Regret: A Great Tool For The Past and Future

Published July 16, 2019


Leading YourselfLearning Agility

We all hate the feeling…looking back at an event, a choice or even an entire season, and realizing “I really missed it. I blew it. I could have done that really differently.” It is the worst. Especially when we know that we really could have done something differently, and just didn’t. Fears, personal weaknesses, lack of courage or whatever…we all have had times like that.

Regrets. “If only I had…” Fill in the blank, and the sick feeling is horrible. And the worst thing about it is that looking back, it is not hypothetical. It is reality. The record stands, the consequences are felt and remain. Yuck.

As I think of this topic of regret, there are two main ideas I would like to impress: Past and Future. The past is for learning and the future is to promote a good kind of fear. More about that later.

Fears, personal weaknesses, lack of courage or whatever…we all have had times like that.

In terms of the past, we can’t undo what we did or didn’t do. Failures of commission or omission both are already done. But, we certainly can learn from them. Just as a good football team reviews game films on Monday in order to learn and not make that mistake again, so should we. Post mortems give us an explanation of what happened, what could have been done differently and a path forward. All great performers look in the rear view mirror—not for wallowing in shame or guilt, but for learning. Here are some points to help guide you through learning from your regrets, in relationships or in your work:

  • Was my failure or regret a result of my being too disconnected, not involved or non-attentive to either a person, or some area of my work?
  • Was my failure or regret due to my not setting limits with someone soon enough? Did I allow something destructive to continue? Did I allow non-performance not to be addressed, allowing bad behavior to remain unchecked?
  • Was the regret related to some way that I handled someone else’s failure or their not meeting my expectations? Was I too harsh? Judgmental? Too angry? Or, did I do the opposite and just live in denial about someone else?
  • Is my regret related to not grasping, owning and living out some area of talent that I possess and have not stewarded? Have I “buried a talent” in the ground because of a fear of failure or some other reason? Is it time to “dig it up?” Does one of my talents need some development in order to reach my full potential?
  • Did I continue to neglect some area of pain, weakness, emotional problem in myself that finally caught up with me? Or a long-standing relational pattern that got me once again?

Remember that regret from the past does not have to be crippling, if used as a wake-up call. We do not have to wallow in it and call it quits or feel like there is no tomorrow. The Scriptures are full not only of second chances (think Peter or Paul), but also a warning and a guide to how we evaluate failure. Scripture contrasts a fruitful way of looking at our past that will result in a better future with a destructive way of looking at our past that only causes more pain and failure.

Consider 2 Corinthians 7:9-11:

“Yet now I am happy, not because you were made sorry, but because your sorrow led you to repentance. For you became sorrowful as God intended and so were not harmed in any way by us. Godly sorrow brings repentance that leads to salvation and leaves no regret, but worldly sorrow brings death. See what this godly sorrow has produced in you: what earnestness, what eagerness to clear yourselves, what indignation, what alarm, what longing, what concern, what readiness to see justice done.” (NIV)

God wants us to use our sorrow over the past to help us change. He does not want past failure to make us feel condemned, worthless or subject to other kinds of emotional recriminations that lead to nothing good, or as He puts it, “sorrow that brings death.” Don’t let that happen to you. See His hand as still active in your life and in your leadership and seek the changes that will give you a better future, beginning with the areas mentioned above. Use the questions above with your team as well.

What about the future? Regret is a great future tool too, if used well. How do we regret the future? By fast-forwarding the movie to the end before we live it. In a movie, every scene plays an important part in where the story ultimately goes. And great writers take that into consideration when they write a scene into a movie. Even though they might like it, if it does not fit the future story line of where they need to go, the don’t write it in. In my book “Necessary Endings” I ask the question “What exists in your work (or life) today that does not fit the future you desire?”

The emotion of regret can help us. Use it to look into the future, and avoid what you do not want to end up regretting.

So, do what the Scriptures tell us to do, all the time: See your current choices and realities in light of the future. The Bible tells us that there is a path that leads to a great banquet, a great reward. And there is a path that leads to loss and pain. Said another way, it always reminds us that each choice, each season, each attachment to a person, each spending of a talent or a resource, and each continuance of a strategic path…goes somewhere. In light of that reality, ask yourself:

  • If I play the movie forward a year, or two years or more, and continue in the strategy I am currently in, where does it end? Probably more of the same? Is that what I want?
  • If I play the movie forward continuing to trust that this key person under my leadership is going to change or perform better, what basis do I have for believing that change will happen? And if not, what does it look like a year from now? Two years?
  • If I do not step out and begin to pursue that particular vision or dream, where will I be a few years from now? Will I regret not trying?

I want you to put yourself into the future that your current reality is leading you toward, and really sit with how that feels. Does it contain regret for the future? Is that future regret something you want to live with? I don’t think so. And the difference in those the Bible refers to as “diligent” and those it calls “fool,” is that the diligent person lives with a future orientation, all the time. They ask, “where is what I am choosing to do or not do today— in my church, or my business or my marriage—going to end up tomorrow?”

In that way, the emotion of regret can help us. Use it to look into the future and avoid what you do not want to end up regretting.

Like everything in life, good or bad, God is able to use it for our good…even regret. Use the past regrets to teach you and use the “future regrets” as a guide to knowing what you want to avoid.



About the Author
Henry Cloud

Dr. Henry Cloud

Clinical Psychologist & Acclaimed Leadership Expert

Leadership University

Dr. Henry Cloud is an acclaimed leadership expert, clinical psychologist and New York Times best-selling author. His 45 books have sold nearly 15 million copies worldwide. He has an extensive executive coaching background and experience as a leadership consultant, devoting the majority of his time working with CEOs, leadership teams and executives to improve performance, leadership skills and culture. Dr. Cloud founded and built a healthcare company starting in 1987, which operated inpatient, and outpatient treatment centers in forty markets in the Western U.S. There, he served as Clinical Director and principal for ten years. In the context of hands-on clinical experience, he developed and researched many of the treatment principles and methods that he communicates to audiences today. After selling the company, he devoted his time to consulting and coaching, spreading principles of hope and life-change through speaking, writing and media. Throughout the same years and until the present, he has devoted much of his career to leadership performance and development, blending the disciplines of leadership and human functioning to helping CEO’s, teams, organizations and family entities. His book, Integrity, was dubbed by the New York Times as “the best book in the bunch.” In 2011, Necessary Endings was called “the most important book you read all year.” His book Boundaries For Leaders was named by CEO Reads in the top five leadership books of its year. His newest book, The Power of the Other, debuted at #5 on the Wall Street Journal bestseller list. Dr. Cloud’s work has been featured and reviewed by the New York Times, Wall Street Journal, Boston Globe, Publisher’s Weekly, Los Angeles Times, and many other publications. Success magazine named Dr. Cloud in the top 25 most influential leaders in personal growth and development, alongside Oprah, Brene Brown, Seth Godin and others.

Years at GLS 1996, 2005, 2011, 2013, 2016, 2021