Choosing What You Won't Regret

Thirteen years ago, as entry #71 for The Rumpus's advice column "DEAR SUGAR," Cheryl Strayed wrote "The Ghost Ship That Didn’t Carry Us." That ghost ship is an alternative version of your own life based on a big choice you didn't make. It's a ghost because you won't have that other life. You have the life that results from the big choices you did make.

I wasn't aware of this famous column until Anne Helen Petersen mentioned it recently.

In Strayed's column, a 41-year-old man contemplates parenthood with his 40-year-old girlfriend and asks how he can decide whether to become a parent. How can he know what he wants to do? He values his child-free lifestyle. And yet, while "I believe I am one of those people who could be perfectly happy without having children," he says, "that doesn’t necessarily mean that I wouldn’t also be perfectly happy with children."

Strayed replies that "the people we might have been live a different, phantom life than the people we are." As for feelings that might push our decisions, if you go for years without detecting a particular feeling within you, then "there will likely be no clarity, at least at the outset; there will only be the choice you make and the sure knowledge that either one will contain some loss." This man, as long as he remains a non-father, may never have an uncomplicated desire for fatherhood, in which case the desire itself can't serve as "an accurate gauge for you."

So here's another way to gauge: What do you imagine your future self will regret?

Choosing an option mainly to avoid regret is "the reason I’ve done at least three quarters of the best things in my life," Strayed counsels.

"The sketches of your real life and your sister life are right there before you and you get to decide what to do. 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?"

Sometimes you don't fully embrace your choice until after you choose it. Strayed recalls holding her infant son and feeling "rattled by the knowledge of how close I’d come to opting to live my life without him."

In becoming a mother, of course she'd left her childless life behind. She could no longer embrace whatever she might have become as a non-mother version of herself. This closing-off of options is not unique to parenthood; it's true for everything. Of the unknowable "life you don’t choose...whatever that sister life was, it was important and beautiful and not ours."

On gender transition

I mention this because, as you readers of Gender Identity Today are already aware, this counsel applies to gender transition too.

Sometimes we have a strong, specific desire to take a certain transition step, a feeling that itself can be sufficient reason to act. You might have a specific feeling about your gender, your sexuality, your body, or how people perceive you — one that's somehow distinct from your feelings about other parts of your life. You may give this feeling its own name, call it out, and call yourself into it.

Or you may not have a conscious and uncomplicated label for "what my gender is," "what to do about my gender," or "how I'll feel most comfortable in my body." If that's the reality of your identity or situation, you may feel ambivalent about a certain transition step. You may wait for a feeling to give clarity, and neither the feeling nor the clarity ever emerges.

In that case, we can instead ask ourselves: Will I regret not taking this step? When we realize that, yes, we'll regret not doing it, we've gifted ourselves with awareness of an important motivation.

We may need to develop the ability and amass the resources to act on our motivation.

Once we make the big leap and take the transition step, we change into a person who has made that choice:

My life used to be different, and now I've chosen this.

It is then that the feeling may come:

How wonderful. This is my life. I can't believe I almost didn't do this.