January 3, 2020 | Samuel Ira

Wistful People Share Their Life's Biggest Regret

“I'd rather regret the things I've done than regret the things I haven't done.”—Lucille Ball.

“Do not brood over your past mistakes and failures as this will only fill your mind with grief, regret, and depression. Do not repeat them in the future.”—Swami Sivananda.

We all have moments that we look back on and wish we had made a different choice. They pop into our brain and agonize us when we can’t sleep at night. They cast a shadow on an otherwise well-lived life. We can never get these moments back, we’ll never be able to relive them and get to experience a different outcome. Instead, they will play over and over again in our minds. A perverse torture we never move beyond, to our therapists’ constant disappointment, no doubt. They come in all sizes, little and big, and they don’t discriminate.

Regrets are hauntings by past decisions that we would all do well to shake free from or conduct some sort of hypnosis to block out the memory forever. But for all the embarrassment, frustration and anxiety they cause us we wouldn’t be the people we are today without having experienced them in the first place. They help us grow and serve as a reminder of how far we’ve come. Here are some of the biggest regrets that Redditors have in their lives—but, fortunately for many of us, there’s still time! We can all learn a little from these stories and maybe not make the same mistakes.

#1 A Child Mourns

My mother passed away when I was eight years old. Cancer. It came to the point where death was inevitable. My dad asked if I wanted to see her and I said no.

Biggest Regrets factsPixabay

#2 Dear Teens: Heed These Words

I was painfully shy and awkward around strangers and the opposite sex when I was in elementary school and high school. I really presumed that I had so few friends because I wasn't the kind of person other people liked. I also presumed my social awkwardness was inherent and something I was completely unable to overcome.

I only found out that both of those are untrue when I was, like, 30. I kind of wish I had my teen years back so I could force myself out of that awkward shell and enjoy my youth a bit more.

Biggest Regrets factsThe Ross Center

#3 Never Heard That One Before

I'm only 20 but I regret spending my childhood reading books instead of joining sports. I feel like sports would have helped me socially and physically so much.

Biggest Regrets factsWaterford Institute

#4 Youthful Take-Backs

Hanging out with a friend instead of visiting my father in the hospital. He died that night and I never got to say goodbye.

Biggest Regrets factsOdyssey

#5 Who Could Have Known

Selling all my bitcoins when they hit $10.

Biggest Regrets factsBloomberg

#6 An Important Lesson to Learn

(Then age 22, now 29) Loaning an ex $10,000. He cheated and never paid me back.

I learned the valuable lesson to never loan money you can't afford to lose.

Biggest Regrets factsStartsmile

#7 Extremely Relatable

Jumping into college right after high school. I had no freaking idea who I was or what I wanted to do.

A lot of money wasted, drugs consumed, and destructive relationships later, I kind of know what I want and who I am…kind of.

Biggest Regrets factsEden Village Church

#8 You’re Ready When You’re Ready

I'm 26. I didn't properly develop my social skills until a few years ago and I only lost my virginity this summer. I wish both would have happened at least ten years earlier. Would have saved me a lot of frustrations and disappointments.

Biggest Regrets factsSteemit

#9 The Night Shift Is Damaging But so Is Comparing Yourself to Others

Started working night shift when I was 20. I am 24 now and finally got a new Monday to Friday day job. But nights have already done their damage, I am shy, reclusive, don't go out much, been single for nearly five years now, don't know how to talk to girls anymore when I am out, don't know how to make new friends. Now my best friends are having kids and I am getting worried that soon I will be on my own completely.

Biggest Regrets factsYouthmanual

#10 So Many Regrets

I’m 25 and here are a few.

Not going back to see my grandfather before he died.

The self-destructive things I did when I was a teenager.

Not trying harder when I was in school.

Ruining a bunch of my relationships.

Biggest Regrets factsWallpaperMaiden

#11 That’s a Big One

Not fulfilling my potential.

Biggest Regrets factsHarvard Business Review

#12 Trying to Look Cool, End Up Being a Fool

We were on a break cause I was being a jerk. In order to get a reaction, I ended the relationship status on Facebook. That resulted in the complete end of our friendship and all. I’ve regretted it ever since. It's only added years of misery to my life.

Regret Breaking Up Factspixabay

#13 Perfect is the Enemy of Good

Ten years or so ago, when I was 24-25, I dated girl A for a while. She was cute and sexy but kind of boring in bed. So I started seeing girl B who was fun and freaky, but more unpredictable. I, being stupid, dumped girl A for girl B. I do regret it because she was a good person and I was a jerk for what I did.

I wasn't ready to settle down in any shape or form, so it fizzled out with girl B as well. I think back to some advice my buddy gave me (after all this): if you find a good woman, lock her down!

Now I'm almost 35 and still single. I've accepted my fate as forever alone and just kind of do whatever I want when I'm not working. My best buddy is a 70 year old ex-IBM guy who looks like Benjamin Franklin.

people man guy free photoNeedpix

#14 So Naive, So Full of Life

I'm 23. Young enough to do what I want...but I have been thinking that since 18. I have nothing to show for those five years that flew by and I had some huge aspirations that I was sure to have conquered by now.

Biggest Regrets factsIntegrative Psychology Services

#15 Lessons From Our Elders

Not talking to my grandfather about his experiences in World War II before he passed.

Biggest Regrets factsUPPSolutions

#16 Out of Fashion

The fashion design industry has been crippled lately to almost a non-existent size, so I have difficulties in getting any work.

Been unemployed for almost 500 days.

Why Professionals Regret Going Into Their Fields factsPixabay

#17 The Dark Side

By the time I got to the last semester of my Master’s degree in counseling, I regretted my choice. It's soul crushing. I was prepared for the burnout that counselors experience from listening to people talk about all their pain, but I was not prepared for the burnout I'd experience after I learned just how corrupt and unethical the mental healthcare system is. I couldn't stand it.

I'm so glad I left.

File:Confused young woman.jpgWikimedia Commons

#18 It Would Be So Practical Now

Not getting a degree in one of the STEM streams all those years ago. Playing catch up now. :(

Biggest Regrets factsWrike

#19 The Day to Day Grind

My story thankfully didn't progress too far; decided on digital forensics in high school, went through a horrible university experience while learning networking, IT security, IT resource planning/management, hacking, said digital forensics as well as some other topics. I looked for a wide array of such jobs for half a year before realizing I absolutely did not want to do any of the actual things that you do when working with any of it.

Learning and thinking about what you actually do when "doing" any of these things seems like a big combination of dull, stressful and thankless to me. It is not the type of job that fits me and my personality.

Image result for digital forensicsWikimedia Commons

#20 Write or Wrong

Got an English degree, entered the writing/editing field. Work is hard to get, but that's not the worst part. There is very little room for creativity and your skills top out fast. I switched fields to software and am much happier.

I would not suggest dropping the English degree, which is still valuable to me, but I would suggest double majoring in something useful.

Why Professionals Regret Going Into Their Fields factsPixabay

21. I Didn’t Know You Cared!

When he called me up the day after I broke up with him to ask me if I was ok.

Yeah. Mistake I've regretted for 13 years now.

Regret Breaking Up Factsshutterstock

#22 Lesson: Don’t Be an Idiot

I left her for someone else because I'm an idiot. The other girl turned out to be a jealous, mentally and physically abusive psychopath who eventually ended up in a psychiatric hospital. My ex, quite rightly, refused to take me back.

Lesson learned.

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#23 I Still Don’t Know What I’m Good At

Not knowing what I'm really good at and want to pursue earlier in my life.

Also, finding out that I have ADHD earlier in life.

nyc travel traveler free photoNeedpix

#24 Surprise Ending

I dated a guy in high school who I was very into. We were both really awkward teens though, so he wouldn't kiss me and I broke up with him because of it. We'd been really good friends before dating but afterward, he didn't speak to me for about a year.

He was a few years ahead of me in school and he'd graduated by the time we broke up, so while we gradually started texting again the first time I actually saw him was at a friend's party. He'd gotten way hotter somehow. As soon as he saw me he strode across the room and kissed me.

That was seven years ago. We now live together and have three annoying cats.

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#25 I Love Him, I Love Him Not

I had some personal issues and thought I wasn't really in love with him. Turned out I was and really regretted my decision to end things. After a few months though, we ran into each other and I asked him for a second chance.

We're together for almost a year now and everything is going great!

