composure. He delivered. He won gold. When asked whether he had put his previous Olympic disappointment behind him, he reframed it entirely. It wasn’t something to erase. It was something that prepared him.
Financial decisions work the same way. Not every investment will perform as expected. Not every strategy will unfold perfectly. But reflection—rather than reaction—builds experience. And experience improves future decisions. Over time, lessons compound just like returns.
4. The most important step is deciding to step into the arena.
In financial planning, the biggest risk often isn’t making a mistake. It’s staying on the sidelines. Olympic athletes train for years for events that may last less than two minutes. They understand the risk. They know a single miscalculation can undo everything. They compete anyway.
We’ve seen something similar with clients pursuing their own goals—launching a business, preparing for retirement, restructuring their investments, making a major life change. The turning point isn’t when everything goes perfectly. It’s when they commit and begin. Long-term goals require participation. They require patience. They require the willingness to endure volatility and adjust course when necessary.
The Winter Olympics remind us that excellence is rarely linear. It’s built through preparation, adversity, and repeated effort. In investing—and in life—the objective isn’t to avoid every fall. It’s to build a strategy resilient enough to withstand them, learn from them, and continue forward. That’s how meaningful goals are achieved: not in one flawless moment, but over time.