Help! Should I Be More Ambitious?

Dear OOO,

I like my job, mostly. The people are nice, the work is interesting, the pay is good, and I have a lot of flexibility. I’ve been here a long time, though, and sometimes I wonder: Am I an unambitious weirdo if I don’t try to level up?

–California

OOO

Surviving the #WFH Age

Need help navigating the always on, always remote life? Ask OOO at mail@wired.com.

One thing you realize after a couple of stints as a workplace advice columnist is that nobody—or at least nobody in the type of “creative class” careers that often lead people to confuse a job with a religious calling—feels confident about where they are in their career. Middle managers wonder if they should be senior managers, while senior managers fret over when they’ll be sent back down. Junior employees worry about whether they’re progressing fast enough or if they’re progressing too fast and will be forced to manage. People who have changed roles many times (hi!) are anxious about people seeing them as flighty job hoppers; those who have stayed in one place for a long time are anxious about people treating them as a piece of furniture bolted to the floor.

The pandemic, of course, has exacerbated all of the above. Being trapped at home all day—simultaneously isolated from most loved ones and with no separation at all from a select few loves ones—can really do a number on a person’s relationship to sanity and reality. And if you’re the kind of person who defines yourself by your job to a wildly unhealthy degree (hi again!), some amount of panic about your professional station is all but inevitable. (It’s not just office workers. Anne Helen Petersen’s recent essay about what she calls “the ‘capitalism is broken’ economy” elegantly knits together the fates of “creative class” employees and service workers, arguing that the real problem is bad business models that demoralize and burn out workers in basically every sector of the American economy.)

So the easy answer, California, is that you are not an unambitious weirdo for sticking around in a role that you like and that treats you well. When everything around all of us feels unstable, there’s not only no shame in holding onto a job like that, there’s a whole lot to aspire to.

And yet! Something in your brain or heart or soul is telling you that a pretty good job with interesting work and good pay and kind coworkers is not in fact enough, and that’s worth taking seriously. Perhaps it’s the larger world’s fetishization of constant advancement, in which case please do your best to tune it out. But perhaps it’s something more, some stirring inside of you telling you that while on paper you have it made, you’re just not feeling it at the moment.

You don’t mention anything about whether you feel fulfilled or satisfied by the work, which makes me wonder whether you do. There is nothing wrong with doing a job for a paycheck without expecting some psychic reward—drawing boundaries between your job and your life is healthy, or so I’ve heard—but your question seems to suggest that that’s not your style. And I wonder how much work that “mostly” in “I like my job, mostly” is doing. Some questions to chew on: Are you having fun? Are you more often excited or filled with dread at the start of your workday? Do you feel challenged? Are you able to try new things? Do you work for and with people you want to learn from?

Some of these questions will feel irrelevant to you, while others will resonate. That last one is particularly important to me personally; the times I’ve truly loved my work have been when I’m surrounded by people who are both smarter than me and supportive enough to teach me things. The common link between all my questions, though, is that they go beyond surface attributes like pay and general pleasantness, and strike at how your job is actually affecting your well-being.

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