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Lessons in Flight Delays

Chase Kerby, CFP®, AIF®
10.24.2025

Like many travelers, I found myself in an airport recently trying to catch a connecting flight back home. Due to a delayed start on our first flight, we knew the connection would be tight. Even after a mad dash to our gate, we arrived just in time to see our plane pull away without us. We were told we were rebooked on the next flight leaving in 10 hours.

It was inconvenient, but this is something that happens to every traveler at some point.

This was a risk, but not an unknown one that would warrant never flying again. It’s simply a reason for margin of safety to be built into the plan. It’s the reason I hadn’t made plans immediately after our original scheduled arrival time. These things happen.

The trip’s larger purpose wasn’t derailed. It just looked a little different.

That day, and the extra time on my hands, offered a simple but powerful reminder: success doesn’t require perfection.

Investing Isn’t About Catching Every Flight

Investors are often conditioned to obsess over timing. And yet, some of the best long-term investment outcomes come not from hitting every perfect entry or avoiding every drawdown, but from participating consistently in a sound plan.

Just like travel, markets are full of delays, reroutes, and unexpected turbulence. A missed opportunity or a temporary setback doesn’t undo the entire journey—especially if you’re grounded in a resilient strategy and maintain the flexibility to adapt.

Margin and Mindset

There’s a reason we emphasize margin of safety. Market downturns happen, sometimes at very inconvenient times. For many investors, that safety may be bonds held in a portfolio, cash savings in the bank, or a high consistent income if still working. That margin buys you time and room. It allows you to absorb the inevitable bumps without being forced into reactive decisions.

Margin alone, though, isn’t enough. Mindset matters just as much. The market doesn’t always reward speed or even precision in the short term. It rewards patience, discipline, and the willingness to stay focused on the long view—even when the itinerary changes.

The Big Picture

The flight I missed wasn’t critical. It was a step in a longer journey. Missing it reminded me that while the details matter, they’re not everything. What’s more important is having a clear destination and the flexibility to navigate there, even when the route isn’t direct.

This principle echoes throughout our investment process. We don’t aim to predict every move the market will make. We aim to position ourselves with durable businesses, diversification, and a margin of safety. We manage risk thoughtfully, accept that volatility is part of the terrain, and focus on compounding capital over time.

Looking Ahead

The market in recent months has had its own version of missed flights—mixed data, interest rate uncertainty, geopolitical risk. Some sectors have taken off. Others are still waiting at the gate. We’ve stayed focused on the plan: identifying quality, managing exposure, and staying patient.

Sometimes you land right on time. Sometimes, you miss a connection. Either way, with the right mindset and a good map, you still get where you’re going.

Thank you for your continued trust.

Chase Kerby, CFP®, AIF® is a Senior Advisor with Rather & Kittrell.

 

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