Where Leaders Come to Think

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Live With Few Regrets


Why I do this to myself?  Sometimes, when I’m feeling contemplative, I think about the end. Which for a person of faith is actually the beginning…sorry, I digress.

I think about my epitaph and what this life is all about. I worry about the dash in between. Have you ever wondered what the ones you love the most will say about you when you die? How about the people who don’t like you much?

I have a desire to leave a positive legacy while sharing our planet and gain momentum so that I may step into eternity having “run the good race” or “persevered” like the Apostle Paul wrote about.

Even writing about this subject makes me realize that thinking about the end of the story is not normal. I’m not normal. Having said that, I’m not sure I was ever created for “normal” – were you?

What if there existed a solid life strategy for the “not so normal” leader who wishes to leave a legacy and live with few regrets? I think there just might be.

How to Leave a Legacy With Few Regrets

  • Enlarge Your Story. Dr. Henry Cloud teaches that we should play the movie forward. You know, think through what the results of your actions are before you begin. That’s wisdom; the challenge is to expand your thinking beyond. Don’t just live life for earthy stuff rather think through your eternal results. This is important because when you add heaven into the mix you will immediately take your focus off yourself and place it on others. I believe this is the secret behind ending well. A successful legacy is about the value you add to others through love.
  • Cling To Hope. Hope is a funny concept. It is the confident belief that despite challenges, pains and sufferings there is still reasons to carry on. Legacy leaving leaders need to cling to hope like it is oxygen because it truly is what fuels the human spirit. Lose hope in anything and you lose everything. Hope says – yes we can. Hope declares – we got this. Hope gives rise to joy and joy gives power to life. Legacy leaving leaders learn that clinging to hope takes intentionality and effort. My experience is that life is mostly challenging and hard. If you don’t believe me, simply watch the news. Finding hope is a mandatory practice if you want to keep your heart alive and in the game.
  • Fail Like a Freak. A freak is freaky because they add a level of insane intensity to anything they do. Normally to be called a freak is a bad thing. However, when it comes to failing it takes a freakish resolve to continue forward. Learning to fail like a freak means learning to learn from our failures. To take every mistake in life and turn it into a lesson of life. The best lessons in life come from the valley and not the mountain. When your pressed and broken I believe this is where you grow the most. So give yourself permission to live with a freakishly reckless abandon – go ahead and get up after life knocks you down. Do it – freakout on failure. The key to failing like a freak is to NOT take yourself so seriously.
  • Build an Inner Circle. We are not meant to travel through this life alone. Developing a powerful inner circle is important. The other day when a family member was sick some of my inner circle gathered and prayed for my loved one. It was so cool. I would hate to think of life without this level of friendship. A person’s inner circle is not the friends from afar or I’m your friend only if you’re in my club kind of person. I’m talking about drop everything friendships that are mutually committed to each others success. A powerful inner circle takes cultivation and care to build. Trust is the key and love is the fruit. At the heart of every legacy leaving leader is a powerful inner circle of committed friends.

When I think of my ending, I desire to step into my legacy. My hope would be that my loved ones can continue to learn, laugh and love through the positive influence left behind. Mostly, I want to be remembered as a leader who demonstrated his love for God and others in a tangible way. I want to be a not so normal kind of leader. What about you?

Do you desire to leave a leadership legacy? (Please share your thoughts in the comment section below.) 



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  1. Tina Z
    Tina Z10-30-2013

    Thanks Mark. Needed this! God Bless you and your family.

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