For those in their 30s (and beyond)
What would you start doing in your late 20s, or wish you would have done in your late 20s had you the time again?
What would you start doing in your late 20s, or wish you would have done in your late 20s had you the time again?
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Finally, something I can answer as a mid-30s schmuck. I’ll give the non-answer first, that I regret nothing: my position in life today is the sum of all of my prior decisions, and I am quite thrilled to be here. BUT, something I could’ve done better, and this is more geared to my early/mid-20s self because I actually figured this out in my late 20s, is playing the long game. I was always focused on my next role, never fully locked in to the present, and it causes a disconnect that leads to suboptimal performance and discontent. I always wanted my next move to be my final career move, and wasn’t open-minded enough to other opportunities. Like being a 24-25yo dipshit thinking it was beneath me to take a year back in seniority for an awesome buyside opp. I was trying to get them ones, when I should’ve been trying to get them m’s (hopefully that early 2000s Jay-Z reference validates my age…). I finally decided to play the long game in my immediate prior role, and it led to me landing what actually is my dream job. Funny how that works out.
For a more superficial answer: running. Should’ve started that way earlier. It’s a great hobby and great cardio. God I’m still such a shitty runner but it’s fun to do 5k/10k/10milers with friends, wifey, colleagues etc.
this is a really fucking dope answer and strangely resonates with a crossroads i'm at currently, so thank you.
Question on balancing travel with future career potential - if you had the opportunity to work internationally but it's either tangential or not linearly related to the career path you're currently on, would you take it? E.g. doing M&A in NYC but an opp to do FP&A in Sydney or London. I've always had this nagging feeling I should work abroad whilst in my 20s, and that it will become harder in my 30s, but recognise now it will probably push me back 3-5 years on my current desired career trajectory...
I wish I had a good answer, but that’s a completely a personal decision. I never had any interest in working abroad earlier in my career, but have a buddy who did a rotation in London and enjoyed it. But for my situation, it never came up because 1) I was not single during those years (with gf-now-wife), and 2) I had zero real international travel experience until my honeymoon, as I’m from more of an atypical background compared to most people in the industry (i.e., broke).
Sounds fun in theory, though.
I think this is so common and something I suffered from as well. Think it's especially so for those of us that grew up middle class. When I was in my 20's, I got so fixated on getting $20 - $30k increases in comp because it seemed huge to me coming from a middle class family. Now in my 30's I realize how meaningless those increases were in comparison to others who sacrificed short term pay for experience and opportunity and are now crushing multiples of me. The future seemed so far way in my 20s as well but it's really true that time keeps going faster the older I get. Not sure if it's an age thing or just simply that I start liking my work more as I progress closer to being an executive, my comp provides a more comfortable life now, etc all leading to a happier life = time feels like it moves fast. When I was 25, 5- 10 years sounded like a lifetime. Now in my early 30's I think back about things from 5 - 10 years ago and it seems so close like I went to sleep one night and woke up 10 years later.
Agreed 100%. The passage of time is wild in retrospect. It might take two entire years to get promoted to associate? Holy fuck we’ll be on Mars by then.
thank you for the insight, very thought-provoking tbh. I think one thing I've learned in my late 20s is I want a sustainable career i.e. not burn out and settle in some dead-end gig that stops my growth and career prospects. Equally, that is a very tricky thing to find with all the disruption and uncertainty in the world atm. How would you weigh up a 'fuck it just go travel / work abroad' for 2 years vs knuckling down and deferring that til later in life?
Hey man, I’m just getting my morning started and seeing this was refreshing for some reason. Thanks for sharing
I ran the NYC marathon. Honestly, cycling is way better on your body. Give it a try.
Yeah cycling is super healthy
Agreed. Hard to say what the butterfly effect could have done if I made one or two or whatever number of different choices. Think I got a top 5% outcome from what I did in my 20s, so objectively speaking a lot more downside than upside if I rolled the dice again.
That said, more vacations and really experience with loved ones/people I care about. Money and career is great, but time is finite.
