When I was kid and I would do worse on a test than I wanted to or had a bad audition for the school musical, my mom would always ask the same question:
“Did you try your best?”
Almost every time, my answer would be “Well, yes,” followed by some kind of excuse as to why trying my best didn’t work that way I wanted it to – the way it should have.
My mom would listen for a bit as I tried to explain my failure, but I knew she wasn’t really interested in hearing the why after I had already confirmed that I had done the best that I could. She’d wait patiently and eventually say, almost smugly, “All that matters is that you tried your best.”
When I was younger, the idea that all that matter was that I tried my best – not whether I won or lost, succeeded or failed – always managed to calm me at least somewhat. Even if I still wished that I had done better (extremely typical type A oldest child Virgo here), I took solace in the fact that trying my best was at least better than not trying my best, right? I gave it my all, I put in the best effort I could, and I did so in good faith. It was kind of like “winning.” It didn’t feel as good, but it was better than feeling like an abject failure.
Over time, “all that matters is that you tried your best” became one of those things that my sister and I teased my mom about any time she said it. We had heard it so many times that it had lost all meaning and it became a silly platitude. “All that matters is that you tried your best,” mom would say. “All that matters is that you tried your best,” my sister and I would repeat in a sing-song voice, laughing.
On this week’s episode of Succession (no spoilers, I promise), Roman meets with an eccentric Zuckerburg-style tech magnate who asks him what he’s worst at, because, he says:
Success doesn’t really interest me anymore. It’s too easy. Like, analysis plus capital plus execution . . . Anyone can do that. But failure . . . that’s a secret.
Failure is hard because it requires trying. It requires having the strength to try something even if you aren’t confident that you’re going to succeed. It requires sticking to it even when things are tough and even if you know that they may not end well. It requires not giving up. And most of all, it requires continuing to do your best even in the face of all of that. These are all things that our parents taught us when we were kids that have gotten harder and harder to do as we’ve gotten older.
When I look back on my failures – the times when I tried so hard and often failed just as hard – they’re always the catalysts for my greatest successes, the things that I’m most proud of. I went to school for theatre management and always wanted to work in fundraising. I got a grant writing job right out of college and another bigger, better one two years later. Two years after that I was offered a stepping stone to my dream job – Director of Development – at an organization that I was so passionate about. It was an assistant director position and it seemed like the perfect fit.
I tried, really hard. I was in grad school at night and woke up before dawn, worked on homework, did the hour commute to work, worked until I had just enough time to pick up some food and take the train to class, went to a 3-hour class, came home and worked on homework until 1am, and then got up and did it all again. I was used to sitting in a corner and writing grant proposals for hours, but this job required face time with donors and the board and other things that I hadn’t done before and, I learned, I hated doing. But I kept pushing because I couldn’t give up. I didn’t want to fail.
Six months in, I got called into the CEO’s office. He told me that if I wanted to be a Director someday (my boss, the current Director, was about to go on maternity leave), I would need to work more and harder; be the first in the office and the last out. He also said that they felt like I had lied to them about being prepared for this position and that I wasn’t where they expected me to be in terms of higher-level development work. I was told to improve, quickly, or they would demote me and decrease my salary.
I was devastated. My entire very brief career to that point had been up and up and up and everyone telling me how fantastic I was. I had foregone time with friends, time with my partner, and trips for this job. I was exhausted from trying so hard, and here I was being told that I was precariously close to being fired.
But part of trying your best is also realizing when you’re failing and doing whatever you can to take care of yourself in that situation. I had an acquaintance from Twitter who had also worked in fundraising and had recently taken at a job at a tech company that was focused on helping nonprofits. I reached out and got an immediate message back that they had the perfect position for me that would be a great fit, and I got hired within days. That was the start of my tech career, and here I am nearly 10 years later. And I won’t lie, it was pretty great to tell my CEO, “you can’t fire me, I quit.”
Without failure, we don’t grow. Without trying our best, we don’t fail gracefully. Without failure, we don’t succeed in the right place and at the right time. The older that we get, the more terrified we are to try our best because what if we waste our precious, waning time and energy only to fail?
But that’s no matter. All that matters is that you tried your best.