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Session 30 - Haunted By Regret

This is part 3 of 4 in our Modern Monsters series.

Off in the distance you see a dark figure lumbering towards you. Its shape is human, but its movement is anything but. You start to run and it only moves faster. No matter your pace, it stalks you vigilantly, hauntingly, purposefully.

What regrets are chasing you now?

When we think of regret, we think of missed opportunities, the wrong words at the wrong time, misdeeds or inaction, or chances vanished in the air. These regrets appear across many dimensions of our life from work, love, education, travel, friendship, finances, and wellbeing. Yet, no matter where in our life regret pops up, there are only four types of regret.

In his book “The Power of Regret,” Dan Pink identifies the four types of regret that are the deep structure beneath regrets we identify in our lives:

  • Foundation regrets - where we failed to set a foundation for our future success and create stability

  • Boldness regrets - where we thwarted our possibility of growth or failed to take a risk

  • Moral regrets - where we failed to do the right thing, according to our own definition of goodness

  • Connection regrets - where we closed doors, failed to reach out, or left words unspoken

When our regrets haunt us, they are much like the undead creatures of D&D and other TTRPGs: spirits and specters born of mistakes and wrongdoing caught between life and death. Regrets in the same way can prevent us from living and keep us from a peaceful death.

Similar to feelings of doubt and shame, our regrets can be our teachers rather than our enemies. While they can interfere with who we want to become, when we learn and heal from them, they offer us a reminder to focus on what is important to us: stability, growth, goodness, and love.

Where we’ve made mistakes setting a foundation for ourselves, the best thing we can do is to start to build that foundation today.

Where we’ve failed to take a risk or invest in our growth, take an assessment on what opportunities are ahead and pursue them now.

Where we’ve failed to do the right thing, apologize, make amends, and repair where you can.

Where we see disconnection, reach out and make the phone call or say what you feel.

And regardless of the regret, if you can’t undo it, find the silver lining, and give yourself the compassion and the commitment to do better next time.

No matter your efforts, you can’t avoid regret. There will come a time when our hindsight will summon that familiar twinge of our own personal error. We all have skeletons in our closet, but the decision is whether we revive them to become the instruments of our own self-haunting or if we finally allow them to rest in peace.

It’s a grave decision to make, no bones about it.

No ragrets, not even a single letter!


Autumn & Jerod


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