I find it striking that palliative care nurse Bronnie Ware found the top regret of the dying patients she encountered to be, “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

Today I have been reflecting on the reasons for why this might be. Is it because others’ expectations are in real tension with our own? Or, is it because the expectations of others are so apparent to us and we do not actually know ourselves well enough to have expectations of our own?

In this video, an interviewer asks people what they would do if they weren’t afraid:

I think one of the most sincere insights in the video comes from the young man who says, “I’m afraid because I could fail.”

Studies show that people tend to have greater regret at the end of their lives over the things that they didn’t do over the things that they did.

Beginning with this in mind, what fear of failing prevents us from living with greater audacity?

I remember an application question for a program to which I was applying that asked applicants to discuss their most meaningful personal or professional failure. This was for a very elite program with thousands of extraordinary applicants. Struggling to come up with good stories of meaningful failure in time to meet the incredibly tight application deadline, I ironically failed to apply on time. However, this question has stayed with me and inspires me to try more things at which I could fail, like blogging about death every single day in 2021.

By intentionally adding things to our lives at which we could fail, we take the meaningful, character-defining risks that make for good stories, a life well-lived, and less regret. But this isn’t just a passing sentiment; it’s demanding. It costs actually doing more real things at which we could fail.