How to Move Through Regret and Disappointment

Each time I facilitate a year-end or mid-year reflection ritual, the question inevitably arises:

How do you get over your disappointments and regrets?

It’s a question that can be asked only by one who is brave enough to create space for reflection in the first place. Indeed, the fear facing those disappointments and regrets is what keeps most people from creating space in the first place.

As we start to slow down from our busy pace, we might stumble into the opening that invites us to look at what the busyness has been hiding. We might see the wounds, neglect, and pain of others that we inflicted, and those we inflicted in ourselves. In the space we create for reflection, what crystalizes is all the ways in which we have fallen short.

Sometimes it seems that the bigger our vision and the higher our standards, the greater our disappointments and failings.

Rabbi Lord Jonathan Sacks captures the emotion of this his introduction to the Yom Kippur prayer book:

The distance between who we are and who we ought to be is, for most of us, vast. We fail. We fall. We give into temptation. We drift into bad habits. We say or do things in anger we later deeply regret. We disappoint those who had faith in us. We betray those who trusted us. We lose friends. Sometimes our deepest relationships can fall apart. We experience frustration, shame, humiliation, remorse. We let others down. We let ourselves down. These things are not rare. They happen to all of us, even the greatest. One of the most powerful features of biblical narrative is that its portraits are not idealized. Its heroes are human. They too have their moments of self-doubt. They too sin.[1]

So if you feel these pains of regret and failure, there’s good news: you’re human. Welcome to the club. 😉

And… it hurts. It hurts to know we’ve let others down. But even worse is the pain of disappointing ourselves.

Why We Must Face the Pain

This past week I created space to sit with my regrets from the past few months.

Our human tendency is to ignore, bypass, or excuse the disappointments. It would be easy to do this year; the events of 2020 give us a ready-made excuse.

But that would be a mistake.

If we don’t address the pain adequately, the feelings of failure and frustration come with us into the next chapter.

It’s like the sand in the bottom of your beach bag that gets into your suitcase. Eventually it infiltrates everywhere. No single grain is heavy on its own, but over time enough sand will weighs you down.

Until it’s resolved, the pain will weigh on our spirit and infect our subconscious, undermining future plans, dreams, and actions. Without conscious resolution, the failure or disappointment becomes a belief about ourselves or about the world.

All emotional pain eventually turns into physical pain. It latches into our bodies, creating physical pain and literally keeping us stuck.

Unseen and unresolved, this pain separates us from ourselves and from others.

How to Move Through Regret and Disappointment

This is where the gift of Yom Kippur comes in. It offers us a framework for working with the pain and disappointment that inevitably arises as we reflect on our year.

Yom Kippur is a day dedicated to healing. It tells us we can reform our ways and shows us the path to move through our failings — not just to get over them.

At the heart of this process is the process of teshuva, returning home to ourselves. Teshuva is not merely about apologizing and asking for forgiveness. It’s a process of realigning with our true nature and returning to our path.

We can do this by using the information from regret. Regret contains a message for us about our values and our path, which we can hear only if we pause to listen. The pain we feel is our cue to listen.

Here’s a 3-part framework for Teshuva, which I learned from Dr. David Bernstein, the Dean of the Padres Institute of Jewish Studies in Israel:

• Recognize: acknowledge what we did and the impact of our actions (or non actions).
• Regret: truly feel the pain of our actions and their impact.
• Resolution: make it right and set a new course for the future.

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1. Koren Yom Kippur Machzor, Introduction by Rabbi Lord Jonathan Sacks, 2nd Ed. 2013, p.xiii. ↩