Picking a Career isn’t easy, so it’s a bit strange that we basically take a bunch of teens and tell them to make life-altering decisions before they have really even started to live. It shouldn’t surprise anyone that many people reach middle age and realize that they perhaps aren’t where they want to be.

So, perhaps to learn from other’s mistakes, one netizen asked women to share their biggest career regrets and what led to it. From bad educational choices to feeling stuck in a role, people poured their hearts out. So be sure to upvote the most interesting stories as you scroll through and share your thoughts in the comments section. 

#1

I regret that we need “careers”. I have two degrees in Art History but ended up a project manager because it pays better than anything in that field does, at least when starting out. Honestly if one could actually live in the US on minimum wage and didn’t have to worry about health insurance I would go back to working in a bookstore and spend the rest of my days stocking shelves and talking to people about books.

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#2

I'm a pediatrician. I love kids, I love building relationships with families and I love learning. The science of medicine never gets boring - it's always changing, it's interesting, there's tons of variety.

But knowing what I know now, I wouldn't do it. Simply, it's really f*****g hard being a doctor. And sure, that seems obvious on its head. But there are so many lies about becoming a doctor that are sold to med students. In my experience, one of them was that the painful, isolating, and exhausting sacrifice of training will yield a better life.

I don't think that's true. Yes, medical school and residency were peak miserable times of my life, but after training, my work life hasn't exactly been that much easier than training. Even my dream job on paper was incredibly hard - I worked 10-12 hrs a day, was on call all the time, had hours of charting to do every night, and was underpaid in lieu of how much cash flow I brought into my practice. I don't think there's anything wrong with wanting a soft work life, or at the very least, a work life where the stakes aren't so high all the time and the work does in fact end.

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#3

I hated my career so much that I switched careers. Don’t be a teacher in the US. It’s a bad choice.

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#4

I hate my career but it is perfect for my kids (hours, autonomy, flexibility)

I wish I had crosstrained into something I could change to now and be my own boss or WFH more.

I’m tired of what I’m doing. Soul deep tired.

Image credits: Icy-Organization-338

#5

My career is mostly regrets, lol. I regret going to law school. I regret doing corporate law. I regret even doing more public interest oriented law. The only thing I don't regret is eventually striking out on my own.

I think if I had the chance to go back in time, I'd have done something in org psych instead - probably some kind of strategic consulting. Basically everywhere I know who went into that line of work confirmed that it is not easy, and can get stressful, but is ultimately dynamic and *fun*. I would have much preferred that type of career (back when I was younger and had the energy) than something as staid and uptight as the ~practice of law~.

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#6

I’m was recently (late) diagnosed with Autism and ADHD. Had I know this all along I would have made completely different career decisions. I cannot stop wondering (yet also can’t really fathom) how different (better? easier? more fulfilling?) my life could have been.

#7

I wish I had the self-awareness to choose a career that was less overstimulating than teaching. I like a lot of things about the career, but I’m exhausted constantly and it really influences my perspective on life.

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#8

Honestly? I regret becoming a teacher. Its all I know how to do, and changing now seems too much trouble (getting another degree, starting again in the workforce, doing networking, etc). The biggest problem isnt even the kids or classes; its the parents. Millenials and Gen X are trying to not be the strict parents we had growing up and are now swinging in the opposite. The parents are insufferable and we have zero to negative support from them. Its a lot of stress daily, and ive started taking anxiety meds because of this. I dream of getting a factory job lmao

#9

I should’ve stayed away from my business degree and done something that I wanted in the hair or makeup industry. I have a bachelors and masters degree. Sometimes I wish I could start all over again but I don’t have money to pay for school

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#10

Yes- i am absolutely not a people person- I work nightshift in a retirement home.
Wish I had taken up data entry or some such job that limited my interactions with humans.
2997 days until I retire.

Image credits: ContentMeasurement93

#11

I went to law school. I 100 percent wish that I did not go to law school. It was a waste of three years and a lot of money.

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#12

I loved my career, but I do regret it. I’m a chef- but it took so much physically, emotionally, and I missed so much. The pay and benefits were never great.

Image credits: Playful-Natural-4626

#13

All I want to do is work with animals. Those jobs don't pay well, though, and I don't have a safety net if I fail financially. So, I work in operations. Do I wish things could be different? 100% absolutely. But, that's life.

#14

Yes, I fell into my career (Recruiting) and completely regret it. There are days I don’t mind it and actually like it, but for the most part I hate it. It’s a very unstable career - when the times are good, it’s great, but when the job market tanks, it gets really bad. I should have done something more creative, technical, or mentally stimulating.