Image result for couplePixabay

#26 Good Luck Analyzing This

NEVER get a psychology degree. There are NO jobs out there and if you are lucky enough to ever find one, you better have a PhD or good luck!

Image result for psychologistNeedpix

#27 One Little Change

I'm a year into a career job (R&D tech for a chemical manufacturing company) and I can't decide if it's the work or the company I don't like.

I loved academic lab work, but industry work is so cold, repetitive, uninspiring, and unengaging.

Image result for lab workerFree Stock Photos

#28 Second Time’s a Charm

Mine is tremendously dumb. We were 18. I didn't think I had that same love feeling and we were headed to colleges an hour apart, so I thought breaking up was the right thing to do.

A few weeks later we're chatting and lightly flirting on AOL instant messenger when she misspelled touché as "tushey." I laughed so hard at this mistake that it made me miss her. She also informed me of a guy she'd had a few dates with, so there was some jealousy. I asked her to a movie to talk (dumb, I know) and I felt a strong attraction again.

I kissed her in the parking lot after and we kind of restarted but with a better foundation. We've been together ever since and celebrated ten years of marriage over the summer.

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#29 Oh, the Humanity!

I'm going back to school now but working with the public has basically depressed me regarding humanity. Some types really want to work with people, but I want less of that. It amazes me how cold, calculating, manipulative, and selfish the general public can be. Even friends. Give them an inch and they take a mile. Unfortunately, I LOVE my field but 1) it doesn't pay well and 2) I can't duct tape my clients' mouths shut.

Image result for university studentFlickr

#30 No Regrets

Age 25. I don't regret anything. Everything that has happened or I have done has led me to be the person I am now and I like who I am now. It's taken a long time to like myself but I'm finally there.

Biggest Regrets factsPillowfights

#31 Getting Schooled

I don't regret my career choice, I just wish I actually went to school for it. I mean, I still could and I might, but I wish I knew when I was 19 to choose computer science rather than theatre.

Image result for computer sciencePixabay

#32 Tell Us About Your Problems, Doctor

I’m a therapist. Don't go into this field if you haven't figured things out yet, and by that I mean, you haven't ever gone to therapy yourself, you aren't used to questioning everything about your life like you would a client, and overall don't enjoy working on self-development and self-care all the time. Burn-out and traumatization are real and take a long time to get over.

Plus, thinking the job is all about helping people is a mistake. It's more like helping people help themselves and watching their messes unfold like a telenovela, but it's real and most of the time you can't do much but sit there and be with them through it all. I liked it, but not after 30-40 clients a week. Also, you constantly need training and reassessing of your skills. It always feels like running on a treadmill going nowhere, no matter how much progress you make with a particular client.

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#33 Debt is a Constant Regret

Going to a private university instead of a public one, and not sticking to my original degree in engineering. Stupid me ends up with $150K in debt and a degree that is nearly useless.

Biggest Regrets factsMoney Sustainability

#34 Always Care About Your Health

I wish I started caring about my weight much sooner. I've lost some good people because they gave up waiting around and I don't blame them at all.

Biggest Regrets factsHabibi Halaqas

#35 Defeated By Society

This will be long and I doubt anyone will see it. I don't care because this is actually for me. I haven't thought about it in a long time and want the memories today. Besides, it beats working.

I regret letting myself lose touch with the first person I loved who loved me back after I was forced to move away. She was a keystone in my life though we were together for a short time and I’m probably just a short meaningless moment in her life.

Like most of us, I was an awkward kid. A huge nerd who was too smart for his own good and that just made it even harder to form relationships at all let alone with girls. I had been hanging out with a bad crowd and knew I should get new friends before I got in too deep.

I was also an honors student so I didn't fit in well with my misfit friends either. They didn’t like me. I didn’t like them. They kept me around to be the butt of all their jokes and generally treat badly. Like I said, I was awkward as heck and my only two real friends lived an hour away from me. If I was lucky, I would see them for a weekend or two each month.

During the school week, I was on my own. I was the perfect blend of huge nerd and a want-to-be heavy metal kid with a lot of Dungeons and Dragons mixed in. I was tall and lanky—probably 130 pounds soaking wet. During, my freshman year of high school I spent my lunches alone reading fantasy novels in the library. There is even a picture of it in my freshman yearbook: Just me sitting alone reading a David Eddings book sporting a mullet and wearing a grey cardigan sweater with a white turtleneck underneath. Oh, and the type of metal wire glasses you see 65-year-old businessmen wearing. The ones with really big lenses the cover most of your face.

I’m in that yearbook photo with a caption about me reading in the library at lunch. Something I longed for each day just to get away. The yearbook itself is crisp and clean. It still looks brand new 20-something years later—not a single signature inside it because I had no friends and knew that anyone who would want to sign it would only write something mean.

One of the misfit kids was a close friend, who treated me differently when the rest of the gang wasn’t around, but he was from a tough background and even then I knew he was headed in a bad direction. We hung out a lot that summer. He was good looking and good girls were always falling for his bad boy charm. In spite of my awkwardness, I could pick up on social clues.

I decided that summer I would cut my hair, ask for new clothes and contacts in spite of us being very poor and try to conform to what I saw other kids doing at least in appearance. I knew that people do judge a book by its cover and I didn’t learn that at lunch in the library. I saw it as a huge defeat to myself, but I was tired of being alone. I still remember asking my father for different clothes and contacts. I had to tell him I was a freak that everyone ridiculed and that I was embarrassed by myself. I could tell he understood even though he thought the world of his son.

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#36 Don’t Get in Your Own Way

Letting the most beautiful girls I have ever met slip past me because of self-doubt and social awkwardness. Once when I was 17 and again when I was 20. The worst part is the fact that both times it was girls in which we really got along and were really into each other.

Biggest Regrets factsThese days I call myself a runner...

#37 All Hustle, No Heart

I’m a software engineer.

While I am competent at my job, I am not as "into" it as my co-workers. I don't do pet projects at home, I don't research the latest trends or look for new, cool programming languages to try out in my spare time. This means I treat my job very much as a 9-5 time punch (in my case, 7-3). I struggle to keep current in my field. I am not much interested in advancing (but that's also partly because I love my current hours and flexibility due to the great work/life balance it allows me). I am at a point where I really need to work for another company because the director is getting more and more difficult to work with, but working on my resume has been really depressing. I don't have any great stuff to put on it because I'm just not into the job.

business woman, using, laptop, sofa, agency, assistant, business, ceo, company, corporationPxfuel

#38 An Interesting Bio

My big mistake was that I didn't go for what I really loved because I didn't have the confidence to do it, which was biology. Somehow, I had it in my head that only super-smart people can be scientists. I understood that people thought I was smart but I knew, for sure, I would be exposed as being mediocre if I took up such a challenging topic. So, I stuck to classes and disciplines that I felt more confident I could just do well in, and that sort of defined how I lived my whole life for a while: nothing too challenging, where I might fail and expose myself for the fraud I was.

For better or worse, at my middling, not-so-challenging job, I got a new boss who just hated me. He, quite literally, nearly drove me insane with how he treated me because he just wanted me to quit so he could hire someone in my place that he preferred. I got so depressed that I really needed some therapy and that is how I came to terms with how much I wanted to be a scientist and how much I loved it. So, the time came and I quit that job and started all over again, working part-time and going back to school. I eventually got my PhD in biology. It is, indeed, a very challenging career where I feel my abilities are constantly being tested, but it has its rewards as well.

File:Research scientist works in the NCATS chemistry laboratory.jpgWikimedia Commons

#39 Straight to the Point

We once had a piano tuner visit my piano class. His first words:

Never become a piano tuner.

Image result for piano tunerWikimedia Commons

#40 Education is Highly Valued By Employers

I'm 31. For me, dropping out of high school and not going to college is my biggest regret. When you are young you tend not—at least I didn't—to appreciate how much more difficult this can make your life.

woman worried nightmare free photoNeedpix

#41 Accepting Yourself Is Hard

Not being myself. I waited until this year to finally admit to myself that I am bisexual. I tried so hard to make myself into someone I wasn't all these years, feel like I wasted my 20s and my life is still so complicated and messed up. Oh, also a furry by the way. I’m 33 years old now.

Biggest Regrets factsCaylor Solutions

#42 Inner Truths

A female friend in college revealed she had a crush on me and had for a long while. She was probably my best friend at the time and I never caught on to this because I'm super gay, and at the time I was super deep in the closet.

