The Road Not Taken

The Lives We Didn't Live… And looking toward the road still ahead

At some point in life, most of us look back and wonder about the roads we didn't take.

The relationship we didn't pursue. The career we abandoned—or never attempted. The place we didn't move to. The child we didn't have. The friendship we let fade. The risk we decided wasn't worth taking.

Sometimes the road not taken was a deliberate choice. Sometimes circumstances choose for us. And sometimes we simply weren't brave enough—or ready enough—to recognize the road while it was still available.

But what exactly are we regretting when we look back?
Are we mourning a genuinely better life we might have had, or are we mourning an imagined life—one whose difficulties, disappointments, and losses we conveniently don't know?

Perhaps regret serves a useful purpose. It can tell us something about who we were, what we valued, what we feared, and what we failed to recognize at the time. But it can also become a trap: endlessly comparing the complicated life we actually lived with an idealized version of the life we didn't.

But eventually another question becomes possible:
What does my regret tell me about the life I still want to live?
Maybe the relationship we regret losing tells us that intimacy matters more to us than we admitted. Maybe the career we didn't pursue tells us that creativity was more important than security. Maybe the adventure we avoided tells us that we've allowed fear to make too many decisions for us.

In that sense, regret doesn't necessarily have to be an argument for going backward. It can be a compass pointing forward.

But turning forward isn't always easy
There are roads that really are closed.

Some choices cannot be undone. People die. Children grow up. Opportunities disappear. Bodies change. Circumstances change. There are versions of ourselves we will never get to become.

And there is a temptation, particularly as we get older, either to deny those losses—"It's never too late!"—or to surrender to them completely—"That part of my life is over."

Perhaps wisdom lies somewhere between those extremes.
We can't necessarily take the same road, but we may still be able to pursue the thing the road represented.

- The career we didn't have might become teaching\, volunteering\, mentoring\, or simply finally making something.
- The adventure we didn't take might become the trip we take in the next year or two..
- The intimacy we didn't allow might lead us to risk greater vulnerability in a relationship we have now.

The person we didn't become at 30 may not be available to us at 50 or 60—but some essential part of that person may still be waiting to be expressed.

“What would I regret not doing with the time I have left?”
That last question can be remarkably liberating. It shifts the emphasis from the life I didn't live to the life I don't want to fail to live now.

So tonight, let's explore not simply what we regret, but what kind of person we want to be with the time that remains?

Questions to consider:

If you knew you had ten good years left, what would you want those years to contain?
What would you regret not experiencing?
What would you regret not letting go of?
What road have you been telling yourself is closed that might actually still be open?
What have you postponed because you've assumed there would always be more time?
Is there something you've wanted to do for years but keep finding reasons not to?
What would you attempt if you knew you couldn't fail—or, perhaps more realistically, if you knew failure wouldn't matter very much?
What conversations would you regret never having?
Is there someone you need to forgive—or someone from whom you need forgiveness?
What do you wish you'd told someone while you still had the opportunity?
Are there relationships you are maintaining out of obligation that you would rather release?
Conversely, are there relationships you have allowed to become distant that you would regret losing completely?
What kind of friend, partner, parent, sibling, or member of your community do you still want to become?

When you look toward the end of your life, what would be harder to live with: having tried and failed at something that mattered to you, or never having tried at all?