Here Are The Five Most Common Regrets Reported By 21 Self-Made Billionaires

By on September 12, 2019 in ArticlesBillionaire News

In America, we often think that making your fortune is the endgame of all endeavor, and that the only thing left to do once you've done it is to start working on the next fortune. But even the self-made billionaires of the world suffer from the universal feeling of regret, and as writer Rafael Badziag recently found, there are some interesting patterns and commonalities that emerge when you ask billionaires about their regrets. He interviewed 21 such individuals for a book called The Billion Dollar Secret, and he recently shared the five most common regrets they feel about their lives with CNBC.

Here's a rundown of what those regrets are:

Missed Opportunities


It turns out that self-made billionaires like Tim Draper (pictured above) can regret missed opportunities just like the rest of us. He told Badziag one of his biggest regrets was back in the early days of Facebook. In those days, the company was valued at about $20 million, but after an intense bidding war Draper's venture capitalism firm backed out, and Facebook's meteoric rise is now history. He also had a similar experience with Yahoo, an investment opportunity that also fell through. As he puts it: "When you spot a great opportunity, don't hesitate."

Not Living In The Moment

Fittingly enough in a conversation about regret, one of the most common reported by highly successful billionaires is failing to live in the present moment rather than fixating on the mistakes of the past or what might happen in the future. Lululemon founder Chip Wilson explained the value of living in the moment like this:

"It seemed to me I was always in survival mode. I was always thinking, 'What am I going to do in the future?' I recognized that I spent probably 40 years of my life not saying, 'Oh, isn't life great?'"

Not Starting Earlier

It's common enough to wish you'd figured out what you were supposed to be doing all along earlier in life, so you'd have that much more experience today. Former billionaire Naveen Jain was in his late 30s when he started InfoSpace, his first company. And he shared just such a regret with Badziaq: "I wish I had done it when I was in my 20s…I would have 20 years more experience to be doing things." Billionaire founder of OSIM International Ron Sim had a similar thought on taking those kinds of leaps now rather than waiting for some perfect moment that might never arrive:

"There is never a right moment to start a business or have a child. But if you don't do it, nothing will happen. So don't wait for the right moment. The sooner you do it, the better."

Not Being Bolder

It's easy to wish you could act with more boldness with the benefit of hindsight, and as it turns out the billionaires interviewed by Badziag aren't immune to this tendency. One of them is Jack Cowin, founder of Competitive Foods Australia, who answered the question of what he would do differently in his life if he could do it all over again:

"I'd be bolder. I'd take more risks…The fear of failure makes you more conscious. The fear of debt makes you more conscious. So I would have more confidence in myself that I could find my way through the maze."

Being Slow To Change

Changing with the times is important for everyone, and some in business are especially aware of its importance. Linamar founder Frank Hasenfratz told Badziag about the myriad changes in the world he's seen over the last 60 years, and he spoke clearly on the importance of flexibility if you're going to be successful over such a long period:

"And if you're not a little bit apprehensive, if you don't think, 'I've got to do better tomorrow, I've got to get a different product or a more advanced product' — if you don't do that, you won't be here for long."

So be bold, start early, seize every opportunity, live in the present, and keep up with the times, and you just might find yourself freer of regret than a typical billionaire.

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