What would you do if you didn’t need money? I have a fair amount coming one day and don’t actually need to work to live a good life (middle / upper-middle class). I work because of this vague notion of “ambition” and because everyone I grew up around is highly competitive and hard driving. I just feel unhappy so often and am wondering what this is all leading to. Scared I’m wasting my life being unhappy / in turmoil cause it’s what my culture wants me to do.

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Try looking up symptoms of an over achiever. I struggled with the same issues but realized that it doesn't lead to happiness. There's always the next promotion, the next job, or another thing to pursue to climb the corporate ladder.

If I were in your position, I would try starting my own business, doing a phd, or volunteering and donating to people in need. Is there something that you've always wanted to do but never took the plunge?

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The problem is when you work a lot and have been grinding for a while, how do you even know what you are passionate about? Hard with limited hours in the day and a brain that is so taxed on work... guess I need to do some soul searching

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Try going to an executive coach. I did that when I was really stressed and burnt out at work. It was the best thing I ever did. She lead me through a series of exercises that helped me identify what motivated me, what made me feel fulfilled, what frustrated me, etc. From there, I was able to pick a better career path that is still very “prestigious” from society’s viewpoint but is more suited to my personality and needs. I am SO MUCH happier and work doesn’t feel like a constant grind and battle.

There are many paths within our profession. You can do so many different things. You will find you will be more successful and happier when you figure out what fits you best.

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Ah that’s interesting! Glad you found what makes you happy!

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It’s a really difficult question. Most people would say “go live on a deserted island” but you may feel depressed all the same because you’d be on the edge of society.
What I would do would be to go study to get the job I dream of without having financial worries. I’d be working for maybe $30k/year but without compromising on stuff I like (home, vacations, fashion).

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Exactly. Many people are like “go buy a farm” or “go just travel forever” but the idea isn’t to be super distant from my friends and family. It’s tricky because the question sorta becomes “how do I retain the respect of the society I grew up in without having to be so unhappy about my occupation?” A caveat being that I won’t be respected unless I’m successful at whatever it is so even if it’s something I like more, there is still this drive to be the best.....or maybe I can just get used to not being respected in that context.

It’s hard.

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I'd be a college professor researching something soo specific in the humanities.

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Even though it wouldn’t be as fun as some of the other options, I think I would devote myself to a cause I’m passionate about. I feel like a life with that kind of purpose would be really fulfilling and make me happier.

Studies have shown that service dogs are happier than house dogs, presumably because of the sense of purpose they’ve been instilled with. I like to think this would apply to humans as well.

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I totally agree, the issue is: what do I like enough to feel truly good / fulfilled doing it every day for years? I’m just not sure I have a good answer to that yet. I hope to find it eventually

Someone I knew was in your position. Void of understanding of what really makes them, they had lost drive and vision for success. What started as an exploratory journey by volunteering at a hospice, has turned to his passion. He now owns and runs 2 hospice facility, and uses his MBB skills everyday to take his babies to new height. I have never seen him this happy, engaged, driven and also successful. But it's not for everyone, as in I can never see myself owning my own business.

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Thank you for your reply. I think the fact of the matter is if I didn’t grow up the way I did I would never have become the ‘high power’ person I am. I need to do some soul searching and figure out what really motivates me and makes me fulfilled.

Thank you everyone for being so kind and not just dismissing my issue with the usual “how can you be upset/lost you are set! Stop being a baby” I know my problems are trivial compared to others but it’s refreshing to have people be genuinely thoughtful in their responses to me instead of mocking.

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So here is what I would do (and may do some version)- currently at 30 if I knew I didn’t have to save for retirement/trying to get out of the rat race, i could use some chunk of the money I’ve put away (I’m sure you have or could put away some quickly) to take some time extended but time limited time off work. Likely plan for one year. I would spend the first 6-12 weeks “detoxing” with therapy, meditation retreats, and an extensive workout/athletic endeavor (think multiple times a week surf lessons, learning tai chi, tackling 6-15 miles hikes). Then, I would lay out my plan for continuing in a lighter fashion those three while I enrolled in some philophosy and writing courses, and began engaging in local politics and community organizing. Think going to all city council meetings, volunteering with a bunch of different places, following local police, district attorney, mayor, state reps closely. I would work to meet people and understand where I felt I could best plug in to help make change. Hopefully by the end of the year I would have a new full time job probably not as lucrative as what I do now working in some public serving role, or working on a local political campaign or in their office, or have discovered a passion project worth going back to school to be formally trained in (city planning, medicine, ecological conservation) If none of this happened, I’d probably go back to consulting and try again every 5-10 years. I believe local politics can really impact lives, but I’d like to get my house in order first. I guess this is how I plan to spend retirement, if I still have the energy.

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I also think these days civic engagement is in and even crusty rich manhattan families would see this as something not to scoff too openly about ;)

If you don't need to work for a living... Can you afford to try out different ideas? For example, I think making cakes and desserts is something I would like so I would try opening a cafe.

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Ok... Maybe I thought something different... Didn't know you had a reputation to uphold. Well this will be no comfort, trying to do something just to impress others ends up badly most of the time. Either people will not be impressed, will only pretend to be or you will not actually feel any fulfillment or a combination of the 3. "Passion" is overrated in the sense that you don't really need that to be successful. I mean, it helps, obviously. But discipline has a lot more to do with making something successful. So, given you have no passion in your mind right now, just try several things, maybe online (best time ever in history to do so) in my example, I would start with an IG page or Youtube channel, try selling stuff, etc. If it fails well it fails! Do you think Uber and Airbnb started out being successful? They were rejected who knows how many times

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I get it OP! I recently came into a large inheritance, and it’s hard to relate to how conflicting it can feel. On one end you feel blessed, on another end you feel shame and guilt because the money was not earned by you. On top of that, it gives you way more choices in life, and we all know the research indicates more choices can leave us feeling confused, depressed, and second guessing ourselves constantly.

I would say invest and sit on it for now, and try not to think about it too much. Just continue to chart your path as you normally would, and eventually the answer will come to you. Something that is both fulfilling to you while at the same time honors the individual who gave this to you.

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OP - from what you are saying I feel like the problem is that you are taking on the pressure of other people’s expectations. I feel like if you solve for that (through therapy or self reflection), you might find you even enjoy your current job. Or find what it is that makes YOU happy. I feel you - I myself don’t know what it is that I might enjoy most in life or be most passionate about. But first step is to let yourself try a few things, and to do that you need to stop thinking of other people’s expectations/judgement

I admire your passion greatly. I’m not advanced enough in my career to feel comfortable taking time off like that but it’s not too far off. I appreciate such a detailed answer.

You may be in a better position than you think - I work at a smaller firm but after about five years they almost certainly would have taken me back. Focusing on your network/relationships can make this happen sooner than you think. My firm has tons of “boomerangs”, including folks who just took a bit of time off often somewhere between year 3 and year 12. I think it actually becomes harder as you approach partner/managing director because it feels like you miss so many opportunities and loose your client ownership for your sales.

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