Embracing Regret

        So I’ve been going through the interview process a lot lately, both as a candidate and as a recruiter, and one of the questions that keeps coming up has to do with the idea of mistake making and regret. It’s a good question honestly, as it gets you to reflect critically on your approach to failure, and whether or not your past has impacted your present in a positive or negative way. Mistakes and regrets can be framed very differently I think depending on your mindset…they can be opportunities for growth and action, or they can be a hinderance and debilitating both personally and professionally…it’s all in how you respond, and how your frame the experience.
        Because of these recent interviews I’ve been thinking deeply about this, and it’s given me the chance to look back on how I’ve reacted to the many mistakes that I’ve made, and how the regrets in my life have impacted who I am as a person and as a leader. I’ve come to realize that the more you embrace your failures, the more you grow and the more you learn. It’s the mistakes in your life that shape who you are, and as long as you open your mind, reflect, and do better the next time around, your mistakes, regrets and failures can ultimately become the most powerful opportunities that you have in your life.
        Luckily, I don’t have many true regrets in my life but I certainly have a few. One of them, which I still think about on a regular basis, has shaped who I am as a leader in a very profound way. You see, almost ten years ago, during my first year as an administrator, I had the opportunity to advocate for a student who needed my support. This student was being bullied by a teacher and needed me to stand up for them. The relationship was negatively impacting this student’s ability to be successful in school, and it warranted a hard conversation and some quick action from me…but as it turned out, I lacked the educational courage to do what I needed to do. I’m not proud of that experience, and it haunts me to this day, but looking back on it, it may just be the most important leadership lesson that I’ve ever learned. From that moment on, every time that I have been faced with a hard conversation, or a difficult decision, I think of that kid…and the conversation becomes easier. Because of that one incident, that regret, I no longer lack the courage that is needed to be a true student advocate, and ultimately, dealing with difficult situations has become a strength of mine…it’s all about learning, growing, and becoming better…and seeing a regret, or a mistake as an opportunity to become a better version of yourself.
        I’ve since reached out to that student, and we talked through the incident from both our perspectives, and I apologized for not being there when they needed me. Our relationship is stronger now than it was and they have forgiven me, which is the next key ingredient to growing and becoming better…forgiveness. People will make mistakes, and it is easy to hold grudges or to judge, and to let it affect you in unhealthy ways. The way to move forward, and to truly own your life is to forgive, and to let it go. I know it’s hard but it’s freeing for both parties. I’ve made a practice of forgiving in my life, and I’ve learned to say what it is that I need to say to people. One of the biggest forms of regret are the things that go unsaid. The times in your life when you didn’t thank someone when they deserved your appreciation, or when you didn’t tell someone you loved them enough, or when you held your tongue when you really should of spoken your truth. Well, it’s not too late…
        I’m asking you all this week to do two things…First, think of a person or persons in your life who deserve to hear from you…either a “thank you”, or an “I love you” or an “I’m sorry”… say what you need to say and get it off your chest…don’t wait for it to become a regret down the road. Secondly, think of someone who has wronged you in some way and forgive them…move on. I guarantee that it will be freeing and it will ease our mind in many ways. Let things go that are bringing negative energy into your life and take control. For my part, I’m off to write a couple of emails to people who need to hear from me and I’m excited about it. I hope that you will take some time this week to do the same. Mistakes, failures and regrets don’t have to be negative experiences…they can be framed as opportunities for growth and powerful learnings…embrace them…hold them close to your chest, and do better. It’s all about your mindset and approach. Have a wonderful week everyone and remember to be great for our students and good to each other.

Quote of the week…

There are far, far better things ahead than any we leave behind – C.S. Lewis


Interesting Articles/Websites –







Great TED Talk – Embracing Regret (Kathryn Schulz)



Inspiring Videos – 





One thought on “Embracing Regret”

  1. This was a great read for me today, especially since we are in the process of figuring out our next move. I, luckily and also, don’t have regrets but reminders that mistakes and failures lead us to the next “thing” is always reassuring.

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