I just turned 30, so hopefully eligible to answer this question. I can start with the things I am really glad I did in my 20s:
Don't worry so much about your job title. I have worked for and reported to people who are younger than me. To many, this would be embarrassing. However, I took a very unconventional career path and made transitions very few have made. I am grateful to be here. It is easy to compare yourself to others and to get caught up in the rat race (many of my friends are VPs in IB / PE whereas I am just a mere Associate in Corp Dev). However, career progression can be measured by many metrics. My fulfillment, compensation, responsibility, and experience are increasing meaningfully each year. I am getting much much better at what I do each year. Similar to what Hugh Myron implied below, don't rush to chase a certain title or pay band. I firmly believe what I am doing now will best position me to be successful in a dream role 5 years from now. Therefore, despite my lagging tittle, I remain motivated and do my best to be content with where I am in life. When you get to your late 20s many of your friends are really killing it career wise (I have friends who founded businesses, received multi-million equity payouts, and / or are on partner track at top \firms). Congratulate your friends and genuinely be excited for them, but do not beat yourself up for not being in the same spot as them. I should know, I spent many years wishing I had done things differently so I could have ended up in their current position. As anyone reading this knows, this is a complete time waste and not how life works at all.
Finally, to address what I wish I had done differently:
1. I am going to summarize all my regrets into a single point that I think will resonate with all readers; I didn't take the risk / the chance. I got a great job offer in my dream city, and turned it down because the risk was higher than a different offer in a T1 city. I had an offer to join a small PE fund with a lot of uncertainty but with partners I really liked, and it could've changed my life. I fumbled it with a few different girls because I wasn't emotionally mature enough to open up and tell them how I really felt. In short, during your 20s you will have these moments where you are smart enough to realize you have a special opportunity in front of you, and you will have two internal monologues; one will tell you to take the chance, and the other will tell you to go with a safer option. Listen to the former, not the latter.
No risk no reward, that's what I'm focusing on now in my early 20s. I can't leave this life with regrets I could've prevented and missed opportunities.
Co-signing point #3 - that mid-to-late 20s metabolism slow down is real.
FT MBA
One thing is maybe have our first child around 28-29 instead of 32-33. I think it would have been easier to have three children if we started earlier. I’m now of the belief that “its never the perfect time” to have kids because we’ll always think of doing more with ourselves. We were lucky to even have kids at early 30’s because of a lucky accident. For context, we were one of the first among friends to have kids, age wise.
Maybe on top of that, buying our first home in our late 20’s would have been better than early 30’s. We barely had enough for a down payment, so it had to be early 30’s for us. But if we could have done it earlier, that would have been better.
without kids or a partner. what would have done if you were still single in early 30s?
It’s a difficult hypothetical for me since I’ve been with the same girl since 19 (I am 43). One thing I know about myself is I almost never think about myself enjoyment. My wife compliments me since she plans our vacations, good places to eat. I might literally live in a sublet apartment well into my 30’s (or a mobile home) if it wasn’t for her. I don’t need much.
So, if I was single in my early 30’s, I would first fight my urge to be the miser that I am. I would go out more with friends, hopefully meet a nice girl. I would probably think of sex all the time, and it would distract me and also motivate me (Read the chapter called The Power of Sex Transmutation in the book Think and Grow Rich). So, basically I would become someone I’m not naturally in a resting state.
I might be more successful. I might be dead. I don’t know.
Fun fact: I’ve been single for 6 months since I was in 11th grade. During that 6 months I was violently assaulted twice both after midnight. I’ve realized that I am best under the safe supervision and management of a life partner and that world is not safe for me.
for those in your 30s (i’m late 20s) how do you balance saving money, rent in nyc, and dating
what kind of wacky either/or scenario did you try to come up with? you can save money and still have a good life dude.......
just wondering if people look back and regret spending a lot of money on rent when they were younger
I think your real issue is going for more luxury at your age. You're in you're late 20s - you for sure should be living in the city. You just have to lower your standards for quality of apartment. I have friends that live in West Village for $4k - $4.5k and in east village for $4k a month. You aren't going to look back when you're older and think "damn, if only I had a nicer apartment in my late 20's" but you will probably say "damn, I really wish I would've spent my 20s in the city when I had the chance"
i agree with you. but have you actually seen those $4k apartments?
Get the apartment. It’s important to save money but not at the expense of your sanity
sounds like you’re in a good spot financially and assuming you stay on your current track you’ll be fine. The extra $1-2k per month isn’t going to be life changing for someone like you tbh. Especially if no debt, etc.
take it from someone who pinched pennies in their 20s…not worth it to miss out on quality of life, especially in your late 20s. Not saying ball out and spend recklessly, but you should enjoy some of the fruits of your labor at this point assuming you have a good foundation set
thanks and very valid point!