She broke down and revealed this one night after we had grabbed dinner and saw a movie—I honestly can't believe I never caught on. I did the only thing I could do, since this was clearly hurting her, and I told her I was gay. She said she had started to suspect that a while ago, but wasn't sure and decided to pursue me anyways.

And this is where I become scared: That night was the last time I saw her. I closed myself off slowly. Stopped responded to Facebook, texts, calls, everything. She was the first person I had told I was gay, and I was not ready for it. She was fine with it though—so fine with it that I think she tried setting me up with her brother at one point, but I was not fine with it at all.

I was so nervous back then about everything, I wanted no one to know I was gay because of this overwhelming sense of dread I had about it, and suddenly someone knew my biggest secret and I couldn't stand it. I got scared, so scared I cut her off completely within a few months.

I still feel bad about it, and I should because it wasn't a good thing to do. I've thought about reconciling a few times, but she's left the state now, moved on with her life, and from what I can tell is a very different person from when I knew her. I'm out now, and finally happy with myself and my life, but this thing I did to a good friend weighs on me.

Biggest Regrets factsOdyssey

#43 Live in the Slow Lane

The day my dad killed himself, I was walking out of the house and running late for class. He asked me to have some breakfast with him but I just yelled out, "I don't have time," and walked out.

Biggest Regrets factsCarnisseria Can Pepito

#44 Don't Give up

Attempting suicide. I don't talk about this much, but screw it. I'm 34.

Trigger warning. This might not be an easy read for some of you.

This is the first time I've ever opened up about any of this in public. Even my family isn't really aware of a lot of this, for reasons I'm sure you're about to understand.

My first time, in a word, was due to bullying.

I was an awkward teenager, and I've got a very Norwegian name that looks like someone ate a bunch of alphabet soup, shot diarrhea of it at a wall, and wrote down the result. I got messed with quite a bit as a result of both facts, ended up being shuttled around between schools because I'd inevitably get kicked out of a school for fighting over it. After a certain point, I snapped. Stalked around my high school breaking stuff, did a few grand worth of damage. They had to call my parents to come grab me, and I was institutionalized for about six months at 16 years of age. I put on a good face, did my time in the hospital, and finally got released. Less than three days later I was in the ICU after a massive overdose of my psych meds. I had to have my stomach pumped, got charcoal, it was a pretty close call. For the record? Having charcoal pumped into your stomach through a tube in your nose isn't really a pleasant experience.

I just got to a point where I felt like the cycle wouldn't end. I'd never graduate, I'd always be miserable, and I'd started having the usual effects of PTSD. Hallucinations, self-destructive thoughts about how terrible I was, scary rages that left me exhausted and cost me a lot of beloved possessions. Panic attacks.

After a few weeks, I got out of ICU and back into the hospital. About a year later, give or take, I was finally out and sent from New York to Colorado, to stay with my dad. If it's because the state said I had to, or if my mother couldn't take looking at me after all that, I'll probably never really know.

Fast forward about 14 years, my marriage dissolved and my PTSD was still mostly untreated. I'd been homeless off and on the entire time, scraping by with odd jobs and teaching MMA to keep myself alive. I kicked off a wicked drug habit that culminated in a pretty sick addiction. I did a lot of things I'm not proud of, and that weighs on you.

To make a long story short, I finally cut that stuff out of my life, and moved back in with my parents to regain some semblance of normalcy. Had enough. Got a job, probably the best I'd ever had to that point. And then I lost it because of the stress of finally treating my disease. I spun out, with PTSD it's a pretty tough fight to keep depression in check unless you've got some serious tools to control it. I started feeling the urge to pick up my old habits, and again just kinda felt like it was going to be more of the same. So, I hit that point again. Gave up. Overdosed. This one didn't go as badly, I was only in the hospital for about a month, and actually got some skills to actually keep it in check.

Since, I've traveled all over America. I started in Maine and found my way all the way out to Montana. Started writing, which worked out better than I'd expect, all things considered. But you know what? I can't say it ever really gets better. Things are stable, but medical care is expensive and I'm still paying the bills for getting put back together again. My last attempt was probably about 3-4 years ago, it left me with thousands in debt. But, things are a bit different now. I've gotten so close to death that I coulda had a nice chat with her, overdosed so badly that I lost control of my bodily functions and almost coded a few times. I know what it's like, and I know how bad of an idea it is.

What people never tell you, and what I'm going to, is that when you get that close? All you can think about is how much of a mistake you're making. It's painful, it's humiliating, and it's ugly. I still flashback to being on the table and having my clothes cut off. Vomiting charcoal, and later pooping it out in one painful brick. They never talk about the look in your family's eyes. My mom came to see me in the hospital while they were putting me together, I will never forget the look of fear in her eyes. Me stuck to a table, covered in tubes and wires and beeping machines.

Strapped down to prevent injuring myself in case I had a seizure. Black rock flowing down my throat. In more pain than I'd ever experienced before or since. One lesson I did take away from it is exactly how mean and selfish the entire act is. What I never considered was exactly how bad it was going to hurt my family, that probably hurt more than almost dying. I still have trouble forming relationships as a result.

Moral of the story is, after having gone through it, and a recurrence, I'm incredibly mellow now. I know how much worse it can be, so nothing phases me. But, I won't lie to you and tell you that the world gets better, or that I got some huge epiphany out of it. My only epiphany is that suicide is really stupid. Life's still hard, that won't ever change. Sometimes I wish I could say some happy platitude about how much more I appreciate every day, but I'd be lying if I said it was the case. You adjust, you move on. My life's probably similar to everyone reading this, it's still just as raw and ugly and real. But, it's also exactly as fun and beautiful and crazy. And I'm still around to live it, so I guess that's a plus.

I'll definitely say that it's the one thing in my entire life that, if I had it to do over, I'd change.

Biggest Regrets factsBody for Wife

#45 The Things We Wish We Could Change

I'm 28 and what I regret most is not killing the guy that assaulted my girlfriend.

He was my best friend in high school, but he had messed up views about women. If they dress a certain way they deserve it. If they flirt with you they owe you. That kinda thing.

She told me months after the fact that he attacked her while I was away for a few days. It took every bit of control to not track him down and kill him then. But I knew she needed me there with her more than anything else.

When I confronted him, I screamed, and I was so mad I cried the entire time. But I never hit him. I knew if I did I wouldn't stop until the cops pulled me off of him.

I took the high road and looking back, it makes me feel like a coward. I should have done something. ANYTHING. But all I did was talk.

Almost a decade later, she and I are still together, and we've both gotten our treatments. She's almost all better now, back to normal. I still have major trust issues. I haven't made a new friend since I confronted him, and I've cut almost all ties with the few I had at the time. I just can't bring myself to do it.

Biggest Regrets factsDem Con Watch Blog

#46 You Can't Go Back

I should never have kissed my ex-wife on Labor Day 1997. It was the worst decision of my life. I wish I would have just told her to screw off and said I had no interest in talking to her at all. She was a virus that destroyed me and consumed my will to live. Then she moved on. That is the only thing I wish I could make not happen in my life. Not failing to save my father’s life or the abuse from my childhood, just her. I regret everything about her.

Biggest Regrets factsPower of Positivity

#47 Regrets, I've Had a Few

I broke up with my partner not long ago, but I'm not exactly sure about my decision, even though it was something I contemplated for some time. It seems like we tend to reminisce on the good things and maybe over-romanticize the past and how things were. Thinking back on the actual problems we had, however, I can recall why things went that way. In that sense, my best answer is that the "oh no" feeling comes and goes from time to time, and I think that's natural. In other words, sometimes even if you think you made the right decision, it’s hard not to have at least some level of regretful feelings about someone you once cared about.

black, couple, diversePexels

#48 An Unexpected Turn for the Better

Why I did it? He smoked a lot and played video games and didn't seem as career-oriented or social as I was at the time. We were in love, but after a few specific incidents where it seemed like he would just be an avoidant stoner forever, I broke off our engagement and painfully moved on.

Why do I regret it now? Ten years down the line, I realized how many interests we shared (music, books, politics, good food, whiskey, humor, hiking) and just how rare that is. He's also gotten his act together and is way more career-oriented than I could have ever imagined back then.

I'm married with kids and so is he, but I think about something I want to share with him at least once a week.

