Leveraging Regret To Make Hard Decisions

Living life with a goal of minimizing your regrets

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👋 Hi, it’s Dipti ! Every week, I share a transformational insight or lessons in leadership, growth, and making confident decisions - aligning your career and life with joy and purpose.

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Photo by Anthony Tori on Unsplash

“Do you have any regrets?”

Most people answer that they don’t have any regrets. The explanation is that they wouldn’t be where they are today. That makes a lot of sense - you become successful through some of your hardest and adverse times in life. Yet, not enough people share about the regrets they do have. The choices they didn’t make, which they think about often.

Regret can be a powerful guide if we choose to learn from it. Instead of dwelling on the past, we can use it as a GPS to navigate our future with more clarity and purpose.

What Is Regret ?

Regret is an emotion that makes us feel worse, not better. It’s an emotion that comes up when we dwell on our past and wish we had done something differently.

Without the label, you can pick up on this as you hear people share their regrets in conversations. It shows up as the following phrases:

“I wish I had taken a chance on this”

“I wish I had the opportunity to do that”

“I wish I knew better back then”

“I wish I didn’t doubt myself to do this”

While some regrets are irreversible, others present an opportunity to take action. The key is recognizing which regrets can still be addressed and using them to inform future decisions.

Use Regret To Make Hard Decisions

Regret is a powerful emotion that can be leveraged for personal growth. You can use this to make some hard decisions about your life, career or relationships. Take Jeff Bezos as an example. He used this framework when starting Amazon, before giving up his lucrative wall street career. He thought about his future self, and came to the conclusion that he would regret not trying, even if he failed at taking this chance of creating what he wanted to.

If you're facing a significant decision, try this exercise:

1. Identify the decision you are considering.

2. Imagine yourself at 80 years old. Ask: Would I regret not making this choice?

3. Fill in the blank: My 80-year-old self would regret not ____________.

4. Consider failure: If things don’t work out, what’s the worst-case scenario? Can you survive it? What alternatives would you have?

5. If the decision still feels right, take steps to move forward.

Why This Works

So often we get stuck in our heads ruminating about the “what if” scenarios and staying stuck in fear in the short term - fear of judgement, failure, or losing it all. Making a decision isn’t to say you wouldn’t be faced with a new set of challenges. But that “what if” energy starts showing up in your relationships, health, at work and in ways you didn’t expect. The indecision carries its own risk: the slow accumulation of regrets.

Your decisions will not always turn out exactly the way you expected them to be, but there is something humbling about life in this manner. There will be learnings, new friendships, war stories and fulfilling experiences along this path.

By shifting your perspective to the long term, you free yourself from the weight of immediate fears and gain the courage to make choices that align with your values and aspirations.

The Top 5 Regrets

In her book the top 5 regrets of the dying, Bronnie Ware documented the most common regrets of those at the end of their lives:

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.

2. I wish I hadn’t worked so hard.

3. I wish I’d had the courage to express my feelings.

4. I wish I had stayed in touch with my friends.

5. I wish I had let myself be happier.

*Source: https://bronnieware.com/regrets-of-the-dying/

Conclusion

Regret doesn’t have to be something you look back on with sadness - it can be something you prevent by making intentional choices today.

So, what is one thing your 80-year-old self would regret not doing? I’d love to hear from you.

P.S - Is it time to move on ? Download my free 10 question guide - designed to validate whether its time for transition from your current role or not. Click here to download it.