I qualify as beyond. Looking back, I would watch my diet more than I did in my 20s. Even if you are not overweight, which I was not, you can still get high cholesterol, which I had at the time. I changed my diet to address the issue. I also probably would have dropped out of Corporate America sooner than I did. I prefer working for myself.
thx for the insight - on dropping out of Corporate America, do you think it's a necessary evil to get to working for yourself? My ultimate dream is some quasi-M&A freelancing / Angel ticket writing, but i've got some way to go experience wise to get there. Do you think it's possible to 'work for oneself' earlier and the notion of experience is more of a mirage for fear?
I am not really sure about what you mean by the first question. It would be difficult to work for a company and work for yourself, especially if it is in a related area of finance. Lots of companies would not let you have a side job unless it is unrelated. The required experience depends on your area of finance.
When you are young, you tolerate a boss that is an asshole because you do not want to get a bad reputation. When you are a little older, you become less tolerant of people who act unprofessionally
What do you do now?
Two things - find an exercise routine I enjoyed, and date my wife more often.
Many others here have suggested it, but clean eating and exercise do wonders. The amount of travel I do doesn't help matters, but I feel like if I had an exercise routine I enjoyed it would be easier to stay in shape.
My wife and I are hitting our 10-year mark this summer. I probably spent too much time either working, thinking about work, or kickin' it with my friends instead of giving our relationship the attention it deserves. Yeah, it's a bit sappy, but now that I'm mid-30s I feel like I'm playing a bit of catch-up.
I had to think about this for a few minutes because as we all know, where you are today is a product of all the decisions you've made over the course of your life. To answer your question in a different way, I'm happy with where I am in my mid thirties, and here are a few reasons why.
Who you marry is arguably the most important decision you'll make. Good ones are hard to come by and they will make you a better person if it's the right partner. I realized at 25 I was looking at her and held on. Married at 29 and kids by 32. As someone with old parents and hated it growing up, nobody had to tell me twice not to wait until mid 30s because 'why the rush?' Friends who are now single in their 30s aren't loving it. For the younger dudes out of college - the ones you want will be locked down quicker than you think. People play it off like I'm not looking for anything serious but next thing you know, you're approaching 30 and a lot of the hottest smartest coolest wife material is already off the market. Don't wait just to wait despite what current trends may suggest.
Set yourself up before you find yourself in a serious relationship when you are no longer able to make decisions with only yourself in mind. Examples would be buy the watch, buy the car/bike/toy, establish a workout routine, establish the annual ski trip with the boys, pack fat lips, etc. Program your life accordingly so when she enters the picture, you aren't asking for permission and she's able to get a sense of your lifestyle. It's a two way street and sacrifices inevitably have to be made, but when you are already wearing the watch you want, easier conversation to say I don't need a second right now versus sorry I'm dropping my bonus on a watch, not towards our future savings/life together.
Working out / looking good and presenting well is a life hack that will get you further than you might think. Halo effect is very real and plays into the whole 'half of it is just showing up' theory. It helps to look the part. Haircut, attire, weight, hygiene all matter and if you aren't already thinking that way, start now as you go into your 30s. It's a game changer that people don't necessarily talk about but has a real impact on your dating life, career trajectory, and general brand as a person.
Don't be afraid to switch industries/jobs/cities. Now is the time. I'm glad I did it when I was single in my 20s and only myself to consider. If you take care of yourself, by the time you move back to a big city after your time working on the mountain in Big Sky, people won't even know you're a 30 yr old associate and think you're 27 like other post MBA people.
It all goes very fast and you don't get it back. If you've been putting off a move or a career change or asking her out, you have nothing to lose by acting now. And everything to gain.
Proud of my 30+ year old cohort for the responses here. I agree and echo pretty much across the board.
The only thing I'd add, which may be surprising, is don't fear getting older. I enjoyed my 20s a lot but at times I look back and realize it was a fever dream. Pushing so hard to establish myself and get points on the board, learning a ton (in some cases the hard way), and navigating adulthood without the backing of bank of mom and dad. I'm extremely proud of those efforts but if a genie came along and granted me the ability to go back to being a 24 year old, I don't think I'd take that deal. It's exhausting to think about lol.
With the benefit of hindsight, I'd probably tell my 24 year old self to chill out a bit but the reality is that semi-neuroticism probably fueled the progression.
Interesting. I love where I'm at now in my 30's but if the genie told me I could go live my mid 20's again I would do it in a heart beat. I had a great time but truly didn't appreciate how fast it was going to go.