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#49 It May Be Painful, But You Probably Made a Good Choice

My biggest regret is thinking that no matter how much I changed for him, I knew in the back of my head that it would never be enough. I knew that in the end he would never fully love me. And that his love was full of conditions. That hurt me the most—the pain I put myself through. I should've let it go months before I did. I wish so badly I didn't go through that because now I have such a hard time believing I'm worthy of love just the way I am. And somehow, through all of this, I still wish I was with him a lot of the time.

Image result for couple fightingPxfuel

#50 You’re Not in Kansas Anymore

A few months had gone by, and I was still feeling like crap about my breakup decision, cause I knew deep down she really loved me. However, as much as I cared about her, I couldn't shake the feeling that I couldn't be the man she needed me to be. I had been OK with my decision.

Then I went on a trip to NYC with a couple of friends. It was... not an enjoyable trip, and to top things off, I found out my granddad had died the week prior so I had to fly back home almost immediately after returning from New York. Suffice it to say, I was ready for it all to be over by day two of this essentially two week trip.

Anyway, about three or four days in my friends and I were out to dinner and they started talking about my ex. All I remember was wanting nothing more than to be home already and to be back with my ex. That's when it dawned on me that I made a mistake and my heart sank.

depression loneliness man free photoNeedpix

#51 You’ll Never Live It Down

I dated a girl for almost two years as a 15-year-old. I started to wonder what dating other girls was like, so I broke it up so we could date other people.

I regret it because I eventually married her and she now brings it up routinely.

young couple, fishingPixnio

#52 Why Can’t We See Things For What They Are?

I dated around and all men were awful. They were just horrible. And here I’d left the best person I knew. I don’t know how it could have worked out any other way, but I’ve regretted it for almost ten years now. He was the love of my life. And now he has a different wife and a kid. I think about him every day. I was such an idiot. He won’t even talk to me anymore.

adult couple dating desk family flirting friends happy holding hands indoors love man people portrait romantic room smiling support table together wear woman woodPxhere

#53 Goodness Is a Rare Commodity

My mom left my step dad and he got remarried to a great lady and is super happy now. My mom told me recently that leaving him was the biggest mistake she ever made because he was the only good man she ever really knew. We all have Christmas at their house every year, but my poor mom has to watch them being happy together every year while she lives alone.

Regret Breaking Up FactsThe Spruce

#54 Lessons Learned

I dumped somebody because we reached that serious stage and I didn't, at the time, want to deal with the extra maintenance, especially as she was high maintenance to begin with. Hugely regretted it instantly. I now make dating decisions based entirely on compatibility. This has made all the mind traffic you get from dating so much easier to handle.

Image result for sad girlPixabay

#55 Lesson Learned

My profession is teaching. I don't regret the years I’ve spent with students, but I am choosing to leave the profession. Undergrad students, laypeople, parents, etc. have no idea what it's really like. There is so much more involved than just learning your content and controlling students. It's a very political and bureaucratic profession in which you will rarely come out on top. It's emotionally, mentally, physically, and financially draining.

Woman in White Dress ShirtPexels

#56 Is There a Doctor in the House?

For anyone considering a career in medicine, think good and hard how much you time you want to spend on yourself/family/friends and decide if being "a doctor" is worth it to give this up. You're going to miss birthdays, anniversaries, meetings, parties, weddings, christenings, PTA meetings, plays, etc. No one really tells you what you're getting yourself into.

Once you're in, you're met with people telling you either that you picked this for yourself so stop complaining (usually patients) or that we did it when we were younger so you can too (senior doctors). You're expected to be tough and work yourself to the bone, then go home and study. Get a blood splash/stick from an HIV positive patient and feel like dying from the ARV side effects? Suck it up. You've been working for 30 hours? Finish the ward work before you leave.

Realistically speaking, at least 25% of the people who graduated with me are on antidepressants or anti-anxiety meds. Then there are more who are just denying their problems or self-medicating with drugs and alcohol. Sure, you can eventually get to a point where you decide your own hours and actually make money (after paying off your mountain of student loans, but even then you're in debt from starting your practice) when you're around 50 years old.

I may be in a bit of a negative spot with my career choice right now because of circumstances, but speak to a couple of doctors before deciding and be realistic about it. "Helping people" only gets you so far and a lot of my fellow students who got into it for this reason had to find another reason to keep going or quit.

doctor white coat uniform service girl physician medicine researcher health carePxhere

#57 The Tables Have Turned

I'm a software developer and while it pays well, I hate being at a computer all day. I'm an active person and desk jobs are tough. Going to the gym during lunch helps.

Code, Coder, Programming, Coding, Start-Up, StartupPixabay

#58 The Grass is Always Greener on the Other Side

My friend dumped his girlfriend of 12 years because he'd never dated anyone but her, they were struggling financially, and he wanted the chance to experience more relationships. Right after the breakup, she finished her PhD and started making six figures. She found someone else and got married within a year.

My friend tried dating a couple of people, but none of them have worked out and he still misses her. He said the moment he realized that he made a huge mistake was when he saw her wedding photos on Facebook and started crying.


#59 I Hope You Solve Your Problems Some Day

I pushed her away because I got overwhelmed. I miss her.

I have this habit in relationships where I always end things whenever I feel overwhelmed. I really, really loved her. But little things start to pile up. I don’t say how I feel because I just don’t like confrontation. And then one day I just didn’t love her like I used to. I don’t know why.

I fell out and ended it. She tried so hard to figure things out with us, but it just... I didn’t want to try. It didn’t seem fair to her to continue this when I’m just going to keep feeling suffocated. And when she tried to help, I felt trapped.

I don’t know why I’m like this. And I know she really cared and loved me. Part of me wants to reach out to her again and really try to mend things, and figure out how to not feel so suffocated anymore. I don’t think it’s anything she did, she was really understanding... it’s just me. I don’t know how to deal with me. And I miss her.

Image result for guy sadPxfuel

#60 Full of Surprises

Non-profit professional here. I chose it because I thought the work was interesting when I was an intern. But what I didn't realize was that positions at the more successful organizations can be very competitive, so I don't have as much choice as I imagined over where I work and what kind of work I'm doing. So I'm dealing with a crappy boss and not getting paid that great to do work that I'm actually not super-passionate about. While the relatively low pay was expected, the other crappy things were not.

Image result for stressed businessmanPxfuel

#61 Waiting It out

I don't know if I should have broken up with him. He makes me happy. I don't think I will ever find a guy as good as him. I think I will regret it because I won't find another guy like him. Loyal, hardworking, doesn't need to look at or fantasize about other women, same goals for the future, weird, smart, funny.

We have different cultures though. He is Indian. I was told his family would never be a problem on this front. After three years, I wanted to move in together because he was moving away for a job. His parents said no because they want us to have our careers established. He risks being disowned apparently if he goes against their wishes. We both want to go into the medical field, so that could take years to become established, and I'm sick of seeing my boyfriend of three years only once a week. When he moves away, that will become once a month if we are lucky. I love him but I need more affection, once a week isn't enough. Texting isn't enough. So I ended it. But I'm constantly filled with so much regret and sadness.

Image result for sad indian guyNeedpix

#62 Glory on the Battlefield

The military can be an enticing way to pay for education. And some people definitely thrive there and find fulfillment. Just be sure to take a closer look at the other options for signing yourself up for what can often be a huge burden…

U.S. Marines sprint uphill during a field training exercise at Marine Corps Air Station Miramar, California. to maintain contact with an aviation combat element, teaching and sustaining their proficiency in setting up and maintaining communication equipment. (Photo Courtesy: U.S. Marine Corps)Health.mil

#63 You Can’t Drink Your Troubles Away Forever

I ruined my relationship with my college boyfriend because of my alcoholism. It had really just started at that time and I didn’t even know how bad it already got. I was nuts drunk and he put it up with so much. Honestly, I had the “oh no” moment soon after. He was the nicest guy ever and he loved me so much. He was so smart and goofy and just a real catch and, last I’ve heard (we have mutual friends), he is successful and married.

I honestly wish the best for him because he is a genuinely wonderful person. I’m sorry I missed out on him, but I’m glad he broke up with me for himself; he deserved better than who I was then. We had a pretty quick breakup and remained friendly. Sometimes I wonder what would have happened, but it’s pointless to think about it now. Plus I probably romanticize the whole thing a little now since it was a long time ago and I have had some really awful boyfriends after him to compare him to.

