What’s your biggest regret?

I've been doing a lot of self-reflection lately and with that have been thinking about all the stupid decisions I've made. From going to class maybe 7 times my senior year of college and tanking my GPA to losing $100k on a single trade, I've had my fair share of full-retard moments. I wish I did an internship in college so I wouldn't graduate and have my only offer be absolute shit. I wish I stayed in shape rather than listening to my fat parents tell me I'm too skinny and it's ok to eat an entire pizza 5 days a week. I wish I focused more on making real friendships in college rather than how many thotties I could smash from my apartments GroupMe. I wish I did all of those, but I did learn from that and they're part of who I am today so it's not all bad. However, if I had to choose one single event, I'd probably choose that trade as that's a shit-ton of money no matter who you are. I'm still chugging along, but that $100k returned at 20% annually over the next 20 years is $3.8M. Sure, that's an aggressive return, but it's not impossible. I plan on having enough money anyways so I won't miss that amount too much, but as previously stated it's still a fuck ton of money (yeah taxes would hit but that's still almost $3M post-tax). I'm sure many of you will think of commenting how not grinding hard enough to get that prestigious investment banking internship junior year or not getting into Harvard is your biggest regret. If you're who I'm talking about, please take some time to look at your perspective on life. Sure, those would be nice, but if that's your biggest regret then you've lived a pretty solid life so far.

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Comments (114)

  • Analyst 2 in IB-M&A
Sep 23, 2021 - 6:06pm

You guys need to stop ms this guy mindlessly. As an independent leaning toward right, I appreciate diversity of opinions on this forum.

  • Analyst 1 in IB-M&A
Sep 22, 2021 - 1:06pm

Can you please elaborate? How old are you; for how long did you disregard health; what do you find hardest to fix right now?

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Sep 22, 2021 - 1:25pm

32 this week. Not going to dump out my purse but I'll broad stroke it.

I played college football and was always pushing through physical pain (knee drained of blood and fluid twice a week my senior year of high school, no meniscus in either knee, misaligned hip, separated shoulders, bicep surgery and more concussions that I can count), so everything is more or less shot - makes working out a pain.

I relied on nicotine for stress relief and since stopping that, I've turned into a stress eater and (when it gets really bad) stress puker. This makes the working out even harder. 

No actual long term health issues yet, but I want to be around for my kid to grow up. So I'm slowing trying to fix the diet, work out, meditate, etc.

Since the quarantine I've really struggled with figuring out if I want to do this shit anymore or what I would do otherwise to make money (golden handcuffs), which adds another layer of stress.

I don't think I've slept more than 4 hours a night, two nights in a row, without drinking or heavy melatonin dosage since I was like 21. 

Long story short - don't do the shit I did to just "cope." It makes it so much harder to return to normal health, if it's even possible. 

Sep 21, 2021 - 9:02pm

I sold 391 shares of GME @ $362.14 after an initial investment of $18k so had $141,596.74. 800% return is pretty solid if you ask me. Bought back in with all my money: 90 @ 353.78 and 290 @ $356.72 and kept buying in small amounts until all my money was back into GME. I was hype and ready to buy the 911 Turbo S I had made on Porsche's website. Sold 398 shares @ $110 on February 3rd. Got in my Camry and ordered $30 of Taco Bell to punish myself for being a fucking idiot.

Sep 21, 2021 - 8:57pm


"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee

  • Intern in RE - Comm
Sep 21, 2021 - 9:26pm

No major ones, at least not yet. Kinda wish I went to a better school but chose to stay closer to home for personal/financial reasons. The biggest personal regret I have is not telling a friend how I felt about her. She transferred schools and I haven't seen her since. 

Sep 21, 2021 - 9:31pm

If you're happy with where you are at in life and your relationship with her as a friend I'd say just leave it be. If you catch yourself constantly thinking about her just yolo it and text her with a "hey I've missed hanging out with you". Chances are if you're both in different schools separated by distance nothing will happen either way so if you want to shoot your shot I say do it bro

  • Intern in RE - Comm
Sep 21, 2021 - 10:08pm

Yeah, I'm happy with where I am in life. It's just one of those "what if" things you know? I think we all have them. Besides we haven't spoken for well over a year at this point and I think she's moved on with someone else last I heard. It's a lesson learned, will never make it again and not just in relationships.