I will acknowledge it's an odd/hyperbolic take and probably overly reactive to the exact moment I find myself in now.
I've spent my entire career so far in NYC and making it through 10 years of scraping to get by, then getting some stability, then getting a bit more stability, then finally being able to take full advantage of where I live all contributed to the idea.
Way more importantly, getting married and starting a family... These were all things I really really wanted and were able to accomplish in my late 20s and currently in my early 30s. The idea of having to go back and do it again is scary!
I should have taken more risk on and moved faster.
A good example is, since i had no assets, using personally guaranteed leverage > other forms. It's cheaper, available earlier in the lifecycle of a business, and there's no risk since you have no assets lol.
Introspection - What do I want out of life and why? Less coasting.
Health Self Education - Learn more about health in general and the aging process. I believe I was intentionally lied to by TBTB that if one eats healthy and works out, then you live to mid 80's and drop dead. Note, this is not how aging works. Your prostate will enlarge, you will get random things breaking, that is aging.
Wisdom - Youth is for risk taking and having fun(within limits). Travel, outdoors, career, moving, all should be done when young. Do not take up mountain biking at 40. Do not try to start a business when you have two toddlers, a wife, and a mortgage.
Confidence - Build it when your are young. Be fit, be learned, dress sharp (as you define it), eat well. Push yourself up the social hierarchy as much as you can, it matters, even if you do not get to the top.
What you think is important in your twenties may not really be true. I do not have a girlfriend. It's ok. I feel not happy. It's ok. I broke up with my girlfriend from college. It's ok. I got fired. It's ok. Time will heal. Yes it hurts, as some have already posted on this board, but in your long term journey, nothing but a wisdom buff if you are open to learn.
Frugality - That fancy watch or car...not really that important, seriously. If you are going to spend, spend on experiences, not stuff. Stuff breaks, experiences turn into memories to get you through your rough times.
Last - baby steps. Overweight, stop drinking soda. Then, go use the stairs at work. Then, eat a salad on Thursday. Not, let me go to the gym, get some power shakes, and attempt to deadlift your body weight.
Hitting the 30 yo mark in a few months. Also, since I am a man, this comment may not be very useful to a woman.
Just wanted to let you fellas know that all this advice is invaluable, especially as a 25 year old.
I’m reading some of these comments and realized that I’m doing/done some of the things you guys wished you did, or doing/done things you did and are happy you did them.
As someone largely operating without the guidance of a mentor or a parent who treaded the path I’m on, this is all validating the decisions I’m currently making. Thank you all for putting all these thoughts on paper.
Love y’all; this is what WSO is all about.
I’d say build something, absolutely anything, that is yours. It could be as simple as a small ecommerce store with a limited budget. But I’m a firm believer that these things compound and over the span of 5-10 years, you could find yourself with a solid side business that might turn into your full time thing.
I’ll do the OP better. I recently finished my thirties… No regrets but things I would have changed in later twenties-mid thirties…
1) Leave Asia earlier. I’m from the US but lived and studied and worked in Asia for well over a decade.
2) Like another poster said, take more risk in career or lower positions when making a switch. I had chances to move to totally different things earlier if I did. That’s totally ok and I’m chill with it now.
3) Be less flexible with people who clearly didn’t respect my time. Your time and energy is limited. Respect yourself.
4) Put up with less BS and disrespect when it came to dating. See number three.
5) Started and committed to skiing earlier. I’ve discovered the joy of skiing (again) the last 3-4 years but I have to be more cautious now so that I don’t shatter my body. I wish I had skied more earlier so I could get better and do more terrain.
The key takeaway is self respect and confidence-based I would say. If you have these issues it’s ok but totally worth reflecting and maybe considering therapy if you can afford it..
I’ll give you some non standard advice:
Push yourself until you break, pick up the pieces, reflect and the do it again.
Do this across a few of your life domains (career, relationships, health, finances etc), before 30.
By the end of it, by your 30’s you’ll have the maturity and wisdom of a 60 year old, and it will allow you to handle anything life throws at you when the stakes are higher.
It’s pretty funny I’ve come to this realisation, but the idea of “what doesn’t kill you makes you stronger” does work. The most powerful lessons are the most painful, so get those done before you’re in the crucial part of your life (30s are typically your make or break).
Jesus man
I had a professor who used to say "your 20s are for reducing the information asymmetries between yourself and the world." Try something, if it doesn't ultimately work, ok well you've learned something and you have time to 'figure it life out' using that new incremental information to guide whatever you do next.