My boyfriend now reminds me a lot of him (just because it’s a happy and healthy relationship and he’s goofy and loves me too, they’re not really similar), and I’m sober now, so hopefully I won’t have another round of “oh no.”

love, wedding party, young couplePexels

#64 School Is Not For Fools!

I was 16 at the time of my mistake, I’m 21 now.

Dropping out of high school...twice. I got good grades. School was easy as heck for me, so easy, I thought I could do better on my own. I was wrong. I dropped out after sophomore year, then again after junior year. Both times I tried homeschooling myself and seriously lacked the motivation. Eventually, I just decided to get my GED and move on. I left school at 16 years old and didn't return ‘til I was 20.

It was the biggest mistake of my life so far. It affected everything. I lost my friends. I lost everything that I thought I was going to improve on and get more of. I didn't get smarter—in actuality, I feel I am less intelligent than I was at 16—five years of smoking pot could be why though.

I can attribute most of my failures and shortcomings to a seemingly easy decision to stop going to school. I was accepted to Simon's Rock College of Bard, an early college for high school students who feel unchallenged, at 16. I feel like I couldn't even get accepted again now that I'm 21. That haunts me every day.

I'm getting my stuff together now, kinda, but I've lost so much. I hope one day I can get back on track to where I would have been, but now I have a daughter and soon a wife...so I don't know. Every day I look up and realize how much potential I've lost. I could be in an Ivy League school. I could be making six figures in two years, whereas now I will just be transferring to an engineering school—hopefully—in a year or so.

Biggest Regrets factsYouTube

#65 Always Be Safe

Not wearing a condom—even though I knew the girl got around a little bit—and contracting genital herpes. Now I have to share my herpes with my wife and she lived a perfectly safe sexual past. I wish she didn't have to deal with it, it's my cross to bear.

Depressed ManPublic Domain Pictures

#66 Sports Are Fun

I honestly and truly wish I had the drive/someone to push me in football. I love the game but football was really lax at my high school and I was a big/fat kid that was used for my size, not because I tried. When I went to college I realized how much I would have loved to play college football but because I never tried in high school, there was no way.

Biggest Regrets factsOffice of the Vice President for Research

#67 A Little Change Can Go a Long Way

Not me, but my girlfriend. She broke up with me because she said didn't deserve me as she ALMOST cheated on me with another guy. She got rid of the other guy immediately though. She told me she needed time to get her act together. I said I'd wait. That was three years ago, now we are happily back together.

adult affection blur boy boyfriend close up couple cute dating daylight depth of field fall field focus fun girl girlfriend grass happiness happy husband joy laugh leisure love man outdoors park people relationship smiling spouse together togetherness wife womanPxhere

#68 Your Other Half

When I realised that I can’t be the same person I was with my ex with anybody else.

girl against the wall girl portrait sad girl portrait free photoNeedpix

#69 Always Have Your Priorities in Order

One of my exes I just never made time for. She was a great girl and we got along well, I just had different priorities at that point in my life.

She brought it up to me twice and put in effort to fix it. She tried scheduling dates, sat me down and talked to me and explained why she was feeling hurt. And I'd change for a week. But then I'd go back to my old ways. I just wasn't committed. I had other focuses, namely my career. Finally, she just said she still enjoyed my company but couldn't call seeing me once a week for 2-3 hours a relationship.

Even after, she tried to stay friends, but the time between my responses got longer and longer until eventually I looked at it and her last text was from over a month ago. I felt too ashamed to respond, though I probably should have.

I don't blame her. She had needs that I was not paying proper attention to. So I guess it's more like she broke up with me, but she didn't want to and only did so because of my behavior. I forced her hand by just not being around.

The important thing was I learned from it. I learned I needed to pay more attention to my partners. I learned that just because I am very long-term focused does not mean that I can ignore the more immediate concerns and justify it with "I'll pay it off in the long run." And that is a lesson that has led to greater success in this area since then.

Girl Looking At Phone, Girl Portrait, Outdoor SceneryPixabay

#70 Blinded by Beauty

I was a stupid kid. A really hot girl decided she wanted to date me, so I broke up with the other girl to date the hot one. Hot girl turned out to be shallow as heck and we broke up not long after starting. Other girl ended up being basically my dream girl. Absolutely beautiful, smart, funny, great personality, down to earth, etc. She and I remained friends for a long time, but even though she still had feelings for me, she wouldn't actually get back with me because she never trusted me again.

beautiful-girl-with-long-hair-and-pretty-eyes.jpgGood Free Photos

#71 Cherish Those Around You

An ex of mine. It’s a long story, but she still haunts my dreams. While we don't talk anymore, we did clear the water a couple of years ago and I got closure, mostly. So I'm not going crazy over her, but a part of me will always miss her. She's a hole in my heart that I carry proudly, as weird as that sounds.

I'd like to add, as I totally missed the point of the question, was that I regret the way the relationship went, and not her. She's the best thing that ever happened to me, and I'll never forget her.

Biggest Regrets factsSoha

#72 Sow Those Oats People

Not sleeping with more people while I still had the chance. I'm 31 and married.

Biggest Regrets factsEarnest

#73 Math is a Wonderful Thing

Not studying math properly in school. Turns out, it's the only thing that matters in this world.

Biggest Regrets factsYouTube

#74 Sex Isn’t All That Matters, Buddy

Someone I know left his wife because he felt the intimacy was awful and he wanted someone with whom he felt he could have great sex. Wife pleaded with him to stay (no kids) but he refused and filed for divorce.

Divorce is finalized about a year later. This guy dates lots of women, but still finds the sex unsatisfactory.

Meanwhile, ex-wife meets this other guy about a year after the divorce and they have that type of whirlwind romance that truly is like something straight out of a rom com. She marries this new guy, they have kids and the perfect marriage. She tells everyone that the divorce was the best thing that ever happened to her and can't believe how happy she is and could never have previously imagined that a marriage could be so wonderful.

The guy, who is my friend, is more miserable now than ever. Constantly says what a mistake he made leaving his wife. Doesn't even go on dates anymore and has not had intimate relations in years.

Image result for divorceNeedpix

#75 I Dare You to Screw Up!

I dated a girl I had a lot of chemistry with, and I dumped her on a bet from my friend because I didn't want to come off as "whipped." Honestly, I don't think we would have worked out in the long run, but it still felt like an awful place to end.

Sad Boy, Coffee, Sad ManPixabay

#76 Major Return on Investment

When I was 16 I briefly dated a girl who was 17. She wasn't in my peer group; she was an "outsider." But she was nice, had curly blond hair. I liked her. She had an old 1970 Cadillac and she let me drive it. I had never driven before, so maneuvering that giant boat on the narrow streets of town was... fun. After a few months, my friends were bugging me about why I was wasting my time with this girl. She didn't smoke or drink or listen to hard rock. So I let us drift apart. She turned 18, graduated high school and then won the New Jersey state lottery for $6M. I should have stayed with her. My friends were all bums.

Image result for 1970 cadillacWikimedia Commons

#77 Don’t Get Around Much Anymore

It hit me when I noticed that two years had passed and she's still the last person I'd slept with.

adult asleep bed free photoNeedpix

#78 Don’t Sweat the Small Stuff

I broke up with a woman I was head over heels in love with over something that, on reflection, was fairly minor. Spent half a year progressively dropping into a deeper and deeper funk. Wouldn't admit it to myself, but I had clearly made the wrong choice.

I was hanging out with a friend when she pointed out to me that she had never seen me as happy as I'd been when I was with my SO. Another friend pointed out that same week that the music I'd been DJing had become much more depressing over the past few months and asked me if something was wrong. That woke me up and made me realize how special she had been. It took another year for me to realize she was the first woman I'd really loved in the way you come to love somebody for who they are, rather than what you imagine them to be.

I never saw her again. I wish I'd never left her. We only would have had six years together, as she came down with cancer that eventually killed her. It didn't change how I felt; I'd take those six years with her in exchange for all the years I have left if I could.

beach, couple walking, golden sunPexels

#79 It’s Not You, It’s Me

I was dating this girl for three and a bit years, and we were doing great.

We left university and she got a job and I didn't get one (for a little while). I got pretty depressed during this time. I went to the doctors and got some help, but it was too much of a strain and I couldn't cope, so I ended the relationship on a very bad day.

