A lifetime of should-ing

the case for an existential crisis

Mount Rainier National Park — July 2017

Recently, I found myself in a room with a group of 20-somethings. The topic that seemed to be on everyone’s mind was what to do with the existential dread they were each grappling with. It transported me back to a time in my 20s when I wrestled with my own set of existential questions. It was an era of rumination and pro con lists.

It wasn’t that I was “unhappy.” It was that I was numb to everything in my life that had “gone right” and should’ve made me happy — which felt even worse. I had worked hard to establish myself at a company that I thought I’d dedicate my career to, only to begin doubting whether I actually liked the role I’d been promoted into. I had a great community of friends from childhood, college, and work. I had a committed partner who wholeheartedly supported me and listened intently as I contemplated the meaning of life. He and I had just moved into our dream neighborhood together. Objectively, life was going very well.

Unfortunately for me, so much of my identity was wrapped up in my work self that the parts of my life that were thriving didn’t hold much weight. The lack of fulfillment I felt at work seeped into how I showed up in my relationships. Despite feeling disengaged at work, I would routinely allow it to take priority and further pull me into a pit of despair, sheepishly canceling on dinner plans with friends when a new project landed on my desk at 5pm. Rather than set boundaries, I worked harder to salvage the thing I felt like I should care about. This went on for months.

When I finally admitted to myself that I needed to kick off a job search, I free fell into my first existential crisis, ill-equipped and lost. I had been so committed to fulfilling my college self’s decision to pursue a career in finance that I hadn’t bothered to pressure test any of my assumptions.

The idea that I should commit to a career based on my college interests assumed that I knew at age 21 what I wanted to do for the rest of my life. False.

The idea that I should commit to the first industry I ever worked in assumed that I didn’t need to experiment with other career paths to conclude this was the only career path for me. False.

I was so caught up in feeling like I’d failed to properly calibrate my career that I didn’t appreciate I was freeing myself from a box that had started suffocating me. All I could think about was the sunk costs of energy and time — the shoulds that would go unfulfilled.

In hindsight, it’s clear why taking a good hard look at myself and what I wanted for the first time set off a series of cascading avalanches in my life. By giving myself the permission to envision and make strides towards a new life, I was coming to terms with the fact that my life had been driven by both societal and self-imposed obligations.

playing within the lines

For most of my life, my decisions were driven by invisible shoulds which manifested as ambivalence. It’s not that I felt like I had no agency over my life, but I often felt indecisive at the trailhead of a big decision. I simply did not know myself well enough to make informed decisions on my own behalf. When I found myself at crossroads, it was easier to flag down others for their advice and hitch a ride to the “right” destination than trust that I would get us there safely.

Growing up, we turn to our parents, friends, teachers, and communities for guidance like our lives depend on it. Because it does. We have no idea yet how to live, how to learn, how to dress, how to be. Through being explicitly told what to do and implicitly observing what we should do, we learn to earn love and acceptance by living in accordance with others’ shoulds. At some point in our teenage years, it’s hard to decipher what’s take-it-or-leave-it advice or societal expectations that demand us to conform. We compliantly squeeze ourselves into a box shaped by who we believe the world wants us to be. For years, we live in that box, allowing the walls of the box to become our reality all while outgrowing norms that no longer suit us. The trouble is: we forget that the box that’s held us captive for so long was only meant to provide a structure for how our lives could be.

A lifetime of playing within the boundaries of the box and turning towards others to define the parameters. Somewhere along the way, we stop turning toward ourselves to ask, "What do I think?”

the case for an existential crisis

There’s never a good time to have your world come crashing down on you. But, better now than later. The further along on your journey, the more fragile life becomes, the more entrenched in the shoulds you become.

It’s not to say that having one life crisis guarantees that you’ve rid your life of future existential dread. You’re just better equipped next time with the right tools and experience so the free fall is gentler, smoother. Contemplating the purpose of your life goes from tumbling down a black diamond to sliding down the bunny hill on your butt. The sooner we shed all the ways we’ve been should-ing ourselves, the sooner we can give into the desires that live dormant within us. Giving the dreams that tug at your heart the space to flourish can only happen if we first allow the avalanches to fall and shake up our current misaligned existence.

The numbness I felt was the result of continuously choosing to ride the gondola in the direction of someone else’s definition of success, moving further and further from my own intuition of a life well lived. When we feel internal turmoil, it’s a signal from our body to rethink our assumptions. While it’s natural to turn to everyone else — anyone else — for wisdom, take the time to experiment with cultivating your self-trust. Your instincts are far stronger than you realize.

Like a muscle atrophies without proper exercise, we allow our intuition to atrophy when we outsource our life decision to others. Start small. Build confidence in your ability to make small decisions with no one’s input but your own. The more I’ve cultivated my instinct and brought awareness to the ways I should myself, the easier it’s been for me to make decisions from a place of self-trust. Trust that I have my best interest in mind. Trust that I’m not living a life of other people’s expectations of who I should be.

the quiet shoulds

The work of separating ourselves from societal and self-imposed shoulds is a lifelong practice. Sometimes it’s hard to differentiate if pushing forward is an act of giving into societal conditioning or an act of discipline. As you build your intuition muscle, the shoulds will become more subtle. Subtle enough that sometimes you’ll wonder if the resistance you’re feeling is just the result of a lack of resilience. Once you put in enough reps, you’ll start to develop an instinct for when it’s time to surrender or time to double down.

These days, existential dread is a lot less pervasive in my life. It instead manifests as little tests littered throughout my days. I felt waves of resistance as I wrote this week’s essay. The piece I had originally intended to publish today was 60% finished when I decided to pull the plug on it. It took until I was halfway to the summit to make this decision because I felt like I should keep pushing through. I had this idea that because the topic had come to me in an early morning meditation, it must be an essay that deserved to be brought to life. Plus, I had a writing class deadline to hit — I should just push through rather than start a new essay. Alas, 3 days and 3 drafts later, I found myself staring at a half-written draft with so little motivation to finish it that I almost forgot what writing in flow felt like. Like gliding down the mountain with the wind at my back, carving a new path through fresh powder.

Thanks for reading — let me know the ways you’ve shoulded yourself in the comments or say hi on Twitter!

Thanks to

Nix 🕊

for inspiring me to visit this topic and to Ryan, Samantha,

Treeckster

, and

Bennett Jacobs

for reviewing drafts of this essay.