Sep 21, 2021 - 10:40pm

Senior in college and the answer is being such an antisocial prick my whole life. I didn't ever want to go anywhere to meet anyone. Same goes for high school, never joined clubs, talked to the same people all the time, didn't party.

Part of it is just my personality and I can't help it. But I haven't made any substantial relationships as an adult. I don't feel particularly sad or lonely, but I think there's a lot of merits in having close people around you. Plan to put that right in 2022 when I start a new job. Already been putting myself out there a little. It hasn't been fruitful, but there's a bit of value in doing new things.

Sep 22, 2021 - 12:22pm

It takes some time. With the way things have been over the last year, I think we've all been a little anti-social. But you can set it right when you move for your job.

Sep 22, 2021 - 1:33pm

You still have 1 more major life event to remake yourself. Any time you move somewhere, you get a new start. When you leave college and start a full-time job, join a few social clubs to find what you like (internal to company and external). I found out that I really enjoyed playing social kickball and drinking some beers with my teammates after. It's only once a week, but every Thursday night, without fail, I go out and enjoy my time with my team. It does help that once you're on a team competing, people will naturally pull for you and it creates a subconscious decision to like you. Use that. Join multiple clubs and find out what you like to do. My friends do volleyball. Another does rec league soccer. Another joined a local table game group. I was as antisocial as it gets in high school and college and played way too many video games. Now, I know that I can still do that but I have at minimum once per week that I'm out there enjoying some time with folks with common interests, and that is enough for me (outside of spending time with my wife). She likes to be busy 4-6 days a week whereas I use all of my energy being an extrovert at work. Have to find a balance.

You still have time. Just put yourself out there. 

Edit: Forgot to say, if you like College Football, join your team's club of whatever city. For example, I joined the Club of School in Boston and instantly had ~30 people to text, chat, or reminisce with. A few years later, and I still talk to a few of them to this day, despite not living in Boston.

Sep 21, 2021 - 11:37pm

I should have dropped out of college instead of sticking around as long as I did. Complete waste of time for me.

  • 1
Sep 26, 2021 - 6:46am

I've seen through your posts that you are a PE-style investor/operator. Do you think that not having a college education would've worked against you in whatever fundraising process / prospecting you may have done with potential portfolio companies? Just saying that even having a college degree probably helped in some way there 

  • 1
Sep 26, 2021 - 12:40pm

Not remotely. I dropped out btw, never finished. Was making more than my profs at the time and could have juiced my business way harder to drive a bigger first exit. That cash would have compounded….

  • 1
  • Incoming Analyst in S&T - Equities
Sep 22, 2021 - 3:29am
  1. Maintaining health and cardio I had when I was young (high school and before). Still fit by most standards, but I used to be able to roll out of bed and run a marathon. Can't now. Health will be everyone's number one answer and you will still ignore it.
  1. Not asking girls out immediately when I first notice them. Another common answer you will still ignore.
  1. Scratching car at 2am after party and too tired to think straight.
  1. Not fixing small problem in car that lead to engine failure later.
  1. Not taking showers immediately after sex or not wearing condoms (yeast infections).
  1. Never getting into a street fight.
Sep 23, 2021 - 12:32am

Asking girls out after you first notice them?

Why?  Wouldn't getting to know them and then asking them out work better?  Or are you referring to hotties you see in the grocery store or something that you'll never see again

  • Associate 2 in RE - Comm
Sep 22, 2021 - 11:40am

Biggest regret in life would be cheating on my then gf (of 3 years) when I was in grad school. I never told her and I will likely take it to the grave, but I became so anxious and paranoid after that, it destroyed our relationship. I still hate myself for it to this day and I don't think I'll ever really forgive myself for fucking that up.

