Do More Reps Until It Becomes Impossible to Fail

People often ask me how I became knowledgeable about aviation insurance.

They expect me to name a course, a book or a mentor that changed everything.

The truth is much less exciting.

I have simply done more repetitions than most people are willing to do.

Over the course of my career, I have helped review and place more than 22,000 aircraft insurance policies. I have answered well over 500,000 emails. I have spent thousands of hours on the phone with pilots, aircraft owners, flight schools, aircraft maintenance organizations and aviation businesses across Canada.

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None of those numbers happened overnight.

They came from showing up every day, doing the work, asking questions, making mistakes, learning from them and doing it all again the next morning.

There were seasons where our team was incredibly busy. I would work all day, head to the airport in the evening to complete my night flying, then return to finish more work. There were even nights when I slept under my desk because there simply were not enough hours in the day.

At the time it did not feel like I was building experience.

It just felt like hard work.

Looking back, I realize every email, every phone call and every policy review was another repetition. Those repetitions became my education.

The same lesson applies in aviation.

No pilot masters crosswind landings after a few circuits.

No helicopter pilot learns to hover perfectly in a single lesson.

No commercial pilot becomes confident after only a handful of flights.

Confidence is earned through repetition.

Business is no different.

Every phone call teaches you something.

Every client teaches you something.

Every difficult claim teaches you something.

Every policy teaches you something.

Those small lessons compound over time until one day people assume you are naturally good at what you do.

They never see the hundreds of thousands of repetitions that got you there.

That is why I chose to earn both my commercial airplane licence and my commercial helicopter licence. I wanted to understand aviation from the pilot's seat, not just from an insurance policy. That experience has made me a better broker because I understand the real-world decisions pilots make every time they fly.

If there is one lesson I hope people take from this, it is this.

Do not chase shortcuts.

Chase repetitions.

The boring work is where experience is built.

The boring work is where confidence grows.

The boring work is where trust is earned.

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One day you will look back and realize that what once seemed impossible has become routine.

Do enough repetitions that success is no longer based on luck.

Become impossible to ignore because you became impossible to outwork.

About Caleb Winterburn

Caleb Winterburn is a Canadian aviation insurance broker with over 15 years of experience helping aircraft owners across Canada. He is a commercial airplane and commercial helicopter pilot and has helped review more than 22,000 aircraft insurance policies.