Thinking of switching careers now, but I don’t know what.

Image credits: heymichelley

#15

I went into business for myself and became a boss, and I hated every minute of it. Never again will I be a boss or own a business especially in this economy.

Image credits: Oldgal_misspt

#16

Yes. I wish I’d followed my heart and gone to school for something I actually love, instead of what would give me the potential for a lucrative career. I’m in a pretty well paying job now but I don’t like going to work, and that sucks.

Image credits: justalilscared

#17

Letting a sense of duty or loyalty determine whether I stay at a job instead of my own well-being. There are jobs that I knew right away were negatively impacting my mental health and I stayed years hoping it would get better or being worried about leaving my coworkers in the lurch. Companies can and have (and will) survive without me. It’s not my fault if they routinely understaff. And my intuition is usually right. If there are red flags I see in the first few weeks, those are unlikely to significantly change. In the future, I will set a timeline and the types of changes I need to see by then if I’m going to choose to stay. If I don’t see them, I’ll have a plan for next steps to (hopefully) move on to another job/company.

#18

Yes. I’m currently working a low pay job for amazing benefits because my husband agreed to take more on money wise. He left me Monday. So now I’m wondering if I can stay in the low pay job and get medical benefits or go get a good job. I regret putting myself in this position. Should have stayed at the higher paying jobs.

Image credits: MaggieNFredders

#19

I regret staying home to raise kids. I need work to occupy my brain. I feel like I have gotten dumber because I stayed home.

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#20

I regret not continuing to only work with big, stable, recognizable firms. I took a chance on a company that was undergoing rebranding and repositioning thinking it'd be really fun and exciting. It wasn't. It failed, and I ended up being associated with a failed company instead of a successful one.

Btw... it failed for reasons unrelated to the re-brand, in case that wasn't clear. Lol turns out they had no money to actually execute the re-brand so... we spent a bunch of money on a logo, effectively.

#21

I wanted to be a doctor when I was in high school, but 17yo me wasn't fond of the path to get there. Mainly, I didn't want to be "stuck" on a 10+ year track, with no way to get off of it without saddling myself with huge amounts of debt.

Do I regret it? Not really. But I did look at becoming a doctor again a few years ago, and wish I had looked back into it a *little* bit earlier, maybe in my late 20s.

I'm in my mid 30s now, and I feel like the door has closed for me. I know I could still do it at any time, as I don't doubt my ability to excel in academic environments, but everything else around it, like opportunity cost, the intensity of residency, the inability to choose where I want to end up for both school and residency - all those things don't sound appealing anymore when I want stability, community and to put down roots. I also know that the grass *can* be greener on the other side, especially in health care in the US, where providers are facing burnout like no other.

If I was to win the lottery tomorrow, I'd likely give it a shot and only apply to schools in areas I'd want to live in, but without the lottery money, it's not worth it since I already make a tech salary that is as high as some doctors.

Image credits: labbitlove

#22

Yes. I'm a teacher, and I'm not happy. I wish I didn't rush graduating when I realized that I wanted to major in computer science. I was already in my third year of college, and I didn't want to spend 3-4 other years at college. I just wanted to graduate on time. Now I look back and regret.

I plan on switching my career. I'm still researching some IT roles.

Image credits: Emeruby

#23

I hated my first career in certain ways. I worked for political advocacy non-profits. The work was often relatively fulfilling but not always. The pay was not great. And the number of insane colleagues and bullies was off-the-charts.

If I had a do-over I may have chosen different majors and tried to go straight from school to UX Research or something that would have been just starting to take off at the time I graduated. However, hindsight is 20/20.

Instead now I’ve made the switch to a relatively well-paying public service role. The change was five years in the making and isn’t perfect, but my savings is already looking a lot healthier and the peace of mind is worth it, imo.

#24

I wish I didn’t get my first job out of grad school which was abusive af, psychopath management, etc. the job ruined my health in ways that I’ll deal with for the rest of my life. I was caught up in competing with peers from school and felt like I needed to stick with this job because it was the only thing I got after graduation. I should’ve had higher standards for myself for how I want to be treated but also be gentler with how feeling like I need to meet certain benchmarks to be “successful”!

