A couple weeks ago I was staring at a pair of shoes in a store window, thinking about how appealing they are in the beginning when you pick them off the shelf, and how wonderful it is when they come in your size. But it also occurred to me that if you wear them out on the New York streets long enough, you get to see their flaws—when they’re not right for the occasion, or when they can no longer give you the arch support you really need.
I had gone out for a walk and stopped because a pair of shoes caught my eye in a window display that framed them well. With everything that was on my mind already, this display was a good metaphor for my sense of identity lately: it takes the right circumstances to make you pause and pick something that works well until something else comes along that fits better, doesn't it? And we switch in and out of these things without questioning how that works for most of our lives.
Now, I could be accused of having a midlife crisis. In fact, that is how someone close to me referred to it. But I avoid the term because “crisis” implies emergency, something that must be attended to urgently and maybe with a little force. It also implies that things were moving along smoothly in some specific direction all the way up to my "midlife" and then, all of a sudden, I reached an impasse with myself and now suddenly “find” myself panicking. Well, things haven't been “smooth” for a long time, by design—I decided that learning to appreciate uncertainty is the price you pay as a creative person, and/or an entrepreneur.
However, it is true that a few years ago it started to feel like something was not quite right. I was here in New York working at an advertising job, finally enjoying a smooth, middle-class life with no obligations (no children, no student loans or immodest debt), when I started wonder if I was somehow blowing it.
It was a question that barely showed up on my radar, and I wondered why I was even thinking about this. Wasn't I exempt from this phase, given that I had never followed the conventional pattern that leads up to this kind of dilemma?
After a certain amount of being tossed around in my life, perhaps I was conditioned to expect that something would come along and take everything away? But take what away, exactly? I knew that my anxiety didn't come from not becoming a Mark Zuckerberg or from making my first million by the time I was 25 or 30 or 35 or whatever. No, I was already past that age now and comfortable with a sense of self that didn't require stockpiling cash or assets to feel “whole.” What I had I was grateful for, and that mentality of trying to force a prediction of “success” at all costs has always escaped me anyway. I was not concerned about career or family goals as part of my life's trajectory either. For some of us—after looking inward about what we are comfortable with, and outward at the world in which we find ourselves—many of us find it genuinely difficult to understand people for whom all that is normal, or even desired.
But yes, a low-frequency anxiety began to reverberate around this line of self-inquiry. Where was I headed? Was I screwing it up? Had I screwed up already?
To some degree, questions like these come from passively witnessing a cycle play out over time and then seeing something anomalous, something that shouldn't be there. When you've been an adult for a little while, you notice—with the exception of disease and death—how things are not so different anymore from year to year unless you make them so.
And this is when things become interesting: you start to ask if your presence has value, and more importantly, what circumstances are necessary for you to be of value...within a cycle that seems to be pretty fine on its own. To be clear, by “value” I'm not specifically discussing a “right” profession or whether you're swimming in the “right” career pool. Career happens when we trade skill and time for a place in society—whatever the profession. I think the question of value comes up for anyone who puts aside time for it, from CEOs to clergy to custodians and everything in between.
Career and profession also is about what we do. And I'm not discussing doing. I'm discussing being.
I decided to address the anxiety by eliminating different ideas about what might be causing it. I developed some hypotheses and tested them out by doing things that were typically outside my normal set of routines. In other words, I wanted to know what I would need to do to feel “correct” about myself. I gave myself what, at the time, I thought was a luxury but clearly was a necessity: the time to get a clear birds-eye view of my life so that I could look a few thousand feet below and make some decisions. I had to get clear about what kind of person I was trying to become 5, 10, or 30 years down the line as an adult. I had to be clear about what was acceptable within the walls of my “fortress” and what needed to go. Here's the distilled version of how I have gone about it.
I made a plan
This is not about where you want to be career-wise in the next five or ten years, or what kind of yacht you'd like to own when you “make it”. This is about the person you'd like to become. It is inevitable that by the time we make it to our thirties, we'll have brought with us some excess baggage—things we didn't even realize we'd been carrying from toxic friendships, faulty relationships, incongruous career decisions, and just naivete. So it takes a little initiative to decide that even if you're completely fine with how you present yourself to everyone out there on Facebook, at a conference, or at your job, that you're not entirely ok with how you are with yourself, that there are things that need change and that you can be improved. It takes effort because nothing really has to change (“if it ain't broke, why fix it, right?”) and you can continue exactly as you have. You can decide that nobody is the wiser, and you'll very likely get away with it.
But you'll know.
You might get better at layering your persona with every progressive year, but you'll know. Until time smoothes things over so well that you forget the difference between what you are and the persona you created decades ago as a kind of coping mechanism. And then you might find that the road ahead of you is a lot shorter than the one behind you, and that changing—reverting—to your better, more authentic self is harder than you expected.
I found my celebrants
At every stage of our lives, we're “air-dropped” into new pools of people who are there to do what we came there to do. Often it's by default (family, neighbors), or for school, or for college, or for church, or to be co-workers, or fellow players on a sports team. Each group presents a hodgepodge of personalities roped together by a common purpose. It's easy to believe, as I did, that common purpose equals common perspective. It took me a while to realize that not everyone in a “group” celebrates what you do, understands you, or believes as you do. I know it's obvious for a lot of people, it wasn't for me. But computing it in my own time made me realize explicitly that it was up to me to stay curious and seek out the few who are generous enough to understand the “why” of what I am at my core, why I behave as I do, or why I make the things I make. You have to stay open to attract the rare individuals who agree with what you're putting out: these are the few who will believe in you, encourage you to produce more of that thing you do. Conversely, this also means you'll have to make space for them by letting go of the many who don't “get” you, the people with whom you have activities in common but nothing else, who are stuck in places you escaped from, or people who aren't capable of dialogue—not because of a language barrier, but a listening barrier.
“Don't do anything you don't want to do.”
Henry Rollins is the author of that succinct piece of advice. It is something I picked up from him about 25 years ago and I've gotten good mileage from it. It is an open invitation to say “NO” exactly when it's time to say it. The trick is to understand the consequence of saying “Yes” to something that is just not in your nature. Maybe you feel obligated not to hurt someone's feelings, or to take a deal that is fundamentally unfair, or a gig that moves you further away from the kind of person you're working toward becoming. For example, a management position in a toxic workplace would be a good example of this kind of thing, as would staying in an abusive relationship: there are always trade-offs with these things, but any “advantage” in cash, status or stability will likely require you to invent or maintain a persona that is ethically at odds with your best self. Or maybe not, if you're ok with that. An old mentor once put it well, “Don't focus on what they're giving you, think about what they take from you.” I miss her wisdom still.
I believe these questions—and their corresponding unease—will come up at some point for everyone, no matter what your profession, skin color, class or geographic location. It's what every person living in modern times has to contend with. It divides people into two broad groups: those who will feel that it is perfectly natural to be pulled in to resolve the questions, and those who will believe it's perfectly fine to ignore the questions by switching to something else instead or kicking the can down the road. I'm not sure if there's a correct group, or a correct way to deal with these things. But I do know that if we remain honest, curious and open, we always know which camp is home. And we're clear with whom we can—and probably should—spend our best selves with.