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Experience Isn’t the Best Teacher: Someone Who Made the Mistake Already Is

Eric Crews
|
10.15.2026
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"The only source of knowledge is experience."

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Einstein was a pretty smart guy, and his philosophy aligns with my traditional approach to learning.

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I make the mistake. I feel the pain. Eventually, I learn from it.

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Having made many mistakes, I have by now accumulated many lessons. And the kind of stories that are great for retelling.

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They’re great because eventually, everything turns out okay.

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But as I get some distance from my 23 days at sea, I think the most valuable lesson I can learn is….to learn my lessons differently.

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There’s another quote that rivals Einstein’s for wisdom.

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“Dumb people don’t learn.

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Smart people learn from their mistakes.

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Really smart people learn from other people’s mistakes.”

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I live most of my life in that middle category. I need to experience something for myself before I can absorb it.

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But my career is focused on making my clients smarter than me.Taking what I’ve learned and helping other entrepreneurs avoid similar mistakes. Saving them money. Sparing them pain.

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Your biggest strengths are also your fatal flaws. 

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I went on this incredible journey, but I’m not sure I should have been doing it in the first place. I had these crazy experiences, and now I have lessons to share. It’s an amazing story.

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The whole trip was worth it…but only because everything turned out okay. 

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***

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In the aftermath - boat repairs, insurance claims - I’ve been reflecting on one key decision I made during the trip. Actually, before it. 

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I didn’t update the maps in my boat’s GPS. They were only a few years old, and I had a backup option. But if my maps had been current, I wouldn’t have had some of the issues I had along the way. A whole cascade of events could have been avoided.

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The thing is: I knew the maps were outdated. I consulted with my captain and boat management company. 

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What I heard them say was, “It will probably be okay if you don’t do it.”

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What I should have heard was, “You should definitely do the updates, but ultimately it’s your boat, your trip, your decision.”

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I am insistent when I give my clients recommendations. I don’t let things slide. But that’s part of my personality and communication style. I’m a driver, and when I feel vehemently about something, I’m not afraid to say so.

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Not everyone communicates the same way. I wish they did (for my sake), but they don’t. So the guidance I got about my GPS wasn’t strong enough (for me). And I wasn’t smart enough to take the good advice.

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Being able to learn from other people’s mistakes requires you to recognize when you’re getting good advice in the first place. 

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***

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Mistakes are inevitable - even with the best advice, we will all make them. The most we can do in that situation is to learn our lessons well.

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But I’m more committed than ever to learning from each other. Not only sharing the mistakes that I’ve already made, but listening carefully to avoid making new ones.  

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