What would you do anyway, even if you knew you'd fail?
A different kind of year end reset, part two
“Everyone forgets that Icarus also flew”
These are the opening words of Jack Gilbert’s classic poem “Failing and Flying.”
The story of Icarus is often presented as a warning: Don’t fly too close to the sun. Moderation in all things.
But Gilbert invites us to rethink Icarus:
In some ways, the story of Icarus is not one of foolishness, but one of hope and human ingenuity. Icarus was imprisoned on an island with his father, and they painstakingly created artificial wings, while keeping enough hope alive to do something nobody had ever done: Fly.
And fly he did. Of course, the fact that he did not listen to his father’s warnings not to fly close to the sun contains the lesson that excessive or reckless ambition is bad—but we cannot forget that Icarus was escaping a lifetime of captivity on an island. Between accepting his fate and wasting away in prison, or escaping and flying—even though he would fail—the latter was clearly better.
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In his poem, Gilbert compares a falling Icarus not to someone who was a failure, but to someone coming to the end of a great victory. I would agree.
Taken this way, the story of Icarus is not one of success, but I think it’s actually better than most of today’s “motivational” advice.
Sometimes people say “What would you do if you knew you couldn’t fail?”
This is supposed to be motivating, but it’s not just unrealistic; it also places the focus of action in precisely the wrong place.
That question assumes that things are worth doing only if you “succeed.” But that assumes that success is an end goal—when success is often a process, or an experience.
A hike, for example, is not a success because it is over—or a failure because you didn’t do all of it—it is a success because you experienced it.
Instead, of saying “What would you do if you knew you couldn’t fail?” I think this question is more motivational and true:
What would you do anyway, even if you knew you’d fail?
This shifts the focus onto choosing risks and experiences and pathways that we still want, even when we are disappointed, face setbacks, or ultimately don’t “win” in.
This isn’t just about escaping mythological prisons or taking career risks. It also applies to relationships. I’ve had close friends and relationships fail—exes and friends I no longer talk to. But a world in which I had never talked to them, or was too scared to try to keep those alive, would be even worse.
Alfred Tennyson lost his best friend at 22, and spent the next 17 years writing a poem, In Memoriam A.H.H. in tribute. From this elegy we have the famous words:
I hold it true, whate’er befall;
I feel it when I sorrow most;
‘Tis better to have loved and lost
Than never to have loved at all.
Initial Questions:
What would you do anyway, even if you knew you’d fail?
What do you criticize others for trying? (Your judgements of others might reveal something here.)
What have you “failed” at but you’re proud of anyway?
What did you love doing before you became ashamed of it?
The next section is paywalled, with further questions, stories, and exercises. Paying members make this work, and also have access to part one of our year end reset (out now) and part three (coming soon). Please consider signing up and supporting us.
Content note: self harm and grief.