I got better and tried to get back in contact with her, but she never contacted me back and ignored me. It makes me extremely sad sometimes as I haven't found anyone else and don't think I will. It's been two years now since and I still get the urge to try something, but I know it's best for her if I don't try.

She has most likely moved on and is in a better place without me.

Image result for guy alonePixabay

#80 What Are You Waiting For? Block Him!

I was the dumped one.

Guy and I had a good connection. I actually really liked him. We had a lot in common. But he ended up ghosting me.

A year and some months later, I get a text and it's him. He's asking how I am. I get the vibe he's looking for a hookup. But I'm in a relationship and tell him to leave me alone.

He still stalks my Snapchat stories on a regular basis.

man holding smartphone, phone, cell, customer service, contact us, model, hipster, mobile, telephone, communicationPxfuel

#81 Sudden Change of Heart

In this case, I was the one who was dumped but I love telling this story.

Got dumped by text by this girl who I'd really, really liked for about a year. We were dating for a while when she decided to end it via text with no explanation at all, although I found out the next day she was seeing her ex all the time we were dating. A month after that, I won the lottery. Never seen someone backtrack as quickly. Told her to get lost.

Regret Breaking Up FactsPixabay

#82 Life Is Totally Unpredictable

I ended it because of school. We planned on getting back together after he was done with school, and I planned on talking to him during summer break. I never saw him or spoke to him again, though, because he died just before the semester ended.

12 years of friendship, eight years of dating. It seemed like a good decision, and I missed him, but we were doing pretty well. And then I got a call from one of our mutual friends. He told me to sit down, and he gave me the news.

It might have been the right decision at the time, but I regret not calling him, texting him, telling him the whole thing was stupid and that I missed him too much during those nine months before he died.

Image result for sad girlFlickr

#83 Point Noted

Do not become an attorney. My soul is dead.

overwhelmed, stressed out, burned out, freak out, call out, break out, job, office, work, humanPxfuel

#84 Well, That’s Encouraging...

I followed what I love. Now I hate what I love. I have no interest in 12-hour daily monotony to collect pennies to buy garbage. I wake up everyday and just wait until I disappear into sleep again. Who cares what you pursue. Money is nothing. Fill those landfills and cash in.

Image result for girl looking windowFlickr

#85 Getting Your Hands Dirty

I got a degree in civil engineering and worked as a geotechnical engineer for five or six years. I HATED always being dirty. I couldn't keep my nails clean. Couldn't wear nice clothes. Had to be in inclement weather all the time. Had to wear safety hats and vests all the time. I couldn't be feminine at all. I mostly just hated working in the rain or the scorching heat most of the time. I also had to travel constantly. It's hard to have a relationship when you're never home to meet anyone, plus I had a dog.

I quit about two years ago. It killed any upward mobility I had in a career.

engineer architecture construction architect civil estate working autocad real business building blueprint ad compass detail drawing project technology archicad architectural background calculator contractor design desk divider element engineering hand holding home house industrial industry measurement meeting object office paper paperwork part pencil plan professional ruler sketch table tool white workplace learning job writing writing instrument accessory homeworkPxhere

#86 Anti Social

Being a social worker sucks. It pays crappy and the jobs I've had have either taken my entire soul and still paid horribly, or been boring and useless and paid crappy while I constantly get yelled at by mentally ill people. I am currently trying to figure out how to leave the field because I dread coming into work every day.

Woman Sleeping on Mattress Covered With BlanketPexels

#87 Say Cheese!

Don’t go into photography like I did. It's oversaturated right now because everyone nowadays thinks they're a professional photographer with their digital cameras. It's especially hard if you’re looking to get editorial or advertising work. Super competitive and you have to almost know someone at an agency or magazine already.

Image result for photographerFlickr

#88 Grief is a Bad Dream You Can’t Wake Up From

Three years ago my father passed away. In the months leading up to his death, he had been struggling with idiopathic pulmonary fibrosis—his lungs were turning to scar tissue and no one knew why—and had been working with Duke Medical Center exploring the possibility of a lung transplant. He had just returned home from a multi-day battery of tests and examinations there and was feeling pretty good about his chances when he fell ill with what appeared to be pneumonia and was hospitalized. He was having difficulty breathing (well, more than usual) so he was put on a ventilator.

Very late the previous night I had returned to my own home, about an hour from the hospital, after a long car trip and was still tired from the journey when I received a call from my mother explaining the situation. We agreed I'd visit the next day when they had more information on his condition and he'd had a chance to settle in.

That evening his doctors decided to put him into (what was meant to be) a temporary drug-induced coma; he was fighting the ventilator and in a lot of pain, and putting him under would give his body a chance to rest and hopefully heal as the machine did his breathing for him. A few days later he was airlifted from the local hospital back to Duke Medical, where he was reevaluated as a transplant candidate. His application was rejected because his condition had deteriorated so far that the transplant board didn't believe he'd be able to survive the procedure or the months of rehabilitation that would follow.

We made the decision to put him out of his misery and take him off life support, and my mother and brother and I watched him pass away. Our decision ended up being validated by how quickly his body gave out; it took less than five minutes for him to go. The staff didn't even have time to bring us snacks.

Did you know that hospitals provide cookies, crackers, soda, etc. to the families of patients waiting to die? I didn't. We thought it was kind of funny, even at the time, but the nurses explained it usually took hours for someone to pass on after life support was shut off, and those waiting usually got hungry.

Two things bothered me about the manner of his passing. One was personal, and what I consider my greatest regret even though I strive to live a life free of them: I didn't make the effort to go visit him the day he was hospitalized. I hadn't known it at the time, of course—no one did—but it would have been my last chance to speak to him. The second was a sort of outrage on his behalf: he had been full of hope about getting his disease permanently managed and returning to some semblance of a normal life, but he got sick; then he was put under with the assurance it was just temporary, and he'd be woken back up in a few days—I took lots of pictures of him getting wheeled out and loaded into the chopper, to show him the adventure he'd been on without knowing once he woke back up—but he never woke back up. It hurt that I didn't get to say goodbye, but it hurt much more that he didn't get to say his goodbyes, to anyone. It took me a long time to get over that.

That night, after his body was taken away for cremation, my now-smaller family returned to our nearby hotel suite and I slept on the sofa in the main room, letting my mother and younger brother take the bed. In my dreams—and I rarely dream—there had been some kind of mistake; my father came to the door of our hotel room and laughed at how inept the hospital had been, mixing him up with someone else, now go help your mother pack so we can go home. I woke up and stared at the ceiling of the hotel room and everything felt wrong for a while until I was able to sort out the difference between dream and reality once more.

Biggest Regrets factsAboutIslam

#89 Hallelujah!

The average career of a new minister (in my denomination at least, but similar in most American Protestant churches) is five to seven years. The education required is a minimum of seven years—Bachelor’s and three year Master’s program. Your first congregation, unless you are amazingly lucky, will be either in the middle of nowhere, falling apart and cannot afford a better minister, or both.

Congregations are aging to death so there is no fresh blood and no new money. You spend so much time and soul trying to help people feel something in their lives to the point where it can become easy to forget to feel your own. Your colleagues vary wildly from great people to arrogant sociopaths who crave attention and power. Guess which ones are in leadership? It’s all very tiring which is why I quit—but it was like losing a dream, a lover, and a career all at once.

Priest, Church, Blessing, Cassock, PloverPixabay

#90 A Family Matter

I’m in cosmetology. I live in the suburbs of the suburbs and work in a small town salon. Granted my mom owns it, but still...

I hate working for my parents and so often I feel payday is just a pat on the head for being a good daughter.

Image result for cosmetologyFlickr

#91 Self Reflection is Growth

I've got plenty of regrets but I'll share my most recent one: Not treating my girlfriend better. I see now that I didn't appreciate her enough, I really didn't trust her enough. There are so many times where I wish I could take back something, kept my trap shut etc., etc. I'm torturing myself.

I go over and over in my head what I wish happened instead. I loved her with all my heart and I still do but she's left me. I’m a wreck right now, I'm extremely unhappy and wish so many things in my life were different. I don't know what to do. Or rather, where to start.

Biggest Regrets factsIndependent

#92 It Pays to Remember Every Action Has a Consequence

I'm 35. I spent the latter part of my high school life doing too much partying and ended up selling drugs which ended up derailing me from my plans for college and a career. I ended up getting in trouble with the law and getting trapped in the system. I did two stints in prison as a result of my mistakes and have only been out and well since the end of 2009. Now I have to navigate the world with a criminal record, which includes two drug felonies.

