How do I figure out what to do with my professional life? Will I always feel helpless and bored?

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How do I figure out what to do with my professional life? I have always been considered a smart and ambitious young woman. I have an honours bachelor degree, a master’s degree from an internationally lauded university and I excel at whatever job I’ve held (which has been at least 10 in the past 10 years). However I find little to no satisfaction in my working life. I’ve tried everything from archaeology to winemaking to high-flying philanthropy to real estate, but nothing sticks. My parents think I’m a “Pollyanna” who just gets excited at the prospect of something and then disappointed once the rose-coloured glasses come off. I don’t think that’s the whole picture. I am a hard worker, very committed when I start out, often even working myself to burnout.

I have an analytical mind, but I don’t think I’m overly critical once the honeymoon ends, as my parents suggest. Will I always feel helpless and bored and pointless at work? How can I find something that pays to have a moderate standard of living, that I don’t hate doing and engages me enough that I don’t feel like quitting? I have many decades-long hobbies and friendships, and studied hard for many years, so I know that I’m not “a quitter” by nature, just with work. Sometimes I think, did I use up all my effort too early in life?

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Eleanor says: Honestly, you might hate work because work hates you, or at least, is relatively indifferent to you. I don’t mean that to sound dramatic or sinister or particular to you. It’s just that work – the apparatus of exchanging time for money – isn’t designed to make you feel anything good. It’s arguably inclined to make you feel pretty bad, no matter how fulfilling the task you’re ostensibly engaged in. This is why even people with high-paid “dream jobs” in social conscience work or creative fields still have long periods where the drudge outweighs the joy, from grants to emails to colleagues to the sheer effect on one’s time. It isn’t an especially emotional or biting claim to say that work doesn’t care about you. It’s a bit like saying a logic board doesn’t care about you: it wasn’t designed to. Professions are designed to connect money and services, and it would be very surprising if a system designed to do that also by coincidence made the people inside it feel good.

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It’s fairly natural that in any relationship, after investing shovels of hope and barrels full of energy, things start to sour when you realise you aren’t getting back what you thought you would.

If we were getting the same hope to frustration ratio from a person – a friend or a relative – it wouldn’t take us long to think that maybe they’re the problem. But the possibility that work itself could be the problem is a little harder to articulate. We don’t want to give up the idea that the thing we spend most of our time doing could be made to feel straightforwardly fulfilling. So the frustration starts to feel like it’s something we could remove if we just pull enough levers – implement enough systems, use enough time-management tools, hone the personal goals a little more. This just might not be true: the undercurrent sense of couldn’t-there-be-more might be an ineliminable part of work.

Treat work as the place you earn the money and insist on separate time to feed the others

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So perhaps the reason you’ve felt frustrated with work is it’s natural to turn on something that continually disappoints you.

That isn’t just a sentence to doom. A bit like the realisation that no relationship can single-handedly make you happy, the realisation that work can’t – and isn’t designed to – sate your spirit can be freeing as well as sad. It means that you can do what many people are too busy (with work!) to do: find things outside a profession that give you what you’re missing.

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You asked how you can find something that “pays a moderate standard of living, that I don’t hate doing, and engages me enough that I don’t feel like quitting”. Perhaps you could try to split these three goals into separate parts of life: treat work as the place you earn the money and insist on separate time to feed the others. I’ve written before that time outside work can (should) be more than just the absence of work: perhaps this is the space to explore the things that feed your intelligence and capability.

It’s a wretched feature of contemporary existence that so much of everybody’s time is spent standing and serving others, lifting boxes, sitting in an open-plan fluorescent office, manning a Cisco phone – whatever you do to pay the rent. Once we realise fulfilment is likely to be outside those doors, it becomes less painful when we don’t find it within them.

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