When I was 23 I quit my job without anything lined up. It was my first job out of college. I had roughly $200 in the bank. I packed my car with everything I owned and sold the rest, listed my bedroom on Craigslist, then drove to Pittsburgh, PA to live with my grandparents.
That was October, 2012. I’m sitting here four years later, back in the city I once gave the finger to before packing my bags.
A lot happened in those four years. I lived in three different states, met some awesome people, met people not worth my energy, and lived in five different apartments (I know). I fell in love with writing and out of love with running (and back in love with it).
I lived in Pittsburgh for two years, four months. It wasn’t easy. I spent eighty percent of that time figuring out what I wanted to do with my life.
And I want to tell you about one of the many, many people who helped me figure it out.
What will you regret in forty years?
“Hey Grandpa, what’s up?”
“Well now, I’m up and you’re up. Are you walking to work?”
For twenty-plus years, my paternal grandparents did not play a large role in my life. There’s no somber backstory—our relationship was affected largely by location. We lived in different time zones, and birthday cards and phone calls took precedent over face-to-face interaction. Living in Pittsburgh changed that. My best memories in that city are having coffee with my grandparents.
I was en route to work in downtown, DC, walking on the cobblestone streets that make me so happy. “I have a random question for you,” I said. “Is there anything you regret? If you had to go back forty years and do it all over again, what would you do different?”
I was born without the ability to think ahead. As I’ve said before, I’m an immediate gratification addict. I think about the things I want now, rather than those that will benefit me in the long run. My grandpa is the one person who’s given me the smallest ounce of foresight. He has 55 years on me, and his ability to look back gives me the smallest motivation to look ahead.
This was a question I wanted to ask my grandfather for years. I just never had the guts to come out and ask.
“I wouldn’t allow the TV on during dinner time,” he said.
My grandfather is a badass. A Princeton-undergrad-turned-Harvard-law graduate, former pilot and partner of one of the largest law firms in Pittsburgh, I always wondered if he regretted working so much. He once told me he worked eighty-hour weeks for the 35 years he spent practicing law. He worked evenings, weekends, and stopped only during lunch to run five miles.
I thought his answer was funny, but could see his point. When you get one meal alone with your family, the last thing you want to hear is the television.
“What else?” I asked.
“Well, there are a lot of things I regret, but I don’t want you writing about it on the internet!
“I regret running so much on paved streets, instead of running on grass or a track, because having both knees replaced was certainly uncomfortable.”
My grandpa is always telling me I’m going to have my knees replaced.
I regret the times I was mean to someone,” he said, “Because those things are awfully hard to take back. I didn’t lose friends many times because of it, but sometimes I did. What do you regret?”
I knew my answers. “I regret any time I eat bad food, and sometimes I wonder if I’ll end up with diabetes one day from all the dessert I eat. Never once have I regretted running. I regret all the times I would become unreasonably angry or upset about something that was not a big deal.
“Most of all, I regret quitting my job when I was 23, because that wasn’t how I was raised. I never quit anything in my entire life then—and I always wondered if things would have turned out different if I gave DC a chance.” I paused for a second and said, “But if I never quit that job, we wouldn’t be having this conversation.”
It was true. I call my grandfather almost as much as I call my parents. Before 2012, I think I called twice a year.
“And you never would have found what you really wanted to do!” he told me.
When I graduated college, I would have taken any job in any city within driving distance of—I don’t know—Earth. When I lived in Pittsburgh and was busting out job applications on a daily basis, my grandfather finally told me to slow down, saying, “I think your first step is figuring out where you want to live!”
“I think you have to realize,” my grandpa said, “That you are going to make mistakes. I’ve done things I’m not proud of. Everyone makes mistakes, and everything turns out the way it should.”
Be grateful for all the F words.
I think the world of my grandfather. His career is unlike any I could ever hope to have. He was the person who carved a path for himself and followed it to the letter—many times to the extreme. He would never leave the office with work left unfinished. He still corrects the grammar of his adult children. If I do not speak in the most literal, precise tense (the fact that I answer the phone with what’s up drives him nuts) he’ll throw a snarky remark right back at me.
For all of my incredible screw-ups—like quitting a job at 23 to waitress for six months—I never expected a man like him to tell me it was completely normal to make mistakes.
Everyone always asks me why I started writing a website, or why I am so willing to be ridiculously open with my life. What I want—more than anything—is for people to know it’s ok to fuck up.
You will make mistakes. You will have things you regret. But everything turns out the way it should. Each one of those unfortunate instances teaches you something you were always meant to learn. You just might have a roundabout way of getting there.
Be grateful for all the f words in your life—your fuck-ups, the friends and family who got you through it, and the times you stood and fought. Everything will work itself out.