Redbird Landing

Overestimating Skills and Flying Into Trouble

Written by Chris Peterson | Feb 12, 2026

If you’ve flown long enough, you’ve probably had a moment where you told yourself, “I got this,” when deep down you knew it wasn’t a smart call. Most of the time, we get lucky, and it works out, but in aviation, luck isn’t a strategy.

The sky is a very unforgiving teacher. You either respect your limits, or you eventually find out what they are—the hard way. In this article, we’ll take a look at how pilots get themselves in trouble by overestimating their skills, and more importantly, how to avoid it.

How Confidence Kills

There’s nothing wrong with being confident. You should be confident when you’re flying an airplane. However, confidence can slowly turn into overconfidence without you even noticing.

Maybe you fly a little lower than you normally would. You land with a crosswind a few knots above your comfort zone. You push your fuel reserves thinner than you planned, and nothing bad happens.

So you do it again, until one day, you get caught. Skill matters, but judgment about when to use it is the key to staying safe. There’s a fine line between capable and cocky.

Real-World Example: “I Can Handle This” Turns Into “I Can’t”

Let’s circle back to the Cessna 150 accident in New Hampshire we discussed in a previous article. The pilot had 675 hours. He wasn’t a rookie. In fact, he had plenty of time in that airplane and knew the area well. He probably thought, “I’ve got this,” when he set out on that night flight home.

But here’s what was working against him.

  • He hadn't flown at night in years. 
  • He wasn't instrument-rated.
  • He wasn't current in anything except day, VFR flying.
  • He was flying over a dark lake with wildfire smoke killing what little visibility there was.

This wasn’t a routine hop. It was a high-risk flight that required skills he didn’t have, or that he hadn’t kept sharp. But he convinced himself he could handle it, which unfortunately, he couldn’t.

I have attended Redbird Migration and several workshops and conventions hosted by AOPA and EAA. Frequently, a speaker at one of these events will discuss decision-making, almost always covering “inherent risk” and “calculated risk.”

In theory, we know flying can be dangerous. We mitigate risk as much as possible to arrive at a calculated risk. The calculated risk is the one we are willing to take to accomplish the flight. If the calculated risk is too high, we don’t go—or we shouldn’t go.

Spatial disorientation doesn’t care how many hours you have. If you don’t have the training and recent experience, you’re not immune. The previously mentioned pilot got into trouble because he overestimated his ability to keep control when there was no visual horizon.

Common Traps

 

Familiarity

You’ve flown the same route 50 times. You’ve landed at your home airport in your sleep. That familiarity can lull you into thinking you can handle conditions that are “just a little worse."

Success

The last time you pushed the weather, it worked out. You made it. No big deal. So you think you can do it again. But each time you push the envelope, the margin for error gets thinner.

Experience

Hours in the logbook don’t make you invincible. One thousand hours of flying the same VFR routes on clear days doesn’t mean you can shoot an approach to minimums in IMC.

External Validation

When people see you as “the experienced pilot” in the group, it’s tempting to live up to the image, even if it means flying beyond your actual capabilities. Don’t let the pressure force you into a bad decision.

How To Stay Honest About Your Skills

Just because you’re legal doesn’t mean you’re proficient. When was the last time you flew at night, flew in weather, or practiced unusual attitudes? If it has been a while, don’t fake it. Get a safety pilot or an instructor and knock off the rust.

Set hard limits and stick to them. Write down your personal minimums and treat them like gospel. Don’t fudge the numbers mid-flight because you’re “feeling good.” If you said you wouldn’t fly at night with less than six miles of visibility, don’t. Better yet, review those personal minimums before you fly.

Ask yourself, “What’s different today?” Every flight is different. Is there more crosswind? Are there lower ceilings or unfamiliar airspace? Take a minute and assess what’s different and whether you’re ready for it.

If you’re hearing that quiet voice saying, “This isn’t right,” then pay attention. It’s a lot easier to explain a late arrival than an accident.

The Bottom Line

Confidence in your flying is earned. The best pilots I know are confident, but they also have humility. They know what they can handle and when to say no. They don’t fly beyond their skills. They don’t bet against the weather. They stay honest with themselves, and you should too.