Don’t Go OTB: A Timely Investment Lesson
March 9, 2026
Written by: Thomas Watson, CFA, CFP®
On our 10th anniversary trip, my wife and I did what we often do on vacations—we tried to fit too much into one day. The morning included miles of hiking and zip lining. By early afternoon, we were strapping on helmets for a guided mountain bike ride I had been looking forward to for months.
As a Peloton rider, I was confident. I understand cadence and output. The plan was to complete a required warm-up trail with a guide and then move on to more advanced tracks the following day.
How hard could it be?
Quite hard, as it turns out.
There’s a meaningful difference between fitness and skill. Peloton builds stamina and leg strength. It does not teach you how to navigate loose gravel, shift your weight on steep descents, or pick a clean line through rocks and ruts.
On flat terrain, practically anyone can ride a bike. Momentum carries you. You don’t have to think much about technique.
Investing during a strong market can feel similar. Buying a hot stock when everything is trending upward feels natural—almost easy. Confidence builds quickly when the terrain is smooth.
But trails change.
The first steep climb was my reality check. Being in the wrong gear wastes energy and traction. Push too hard and the back tire spins. Shift too late and you stall. You have to anticipate the incline and adjust before you’re grinding halfway up it.
In investing, diversification is your gearing system. Portfolios built for only one environment—high growth, low volatility—can struggle when rates rise, valuations compress, or sentiment shifts. Adjusting allocation thoughtfully before the hill arrives matters more than reacting once you’re already under pressure.
The descents were even more instructive. Instinct says grab the brake hard. Experienced riders know that over-braking—especially with the front brake—can reduce control and increase the odds of going OTB, or over the handlebars.
When markets get bumpy, going to cash can resemble grabbing that left-hand brake. It feels protective. But abrupt, emotion-driven exits can lock in losses and make it difficult to reenter when conditions stabilize. Some of the market’s strongest recovery days often cluster around its weakest periods. The goal isn’t to eliminate volatility; it’s to manage it without overreacting.
What made the biggest difference that day was our guide. He knew where traction would fail. He signaled obstacles before we saw them. He set a pace appropriate for the terrain—and for two riders who had already put in a full morning of activity.
In markets, a thoughtful advisor plays a similar role. They can’t remove uncertainty, but they can help you avoid preventable mistakes—overconcentration, panic selling, or taking on terrain that doesn’t match your long-term goals and risk tolerance.
I was humbled on that trail.
I found myself walking my bike for much more of the track than I’d like to admit. My ego was bruised. But I didn’t hurt myself—and that was no doubt thanks to our guide.
Safe to say, we did not proceed to the more advanced trails.
Investing has a way of humbling people too. Confidence built on smooth stretches doesn’t always translate to technical terrain. In both mountain biking and markets, the objective isn’t proving you can conquer the hardest trail.
It’s finishing the ride safely—and being ready to ride again tomorrow.
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