#25

I hate my career. HATE it. And there’s a million things I wish I would have done instead, but realistically I don’t think I would have been capable of it at 18. For the most part, I think I made the best choices I could have made given who I was and what I was like back then, so I’ve mostly come to terms with my career field at this point. My biggest regret is staying in a toxic job as long as I did

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#26

I regret thinking that I had to obtain a graphic design job after college (my associate degree was in commercial art)…I heard so much from my parents and teachers about how fine art would turn me into a starving artist. But I didn’t start actually making money until I got back into making art in my 30s. The graphic design jobs don’t really pay much and they’re so much more uninteresting to me.

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#27

Mine is lack of.

I’m a nursing school drop out. I want to go back but all my hard work is down the drain. I’d have to retake everything. Definitely want to do health care just not sure what area. I’d love remote. I chased guys more than my career while I took care of my dad. I make decent money and love my job but I wish I would have finished.

#28

Wish I hadn’t gotten my masters in education and been a classroom teacher. I should have done something totally different. I have learned some valuable lessons from that and was able to travel the world as a teacher though so that was cool

#29

I was an engineering major, switched to a career in medicine.

Some days/weeks/months I think I should have just stayed out of medicine. I’m burned to a crisp.

#30

This is comforting, thank you for asking this. My career is my biggest regret. I’ve spent an upsetting amount of money in college and grad school only to realize they all weren’t good choices. I didn’t know myself in my 20s and I had a lot of childhood trauma to work through. I didn’t even apply to the right grad schools that could have set me on a better track. I gave up on all of it and became a stay at home parent, which I love. But it kills me a little that I know I could have been great if I had narrowed in on the right field. I know I’m above average intelligent and people only see me as a mom.

Image credits: Sea-Psychologist

#31

Not a regret really just I wish that I started working in disability support earlier and found behaviour intervention as a career earlier. I’m 42 and have had a wonderful career so far and been able to meet some of the best humans it’s possible to meet and hopefully helped to make change in their environments and situations for the better.

#32

I would go back and tell my 19 year old self to grow a backbone and tell the bosses of my first few ‘real’ jobs to suck a fat one.


I was scared about making waves, didn’t advocate for myself and was terrified to ask questions. The ’Directors’ were big scary powerful guys in suits with money and connections, and they made sure you knew that. Looking back, a lot of things that happened were due to p**s poor management, bullying, harassment, discrimination and manipulation. There were a number of things I could have done to be higher performing in those roles, but as an entry level employee with no guidance, I had no frame of reference. I know now that those Directors are just average guys with average intelligence and average skill sets with connections to local business networks who were making it up as they went along, but at the time it didn’t feel like it.

#33

I wish I would have stuck with foreign languages so i could be working as a translator or interpreter rn. I still learn languages for fun as a hobby, but i am not professional skill level in any of them. French was my first college major, then I bumbled around for a loooong time and only have a 2 year degree I dont use now ??‍♀️

#34

I regret most of my career. I just kind of fell into it because I couldn’t choose a major and stick with it. Now I work in marketing automation. I should have stuck with my original plan of nursing school because there are so many more paths I could have taken that I just didn’t know about at the time. I thought the only option was working in a hospital, a grocery store, or an old folks home.

#35

Thinking I need to decide on a “forever career”. It only makes me constantly dissatisfied. It’s such a big thing to figure out! Now, I view it as “what can I do in the short to medium term? What supports my life goals/priorities?” I re-evaluate occasionally. Do I need a change? How big of a change - is a slight change in responsibilities enough? Can I talk to other people who do other jobs to see what I might be able to work towards? This also ensures I stay open to new opportunities that I would’ve never thought of. There are so many jobs I didn’t even know existed when I graduated from university and I continue to learn about new ones. Who knows where I’ll end up!

#36

Not getting permanent part-time minimum while pregnant with my first child, I was casual and allowed them to reduce my hours because I was young/stupid and it was my second job I ever got so didn’t really understand what to do or even how to navigate these situations.

I now understand what they were doing was discrimination and i should have taken it further with upper management.

#37

I stayed in the exact same job for seven years in my 20s. I stayed because I was happy, but now I’m realizing it was about five years too long. I should have been trying new things and growing my career. I feel behind now.

I kinda also wish I would have gotten an advanced degree (Masters or law) in my 20s. I know it’s possible now, but it’s a lot harder when I’ve been away from school for a decade and also have to pay my own health insurance.

#38

I regret my degree in Classics, my family told me to study something I liked and become a teacher...oh well, there are not enough jobs for Latin and Greek teachers, so now I'm stuck working a job I hate for a company I hate and it's making me sick.
I should go back to college and study they say...