Did your life turn out the way that you envisioned it would when you were younger?

We all have different versions of ourselves that we grow into and out of, and these versions of yourselves may have had different dreams or expectations about life than you have now. When you were little, maybe you wanted to be a scientist but ended up working in the arts instead. Maybe you thought you’d marry your high school sweetheart, but ended up meeting someone who was a better fit for you after you graduated. Perhaps you wonder how life would have been different if you had gone to a different school or decided not to have kids. We each make hundreds of decisions a day, and it’s natural to wonder if some of them were the right ones in hindsight. This line of thinking often leads to complicated emotions, like grief or regret.

We think of grief as something that is reserved for serious situations, like when someone passes away or there’s a natural disaster. These situations do cause grief, but many others do as well. Some grief specialists define grief as “the conflicting feelings caused by the end of or change in a familiar pattern of behavior.”

The grief you feel for the life you thought you’d have can feel conflicting.

Even when you’re really happy with where you are, grief can pop up unexpectedly when you think of everything that could have been.

Grieving the life you envisioned for yourself doesn’t mean you don’t like your life. It doesn’t even mean that you didn’t make the right choices. We all feel curious about what life would have been like if we had made another choice.

In an advice column years ago, writer Cheryl Strayed answered a reader question about how to make peace with a life altering decision. In her answer, she described how we all have versions of ourselves that will never be. She describes viewing that version of yourself that is not to be as sailing away on a ship.

“One is the life you’ll have, the other is the one you won’t. Switch them around in your head and see how it feels. Which affects you on a visceral level? Which won’t let you go? Which is ruled by fear? Which is ruled by desire? Which makes you want to close your eyes and jump and which makes you want to turn and run?

I’ll never know and neither will you of the life you don’t choose. We’ll only know that whatever that sister life was, it was important and beautiful and not ours. It was the ghost ship that didn’t carry us. There’s nothing to do but salute it from the shore.”

Whether it’s due to our circumstances or the choices we make, it’s not possible to do everything you want at all times. Life forces us to make choices, and even though it’s a natural part of life, it can feel incredibly painful to watch a possibility slip away.

As we get older, we tend to become more comfortable in our own skin.

We learn how to scale back and see the bigger picture so that everything doesn’t feel so immediate and urgent. We become more familiar with what works for us and what doesn’t, so we care a little less about what others think and a little more about what we think of ourselves. This sense of settling in to who you are as you get older can be a great feeling. It’s freeing and empowering to realize that you are comfortable with who you are. This can also bring up feelings of comparison or even grief at the paths we didn’t take when we were younger.

Remember, everyone feels this way, even if they hide it well. Life is short, and there’s just not enough time or resources for everyone to do everything they want all the time.

Learning how to have compassion for yourself in moments where you feel grief can help you navigate through.

You’re human. Even if the choices you made weren’t objectively the “right” ones, they were the right choices at the time. You did the best you could with the information and skills you had at the time. If things didn’t work out for you as expected, you can take note of what you could do differently next time and forgive yourself for what happened. Dwelling on things in the past doesn’t help to change the present or the future – it just distracts you from what’s going on in your life right now.

You are where you are today for a lot of reasons, including decisions you made in your past. Not everyone is happy with where they are currently, which can bring up complicated feelings like disappointment. It’s normal to be curious about where other paths would have taken you and what you would be like if you had chosen differently.


If you’re looking for more support in managing the grief of your unlived life, working with a therapist can help guide you through the process in a way that works for you specifically. Get in touch with our office today to get started.