Sep 23, 2021 - 12:44am

Dude relax, its your gf, not a wife of 5 years or something.

just fing lol at a  BIG regret in life being related to a college GF who was likely taking dicks from half the biz school class behind your back

  • Prospect in Research - Other
Sep 22, 2021 - 9:39pm

That's your biggest regret? Seriously? I'm a longtime lurker here so I've witnessed your descent into horny hell over time, but damn man. There's gotta be something more. 

  • Incoming Analyst in S&T - Equities
Sep 23, 2021 - 12:35am

I did the same in high school. Turned her down in front of all my friends while I was still a virgin. Random hot blonde came up to me and asked in the gym. Wanted my red face to go away before acknowledging, but by that time she left. Such a pussy damn. Never had anything like that happen again.

  • Analyst 1 in IA
Sep 22, 2021 - 1:27pm

staying in a long-term relationship way longer than i should have and missing out on a lot of pussy. don't get me wrong, i am with someone now who i absolutely love and want to marry. my issue is that i missed out on a lot of experiences that i could have been in had i dropped that old girl years prior

Sep 22, 2021 - 2:46pm

Succumbing to ego. I spent 7 years agonizingly striving to get into medical school because I was so tied to the egotistical idea of becoming a doctor and walking around with that title after my name. I got two substantial degrees out of those 7 years so it wasn't like I wasted all that time on fluff classes and subjects but I wish I spent those 7 years in finance as I would be worth much more financially now than I am. Ego is poison and it is the curse of the male sex.

Sep 22, 2021 - 2:51pm

Finished junior summer internship but didn't get full time return offer. I had Study abroad plans for Senior Fall. I was set to start my semester there, I flew over to the destination and flew back home after two days over fear of recruiting and being left without a job post graduation. I also had panic and anxiety but I should have stuck it out and gained that life experience and partied it up.

I ended getting a full time offer during senior fall recruiting but was only there for a year and it was toxic and was unemployed for 1.5 years after. I was set back in my career and lost time.

So I guess the decision to fly back and cancel my study abroad trip really cost me

Sep 23, 2021 - 11:21pm

I lived at home with parents and I still do tbh.

I was applying for jobs but landing nothing, I did side hustles, freelance work, trading etc. to remain occupied. I wasnt having any luck until after 1.5 years a recruiter reached out about a role and I was able to land it, but man that was  a tough and depressing time.

Sep 22, 2021 - 5:59pm

No major ones but for a long time I regretted not taking school more seriously when I was younger.  I was an a minus student through high school.  I studied but did the minimum to get decent grades.  I spent too much time playing sports because I liked it better than school work.  

  • 3
Sep 23, 2021 - 3:54pm

Same, I did well in school but felt I could've done better. Maybe somethings might have been easier, but hey I still got what I want so can't really say I regret it too much.

Sep 22, 2021 - 7:18pm

Missed so many oppurtunities to get laid bc im socially challenged. It actually is a big problem for me.

I guess my life is kinda good given that this is my biggest regret tho ha

Sep 22, 2021 - 9:07pm

In college I used to hook up with a girl who literally lived 5 doors down from me but I always made her come to my room bc I was too lazy to walk to hers. I still find it hard to believe I used to turn down a nut bc I couldn't get myself to walk 100 feet down the hallway.

  • Analyst 1 in HF - Other
Sep 22, 2021 - 10:34pm

Wish I didn't take the shortcut and cheat on an exam in college. Got an F, got a mark on the back of my transcript saying what happened, and dropped the major due to being unable to finish the major on time. Now my b-school prospects are even slimmer and GPA is down in the low 3s. Don't cheat people, it's not worth it. If you really are going to, make sure you damn well won't get caught. 

  • Incoming Analyst in IB-M&A
Sep 23, 2021 - 12:35am

My biggest regret is probably not having the strongest social life. I have friends around me that I hang out with every day but I look at others and see that they have such a strong friend group and they are always having fun and I get FOMO. I am pretty successful from a professional point of view (top leadership on campus, IB FT lined up etc.), but I think that has come at the cost of an optimal social life. I am pretty boring and honestly, kind of a hardo right now on a campus which is not very driven. This is something I am trying to improve but I really just regret that I don't have as close a friend circle. Honestly at this rate I am probably gonna be that IB/PE VP at 30 that isn't married and all he does is work, which sounds kinda dreadful.

