Regrets? Thankfully, I’ve had a few

I had a great chat recently with a successful businessman – a man in his 60s who has made money in a lot of different industries and lived through both good economic times and bad.

The conversation eventually turned to the subject of the opportunities he failed to capitalise on. It was amazing to hear that even for someone so successful, there have been countless missed opportunities.

He told me stories of businesses he could have invested in and markets he could have gotten into that would have earned him untold extra millions.

It ended up becoming a conversation about regrets – of the downside of being timid or short-sighted and not going after things with sufficient aggression or conviction.

I then asked him what seemed like an obvious question: How many things did he almost go into that would have been a disaster?

He looked at me and smiled. I could almost see the hundreds of near-misses running through his consciousness.

Up until that point, as the conversation flowed, he was becoming obsessed with his mistakes and oversights but he didn’t for a moment consider the kind of reverse luck that he’d had along the way as well.

He then opened up to me about all the things he nearly went in to – the companies that went bust, the people who were crooks, the markets that crashed. Luckily for him, for whatever reason at the time, he simply passed on them.