For anyone who is age 50+, if you could travel back in time to advise your 20-something self regarding careers and you would not change history in a negative way (i.e. if you have kids/grandkids, that would not change), what would you tell yourself?

20 Comments

1. AnonymousFebruary 1,2026 at 1:29PM UTC

   I would take more credit for things. I have been well-suited to roles that keep everyone ELSE’s work running smoothly. Mostly behind the scenes, and so I have found myself without good concrete accomplishments to show off even when I have been effective.

2. AnonymousFebruary 3,2026 at 1:33PM UTC

   Do not concentrate on getting married and having children. Work on making a career and setting myself up financially and being financially independent. And never relying on anyone else.

3. AnonymousFebruary 3,2026 at 2:00PM UTC

   Have a plan: 5 years, 10 years, 20 years. Be intentional of what you want. Don’t listen to what family or romantic partners believe what suits you best. Document everything. And avoid partners who see you as long-term investment for THEIR comfort and security. Gold diggers come in all shapes, sizes, and gender.

4. Diana SchneidmanFebruary 4,2026 at 1:55PM UTC

   I majored in secondary education many years ago so I could take liberal arts courses. Classroom discipline was something that I sucked at. I thought college would teach me how to do it. It didn't. So I completed student teaching, I knew I couldn't do a full-time job of it and I never did

5. GirlBossanova934974February 4,2026 at 4:42PM UTC

   I wouldn't change anything about my career choice or education. The education was rock solid and provided a huge advantage over the years. Never ever underestimate the value of a good education with first class instructors and materials.

   One big regret? Never ever assume there is any loyalty in the workforce. Times change. Managements change. The minute you sense the culture has changed for the worst, be gone! Don't stick around with people pleaser managers.

   Last, do not wait for layoff slips. Transfer, find another company, go back to school, whatever. In my career, I checked out of a few organizations when I felt the financials were going south in a hurry. I was long gone when the layoffs hit.

6. AnonymousFebruary 4,2026 at 5:22PM UTC

   I would tell myself to take advantage of every learning opportunity possible, build positive relationships, never gossip, and set aside a good portion of my salary in a separate savings account. I would not want to change my career, as I am still loving it even at 70!

7. AnonymousFebruary 6,2026 at 1:17PM UTC

   Oh my gosh. I am nearly 60. I made a mid life career change that I wish I had not; Mostly I had made the change due to 'imposter syndrome' and doubting my abilities. So, my advice to my late 30's - early 40-something self would be: Stay the course, until you have tried everything. Network better. Believe in yourself. And for gosh's sake, don't blow up a job for some relationship (that isn't a committed, mutually encouraging, one).

   At 20 something, I was still figuring a lot out. But at 30 something, I wish I knew then that I was as capable as I am, and that I could have succeeded in my original career path.

8. AnonymousFebruary 6,2026 at 1:36PM UTC

   Work strategically to develop you and your career path so you will love what you do and you love yourself. Become self sufficient with investing and assets, even if it’s slow so you don’t need to rely on a job or a person entirely. Set yourself up for the most freedom possible and position yourself in a place where you can make the choices you want because of the choices you’ve made.

9. AnonymousFebruary 6,2026 at 1:44PM UTC

   I would have told myself not to put my life on hold for my kids. I was rising up in my career and had a baby. I decided not to pursue the higher ranks so I can, but now I regret it. While I have NO regrets about raising my child, I had a lot of flexibility, but I really could have done both.

10. AnonymousFebruary 10,2026 at 5:15PM UTC

    That’s very interesting! Most people have the opposite regret. My Mom worked and loved it. She liked me and was super devoted but loved working and being autonomous too. I still have no idea how she managed it all. Our home was spotless, she made beautiful meals, made sure I had what I needed and worked a full time high powered job and managed a weird but lively social life. She was a widow. Because of her example I’ve always worked and even though I’ve been married for over 30 years have maintained my autonomy.

11. AnonymousFebruary 7,2026 at 1:36PM UTC

    I would have followed up on a technology company’s recruiter’s advice to email him with a letter of interest for a sales job. He was already impressed with my sales skills at a large retail store in the 1990s that is still operating but struggling. I’ve worked at the retail store on and off 2x, but switched careers from retail to education.

