Most of us have a regret or two that's affected our success and happiness. Even those who have climbed to the peak of success, like billionaires, have regrets. When we learn that even people at the pinnacle of having it all still regret some things that held them back, it makes us feel better.

That's why the book The Billion Dollar Secret, by Rafael Badziag, caught my eye. Badziag recently shared on CNBC's Make It what he learned from interviews with 21 self-made billionaires (like Chip Wilson, founder of Lululemon, and venture capitalist Tim Draper) about the top regrets they had on their way to making a fortune. One regret in particular really stuck out to me as having the most potential for dramatically holding you back from success.

Too much waiting around for the right moment.

You know the drill here. That perfect time will never come. Guaranteed.

Said billionaire Naveen Jain of his first company, Infospace, which he started in his 30s, "I wish I had done it when I was in my 20s, I would have 20 years more experience to be doing things." This matters because, "You learn a lot more by doing it yourself than by learning from someone else." 

By far the most common thing I hear from people I coach who desperately want to leave their corporate life behind, but haven't yet, is this: "I'm not ready yet" or "Now isn't the time."

And when I poke at what remains to be done before making the move, it's incremental, tiny things, not massive blocks of preparation still left to be done. It's stalling.

The right moment won't hold up a blinking neon light. It won't all lock into place and then send you an alert, like one of those restaurant buzzers that tell you your table is now ready. You've got to make a meal of it before you're no longer hungry.

So when is the right moment?

I made a big decision four years ago to leave the corporate world behind to broaden my platform for making a difference via the spoken and written word (as a professional speaker and writer). People ask me all the time how I knew it was the exact right moment to leave. I didn't.

But one trick helped me. Oftentimes, we'll convince ourselves that it's not the right moment because we're taking so much information in and considering a vast number of variables to discern if it's the right time to make a move on something we're longing to do. So simplify.

Reduce the noise and boil the decision down to only a key question or two as to whether or not it's the right moment. For example, here was the key question I used as I debated leaving corporate: "Will I have a broader positive impact on people now (and later) if I stay in corporate or launch my entrepreneurial venture?" I just kept returning to this same question over and over again as internal false objection after objection arose. The answer came up consistently the same, and so I knew my decision to leave corporate was right, and that the time was right.

This is what happens when you stop waiting and just start.

Virtually every person I've talked to who finally made the leap to do something they were longing to do, whatever that was, all shared the same sentiment.

"What was I waiting for?"

It's natural to hesitate. But the problem is that the more we line up our sight through the scope, the more the scope of what we long to do shrinks. We compromise. We rationalize. We don't realize that we're just delaying happiness.

So much of what we do is born out of two things: love and fear. And far too often, it's fear born out of practicality.

All it takes is a strand of reassurance that you've made the right move (which comes quickly if you've planned well--without obsessing), and it immediately makes all the factors that were holding you back seem overstated and irrelevant.

Learn from those who have accumulated much so you don't accumulate regrets.

Published on: Sep 14, 2019
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