I’m desperately unhappy with my job, but my boss relies on me. Should I quit?

<span>‘Every day I get more fed up and depressed about having to do a job I resent and am bored by.’ Painting: The Fruit and Vegetable Costermonger by Louise Moillon.</span><span>Photograph: Artimages/Alamy</span>
‘Every day I get more fed up and depressed about having to do a job I resent and am bored by.’ Painting: The Fruit and Vegetable Costermonger by Louise Moillon.Photograph: Artimages/Alamy

I work for a small company; there are just three of us. My boss, who is the owner of the company, hired me to manage it while she stepped back before having her first child. She’s since had a second child. At the start, I loved my job. It represented security after several rocky years. But as time has gone on, I’ve become increasingly disillusioned with my job and the industry I work in. I desperately want to leave.

I’ve been working on a side gig for 12 months in my free time and it’s starting to take off. If I had extra time to spend on it, it would make a huge difference. My dream would be to take a part-time, mindless job to help pay the bills, but I feel trapped in my current position. My boss is stressed. She’s struggling to cope with parenthood and being the main breadwinner in her household. If I left, I would put her in a difficult position. While we’re not close friends, we have become friends of a sort over the years, and I am aware of how much she has to deal with at home. Of course, I could just wait and see how things pan out, but every day I get more fed up and depressed about having to do a job I resent and am bored by.

Do I put my own selfish needs first and hand in my notice, or should I be a good person and stick it out until the chips fall where they may?

Eleanor says: The question here I think is: would this job, this boss, take care of you in the same way?

It’s common for us to wind up with feelings of obligation, attachment and reciprocity to a job. We spend so much time with our bosses and go through so much for them that we can develop relationships that feel for all the world like friendships, setting aside the fact that one pays the other.

Related: While I love my job, I resent having to work at all. Any advice? | Leading questions

But there are an awful lot of people who’ve approached their job through the lens of friendship or benevolence and found out the hard way that the job wouldn’t do the same for them. You say you’re “desperate” to get out of this situation. If you’re going to make massive sacrifices in your life – setting that desperation aside to do something supererogatory for the boss – I think you’d want to be really sure they’d do the same for you.

The general rule of thumb is “no”, not because every boss or job is a schmuck, but because that category doesn’t apply. Because they’re bosses, it’s their modus operandi to do what makes sense for them. Kindness and favours at work aren’t unheard of, of course – but they’re not usually the norms by which businesses (even small ones) operate.

So unless you have good reason to think this boss and this job would do a symmetrically high-cost favour for you in return, I’d be careful about setting too much of yourself aside for them.

That said, it does sound like it would be important to minimise the impact of leaving, given your boss’s personal circumstances. Don’t do the thing where you avoid a conflict with someone because you’re afraid of hurting them and paradoxically wind up doing far more hurt by putting it off, deceiving by omission, making it a nasty surprise.

You could bring this up with plenty of notice. Could she not hire someone to do your job at the rate she’s currently paying you? Could you find or train a replacement? Try to look for ways to manage this transition that abide by some of the “friends of sorts” feelings you have without just making it the case that you’re doing a big favour, at your expense, indefinitely.

It’s worth remembering that things in our professional lives often feel much more personal to us than they do to the other half of the interaction. You have to conduct yourself in a way that’s fair to them, but remember “fair” doesn’t necessarily mean the same thing as “benevolent”. Just as it’s “fair” for workplaces to make decisions that maximally benefit them, it’s fair for you to do the same.

• This letter has been edited for length and to remove some personal information.

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