The wrong trophy

Photo by Giorgio Trovato on Unsplash

I’ve always been a pretty future-looking, goal-oriented person. What classes will I be taking my freshman year? What will my high school GPA be when I graduate? What college will I go to? What will my first job be? When is my next promotion? It never stopped. After every milestone, there’d be another achievement waiting there for me to grasp it. Achieving things has always been how I felt appreciated and loved. So I kept achieving and achieving and achieving.

As a kid, this way of living gets you labeled as an “overachiever” pretty quickly. An A+ on an art project followed by a perfect score on an English paper followed by an honors class, all while being well-behaved and prompt. Being a teenager was really hard for me; my internal world was a tough place to be. But I thrived under pressure, and achieving made me feel good. So, despite my toughest days, I kept achieving and achieving and achieving.

After school, I struggled to nail down a career path that resonated with me or an industry I wanted to grow in. I just knew I wanted to achieve, and I wanted to be successful — that was it. When I started my career in tech, taking on more responsibility was easy. I excelled in most everything I tackled, and I was determined to climb the ladder in front of me. And I did.

Despite my career success, my personal world was in shambles. Just like being a teenager was really hard for me, so was being recently divorced. Doing things like checking my mailbox or scheduling a doctor’s appointment were nearly impossible for me; it was just too much to handle. But I thrived under pressure, and achieving made me feel good. You don’t get accolades for checking your mail, but you get accolades for climbing the corporate ladder. So I kept achieving and achieving and achieving.

I was eventually able to turn myself upright and do boring human tasks again. Hooray! It took a few years and some help, but I got there. My friends and colleagues noticed a difference in me, and I did, too. My overall life improved while I continued chasing success — but now perhaps in a slightly different way. I needed a bit less external validation to confirm that I was a person worthy of love and appreciation. My overachieving tendencies died down just a bit. I no longer had to give 150% in relationships where I received little. I no longer had to have it all together. But old habits are hard to break, and I kept achieving and achieving and achieving.

As I progressed through work and life, my achievements really started to accrue. And after years of pushing and climbing and achieving, I found myself in an usual situation.

I lived in a beautiful house with a big kitchen, a nice garden, and wood floors (like I always wanted). I had a nice, reliable car, and I had plenty of money to pay my expenses, save, and spend. I was surrounded by great friends. I had cute pets, a leadership position at a start-up, and I’d done plenty of traveling across the country. I had a really wonderful life. I was (and am) so grateful.

One of the things you don’t stop to think about when you’re an overachiever that ties their self-worth to accomplishing things is that, eventually, you’re going to turn 30 and have accomplished most everything you ever wanted. You push so hard for decades to be “successful,” but when you realize you’ve achieved all the success you desired, it doesn’t feel quite like you imagined. There’s still an emptiness and a longing for more. You don’t know how to feel content. Perhaps, all this time, you were chasing the wrong trophy.

So, as you might imagine, this situation is pretty world shattering.

I had no option but to detach my self-worth from achieving things, alongside having to find a new way to experience pleasure in everyday life. I was starting from scratch in a lot of ways.

I decided to keep a strange dog I found in the woods. I moved to a new state. I met new, interesting people. I forced myself outside of my comfort zone of being-good-at-everything-because-I-only-do-things-I’m-good-at. I opened myself up to being supported by someone warm and caring. I began to feel detached from my demanding, stressful job, and I left it altogether over the summer. I let my body rest for the first time in a long time, and I went quite a long time without achieving anything (to my standards, anyway). My life has changed a lot this year.

And here we are, present day. Trying to find worthiness and fulfillment while writing essays in coffee shops. Looking for ways to make a living that are less about achieving, achieving, achieving and more about using the skills I’ve developed to contribute to the world in a balanced, content way. Finding joy in simple, random things and appreciating the way things change. Still working on it. I’m getting there. (But not in an over-achieving sort of way.) Wishing you, dear reader, the absolute best.



Operations leader, mindfulness fan, and a big creative.

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