Unpacking Regret: From Broken Dreams to Greater Fulfillment

In my last blog post, I talked about how taking time off can help us step back from daily life and make strategic choices about how we spend our time. This action can help us live with less stress and more meaning.

But what if exhaustion and overwhelm aren’t the problem? 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, of course. 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.

Man with head buried in 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 ways to deal with it effectively, which has been essential for me to get out from under its shadow so I could move on to a more fulfilling life.

First, we need to gain perspective. And to do this, we need to start by understanding our tendency towards all-or-nothing thinking.

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 so we can fully appreciate all aspects of a situation. 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.

Woman lying on grass smiling

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 the peace corps volunteer/doctor/artist 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.

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

Lighthouse at dawn with calm water

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. (They are, it turns out, drafty. And they have very tiny staircases.)

And yet I didn’t let the dream go. Not for a 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 large 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.

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 - a significant problem for a professional musician.)

Hands form a heart with the sun shining through

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 some of my deepest values, born out of accumulated wisdom and deeper maturity. Most importantly, I found a way to integrate these life-changing truths into my new life, which I’ll get into more in my next blog post.

But let’s not get ahead of ourselves.

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 this summer just making friends with the idea. As a therapist once wisely said to me, it’s perfectly fine to just allow for the possibility for a while. Let the regret out into the light of your consciousness and give it some space. Let it breath.

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.