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Dealing with Regret for Greater Happiness and Fulfillment

Summary: We all have regrets. A financial misstep. The ill-advised remark. That college incident involving a bicycle, some alcohol and you with no clothing. But what about dealing with regret that's bigger and more painful, and is weighing you down? This blog helps you get a handle on a big regret that's keeping you stuck.

Dealing with Regret for Greater Happiness and Fulfillment

What if a sense of deep regret makes it difficult for you to truly experience a fulfilling life?

We all live with some level of regret. In many cases, these are relatively small regrets – maybe an unkind word we’d like to take back, an ill-advised purchase, or a friendship we let fizzle. The type of regret I’m referring to, though, is regret over important goals we set for ourselves but didn’t meet, or a big dream we had but never fulfilled. 

How regret can weigh us down…

Stressed man holds head in his hands

Research indicates that regret over actions not taken affects us more than our missteps, often leaving a lurking sense of the road not taken that can have a lasting negative impact. 

I’ve felt the weight of this type of regret myself. I have also found some ways of dealing with regret. This has made it possible for me to get out from under regret’s shadow so I could move on to have new goals and dreams that align with who I am now as opposed to who I used to be.  

An important first step is to gain perspective. And to do this, we need to start by understanding our tendency towards all-or-nothing thinking. 

Our tendency for “all-or-nothing” thinking doesn’t help…

Woman lies in flowers, smiling.

Here’s how this type of thinking can work with regret: You didn’t fulfill your dream of becoming a peace corps volunteer/doctor/artist as you’d planned. As a result, after every success or achievement there’s a lingering thought of, “but I didn’t…” – a lurking regret that taints every new accomplishment.

Psychologists have a fancy name for this this all-or-nothing mindset. It’s called “cognitive distortion” and involves “thinking in extremes. You are either a success or a failure. Your performance was totally good or totally bad. If you are not perfect, then you are a failure.”

All-or-nothing thinking means oversimplifying things that are in fact complex and nuanced. Oversimplification prevents us from taking a deeper look at a situation so we can fully appreciate all aspects of it. If we don’t examine our regrets carefully, all-or-nothing thinking keeps us stuck. We never take the time to more fully understand the regret so we can move past it. And dealing with regret in a healthy way becomes all but impossible.

Our tendency towards “magical thinking”

The tricky thing about a goal or dream that remains unrealized is that it stays in an idealized state. Since it didn’t come to pass, there’s no experiential evidence that the life we dreamed of would have been, alas, imperfect. Sure, there would probably be some great things about being an astrophysicist or professional dancer as you’d planned. But there would also have been challenges, limitations and irritations you can’t foresee.

When we’re busy dreaming, we tend not to account for this inconvenient truth. If we don’t make the effort to set aside our rose-colored glasses and take realistic look at our past dreams and goals, we risk idealizing them to the point where they can ruin our experience of the life we’re living now.

Dream big, but…

Growing up in on the outskirts of my small, bucolic hometown, I had lots of time to dream, and boy, did I. My goal was be a professional clarinetist playing for a top professional orchestra while also living in a lighthouse. Like, on the ocean. In Maine. Where there were no full-time professional orchestras.

Lighthouse on a rocky shore at sunset

While the flaws in this dream are glaringly apparent to my now older and wiser self, to my younger self the dream – in all its inherent dreaminess – seemed perfectly achievable. Over the course of my time in college as a music major, it became clear to me that the life of a professional musician wasn’t for me. And, also, I wasn’t going to live in a lighthouse. (Which is OK. They are, it turns out, drafty. And they have very tiny staircases.)

And yet I didn’t let go of the dream’s hold on me for a long, long time. 

Even as it became obvious that this dream was unrealistic, I allowed it to stick around well past its expiration date. It remained lodged in my consciousness and colored my experience for years to come like a stone stuck in my shoe.

Most painfully, I didn’t let my greater understanding change how I perceived myself. I allowed myself to feel like a failure for not achieving my goal even when it became obvious that the goal itself was completely unrealistic, not to mention at odds with who I was as a person. I maintained this disconnect for years, allowing the dream to live in isolation from what I understood rationally as possible. In my mind, this became a failed goal, but the real failure was in not dealing with the (misplaced) regret.

…remember to revisit those dreams based on new realities

Many years later, once I made the effort to truly unpack the dream, I began to understand some life-changing truths. I understood more fully the idealistic circumstances that allowed the dream to take root and grow. I became more comfortable with the pleasant and not-so-pleasant things I’d learned about myself over the years. (For example, I came to understand that I really enjoyed playing the clarinet but really didn’t enjoy performing. This is a problem for someone who wishes to be a professional musician.)

The process of unpacking my dream also allowed me to dig deep into my own psyche and ask myself some important questions. As a result, I discovered my real priorities in life, born out of accumulated wisdom and deeper maturity. Most importantly, I found a way to integrate the insights discovered by this personal growth into my new goals and dreams.

If unpacking a long-held regret is an idea you’re just warming up to, I’d like to kindly suggest that you spend some time just making friends with the idea. As a therapist once wisely said to me, it’s perfectly fine to simply allow for the possibility of something at first. Let the regret out into the light of your consciousness and give it some space. Let it breath. 

Dealing with regret is a process that takes time. There’s plenty of time to roll up your sleeves, unpack it more fully, and seek the valuable insights it has to offer. Let that process wait. And remember to be very, very nice to yourself; just starting this process is a huge act of bravery.

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