12. Christi LopezFebruary 9,2026 at 1:52PM UTC

    Oh my goodness...I was a hot neurotic ball of stress in my 20s. Such a perfectionist and so worried about what everyone else thought (thanks, Mom). I wouldn't necessarily change my career path. I fell into secretarial work because I got tired of school, but the customer service skills, the proofreading and computer skills...the confidence that comes with doing a job for 20 years...all of that was a fantastic foundation for my current career as a graphic designer. Everything has landed me where I am, and I'm happy here. I would, however, tell myself that no one cares. It's OK to make mistakes. It's part of learning.

13. AnonymousFebruary 10,2026 at 5:08PM UTC

    Do not get involved in gossip and drama no matter how compelling! Become expert at the things no one else wants to do. Trust yourself and be kind!!! Hang out with the colleagues that are going places and not bitching and complaining. Do not, I repeat DO NOT get involved or condone bullying of any kind. I’ve had several situations in my long career where bullying was happening and I got

    way too involved in trying to

    stop it. There comes a

    time when people have to stand up for themselves. Do your best not to drink at company functions …

    but don’t make a big deal about it. Stay away from idiots

14. BarbaraFebruary 10,2026 at 5:21PM UTC

    Oh!!! One more thing!! Take full advantage of your company’s 401k. Save at least 10% of every dollar you earn and pop it directly into a ROTH IRA. You will not miss the money. Thank goodness for auto deposit! Learn about investing from reliable sources and stay away from get rich quick schemes. Never co-sign for anyone, lend money or buy a house with someone you are not married to.

15. AnonymousFebruary 12,2026 at 2:24PM UTC

    Don't go to law school.

16. AnonymousFebruary 12,2026 at 7:35PM UTC

    I'm curious. Why not?

17. AnonymousFebruary 27,2026 at 2:06PM UTC

    I didn't want to be a lawyer and still have never worked as a lawyer despite finishing law school and passing the bar. It just wasn't what I wanted to do - let my parents talk me into it.

18. WendyRMFebruary 13,2026 at 3:21PM UTC

    If I could do that, I'd tell myself to study interior design or even become a market researcher. However, I'd probably never meet my husband that way.

    I'd tell myself to get out of retail asap. And while admin jobs are a good backup plan, to pursue work more aligned with me as an introvert. I'd also tell myself that while hard work is important, to make connections and network. While networking was important back in the day, it's not nearly as important as it is now. You used to be able to get work on your merits but now it's all who you know. I'd also tell myself to make better financial and health decisions. And to see a therapist who could help with childhood emotional neglect issues.

19. Tami CannizzaroFebruary 13,2026 at 4:04PM UTC

    While I've really enjoyed my career (and still do), there are a few things I wish I'd learned earlier. 1) "Don't turn it down until they make you an offer". In other words, when an opportunity presents itself, don't say "no" until you've actually spoken to someone about it, then followed through until an offer is made. I want to be the one to decide if the opportunity is right for me or if I want to decline. 2) Remember to leave the party while you're still having a good time. It's easy to get caught up in a position/job that you love and miss the fact that you've been there awhile, maybe the company isn't promoting you, after this many years it's going to be harder to pivot to a new company. Time to look for something else. 3) Be a bit more strategic at work if you want to advance up the ranks. I did advance, but it took more time than it should have. I was the person who always delivered vs the person who was more "showy" and caught the attention of the higher-ups. Learned that lesson along the way. 4) One thing I would NEVER change: Be Kind. Always. Especially to those at the lowest levels in the organization. They are the ones who can, and will, help you out of a pinch when you are scrambling. It can make or break you.

20. AnonymousFebruary 23,2026 at 1:42PM UTC

    1) Stay in school! I left school for a job I loved and built a great career in a completely different industry. While I loved my career, I think I could have been just as happy with my original choice (teaching). A teacher's schedule would have made it much easier to raise a family. BTW - I finally went back to school and finished in my 50's.

    2) I would not have said no to the promotion I was offered right after I returned form maternity leave. I had an 8-week-old baby and was exhausted and did not think I could do it. I could have and should have. It took 10 years for an opportunity like that to come along again.

    3) SAVE! I did a mediocre job at saving for retirement and now I'm terrified. Looks like I'll be working until 70 to make up for it.

    As for the rest of it, I would not have changed a thing. I fought for flexible work arrangements back in the 90's when it was not really a thing. I fought for - and created - a Mother's Room to help myself and others have a safe place to pump at work, allowing me to exclusively nurse while working full time.