I never really thought about the consequences of my actions while I was screwing up and honestly was in such a strange state that I didn't think about living long enough to deal with my mistakes.

Now I am in a good place in life with a wonderful wife whom I love more than anything. I have mended all of the bridges that I burned during my madness and life is good but those mistakes I made when I was younger will never go away.

Man Looking Outside Near Clear Glass WindowPexels

#93 When One Door Closes

Dropping out of a full-ride scholarship engineering program to become a full-time pothead working with kids. Things have changed, now I’m in the field without the degree so it all worked out. I’m getting the same pay as if I graduated the school.

Biggest Regrets factsThe Modern Man

#94 Career Choices Are Hard

I'm 28. I wish I had developed a more concrete plan for my career earlier. I sort of had this strange assumption that if you get a degree from a respectable college it would make numerous avenues of employment available to me.

I'm trying to break into a field that has nothing to do with my degree and I have no relevant internships either. It's a serious barrier to overcome despite some reasonably impressive credentials I have obtained outside of college.

Biggest Regrets factsPro-Essay-Writer

#95 Not What I Signed Up For

Don't let the reason you go into something be that you are curious about it. You shouldn't be "curious," you should know as much as possible about the thing.

You should know what "insert job title" actually does on a day to day basis when you choose that path. Because your impression of what it's like may be completely—completely—off. You might not even have a real image of it, you just think it might be cool. That's that curiosity again—eliminate it. Educate yourself about what someone in the middle of "your" supposed path would be doing and actually consider whether that is something you personally would enjoy.

Take anything and everything into account, think through it, then decide. If doubts come up, re-evaluate. It may never be too late, but it is always better to change your mind sooner.

Woman Closing Her Eyes Against Sun Light Standing Near Purple Petaled Flower PlantPexels

#96 All That Effort, No Reward

Don't start a PhD without being 6prepared and aware of the stress you're going to put yourself into.

I don't regret doing it per se, but it's a serious and much bigger commitment than many folks realize.

Image result for graduationFlickr

#97 Conforming to Societal Norms Means No One Wins

I'm 31. My biggest regret is saying yes to a marriage proposal when I was 23 that caused me to waste a good part of my 20s engaged to someone who I knew wasn't a good match in the first place. I did this heavily because of family and outside pressure.

Biggest Regrets factsVIX

#98 You Never Stop Learning

Not paying enough attention in high school. I barely passed and didn't actually learn much of anything. Going to really regret that one.

Biggest Regrets factsGifted Challenges

#99 Marriage Isn't for the Uncertain

I'm 30. I got married at 21. I really wish I'd had the courage to break up with him before we got married. Instead, I walked out a year after the wedding. I'm sure he hates me now but if he knew how disastrous my love life was for eight years after, he might get some peace.

From the alcoholic who almost hit me that one time, an older man, to the washed-up wannabe musician who lied about his height to the second older guy who wanted to be with me but couldn't handle it but did I want to move to Australia anyway?

I have somehow ended up in a healthy, loving relationship, but darn, I have some seriously bad romantic decisions I regret.

Biggest Regrets factsBlikk

#100 Times Have Changed

I went to law school, passed the bar, then realized I didn't like being a lawyer. I regret it, but a lot of the reasons I didn't like it were due to personality changes of getting older, so I don't think that I could have predicted my feelings in any way.

Now I own a piece of paper worth more than my house and work in a traditionally underpaid industry trying to dig myself out.


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#101 Rising Above the Crowd

After high school, I started working at a factory. Lathes, welding, shipping/receiving. Was good pay ($16/hr) and I advanced to management positions in a few years. For a non-skilled laborer, 35-40k a year was great.

I hated going to work everyday though. I hated most of the people working there, 20+ year lifers who thought the company owed them dearly because they had been there so long when, in fact, they were easily replaceable by someone off the street and a couple weeks of training. Someone actually eager and willing to work. I liked the company and they really cared about their workers, but the entire culture was very toxic and not somewhere I wanted to be. So I studied for hours on the side (working 12 hour days), took any certification courses I could, and moved three hours away from friends and family to pursue my passion. Four years later, I'm making three times my original salary doing what I enjoy.

Had I remained doing my original job just for the safety of the salary, I never would have had a career I enjoyed—and many people who did make that choice likely regret it.

My point is that not everyone has the drive to pursue their passion and go out there to try and make something for themselves. You see it all the time in the factories or similar workplaces; people who chose complacency and familiarity instead of pushing themselves. Don't fault yourself for providing them a good opportunity.

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#102 Breaking Multiple Stereotypes

I chose to go into the computer field despite never being that interested in it. I was always "the smart girl" who "could be anything" and therefore felt some sort of weird pressure to go into a certain type of field because I needed to represent our underrepresented gender and not "waste" my intelligence. My personality always pushed me towards what were normally boy hobbies/interests.

I don't even know where all the influences came from, but I always felt like I should not look for a career that was generally "women's work." Of course, this was really just as bad as a woman going into "women's work" because of being a woman, because it blanket excluded fields that I now realize I probably would have enjoyed much much better. I spent high school and some college years working for the public library and I LOVED that job. I have never loved a job that much since.

It's probably what I should have done with my future, but high school me saw that as "women's work" and not "important enough" and thus avoided thinking about it seriously as a career. Of course ten years ago, being a librarian became cool and edgy, so meh on me.

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#103 Never Mix Business with Pleasure

My wife would say, "If you want to be an artist, don't get a Master's of Fine Arts—become a welder. You'll make a LOT more money, and can still make art in your spare time." She has an MFA in Metalwork and Printmaking. She works for a world-class art museum as an Associate Curator and has been there for 19 years.

She wouldn't qualify to be hired for that position now—she'd need a Doctorate. They aren't even hiring SECRETARIES unless they have at least a Master’s, because there are so many Art-Degree Grads out there. I have a "high school, and some college" education. I make more, don't have to work weekends, and can still make art, too.

Image result for artistUSN History

#104 People Should Mind Their Own Business

We tried doing long distance for longer than we'd actually been together in person. I didn't know how hard that would be and ended up breaking it off because I thought that me being attracted to other people was a bad sign. It didn't help that there was a guy seriously preying on my insecurities and telling me I would probably break up with him anyway only because he was trying to get with me. I have regretted it every day once my muddled mind woke up.

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#105 Hopefully This Time Will Be Different!

I broke up with my eighth-grade boyfriend. Regretted it later when I realized how amazing and good-looking he really was. We kept in contact through social media but didn't speak much after. Flash forward ten years, I was back in my hometown and was honestly just looking for a hookup before heading back home. Ended up being the best date ever, we started dating shortly after and now live together.

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#106 Music to My Ears

Getting a music degree is far from the best path to building a career. Were you the best in your city? The best in your state? Top five percentile in international arts camps? Doesn't matter, you probably won't get a gig.

Even the very best music schools in the world have crap job placement percentages.

Here are your options: Join a military band (no thanks) or work on cruise ships for crap pay (did that, it will burn you out fast). You will not get a better gig. If you do, it will likely be the equivalent of minimum wage once you factor in driving, rehearsals, etc—and that's excluding the personal practice time you need to keep yourself capable of performing these jobs.

Or you can hustle for odd jobs as a freelancer, but that means a stressful lifestyle and highly variable income. Good luck having a family...

Do yourself a favor and major in something else!

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#107 A Word to the Wise

I'm about 50. I actually enjoy my work (software product management), but I think I took far too long to land where I am. The internet is full of opinions from the young and mostly inexperienced. I say this because of the number of people who think hard work pays off (this is conditional), or the most competent rise into management (think political races with all the sleaze, lies, etc.).

In short, you need to manage your career. Employers will happily pay you for less and put you into a dead-end job if you let them. In a professional office setting, it seldom matters how much you work, but it does matter about perception. That is probably the biggest thing I learned, and goes against the grain of who I am. I hate beating my own drum, but it's become clear that this is required to move up.

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#108 Only Two Possibilities

Paralegal. The work can be really stressful because you're either dead inside or get too invested in your clients and in trying to keep them from panicking. Add to that that the only upward mobility is really to go to law school... and yeah, not worth it. I did it for four years before having a heart to heart with myself and going back to school to swap careers.

