Make It Work: Not All Ambition Is Good Ambition

Yesterday, I quit a job. I told them it wasn’t a good fit, but the truth was that I just didn’t care enough to make it actually work. That was a hard thing for me to admit — although, unfortunately, this is far from the first time I’ve been through this.

Over the last year, I’ve advanced militantly through a series of freelance gigs, and in each,  I’ve found myself in a disconcerting feedback loop: find job, impress higher-ups with an avalanche of enthusiasm, cultivate a high level of expectation, hit a roadblock in execution, falter, grow bored, withdraw, and then eventually depart. Every time, it was easy to rationalize the breakdown as circumstantial.

“My emails were never responded to,” I would say. Or, “They never gave me feedback on anything! How was I supposed to know what to do?”

On some level, I’m right. Those types of problems are difficult to circumnavigate, if not downright annoying, but you’d be hard-pressed to find a single working environment that’s not theater-floor-sticky with structural issues. Yet, other people survive — they even go on to, you know, thrive. They write books, tour the world, get promoted, make tons of money, and go to bed, each night, content to know that they’re working very hard at something they’re extremely good at. (OK, LOL on that last one, but you know what I mean.)

So, what was my hang up?

My expectations for accomplishment were way out of line with the reality of my present motivations. Truth: I hadn’t been taking jobs because I wanted to climb the ladder at a given company and/or had any clue about What I Want To Do. Rather, I’d been unconsciously aiming to preserve a lifestyle — and a level of personal freedom — that I deeply cherished. I loved being able to spend weekdays exploring New York City, when museums are actually empty and a matinee film might cost $8. I loved losing entire afternoons in books, being able to travel spontaneously, and most of all, I loved being able to spend meaningful, regular time with my friends.

This was an uncomfortable kind of ambition. Not only did it put me at odds with most of my peer group — it put me at odds with the woman that I had always imagined myself to be. I’ve always liked to think of myself as relentlessly hard-working; a hustler. Somebody who will do whatever it takes. The reality, though, is that any person only has so much “whatever it takes” in them, and it’s a reservoir difficult to tap unless you sit down and are very deliberate about defining your reasons to do so. For example: you’re thrilled by a certain project. For example: you’re putting your children through college.

Or, most pertinent to my case: pushing your boundaries, and mastering new skills as a result, matters to you.

I had been throwing myself into Big Roles at Big Companies due to an abstract awareness that I should be “achieving” things, defining no real goals for myself there, and then getting flummoxed when I was unable to tap my personal reservoir of hustle. In retrospect, this all seems painfully obvious. While enmeshed in the cycle, though, I had been too overwhelmed with the deadlines and disparate needs of a sprawling client roster to realize what I was actually doing to myself. I was setting myself up to fail.

Part of my problem was that I kept taking on open-ended, part time, only-vaguely-defined gigs at companies that I wasn’t particularly excited about. I had a steady paycheck, sure, but I worked too few hours to really acclimate to company culture and understand the ins-and-outs of project execution. It was cumbersome, at best, to formulate and execute major initiatives while working 15 hours a week remotely. The road of minimum accountability ran both ways, I realized. Companies that ask for this were looking for minimum overhead for maximum outcome — and, as a result, we were both losing out.

I’m making myself a new promise. From now on, I will focus on specific projects with articulated deliverables — five emails, one in-depth report, two 900-word columns a month. I will make sure I know exactly what I am showing up to the table to deliver, so that I can focus on getting it done, and then move on. If a specific company isn’t blowing my mind, I won’t have to pretend to drink the Kool-Aid. The parameters of my role will be baked in from the outset. I will heave a big sigh of relief.

This approach protects my spare time as a creative resource, which helps me use it much more productively. Satisfied that my job is “done” for the day, I can happily lose myself in a good book or a long evening of aimless, just-because writing. I can finally go see the Yoko Ono exhibit at the Museum of Modern Art. While none of these things are quantifiably “valuable,” they’re deeply worthwhile in the sense that they continually restore my personal reservoir. They also spark the kind of ideas that lead to… well, who knows where?

That’s kind of the point. In the big picture sense, I know I’m still searching for the thing that will be My Thing. In the meantime, I know I need to keep a paycheck coming in, and I know I need to continue refining and growing my skillset, but I don’t want to be conflating my personal priorities with those of a company I’m employed by. It’s helpful for me to be continually reminding myself, “These are things that matter to me. These are the things that actually make me feel good.” It’s how I will find and recognize the thing I want to really throw myself into it — and how I can ensure that I’ll be totally prepared to do that, when the time comes.

Explaining this revelation to a friend over Slack yesterday, she passed me an old column by Cheryl Strayed, still achingly relevant: “Don’t lament so much about how your career is going to turn out. You don’t have a career. You have a life. Do the work. Keep the faith.”

I think I am the woman I thought I was. I think I may also still turn out to surprise myself — to become somebody that I never imagined I might be. I’ve been doing the work. I just have to work on keeping the faith.