The first time you jump out of a plane, your brain goes into full alert. Every instinct screams: “What are we doing? This isn’t safe!” The fear is loud, obvious, almost primal. And in some ways, it helps. You’re hyper-alert, extra focused, calculating every move.
But here’s what surprised me: fear doesn’t disappear with experience.
It evolves. I’m now approaching the milestone of 200 jumps, and the fear I feel today is very different from what I felt on jump one. It’s quieter. Trickier. More dangerous.
At this stage, I don’t fear the freefall. I fear the subtle overconfidence. I fear the moment I skip a checklist. I fear the one percent of complacency that slips in when things feel routine. In skydiving, that’s when most accidents happen. Not during the early, terrified jumps, but later, when the mind starts saying, “I’ve got this.”
And it made me wonder: what’s the equivalent of 200 jumps in the workplace?
In leadership and high performance, fear at the beginning is about failure. What if I mess up? What if I don’t have what it takes? But as we grow, succeed, and gain credibility, the fear often shifts. At that point, it’s not fear of failure. It’s fear of blind spots. Fear of assuming we’re immune to mistakes.
And science backs this up. A study published in Organizational Behavior and Human Decision Processes showed that experienced professionals often overestimate their ability to avoid errors, especially when tasks become repetitive.
It’s called the overconfidence bias, and it tends to show up after we’ve become good at something.
The Dunning-Kruger effect, often misunderstood, actually tells us that the mid-zone of competence is when we’re most susceptible to thinking we know more than we do.
And in leadership, this looks like:
- You skip due diligence because you’ve done this before.
- You dismiss junior input that challenges your assumptions.
- You make decisions fast, without updating the mental model.
So here’s the uncomfortable truth: the biggest risk isn’t lack of experience. It’s the illusion that experience equals immunity.
True mastery, in skydiving or leadership, is staying vigilant even when it’s easy. It’s remembering the checklist even when you’ve done it a hundred times. It’s staying curious instead of operating on autopilot.
As a coach, I’ve seen it first-hand. A senior executive makes a call without checking with the team because this is how we’ve always done it. A high-performer resists feedback because they’ve got the track record.
The result? Slower adaptation. Missed signals. Unforced errors.
This week, ask yourself:
- Where in your life or leadership have things become too familiar?
- What small steps could help reintroduce awareness, curiosity, or structure?
- Is there a checklist you’re skipping, mentally or practically, because it feels safe?
To your continued growth,
Lison
PS: If someone has forwarded this to you, you can subscribe here. It’s free. Your information is protected. And I never spam. Ever.
Whenever you are ready, here are a few ways I can help:
- Join my 1-1 coaching program designed to elevate your performance, leadership, and positioning. Whether you’re looking to gain clarity, strengthen your leadership presence, or take your career to the next level, I’ll help you achieve tangible results. Book a call to explore how we can work together here.
- Book one of my workshops or keynotes for your team to elevate energy and performance. More information here.
- With my first book Act Before You overThink to learn how to make better decisions faster and liberate your mind from the constant chatter that hinders your potential. You can buy it here.
Responses