Mid 30s man here, and the fact that I’m aging is starting to weigh down on me. I didn’t really have a fun time on my 20s due to my social skills taking a while to develop (grew up in an abusive household, which probably caused it), dedicating myself 100% to studies and work as I didn’t have any friends and then COVID once I found a good friend group.
I feel like I missed out on a lot of normal experiences in life, and now it seems too late to catch up – my friends all moved either out of town or the suburbs, normal 30s stuff, and the only person I hang out with regularly is my girlfriend. It is also weird because I did end up “making it” – I have a high paying job, high net worth for my age that will probably allow me to FIRE in my 40s, etc, but I still feel empty due to not having “lived” enough when I should have.
I know that having the fun carefree 20s experience is not the be all end all of life, but it is the time that most older people I know remember with most fondness. I didn’t really care about what I was missing until now that I can see middle age approaching. For those who have been through a similar rut, how did you get out of it and start looking forward to your future and fully enjoying the present again? I’m wondering that what I’m feeling might actually be some sort of depression.
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I can relate to many things you said. So while I don’t have a great answer for you, I do send you my support.
Carefree 20s doesn’t exist, it’s a myth that only works for trust fund nepo babies or if you’re headed to be fucking broke as shit
I think millenials (or GenZ) are the only ones to have it illuminated so clearly
If you’re chillin in a dead end job (and ur not a nepo baby with a Hollywood mail room waiting whenever you decide to work), you’re just insanely stressed out and IG is shoving other peoples success in ur face
Or, you’re grinding your ass off to escape the permanent underclass. Doing THAT while also truly socialmaxxing is damn near impossible and I wouldn’t give yourself a hard time about it
I tried to do both and sorta did but then something else broke – I was in horrible shape and that is an extreme drag in social life (even with guys). It was just not possible to max out all 3 of social, job, health.
(I personally should have done job and health. Social life would have been ez if successful AND jacked, but never got to find out)
That being said. If you don’t have kids yet and you’re rich, what’s stopping you from going HAM at your current age?
I kinda feel you, but I don’t think you missed your life. People romanticize their 20s a lot, and they romanticize their teenage years too, especially because of social media and this whole idea that those years are supposed to define your personality.
That said, I get you. There are things I’ll never experience either, like silly teenage dating, for example. And there isn’t much to do about that except make peace with it. But for most other things, what’s actually stopping you from going after them now? There’s no age limit for pursuing a dream or building a life that feels good to you.
Try to give yourself some credit for what you have now: everything you built, everything you survived, and everything you accomplished. That’s your journey, and it was necessary to get you to the mindset you have now. From now on, it’s about the future.
You want spontaneity? Go travel somewhere impulsively for a weekend. Stay out too late with friends. Go to concerts, meet new people, try things you always thought you were “too old” for. Most of those limits are imaginary.
Your 30s are a totally different thing. You still have energy and willingness, but now you also have experience, maturity and money. Friendships become intentional instead of automatic. Fun becomes something you plan instead of something that randomly happens after class on a Tuesday night. That doesn’t make it worse. Just different.
Enjoy the present. Can’t change the past and you may not get to tomorrow
The emptiness you are describing despite having built everything on paper is one of the most disorienting feelings a man can have because it removes the story you were telling yourself about what would make you feel okay.
A few honest things from the other side of a similar rut.
The youth you are grieving is partly real and partly constructed. Some of it is genuine loss, the carefree experiences, the close friendships, the feeling of time being infinite. But a lot of what people remember fondly about their 20s is a selective highlight reel. The anxiety, the uncertainty, the lack of direction that most people felt in that decade gets edited out in the retelling. You are comparing your full unedited experience to other people’s curated memories.
The abusive household piece is worth sitting with more than you might have. Growing up in that environment does not just affect social skills. It affects your ability to feel safe enough to enjoy things, to be present, to let yourself have good experiences without waiting for something to go wrong. That background tends to produce high achievers who feel fundamentally disconnected from their own lives. That is not a coincidence.
The FIRE plan and high net worth are real accomplishments but they are future focused by design. You have been living for a destination rather than a present. That habit does not switch off automatically once the destination arrives.
What you are feeling is probably some depression but it is also an invitation to build something different now. Not to recover a lost decade but to actually be present in this one.
What would enjoying your life actually look like right now if you let yourself define it fresh?
No idea. I was pretty reclusive during my college years, basically just went to class, worked when I had a job, played games at home. I talk to friends and during those same years they were doing all kinds of stuff. They had multiple partners, all types of adventures, lots of crazy stories. Same kind of story goes for the rest of my 20s. Even with a better job and more financial freedom and less worries, I just did the same thing, sat at home, played games. Can’t change it. I’m a year out from 35 and still pretty much am the same way. Shit I’ve never even dated and I highly doubt that or myself will really change significantly in the next 5 years, let alone 15, and so on.
Make sure your kid has a better life. If you don’t have a kid, then u have to find something fun and fulfilling to fill that void
Stopped using social media which reduced FOMO/comparison, therapy to accept yesterday and focus on today, started doing some of the things that I couldn’t during my younger ages (like martial arts), really lucky to have found a wife who has similar goals in life and pushes me forward. Not necessarily in this order.
My family was broke during my late teenage years to early 20s, I was chronically depressed, family was in low to moderate chaos constantly, could afford moving out in late 20s at best. I could never dedicate myself to studying because I was always low on fuel (and I’ve got ADHD which didn’t help) to give you more perspective.
You’ll have to spend a few years to catch up with yourself. I’m not joking, it’s going to take at least a few years to build acceptance and move on.
But it gets better from there. I’m still not fully there, because I couldn’t get over the emotional habits I’ve built about self-control and limitations, but I feel that I’m halfway through. I still question my progress everyday, and maybe I won’t live to see that I’ve done it (like what if I die today?), but after having thoughts like this, then I see positive results that I couldn’t a decade ago. Feels a lot better and more fulfilling.
Whatever you had have in those ‘lost years’, you had coped to your best ability. Now it’s time to stop coping and start living.
Honestly, the people who reminisce most about their 20s are usually the least happy people I’ve met. They’re usually the ones who at some point took “being an adult” way too seriously and forgot how to have fun. Just keep living and doing interesting things, because you get over it by not letting life leave you behind anymore. The more memories you make, the less important the ones you didn’t make start to seem.
What that looks like for you might also be different than for other people. But you just need to keep making the decision every day to enjoy life. A lot of people who had fun in their 20s might have 5-10 years of really good memories that they think about for the rest of their lives. You can’t go back and change the past, but you don’t need to, because, while they’re living in their past, you can choose to make 50-60+ more years of great memories instead.
If you have the money you can do whatever you want because you’re still young.
I do feel my life is much better in my 30s than it was in my 20s. I mostly let the bad memories make me feel thankful and glad for the present. My life got better likely due to a combination of dumb luck that hadn’t materialized yet when I was younger and hard work. I don’t think I’m too old to do or enjoy those things I didn’t get to do when I was younger. I’m happy I get to do them now
I recognize that I have the experience to decide what a good time actually entails and don’t have to waste so much time with things young men don’t realize are objectively terrible times. Look what young guys do. Clubs, 40s, perving out younger people showing up to the wrong concert, vacations where you exercise, driving around wasting gas, it’s a never ending parade of things only young people could possibly pretend to enjoy. I don’t mind missing most of that for being poor. I’ve tried it, my god it was all horrid, even when I was supposedly the right age. You now have the information to make better choices about leisure.