Sep 23, 2021 - 11:31am

For whatever reason people think that college is the pinnacle of our social lives. Sure, it is the only time in your life you are in close proximity to people your age but life goes on. You'll meet interesting people throughout your 20s, just gotta make the effort to actually become friends with them. 

  • Intern in IB - Gen
Sep 28, 2021 - 6:08pm

As a girl who goes to a "party" school and has been in friend groups before, those big groups you see on social media don't actually last. Whenever you see a huge group hanging out around campus or at parties, chances are they're not even close to each other besides from a few people. They might have acquaintances, yes, but they actually have very few real friends. Usually drift away by the time they're junior/seniors. If you're moving into a new city for your full time job, focus on meeting as many people as possible but also know that only very few will be your true friends that stick around and they might take time to find.

  • Associate 2 in IB - Cov
Sep 23, 2021 - 12:47am

Not taking steroids/PEDs in high school

I was an above average varsity athlete (Baseball and track)

Didnt quite have what it takes to continue playing at D1

the D1 athlete lifestyle (for REAL sports, not lame ones like squash) is UNMATCHED.  

Sep 23, 2021 - 7:20pm

Lmao if you think you needed steroids just to go D1 then you weren't good enough to begin with. Also D1 lifestyle is much tougher than you'd expect unless it's football / basketball. Even baseball is tough as you have to go to class unless you're at a top ranked school (for baseball)

Sep 23, 2021 - 2:48am

I think my main one is not pursuing Karate longer. Seems random but here goes...

Joined the sport around 5yo, and became a black belt at 9yo (which I'm sure wasn't even legal lol). Kept going and training but I couldn't get to the next black belt level before 18yo, so as I was growing up I was rly losing motivation for the sport because I was teaching a lot of the time (despite only being like 10/11/12...) as there was no real reason to start training for the next level that early. As a result it felt like I wasn't learning much and was just being used to teach while simultaneously paying for lessons.

Eventually left the sport at about 14/15, for the same reasons I spoke about before + general teenagery things like focusing on school, wanting to get part time work and spending time with friends. I didn't really consider it until recently but seeing it become an Olympic sport this year does make me wonder how I shut off a path very early on in my life for simply not enjoying something.

I'm still happy where I'm at, joined a decent firm as an apprentice after getting A Levels last year - coming up to the 1 year mark now, with a great team as well! Heck, I've even got a coffee chat with the Branch CEO this morning! But I've started to wonder what could have been if I just decided to push through a little more

Most Helpful
  • VP in IB - Gen
Sep 23, 2021 - 8:58am

I think nothing good can come of this thread. What's done is done and the younger folks are not gonna learn from other people's fuck ups. That's just human nature. If it were that easy, everyone would be fit, smart, rich, etc. It's also perfectly fine to screw up in life. 

My frame of mind is that I don't have regrets. I made the best choices I could based on the situation/feelings at the time. Should I have focused a little more on school work then hanging out with friends? Sure...and I knew that and the consequences at the time. Still chose to hang out with my buddies and made some incredible memories. At the end of the day it all worked out. 

Also, don't think all your regrets were bad choices. Could have gotten laid A LOT starting as early as middle school. I was way, way too shy to make a move back then. But in hindsight, maybe I dodged a bullet. No way I could've handled knocking up a girl. 

Forgive yourself, but never forget, that way you can learn from your mistakes. Most people on here are young enough where it's not too late to make some things right. You may not be the most successful person in the world, but chances are, if you're on this forum, you're in the top 10% of the WORLD based on professional success, education, and wealth. 

Sep 23, 2021 - 10:21am

I've had zero regrets in my life ever since I changed my way of thinking from being "results-oriented" (how I was for the first two decades of my life) to "process-oriented" or "decision-oriented" (how I have lived my life ever since)

Obviously, things in life can go wrong, but if you are honest with yourself and you acted or made a decision based on the best information you had at the time - then you shouldn't have any regrets even if things go wrong. 

