Don’t Play it Safe!

Last week, I went on my annual planning advance with friends Shane Benson, David Farmer and Daniel Harkavy. One of the more memorable moments was when Daniel reminded us:

“The older people get the less risks they take. This is how we get old in our thinking. The opposite should be true. The older we get the more risks we should take.”

To do this, to avoid getting old in our thinking, we have to honestly answer this question about risk-taking: “Do I still believe the best is yet to come?” If not, we trend toward playing it safe — playing not to lose rather than playing to win.

This certainly isn’t a plea to throw caution to the wind. As we always discussed last week, “Take unrecoverable risks off the table.” The tension then is how do you balance risk in your life? The key is understanding how to apply an important principle when taking risks in life: You can’t eliminate risk but you can manage it. When you manage risk, you’re actually giving yourself a gift — the gift of still believing the best is yet to come.

You’ve heard the old line: “The journey is more important than the destination.” Honestly, I’ve always been a bit skeptical of that line but in this case, it’s true. Journeying through risk because you believe the best is yet to come is a gift to you and the people in your life. You keep your head up and move toward a greater vision than before.

Another quote that we discussed last week came from actor/director Clint Eastwood. He’s 91 years old and currently directing an upcoming movie. When asked why he keeps going his answer was simply: “Don’t let the old man win.”

In other words, keep going, keep moving, keep trying, keep taking risks. After all, the older you get, the more risks you should take.

FOR You,

PS. To help you manage risk in your career, we’ve created the Career Risk Calculator on my website. It’s free and you can take it by clicking HERE.


  1. William E Gill on July 20, 2022 at 11:15 pm

    I needed this and I will ponder, consider and think about this as I am one in the boat. Shall I try to walk on this water? He did say come many times and my human brain said the boat seems safe I’ll believe but stay in this safety. At 65 the fight with this old man is somewhat difficult especially when trying something new like walking on water.

    • Jeff Henderson on August 12, 2022 at 10:15 pm

      Keep moving forward.

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