Make Mistakes—But Live & Lead with No Regrets

Published July 9, 2019

I labored over the letter for about a week. I tweaked the words and added sentences. It needed to say some important things. I wanted to get it right and it needed to be understood properly.

Finally, it was done! I knew the letter said all I needed to say. And I knew it would warm his heart. I addressed it, stamped it and put it on my desk, ready to post. I felt so good about getting it done.

The letter was for my grandfather who, due to my father’s mental illness, had raised me. Grandfather was a great business leader and was truly my mentor and hero. With his encouragement, I had left India for Australia when I was 17. But I didn’t have much personal interaction with him after that because international communication was still very difficult. When I was about 21, I had multiple promptings to write the letter to thank him for being such a blessing to me and to let him know that his efforts were bearing good fruit in my life.

In my busy-ness, the letter remained on my desk. Assignments, books and lists piled on top until it was out of sight and out of mind. Then my Mum called with the news that he had suddenly passed away.

For many years, the letter haunted me. The self-punishment for my procrastination went on and on. There is a spiritual battle going on in our minds—and destructive thoughts can stop us from reaching our destiny.

Ironically, my breakthrough finally came through one of Grandfather’s lessons. He had said many times, “Son, it’s okay to make mistakes but don’t allow them to rob you of your future. Learn from them. Then live and lead for the better—without regrets.”

That day, knowing it was exactly what Grandfather would advise me, I decided I would stop re-visiting my mistake and stop punishing myself. To make this a reality, I sat down and wrote down the lessons that I could learn from it. Then I listed how it was going to help me become a better person and leader. Since then I have had to repeat this exercise many times.

Once you stop taking risks, you stop innovating and then you stop leading.

The truth is, you can’t lead effectively without taking risks. And when you take risks there is always the possibility (even probability) for mistakes and failure. If you allow it, the pain and regret from these mistakes will paralyze you and stop you from taking risks.

Once you stop taking risks, you stop innovating and then you stop leading.

Here are seven keys that can help you live and lead with no regrets:

1. Know that you are human and not yet a perfect being.

Fear of failure is one of the top things that stops people from taking risks or making changes. One of the best ways to overcome this is to understand and declare yourself to be human and that you are not perfect yet. The more of a perfectionist mindset you have, the more regrets you will carry. The sooner you can be free from it, the more you can enjoy living and leading. The Bible is full of stories of imperfect people who made a lot of mistakes, yet God used them in amazing ways. The same God can use you.


2. Develop a habit of writing down the mistakes and the lessons learned.

Much of the Old Testament is essentially this: a collection of mistakes and lessons learned! By writing your mistakes down, you break their invisible power over you. The lessons you learn and write down from your failures can become great wisdom to build your future on. And, when shared appropriately, they can help save a lot of pain and heartache for others too. Who knows, this might become one of the best things we leave behind for future generations.


3. Evaluate things in the light of the knowledge, skill, information and resources that you had at that time, not now.

Hindsight is such a great thing, but it can also cause us to have unnecessary regrets and make us ineffective as leaders. As you look back, I am sure there is a mountain of things that you would do differently—I know there is for me. But the main thing to ask yourself is, “Did I make the best decision with the knowledge, skill, information and resources that I had at that time?” Don’t judge
your past decisions on your present knowledge.


4. Practice forgiveness—learn to forgive yourself.

We usually think of forgiveness in the context of forgiving others, but we also have to learn to forgive ourselves. Living with the pain of regret is just as destructive as living with the pain caused by others. Some people become a prisoner of bitterness over their own failures or mistakes and they never achieve their God-given destiny. Forgiveness may be a common word, but many have not understood its power: accept God’s forgiveness, then learn to forgive yourself and be free from the regrets of the past.


5. Learn to forget and press forward.

Most of us get frustrated when we forget things. However, intentional forgetfulness is a helpful practice in living a life of no regrets. In Philippians 3:13-14, Paul addresses this beautifully, Not that I have it all figured out, but I have got my eye on the goal and I am choosing to forget the things from the past and I am pressing forward to that goal. (My paraphrased version.) Paul spoke from a messy past where he had been part of a murderous team that slaughtered Christians in the early church. Peter is another great example from the Bible; he denied Christ, yet we never hear him beating himself up with the regrets for his mistake. Both of these leaders could have allowed the guilt and regrets from life to stop them from entering into the new life that God had for them, but they didn’t. Similarly, all of us have some things that we just have to draw a line and leave behind, choosing to forget and move forward so we can thrive in the new season of life and leading.


6. Develop a cheering squad.

To be effective leaders, we must have strong accountability, and most of us have teams and boards to facilitate this important role. But I wonder how many of us have a team that cheers us on, that continues to speak life and encouragement into us, send us text messages, emails, cards—just to champion us as we move forward? We have many people to tell us when we do things wrong, but do you have people in your life who affirm and build you up? We will fail and fall. When we do, it is important that we have people in our life who will help us get up and encourage us to learn and keep going. I believe that for leaders to thrive, we need both good strong accountability and a cheering squad that champions us as we move forward.

We will fail and fall. When we do, it is important that we have people in our life who will help us get up and encourage us to learn and keep going.


7. Live knowing that your best is yet to come.

When we start to feel that our best is behind us, the power of past mistakes and ongoing regret can take deep root. But when we believe that our best ahead, we know that yesterday’s mistakes are not going to define us. Our past may be full of mistakes and failures, but God always gives us another chance and He is able to bring beauty from ashes if we continue to allow Him to mold and shape us. Develop a deep conviction that your best is yet to come and strive to make the future better than the past. When we lead and live this way, regrets can’t take root.

Since ‘the letter’, I have had countless more opportunities to write down my mistakes and lessons learned. And, as I lead and take risks, I know there will be more. But I consistently choose to apply these keys, so I can continue to live energetically and lead effectively—without regrets. Will you join me?

About the Author
This is the author headshot of Jossy Chacko.

Jossy Chacko

Founder & President


Jossy Chacko is the Founder and President of Empart. He uses his gifts as a communicator to challenge business and spiritual leaders to capture a larger, God-size vision.

Years at GLS 2016

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