Coach’s Corner Blog

The Top 5 Leadership Regrets I Hope We Can All Avoid

May 6, 2015 by Leave a Comment


I recently came across an interesting article, The Top 5 Regrets of The Dying, which are listed below:

  1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
  2. I wish I hadn’t worked so hard.
  3. I wish I’d had the courage to express my feelings.
  4. I wish I had stayed in touch with my friends.
  5. I wish that I had let myself be happier.

My parents passed away a decade ago after a slow decline during the previous decade. My father was pretty stoic and never waxed philosophically about any regrets and my mother tragically lost her ability to communicate when I was twelve, so there were none expressed there either.

But during my career and especially now, I see a lot of clients and friends nearing the end of their working careers. I thought about what regrets seasoned leaders should consciously avoid now so the pangs of potential regret could be muted.

Here are some thoughts for you to ponder about how to leverage your influence to make your mark on the world that is good for you, your family and friends, your organization and your community.

1. Live the Life that you want

Man is truly great when he acts from the passions. – Benjamin Disraeli (1804-1881)

When we are focused primarily on those things we have developed a passion for, great things happen.  We become passionate about something because it captures our imagination and we develop an almost unconscious competence for it.

It’s in everyone’s best interest to provide as much time and focus for that and to shed the other parts of our work that can be best left to others.

It’s not just about jettisoning the tough or unpleasant parts of our job, but in finding others for whom that work fulfills their passion or skills and may be critical to their development.

2. Find time to smell the roses – NOW

As they say, on your deathbed no man ever said he wished he could have spent more time at the office.

Make some choices and provide time for your personal, professional and spiritual development. Take that class, make that trip and go watch your children’s activities as they grow up.

Don’t be so afraid of what you’ll miss at the office. Work to live; don’t live to work.

3. Express yourself more effectively everywhere

Be willing to assert yourself because you have something to say that matters – not just to be heard. Don’t pick fights, but stand up for what you believe.

I recently came across a very interesting way of thinking about this. In his upcoming book, Marshall Goldsmith asks this sequence of questions to provide structure for what you may wish to weigh in upon:


4. Stay in touch with friends

I came across a saying not long ago: “whose door could you knock on that would not let you in?”

Granted, we may have lost touch with some folks, but it does not mean we cannot reach out and make an effort to reconnect. Facebook and other tools can create great ways to find folks, and who would not be flattered to be thought of?

A true friend is someone that the connection was forged long ago. Make it happen. Most are flattered you reached out.

5. Happiness is a choice – decide!

Do not confuse being CONTENT with being HAPPY.

Our fears and worries often constrain the range of choices we perceive ourselves to have. Your choice to be happy does not deny others their right to do so – it’s not a zero sum game.

Look for the joy in things. Laugh and have a little more fun.

I hope that by considering this, everybody will win!!!

Ask yourself:

  • To what extent are you acting from your passions rather than just doing your job?
  • Are you finding time to “smell the roses” now or are you waiting patiently for the time to be right?
  • When was the last time you reached out to that old friend you think about every so often? What happened?

I look forward to your thoughts and comments.


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