Anything you would like to have done differently? What is you biggest regret during your 20’s?

31 comments

  3. A few things. One, I mistakenly believed that my next step in life would manifest itself naturally (easy to think, since up to that point everything kind of did), so I wasn’t proactive enough in figuring out next steps. This led to some lost time. Two, I did get kind of sucked into the conspiracy theory rabbit hole and some New Age spiritual stuff that was a grift, though I dropped that and consider it to have been a learning experience.

  4. Great question to ask

    Probably not travelling further afield whilst it’s easier (house, pets, partner,etc). Feel im making up for it now but just so much more consideration needed

  6. **1) Start investing as early as possible, even if it’s just a little bit. And keep it simple, boring, and profitable.** $100/month into SPY/VOO (10% average annual return) from age 25 to 35 would have turned into $21K… or nearly double the amount saved. Compound growth is the most powerful force in the universe. Increment that up as you earn more into your early and mid 30s and suddenly you’re sitting on six figures of investments. I didn’t start doing this until early 30s, and wish to goodness I had those lost 5-8 years back.

    **2) Develop and maintain a 2-3 times weekly workout schedule, and stick to it for life.** Trying to rebuild physical health in your mid and late 30s is a bitch when you spent the decade prior treating your body like a dumpster. I didn’t do this until my mid 30s, and its an uphill climb every step. Develop those habits early and never abandon them.

    **3) Pick a lifetime sport (bowling, golf, tennis, swimming, whatever) and practice it once a week, every week for life.** Do this aside from your workout schedule. It’ll keep you active, away from screens, and give you a community at both a global and local scale. It’s important to spend time away from home, especially now when everything is at your fingertips with social media and smart phones. I was a two sport varsity athlete in high school… then just stopped everything. I picked golf back up in my mid 30s, and wish I had all those years of practice and fun back.

  8. Living to match the expectations of my parents. It took me too long to realize I should have choices and expectations of my own, instead of a living based in what they wanted for me.

  9. Nearing 30, I regret caring about what people thought of me and chasing women who didn’t care.

  11. I guess allowing myself to get talked into going to college before trying to get my mental health addressed. I was a mess before I had my first day, of course it blew up in my face.

  12. > Anything you would like to have done differently?

    – Should’ve invested earlier
    – Should’ve started working out and gotten muscular
    – Should’ve taken more risks

    > What is you biggest regret during your 20’s?

    Should’ve slept around more. If I could go back, I’d take those missed opportunities.

  13. I regret not being social enough. I encourage all my younger family members to be as social as possible.

  14. Not taking risks!

    I was raised in a pretty strict household and was never encouraged to take risks. I’ve always steered towards the cautious route; I started working a “real” job at 18 while commuting to college and living with my parents, went to an all boys high school which means I didn’t date around much, and even now still live in my hometown and work for the same company 20 years later.

    Sure, I started investing early, paid off my student loans very quickly, and am vested in my company’s pension plan, but I always wonder what could’ve been if I’d taken more risks in my 20s. I regret not moving away to college and then moving away after graduation. But, ultimately, I am happy. I will just always wonder.

    Remember: your 20s is your time to take risks. You will never get that time back. Take advantage.

  16. I didn’t get a sleep study or have my Testosterone checked. I finally did both at about age 35 and found out I had severe complex sleep apnea and very low testosterone. Passed up some of the best years of my life feeling like garbage all the time.

  17. Biggest regret:

    Running away from my pain, trying to drown it in alcohol and in general clinging to a mindset of “I need to be strong and I can handle it on my own – I don’t need help”.

    What I would have done differently:

    Finished an education in some kind of trade, so I had a base to build on.

  19. Being active about relaxing, what I mean is don’t “relax” just because. Relax after you clean, after your work, after a meal, after exercising, etc. Don’t relax just because you’re feeling lazy.

    Save money, even if you don’t invest it, saving alone will give you peace of mind to know that an accident or illness won’t cripple your ability to pay the bills and stay above water.

    Most important, don’t dwell in regrets or “missed time”, we can literally, as humans, only experience the present moment.

  21. I got married at 22 and am now divorcing at 30.

    While we made many memories and I had some great times, I regret forfeiting my most “sexually-charged” (for lack of a better term) years to a woman who ended up cheating on me anyway.

    I mean, I spent half a year backpacking Europe.. all while I was in a relationship, for fucks sake.

  22. Dated a girl for way too long even though I knew the whole time she wasn’t right for me at all. I was afraid she might be my last chance to be in a relationship. So far I wasn’t wrong but it might also be a self fulfilling prophecy that I could have avoided if I just broke up with her early on.

  23. Not investing earlier
    Not spending more time travelling
    Not doing more to expand social circles
    Should have spent more time focusing on improving myself than chasing girls and comparing myself to others

  26. Not hustling more when I was unemployed. I was really down about my life in my twenties and I had a rough time.

    But one of the best things I could’ve done would have been to swallow my pride and take any job. Just to have a purpose in the morning and make some money.

    I had too much pride and I regret that. I have a friend who to this day still feels that way, that many jobs are beneath him. He still has no career to this day.

  29. I (47M) was too serious in my 20s. I focused on my career and starting a family too much. I regret not a) dating more before settling down, and b) Not building a friend network more. I also wish I had spent more time getting exercise. That shit catches up to you when you get older.

  30. Why didnt I read a book about communicating properly with partners. Big fuxk up. Don’t get me wrong, I am married with kids. But I could have done better with people I knew . Friends and partners. I was too wrapped up in my work and making the bottom dollar.

  31. Being a simp most of the time and I regretted chasing people that ain’t worth my time

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