Prompt: What Does Success (and Failure) Mean to You?

Note: Full access to prompts like this one, as well as the prompt archives, is reserved for paid subscribers here at The Mending—upgrade now for access. Free subscribers enjoy this preview!

As I write this, graduation season is upon us. Inspirational commencement speeches are recirculating around social media, and graduates are opening congratulatory cards filled with reflections on and wishes for success.

As I attend “promotion” ceremonies for my two sons this week (one’s being promoted to middle school and the other to high school), I keep thinking about what wisdom I want to impart to them as they move into the next chapters of their lives.

To be honest, this season has made me nostalgic about my own commencement ceremonies—specifically, my high school graduation.

At the end of senior year, my class voted me “most likely to succeed”—the words are permanently printed below my yearbook photo. I was an extremely successful high school student—academically, socially, and involved in all sorts of extracurricular activities. I was a high-performing, overachieving student and graduated at the top of my class. As class salutatorian, I can’t recall much of the speech I gave, but I’m pretty sure I quoted Matthew 7:7 (“Ask and it will be given to you; seek and you will find; knock and the door will be opened to you”).

After I graduated from high school, I went off to the University of Illinois at Urbana-Champaign, succeeded in every traditional sense of the word there, landed a dream job right after graduation, got married, and adopted a dog—I was crushing it!

But then, life fell apart and fantastically so.

Twenty-three years later, and my forty-one-year-old self cringes at how many times I’ve asked and not been given, sought and not found, knocked and had doors slammed upon me…

To my high school class of 2003,

I regret to inform you that you voted me “most likely to succeed,” but I have failed remarkably.

Well, this is where my mind goes, at first…

I’ve spent most of my life striving to be successful, to be chosen, to have it all put together and figured out.1 But there have been many times when I haven’t been chosen, when I’ve failed myself and failed others, when I’ve lost nearly everything.

I could continue with a litany of failures and losses—of all the dramatic and traumatic ways life has not worked out for me—but I’m going to refrain from doing so here. What I will say is that I can look back at my life and see all the ways I have not succeeded.

Even now, especially now, as an adult living in the high-performing culture of Silicon Valley and Stanford University, comparison can leave me feeling like a nothing and nobody.