Regrets come only when you kid yourself.

Sep 24, 2021 - 2:45pm

You can make the best decision and still have the outcome be bad due to unforeseeable events or things outside your control (or vice versa). If you only pay attention to the results you might think of yourself (or the project, or investment decision, or whatever it is) as a failure, whereas your decision making skills might have been correct all along. The baseline should be thinking "given all the information I had, was it the best decision" (decision-oriented), not "was the outcome good or not" (results-oriented). 

He's not saying you shouldn't care about results, obviously that's still important, but judging someone's actions based on results is flawed and can lead to punishing good decision makers who got unlucky or rewarding bad decision makers who just got lucky. 

For example, I graduated with my MBA in June 2020 with 6 figure debt and no job. Based on the results it would have seemed like that was a massive mistake, but even then I trusted the process and didn't regret it. When I was applying and enrolling, taking on the debt for the MBA was still the smartest move forward. And ultimately it proved out to be correct, I got my job, it pays more than double what I was making pre-MBA, even after debt service I have a higher cash flow, and it's the industry/work I want to do. If I judged myself and looked at my actions purely based on what the results were at the time I would have been much harder on myself than I was. The things I was hard on myself were things I rightly should have done better, having had the knowledge to do so, like networking more. I wasn't going to beat myself up about the decisions I made that were the right decisions but then someone decided to eat a bat and fucked up my results. 

  • Associate 1 in IB - Gen
Sep 23, 2021 - 4:41pm


Catch myself regretting not going to Bonnaroo one year cus I was still in student loan debt. Should have yeeted it on the credit card instead of being a narc lameo. 

Not my biggest regret - but similar thing with me and my homies going to EDC. Now, that EDC ticket is relative chump change.. while my homie had a blast and hooked up with hoes 

Sep 23, 2021 - 2:03pm

Here are my two cents. Feels good to get these off my chest. Not many people talk about mental health these days.

1. Leaving B school to work full-time because I got married young (20 yrs.).

2. Not taking my side hustle seriously (I was first to market. Competitor sold for $3m last year).

3. Moving in with my parents to focus on school. Damaged marriage and got too comfortable.

4. Not taking networking or school activities/clubs seriously.

5. Turning down key interviews because of social anxiety/fear of failure.

6. Having a child while still in grad school (don't regret baby girl, but regret timing).

7. Overall, not taking life seriously enough.

Sep 23, 2021 - 2:48pm

No regrets. I have had a range of experiences and all of them helped me in some way to get where I am today. Even the bad experiences were valuable. Dealt with a complex medical issue well into high school but resolved it before college. I appreciate everything I am now able to do because it's only been four or five years living a normal life

Sep 23, 2021 - 8:20pm

1) Dicking around in high school. Had a 1540 SAT score, but low GPA. So I ended up a worse school than I otherwise should have gone to. 

2) Not drinking enough milk lmao. I'm about 5'10, but my two brothers are 6'3+. Kinda salty

Sep 24, 2021 - 7:56pm

all of it yet none of it


Look at all these wannabe richies hating on an expensive salad.

Sep 25, 2021 - 1:43pm

Taking care of my health, i.e. exercise, diet, sleep. I've yo-yo'ed like crazy - and the last time I put on a ton of weight, I ended up being pre-diabetic, on a road to heart attack. Worst I've ever felt like. 

Also, not getting my ADHD diagnosis before my early 30s. Always had a suspicion. 

Sep 25, 2021 - 11:08pm

Some days I wish I could go back to my senior year, apply to a lot of the "party" yet solid academic schools I wanted to and do more career inspection (I got wait listed at a few T30 schools but was too lazy to retake the SAT which was my weakest part of my app, had a <2000). I was in tunnel vision and spent most of my senior year gaming rather than looking at different careers (a lot of people I knew the summer before senior year/freshman year in college shadowed different professions to get an idea -- I wish I did that).

Sep 27, 2021 - 4:28pm

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