Help! Should I be more ambitious?

Dear OOO,

I love my job, above all. The people are nice, the work is interesting, the pay is good and I have a lot of flexibility. I’ve been here for a long time, though, and sometimes I wonder: am I a weirdo with no ambition if I don’t try to level up?


One thing you realize after a few stints as a workplace advice columnist is that no one – or at least no one in the type of “creative class” career that often leads people to confuse a job with a religious vocation. – does not feel sure where it is. in their career. Middle managers wonder if they should be senior managers, while senior managers worry about when they will be fired. Junior employees worry about whether they are progressing fast enough or whether they are progressing too fast and will be forced to manage. People who have changed roles several times (Hi!) worry that people see them as flying hoppers; those who have been in one place for a long time are worried that people will treat them like a piece of furniture bolted to the floor.

The pandemic, of course, has exacerbated all of the above. Being trapped at home all day – both isolated from loved ones and without any separation from a few loved ones – can really do quite a bit on a person’s relationship to reason and reality. And if you’re the kind of person who defines you by your job to an extremely unhealthy degree (hi again!), Some panic about your professional position is almost inevitable. (It’s not just office workers. Anne Helen Petersen, recent trial about what she calls “the economy of ‘capitalism is broken'” elegantly combines the plight of “creative class” employees and service workers, arguing that the real problem lies in the bad business models that demoralize and are depleting workers in virtually every sector of America’s economy.)

So the easy answer, California, is that you are not a weirdo with no ambition to stay in a role you love and treat you well. When everything around us feels unstable, there is not only shame in keeping a job like this, there is a lot to aspire to.

And even! Something in your brain, heart, or soul is telling you that a great job with a great job, a good salary, and kind colleagues isn’t enough, and it’s worth taking seriously. Perhaps it is the fetishization of constant progress in the world, in which case do your best to rule it out. But maybe it’s something more, some fuss inside you telling yourself that on paper you did it, you just don’t feel it right now.

You don’t say anything about whether you feel fulfilled or satisfied with the job, which makes me wonder if you do. There’s nothing wrong with doing a job for a paycheck without expecting psychic reward – drawing boundaries between your work and your life is healthy, or that’s what I’ve heard – but your question seems to suggest that is not your style. And I wonder how much work is done “mostly” in “I love my job, especially”. Some questions to chew on: Are you having fun? Are you excited or scared more often 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 not seem relevant to you, while others will resonate. The latter is particularly important to me personally; the times I’ve really enjoyed my job have been when I’m around people who are both smarter than me and supportive enough to teach me things. The common link between all of my questions, however, is that they go beyond surface attributes like pay and general enjoyment, and hit on how your job actually affects your well-being.

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