I'm early-thirties and ascribe to this train of thought. Good stuff.
At this point I don’t regret a whole lot.
I was an average student in college but when I had set some directions and goals in my first job I was laser focused in achieving all of them. And I put it above my social life but still was able to find time for both. Would say holding yourself accountable for your actions is most important
Echoing the prior comments about staying active and keeping office evening Seamless on the healthier side. Went from college athlete, fast metabolism, to getting injured / 5+ year journey to recovery in my primary sport and gaining 30 lbs within a couple years of sitting behind a desk at all hours. Now just getting injury-free/active again in mid-30s.
Additional thoughts on exercise:
The only thing I will add as these are all great responses.
Your real life starts at 35. Before then you don't seem time a gift because it is in abundance. Be careful who you spend your time with, and on. But, at the same time, go out to that big party, learn to work hungover, but mostly honor your commitments, to your work, family, and teams.
Have kids earlier than you think, believe 30 is the perfect time.
Advice to women, you cannot have it all. America and the world is really bad at your explaining your healthcare across the spectrum. I assume this will get me MS. It is really hard to have a kid after 35, like REALLY hard. Freezing eggs doesn't always work, I know a c-suit(almost) head of finance at something in a BB bank, she waited too long. She is an awesome person. Once you hit 40 you hit peri menopause, at 50 you hit menopause, these are very strong phases of life that are affected by your hormones.
This is for both men and women, if you don't think family is the most important thing in this world, you are kidding yourself, by 30,35, and latest 40 you will know if you are going to be the next Bill Gates....you aren't.
I know you meant this from a fertility standpoint, but this advice is valid for both men and women. It's been mentioned all up and down this thread, so I won't belabor the point but... the dating options contract quickly after your late 20s. If you spend your 20s and early 30s enjoying the single life (which is totally fine!) you can't really complain that all the good partners are taken. In some ways this goes more for women than for men - I know a lot of single women who complain about not being able to find decent guys. But it obviously goes both ways. The wife/husband material people get picked off and locked down fast.
As for kids... it's all well and good to think that having a kid at 35 is hunky dory, and it is. But if you want multiple children, you gotta think about the long term. It's 18 months between kids at best. If you start trying at 35 and you want 3 kids, you are probably 40+ by the time you're done. And yeah, if your wife is younger the fertility part is easier, but it also means they may not be in such a rush, and you have to think about whether you want to be 60 when your kids are getting their high school diploma.
Agreed, and I mentioned it above. Think having kids at 30 is sweet spot.
Spend 50% less time on message boards.
Message boarding is probably a result of not having the same interests as close friends or spouse (if you have any); geographical distance; and new ways of communicating.
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Wish I spent less time optimizing Excel models and more time optimizing my hairline.
Mid-30s. Wish I would have had kids earlier. Always some reason: fund's having a bad year, time's not right blah blah. Once you want them and you hear friends struggle as they get older, everything changes.
That and just bet bigger on my all my convictions in my 20s. Got a lot right that I let others talk me out of across both work and life.
Good one on the conviction. If you're in your 20's and really have conviction in something whether it's starting a business or an investment / stock / crypto, just do it. Same as above I had several that people talked me out of that I still think about before going to bed. If you're young I think you're better off just risking it when you have the conviction. You have time to get it back if you're wrong but at least you tried and don't have any what if's. Just don't confuse conviction with taking a risk due to impatience
Build the habit of working out consistently so it becomes an automatic thought to find time several days a week to move your body.
Be thoughtful about who you give your time to professionally and personally. Find a group of people (friends, mentors) that truly have similar interests and development goals…don’t just spend time with “friends” that exist because of happenstance proximity/partying. Date purposefully, talk to everybody (face to face >>> device communication), network constantly, and give/add value multiple times before you ever ask for something from somebody.
Spend time thinking about long-term goals (in your 20s it is really easy to live life day by day without thinking about what you should be doing consistently to move you closer to where you want to be in 1, 5, 10 years).
Be appropriately skeptical of management when it seems like they are telling you all the things you want to hear. “You’re crushing it!” “You need to take a 3-5 years view…you’re on the cusp of a giant compensation inflection in your career.” In my 12 year span at one firm I regret not seeing more advice from outside/neutral parties on career trajectory in my role.
Have kids sooner and have more of them. I guess I can still do the second.
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