Sitting with failure
and becoming its friend
About three and a half years ago, I found myself sitting in one of my professors’ windowless and cramped office with tears in my eyes as he told me that I needed to accept that failure is part of life. But failure was not an option, especially as a journalist. I’m pretty sure he was the one who taught me that.
I used to joke that crying in his office was a rite of passage for journalism majors at my school, but maybe I just said that to make myself feel better. Laughing it off felt like the only way to shrug off his words without actually accepting them.
At the time, I thought he was warning me. There I sat, a 4.0 student, former valedictorian, high achiever. I hadn’t failed yet. He must have been telling me that I should accept failure because the longer I avoid it, the worse it will be when it finally catches up to me. The higher you climb, the harder you fall.
My junior year of high school, I was voted Most Likely to Succeed. At the time, I was at the top of my class and had plans of studying business in college. Seven years later, I’m about to finish an MFA program with dreams of being a novelist. After I graduate in December, I have no clue what I’ll be doing or what my life will look like.
I sometimes wonder if my classmates had known exactly what my life would look like in seven years, would they still have voted for me? Would my MFA and journalism degree (that I’m barely using) look like success to them?
Maybe voting on which teenager at school will likely have the most success is something we should phase out. Receiving the title felt like a mini confidence boost until it crashed into feeling more like a curse, an expectation that can never be reached because success is not so easily measured.
And then not getting the same title my senior year felt like losing a game I never signed up to play.
I have one semester left of school. After that, I will probably never be a student again, just a student of life. Since kindergarten, I’ve been a hard worker and a diligent pupil, but it took attending grad school to finally learn how to sit with failure.
At my MFA program, we are graded a bit differently than I have been in the past. Since art is subjective, most of the time all you need to do to get an A is turn in your work.
This kind of evaluation system would be easy to take advantage of. Just get something down on the page, even if it’s bad, and earn a masters degree with little to no effort. But people don’t pursue post-graduate education in the arts without a passion for their craft.
I’ve been liberated. Now, my work is propelled by my own ambition and drive. I’m not striving to please a teacher or check off a list of assignment criteria, but I’m using the structure of my classes and their deadlines to encourage me to work on the things I’m excited about.
For the first time in my life, failure is allowed. It’s almost encouraged. There is no punishment for trying something out, even if it ends up being terrible. I can still make straight-As while making tons of mistakes out loud and on display.
If you had asked me a few years ago what my biggest fear was, I definitely would have said failure. I even wrote an essay in college called “Atychiphobia” which refers to an intense phobia of failure. In many ways, this fear has defined my life.
Thinking back to sitting in my professor’s office, I now see his insistence that I accept failure in a new light. I no longer view it as a warning, but as a gift I wasn’t ready to receive. He wasn’t saying that failure is worse when you delay it, but that when you learn to sit with failure, to befriend it, you actually find more success.
As a writer, I get rejected a lot. I’ve been rejected from literary magazines, MFA programs, summer workshops, agents, you name it.
Rejection still stings no matter how many times you face it, but I no longer fear it. I’m glad I got rejected from other MFA programs because it solidified my choice and directed me to the program where I would learn so much and meet amazing friends. When I get rejected from a magazine, I don’t think “maybe I should quit writing altogether,” I just accept that the work wasn’t a good fit for the publication or that it may need to be revised again.
Fearing failure holds you back. If you only do the things that guarantee success or acceptance, you will never try anything new. You limit your opportunities. What if your dream is waiting for you behind the door that you’re too afraid to knock on?
Coming from a former winner of the title Most Likely to Succeed, the best way to guarantee success is to embrace failure. To try things even if you think you will be bad at them. To go for opportunities you think you will get rejected from.
In many ways, I am unsure if I have gotten over my fear of failure, or if I have simply redefined failure. Rejection isn’t failure; you’ve successfully put yourself out there. Trying something that doesn’t work is not failure. Imperfection is not failure.
But even when you do fail, or you feel like you have failed, you still have the opportunity to try again. Let it redirect your steps and propel you forward.
Failure is a part of life. I say this as a gift, not as a warning. It is better to try and miss the mark than to never try at all.
Sincerely,
Caroline Cherry




I think I say this every week but this is def my favorite essay yet
As a someone who’s also been a lifelong hard working student, and a perfectionist, I can’t totally relate. I think that one of the biggest challenges of being an artist/writer is learning to be ok with failure, and the messiness of the creative process. Failure is how you learn and grow—it’s just a fact of life.
Thank you so much for being honest about your struggles with failure in this post! I know you may not always feel it, but I think you’re doing great👍