Would I be happier having done something society expects ?

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I’m going to venture an unpopular opinion.

It depends on what’s at stake.

If “doing what society expects” is reading that popular book or trying out that new restaurant, you might find you like it.
If it’s making new friends, you might find people who you find mutually enjoyable and beneficial.
But big stakes like marriage and children, where you’re taking responsibility for others well being and vice versa, you really need to do what you want and what’s best for you. Somebody mentioned about arranged marriages, but societies with arranged marriages also tend to have strong social supports for the couple and the children, who can help out in times of stress.

But going along with the crowd (assuming you’re not doing anything immoral or life changing), tends to be a trade off. You’ll gain in one area and lose in another.

If everybody abided by the status quo, we'd all still be wearing furs and living in caves. We would never have learned how to farm or how to domesticate animals. We would not have learned to make pottery using clay. We would never have learned how to make glass, how to can food, or how to create all of the many things that our technology does.

While many people find comfort in being part of the crowd, without someone to blaze new pathways our society would never evolve and progress.

In terms of my own situation, I spent most of my life trying to fit in. I made friends. I dated. I wasn't happy with having friends or a significant other because we were always out and about doing things when all I ever really wanted was to stay at home when I wasn't at work. It wasn't until I was 59 that I finally learned that I was autistic.

The last four years since my diagnosis have been quite happy for me. One thing I did after learning that I was on the spectrum was to move away from a large and noisy city to a small rural community. I used this move to end the few friendships that I had had. I also used this as an excuse to end a relationship.

Since moving to my current home, I have become a reclusive introvert. When I was not at work or running errands, I was home. Without friends or a significant other in my life, I had more time to rest, relax, and to unwind following the stress of having had to interact with others whenever I was out and about.

While my life may not be ideal and would certainly not be a good fit for all people, it works for me. Since this is my life, that's all that's really important.

So long as you are happy and are not doing anything that harms another, why shouldn't you be the person you were meant to be instead of being the person that society expects you to be?

If I did everything that society expects of me, I'd be a very miserable person and I'd be in the psych ward right now.

Possibly if doing something society expects of you makes you happy.

Otherwise maybe you'd just be differently miserable with different stresses, doing things society expects of you for the approval of others while feeling unfulfilled for it.

Depends what YOU want to do with your life. If you feel compelled to be a travelling rockstar you'd probably be unhappy doing just about anything else, including the "normal," societal expectation stuff. If you feel you Must become an engineer because that's your idea of self actualization, you'd likely be unhappy doing other things - including having a partner and kids.

Or maybe you'd be unhappy doing almost anything or nothing at all Because you're frustrated that you don't know What you Want to do or become because nothing really stands out as the right fit you Must pursue.

Peoples' happiness and internal thoughts about themselves and what they're doing with their lives are very personal and unique to them. So, asking a bunch of strangers on a forum whether You would be happy doing abc or xyz or not is kinda moot. Only YOU know if you'd be happy doing ____whatever or you not. Depends what makes You happy and we are not You. So, you tell us.