Living Life with No Regrets

by Tom Koulopoulos

Living Life with No RegretsPutting one foot in the grave today can make you a better entrepreneur and a happier person.

One of my best memories of the late management icon Peter Drucker was him telling me that the greatest misconception about the entrepreneur’s mind set is that they are risk takers. That may be the way they appear to most people, but in the mind of the entrepreneur what he or she is doing is anything but risky. The reason entrepreneurs take out second mortgages, max out their credit cards, and plow every ounce of energy into their company is because in their mind the idea is always a sure bet, or to say it another way, they refuse to compromise on their dreams.

“Most often waiting for the right time is just waiting for a new set of excuses to show up.”

All too often, however, we fail to pursue a dream because we are compromising a long-term need with a short-term want. For example, colleagues who talk about one day owning a business or writing a book but fear the financial risk or can’t seem to find the time, or friends who make compromises in their lives because they fear confronting a near-term personal challenge. The reality is that you’re either committed to a dream or you’re not. Most often waiting for the right time is just waiting for a new set of excuses to show up. Think about your dreams as you would a committed relationship. Your dreams are life partners–give up on them and you’re partly giving up on yourself.

The one thing that is absolutely certain, when it comes to pursuing a dream, is that only you can define what you’re willing to bet and what constitutes an acceptable risk. I recall starting my first business at a time when I was making a great salary with a great company. When I began presenting my plan to friends and even relatives I was shocked that not absolutely everyone was enamored by it. I even had one very close friend tell me I was flat-out crazy and a relative who told me it was the biggest mistake of my life. For me it was a no brainer, I had to do this or I just would never forgive myself for not trying.

I’m not saying that you shouldn’t be prudent, rational, or logical, but never at the cost of your dreams and absolutely never by abdicating their ownership.

Clearly not every dream ends up a success story–not even the majority of them. Most will die relatively quickly. But while you may be able to justify putting off a dream due to probability, you may never be able to justify it to yourself.

In fact an HBR article by Daniel Gulati, which asked professionals what their top five career regrets were, listed “I wish I had quit earlier” and “I wish I had the confidence to start my own business” as the 2nd and 3rd most frequent regrets.

That’s interesting in retrospect, but how can you figure out today what you will regret most not having done later in life?

Here’s an easy exercise I’ve been doing with colleagues and friends for years, which answers that. I’m especially fond of using it with folks who are facing very tough life and business decisions. Try it out and see what your answers tell you about which things you can’t compromise on.

Your Last Day On Earth

Pretend today is your last day on earth. There is no debate or backdoor out of this. When the day is over you will cease to exist. Let that sink in for just a moment. Now that you’ve had a minute to think about your imminent demise, take a deep last breath and list the first three things you would most regret not having done or attempted to do in your life? Don’t think long about it, just jot them down quickly. Be specific, and rather than listing broad categories that are end results (i.e. having made a billion dollars), list the things on the path to getting to your result. For example, instead of “being a good parent” think of “spending more time with my kids.”

“…take a deep last breath and list the first three things you would most regret not having done or attempted to do in your life? “

Likely your list is much longer than three items, and it’s good to jot as many down as you can. But I’m not after your bucket list of “Gee, wouldn’t it be nice to climb the world’s seven tallest mountains…” but instead, the things you absolutely won’t forgive yourself for not having attempted. I call this the list of “Unforgivables” because these are the things that, no matter what the risk involved, you will never forgive yourself for not doing.

Now look at those top three and ask yourself what you did today to act on them. What did you do last week? Last month? What about in the last year?

If these really are your top three unforgivables then you’d better have a long list of actions supporting each one. If not, then get ready for a very long list of regrets.

“What is most important in life, and in business, is that we live up to the promises we make to ourselves.”

When I do this exercise with people I’m not judgmental about their lists. We each have priorities in life that we chose for our own reasons. They may be good reasons to us and not so good to others. What is most important in life and in business is that we live up to the promises we make to ourselves.

Oh, and by the way, as an entrepreneur you can also guess that running your own business had better be in the top three items on your list.

Is that risky? If you really want to be happy with yourself the better question is, “will you regret not taking the risk?”

This article was originally published on Inc.

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Thomas KoulopoulosTom Koulopoulos is the author of 10 books and founder of the Delphi Group, a 25-year-old Boston-based think tank and a past Inc. 500 company that focuses on innovation and the future of business. He tweets from @tkspeaks.

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