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Gila Gam

Reframing Regret: from Hindsight to Insight

Bad things happen to all of us, right? Some people even believe they come in three. I have yet to experience that ideal day when everything goes perfectly according to plan. My days look more like the Robert Burns famous line: “The best laid schemes of mice and men often go awry.” But the thing is with any plan, or when going on an adventure, is to not define the journey while you are still on it. Going off to the unknown to experience new things is about making the world your university; meaning being committed to continuous learning. There’s something to learn from every person, every interaction, and every experience. In essence, this is called hindsight, looking at things after they’ve happened and considering the alternatives, the road and options not taken. No, the idea is certainly not to be a “Monday Morning Quarterback.” Hindsight is a powerful tool when it is used in the pursuit of knowledge and understanding of what happened and what could be learned to do better in the future. It’s important not to confuse hindsight as a constructive heuristic approach to learning with hindsight bias, which has the emotional undertone of pessimistic resignation and regret. Use hindsight as the accumulated wisdom that comes from reflecting on past events to help build the future you envision.


Use the power of constructive hindsight to grow in your self-understanding, courage, and commitment to continuous growth. Beware of the 3 dangers of hindsight bias: Coulda, Shoulda, and Woulda. Dwelling on what should have, could have, or would have happened is unproductive if not outright harmful. Everyone experiences regret in life. It is one of the more difficult emotions to deal with. It is OK to feel sadness and pain. But that gut-wrenching, all consuming, agony is a wasted emotion. The past is done with and gone. Accept that we are all fallible creatures. Mistakes are inevitable. They are a part of life, of living fully, striving valiantly, and daring greatly. But even if you try and play it as safely as possible, it’s a given you will make mistakes. Therefore, give yourself the credit that the choices you make in the moment are the right ones when you make them. It is only when you live out the consequences of the decisions made, that you can truly determine their merit, or “rightness.” Recognize that what may seem like the right choice now may be the wrong choice later on, and vice versa. Thus, what truly matters is how quickly you resolve missteps, what you learn from errors, and how you use the insights to move forward and get on with your life and goals. Instead of feeling regret, use the power of hindsight to look for the lesson. In other words, regret is wishful thinking. It changes nothing. Alternatively, using the new knowledge acquired with the passage of time can be a powerful success strategy.


Hindsight is a precursive to learning. But be careful not to become data rich and insight poor. Be sure to look at your choices, actions, and behaviors to ask the right type of questions to identify the right answers. Beating yourself up about the things that went wrong, doesn’t help things go right. Don’t regret anything that has taught you valuable and worthwhile lessons. Replace regret with reflect. To reflect is to try and understand what your regrets are trying to tell you. It means looking for insights in order to draw lessons from the experience. The goal of reflection is to move away from regret to make better decisions and take action toward better future outcomes. The ultimate goal being to live fully. Here’s how to manage regret by reframing your thinking to transform negative emotions into positive actions:



Reframe Regret to Rise Up:


Redefine possibilities

Identify viable options

Select your action steps

Exert yourself vigorously


Ask reflective questions:


  1. What do you regret? What keeps you up at night weighing you down?

  2. What about the situation elicit strong emotional reactions?

  3. What is the biggest impact on your life today?

  4. What would you do differently if given the chance?

  5. What is holding you back and getting in the way of moving on?

  6. What alternative universe could you imagine if this didn’t happen?

  7. What are the positives of the experience, the courage and strength that you have gained?

  8. What is the pivot point, the opportunity still in your line of sight?

  9. What is still left undone?

  10. What are you excited to try out on your new path forward?


Remember: life is meant for exploring and experimentation. You are likely to fail many times, but “nothing ventured, nothing gained.” When you accept that risks must be taken and setbacks must be experienced in order to achieve anything meaningful, then you recognize the futility of regret because there’s a valuable lesson in everything you do. Your life’s lessons allow you to grow. The biggest risk is not to take any risks, and the greatest regret is an unfulfilled life, or a life not lived fully. As you reflect upon your wins and losses, accept the whole package and seek the lessons to apply in the future. Take intentional action to keep doing the things that really matter to you. Be open to change and new opportunities along the self-actualization journey. And most importantly, once you reach success, don’t linger in the comfort zone for too long. Celebrate your accomplishments but beware of resting on your laurels. Move on to something new and continue to be relevant and have impact.


Life is made up of a series of changes, choices, and consequences. The choices you make today will make sense in retrospect with time and reflection. The road is windy and slippery. Embrace the wobble. Keep walking and trust you will figure out your own way. So, turn the insights into foresight. Strap on your parachute and take a leap.





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