break point

when does it make sense to pivot?

Hiroshi Nagai, Tennis Court

Lately, it seems, everyone I meet has dreams of quitting their day job. My scene partner in acting class works at Google but wants to play television roles. The woman sitting next to me at jury duty was reading a book titled The New Reason to Work. My boss resigned last week to take a career break. His first stop: Paris, then a yoga retreat in Greece.

It’s no secret that corporate life can be grinding, frustrating, downright soul sucking. There’s doing your job, and then there’s the game you have to play in order to make a good impression and advance in your career. I’m reminded of that controversial Nike commercial that’s been running during the Olympics. It challenges us to answer the question “Am I a bad person?” while flashing a montage of some of our most beloved athletes at their fiercest moments:

I’m single-minded. I’m deceptive. I’m obsessive. I’m selfish. Does that make me a bad person? Am I a bad person? Am I? I have no empathy. I don’t respect you. I’m never satisfied. I have an obsession with power. I’m irrational. I have zero remorse. I have no sense of compassion. I’m delusional. I’m maniacal.

It concludes with the provocative statement: Winning isn’t for everyone.

Although I’m pretty sure the ad is meant to be tongue-in-cheek (we’re not meant to take it seriously, guys), a less sardonic argument can be made about climbing the corporate ladder: it requires a thick skin, a degree of ruthlessness, shameless self-promotion, and political cunning. You have to present yourself in a certain way to curry favor with those at the top. Being nice is a flaw. What friends see in me as calm and poise, executives in a meeting room see as “passivity,” and by implication, weakness.

Most people feel ambivalence toward their day job because even if they hate playing the game, they’re getting something valuable in return: money, status, validation. In Drive: The Surprising Truth About What Motivates Us, Daniel H. Pink distinguishes between Type X and Type I people. The former are motivated by external rewards, while the latter are motivated by intrinsic desires and the rewards are just the cherry-on-top. If you are self-motivated and passionate about building your own product or publishing a book or performing on Broadway, it’s probably not a question of whether to throw off the golden shackles but when. (By the way, if you’re in this boat, I highly recommend this episode from David Nebinski’s excellent Portfolio Career podcast.)

Once my job gets unbearable, I’ll quit. The problem with this thinking is that we’re much more resilient than we give ourselves credit. You might never reach your breaking point, and even if you do, you may leave a bad impression. People can always tell when someone is miserable and disengaged at work.

Instead of waiting to reach your breaking point, I think it’s better to leave on a high note, to figure out what your “break point” is. This might be a crude analogy, but if you think of a job as a tennis game where your employer is constantly serving you harder projects that you have to best, at which point have you accumulated the points you need (skills, experiences, money in the bank) in order to have an opportunity to win the game on the next serve?

I think what people get wrong about career pivots is that it doesn’t have to be a 180 degree change. A pivot is literally a central point at which a mechanism turns: you can keep your day job while exploring other options. Of course, you can only do this if your day job isn’t too demanding, and even so, there are tradeoffs: you won’t have the time and energy to work towards a promotion. You’ll be doing the minimum to keep your job, and that’s O.K. We can’t operate at 100+% all the time. We go through seasons in our careers.

In some ways, the people who can’t juggle both a day job and a passion project have an easier time. They don’t have to waffle between the two. If you’re not one of those people, I think it’s useful to figure out how much you need in order to comfortably quit: set a time horizon and be honest about what’s realistically achievable in that time and what kind of lifestyle you want to sustain. Maybe you want to keep your current lifestyle or you’re fine downgrading to a smaller apartment or fewer vacations. It’s not an exact calculus because you will always feel like you need more money. But there’s no point in hoarding money unless it can be spent on what’s most important to you, and for a creative, the most important thing money can buy is time: weeks, months, and years to do what you love.

At the end of the day, you have to take a leap of faith and not let desire get in the way:

The way something comes into our life is because we have chosen it. It was the result of our intention, or we made a decision for it. It has come into our life in spite of desire. The desiring was actually the obstacle to its achievement or acquisition. This is because desire literally means, “I do not have.” When we say that it isn’t ours, we put a psychic distance between ourselves and what we want. This distance becomes the obstacle that consumes energy.

— David R. Hawkins, Letting Go: The Pathway of Surrender

You know the saying, we see what we want to see? The same is true here. When you believe that your destination is far and involves enormous sacrifice and striving to reach, then that will become your reality. You might never even get there. Instead, if you orient yourself around the belief that you’re already where you want to be, you’ll be doing the work and living the life instead of psyching yourself up for all the obstacles along the way.