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#109 What Am I Looking For?

I think I was looking for something perfect. I don't know if I was wrong or not. She was a homebody and I'm a very active social butterfly. She also had some depression problems and we both felt like I wouldn't be able to support her in a way that wouldn't come across as me just waiting for her to get better.

Now I just wonder, mostly, if I really know what I want or if I have a romanticized skewed version of love that I'll never really achieve.

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#110 You’ll Always Wonder What If...

It all hit me when my ex died in a car accident. We were married for almost six years. I was so young, had no idea what I was doing. I wanted a divorce and can’t even remember why. Our son was seven. Now he’s 18. He was the kind of man that was good at everything and a very hard worker. A man’s man and a family man. Before he died, we were talking about getting back together. He was my best friend.

File:Dusk with a beautiful sky.jpgWikimedia Commons

#111 Why Does Life Have to Be Like That?

When I started dating other people, I realized I had made a mistake. She was my first love. Two years in, we broke it off as I was heading for college and she was still in high school. By the end of the relationship, I was putting myself way ahead of her in terms of priorities. I treated her like she wasn't as important as she was. Cut to almost ten years later, she's engaged and living across the country. I lost the sweetest, most beautiful, intelligent woman I will ever know. She's the only person I've dated who I ever cared about that much.

Image result for sad manPublic Domain Pictures

#112 Sold a Load of Goods?

I work in advertising, specifically in a Media Agency.

It's not like Mad Men. Sure there are some fun parties, and freebies. However, the pay sucks, the hours suck and you start to become jaded and hate everything you see online or on TV.

Clients also tend to be pretty dumb.

Image result for boardroom presentationPiqsels

#113 Moments of Weakness

I yelled at my grandma for complaining about something—I don't remember what it was, something stupid—because I was tired and it was cold and after midnight on a day I had to wake up early to go teach kindergarten and she was sick.

I woke up 2 hours early to my mother crying so hard I could hear her across the house. My grandmother died about 2 hours after I yelled at her. I still haven't forgiven myself for it and I'm not sure I ever will.

Biggest Regrets factsDr. Jennifer Thomas

#114 My Calculations Tell Me...That This Sounds Pretty Rough!

If going into accounting, do NOT fall into the trap of working for large public firms. Colleges hype them as the best option in the industry, and make it seem like passing the CPA is the only way you will be hired. That, however, is not true.

You are a cog to them. Nothing more, nothing less. You are a means to an end, a machine meant to spit out reports, perform taxes, and never make a mistake. Not only that, but you are easily replaceable. Graduating senior accountants happen every year, after all. Unhappy? Take a hike. Underperforming? They'll try someone else (I’m speaking in generalities here from personal experience. I am sure there are a few good ones, so take that for what it’s worth).

Get out there and learn about all of the amazing careers that exist for accounting. Private, corporate, charitable, managerial, farming, statistical, etc. If there is an industry, there's a position for accounting.

Find what fits you best, and what makes you happy.

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#115 Tough Decisions Hurt

I had a realization about my breakup that has been messing with me mentally for a while, but it's also been an enormous eye-opener because of how unhealthy our relationship was. She validated and encouraged me in everything, but never pushed me. I got complacent in a lot of lazy, losery behaviors because she accepted it, so why should I change anything?

It's taken me a couple months to realize: I didn't break up with her because I was sick of her, I broke up with her because I was sick of who I was becoming and how dependent I was on her to feel good about myself. The simple fact of the matter is that I would never pull myself out of this hole of self loathing if I didn't force her out of my life. That being said, I miss that unconditional support and it is almost impossible to go on at times without it.

It still stings every day, but at least it’s usually always a little bit less than the day before.

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#116 Loving Partners Don’t Grow on Trees

When I realized that it’s more difficult than I thought to find someone that you truly connect with, like we did. And when I realized that dating and having sex with other people really sucks. It’s not nearly as easy and exciting as it looks on TV. It’s really hard to find someone you like and want to be with. We had our problems, but some things about him I can’t find anywhere else.

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#117 Reasons Matter

Law. I feel like I was born to be a lawyer and have a good gift for certain skills that go well with law. But I strongly advise against it UNLESS you want to do it regardless of money/prestige/anything. We already have too many lawyers and jobs can be tough to come by. If you are only in it for "the money," or because you want to do something that sounds good, or your parents are pushing you into it, or maybe you think it will help you get dates, or you are just putting off going into the real world—don't do it!! Don't take the LSATs, don't go to law school, and don't try to become a lawyer.

Like I said before, I am not going to knock anyone who truly wants to be a lawyer because, after learning what real lawyers do, they actually want to do what we do. I do a lot of research, reading and writing every day—not to mention analyzing cases and discussing/working on case strategy and arguments. I personally love it. But if your reason is not that you sincerely believe you will enjoy the actual work for the rest of your life and believe you were meant for this line of work, stay away.

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#118 All Work No Play

Do not go into game development because you like to play video games. You won't make it past the first semester.

Do not go into game development because you like to make games. You might make it through the courses, but the industry will chew you up and spit you out in a year.

Go into game development if and only if you LOVE to make games, and even then only if you don't mind sacrificing your life for the next decade in the name of your love.

Every year, in every CS program across the country, a few hundred neckbeards with poor hygiene flood the first-year classes, and every year...90% wash out of the program as they realize that making games is NOTHING like playing them.

The ones who last aren't much better off: They get to go into an industry with only a handful of good jobs and truckload of bad ones, so the competition is frighteningly stiff. If you don't get incredible grades and make friends with connected people, plan on spending the first couple of years being pushed to your limit to develop crummy games for lousy pay. Games that may never see the light of day. Most of your peers will leave the industry in the first six months. You will, in all likelihood, be among them.

The problem is that there is a whole lotta money to be made in the game industry, so there are a quite a few investors ready to dump money into the first startup that promises the moon and the stars. Those start-ups then get to cut corners and pay fresh grads to chug out a barely-together game at light-speed. You will get calls in the middle of the night saying that the testers found another bug and if you don't turn this trash into gold by the end of the week, you'll all be out of a job.

Of course, if you DO manage to get really good and beat out your competition, someday you might be in a job that is fun and doesn't eat up all of your time without your permission.

But you'll be in the minority.

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#119 Red Pilled

I’m a pharmacist. I went through five years of training, only to be viewed as a shopkeeper. With my degree, I can't just go into another field without starting again, and my wife would kill me. Every day I go into work my soul erodes away…

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#120 So... You Regret It Because He Was Nice, or Because He Got Rich?

Back in freshman year of high school, I dumped this guy who had been nothing but nice to me for a guy who treated me like garbage and played around. The guy I dumped got a new girlfriend not long after, and they've been dating ever since. He turned out to be the class valedictorian, got into an Ivy League college, and was hired by a multinational company. So, that was that, I guess.

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#121 Dreams, Meet the Harsh Reality

Nursing sounds like a great career, but make sure you know what you're getting into. The pay can be great, but you'll be working weird hours and spend a lot of time as the butt of every single problem in the facility. Talk to some actual working nurses. Research the crap out of healthcare worker burnout, and how cost control measures affect nurses.

Know that you are costing your facility money, not making it, and they will make every effort to cut costs on your end. Know that your employer will throw you under the bus at any opportunity. Just do your research before you chose a career thinking you can actually help people, only to instead end up a burned out mess in a couple years because paperwork is more important than actual patient care to your employer.

I would go back to nursing in a heartbeat if I could actually help people, but that's not what most employers want from their nurses.

Image result for hospital nursePixabay

#122 Changing the Course of History

I never had a career path, just jobs, but my regret was hiring university students for casual factory work and then helping them get into well-paid positions within the corporation.

25 years later and they're still in the furniture industry. They were supposed to be pharmaceutical chemists and pathologists and doctors. I wish I'd fired them.

Image result for furniture industryPixabay

#123 Bon Appetit!

For anyone thinking of a career as a cook or chef: You most likely will not become the next Gordon Ramsay or Bobby Flay. Instead of starring in your own Food Network show, you'll most likely enjoy the following:

  • Long hours, little pay.
  • Never having a Saturday night off.
  • Mad knife skills and asbestos hands.
  • Fluency in restaurant Spanish (mas platos!).
  • The pleasure of working with some of the most insane, talented, funny, criminal, medicated, loyal people you'll ever meet.

Image result for restaurateur'Flickr

Sources: , , 



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