21 Things You'll Regret Every Time


Living life "with no regrets" is often said in the context of looking back, as if it were purely about a way of viewing things you've done in the past. But what about taking a more active role in living with no regrets?

Living well is an art, and there's no playbook on how to do it. But just like there are certain Decisions You'll Never Regret Making, there are some that many people almost always do. "Not reading this list" might just be one of them…

1. Sending an email when you're angry

You want to hit send so bad. You've had time to craft the perfect response. George Costanza's "jerk store" one liner. Your finger rests on the enter key, promising to deliver an immediate catharsis. Right? Wrong. Just wait — the Internet isn't going anywhere. Take a breather and come back to it in an hour, or if it can wait, a day. Still want to send the email? Fine: that probably means that it's strategic, and will do more for you than provide a transitory relief for your frustration.

2. Sending a naughty text photo

If you thought sending angry emails was all about instant gratification at the risk of longterm risk, just think about the downside of sending this… Unless the recipient ends up being the person that you will indeed spend your life loving and trusting, you've put yourself in a very compromising position, figuratively and literally. And if the person on the other end does end up being your life partner, you'll have plenty of time to show them the genuine article in person anyway.

3. Cheating on your spouse or girlfriend/boyfriend

Besides the obvious moral failings, there is just no outcome from this that works out well. Either you get caught and face the external repercussions, or you get away with it and face the internal guilt.

4. Telling off your boss upon quitting

If you've never fantasized about telling your boss off, you either work for an incredible person or are self-employed (or both!). It's normal. And yes, it would feel incredible to reenact this fantasy when you're quitting and have nothing left to lose. The problem is that you do. Networks like LinkedIn and Facebook mean that your industry is smaller than ever, and word gets around. So maybe try fantasizing about how successful you'll be at your next job instead. (See also: 10 Fun Ways to Leave Your Job)

5. Putting off an artistic passion

It doesn't have to be a career and you don't have to be good at it, but allowing yourself a little time each week to scratch that creative itch can provide immediate mental benefits: relaxing, refocusing, and exercising your brain in a different direction. Conversely, depriving yourself of a hobby you're yearning for can be mentally taxing, causing resentment towards the people and things that are otherwise monopolizing your time.

6. Not spending enough time with loved ones

Very few people on their deathbed wish they had spent more time on TPS reports.

7. Making all your vacations about relaxing, instead of adventure

You work hard, you're stressed, and sometimes you want to lie on the beach. Sure. But when you're on said beach and a local offers to take you on a tour of a hidden waterfall, or your travel buddy wants you to come shark diving with him… go. Naptime is beautiful but it doesn't last — memories and photos with a great white do.

8. Under-budgeting a trip

This doesn't mean, "go on expensive vacations." Plan the trip you can afford, of course. Just don't be unrealistic during the planning face and lowball yourself — you'll end up spending the entire trip agonizing over each additional $3 margarita (well, at least while you can still feel pain).

9. Forgoing sunscreen

Speaking of painful trips…

10. Lying on a resume or job interview

Like cheating on a loved one, this type of cheating can also only lead to two undesirable outcomes upon getting the job: 1) your employers find out and fire you, or 2) they don't find out, and you spend every waking moment living with the specter that they may find out.

11. Staying at a dead-end job

Working at a job you hate can be a necessary evil if it's getting you somewhere. If it's not, every day you stay there has potential to become a regret. Get out! …Just don't lie on your resume to get a new one.

12. Holding grudges

Even the verb "holding" implies that it requires effort on your part.

13. Extensive self-deprecation

There's a time to be cute and poke fun at yourself, and a time to be confident and sell yourself. Know the difference.

14. Letting irrational fear dictate a decision

Fear can be useful – indeed, evolution designed it as such. "Run away from a charging mastodon." "Lock your doors at night." Theses are fears that have value. But irrational fears — often those that are based on embarrassment or on the perception of others — can be dangerous, and can lead you to avoid risks that, looking back, you'll realize weren't really risks at all. (See also: You're Blocking Your Own Success -- Here's How to Stop)

15. Not approaching that beautiful stranger

See "irrational fears," above. Rejection shouldn't stick with you. The thought that you missed out on your soul mate might.

16. Taking Latin

It's a dead language. Yes the classics have value and yes and it will help you on your SATs, and no, it's still not worth it. Learn a language that lets you interact with living human beings instead.

17. Dropping out of school for no good reason

Some very famous, very successful people have dropped out of school. And some of them didn't even have a reason beyond knowing it wasn't right for them. But at least that's a reason. If you don't know, don't drop out. Even if you're forced to take Latin.

18. Not telling loved ones how you feel

You may have less time with them than you think.

19. Letting friends you love slip away

Friendships can run their course and that's OK — this doesn't mean you need to perpetuate every relationship with everyone you've ever cared about. But being busy isn't a good reason to let those you do care about slip away.

20. Perpetuating dead friendships

People change, circumstances change. Appreciate friendships for what they were and be thankful. Don't spend time and energy on those friendships that are no longer meaningful to you in the present.

21. Taking that last shot at the bar

Go home, you're drunk.

Vehemently disagree with one of these? Wholeheartedly endorse one? Let us know in the comments — you may regret not speaking your mind!

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Guest's picture

Have you even studied Latin? Because just from this statement, it sounds like you have no idea what you're talking about:

"It's a dead language."

Perhaps dead in the sense that it is no longer widely spoken, but trust me it's living in countless languages today. Studying Latin will give you the tools you need to better understand the grammar, vocab, and syntax of all Romance languages.

"Yes, the classics have value and yes and it will help you on your SATs, and no, it's still not worth it. Learn a language that lets you interact with living human beings instead."

Coming from someone who scored in the 96th percentile on the GRE and graduated with a MA at the age of 22 and is now putting my writing skills to good use in a successful career, I'm living proof that studying Latin is worth it. One former tutoring student of mine was an excellent Latin scholar and he received a perfect SAT score. Now Ivy League schools are fighting over him. So excuse me if I think that academic excellence is "worth it."

As for the social interaction argument, working closely with my fellow classical studies scholars was a great way for me to make friends. We formed study groups, hosted potlucks, and debated the merits of movies like 300 and Gladiator. Many studied abroad for politics or archaeology, and continued to make long-lasting bonds with others.

The rest of your points make sense, but this one doesn't deserve to be on your list. Learning Latin was one of the best things I did in college, and I don't regret it one bit.

Joe Epstein's picture


Unfortunately, I did indeed study Latin as well. And I do indeed regret it.

Like your friend, it helped me immensely on my SATs, which in turn helped me immensely with college applications.

I still wish I took Spanish. Or Chinese. Or any language -- all of which could also encourage study groups, potlucks, movie watching... -- that would allow me to interact with millions of other people across the world in their native tongues.

But if taking Latin worked for you, I say macte virtute! Factum optime! (I never said I was good at it.)

Guest's picture

Hi Alyssa,

I understand your point of view, but personally I'm on Joe's side. I studied Latin as well and I regret it now. I went to school in Germany and when you chose Latin you were stuck with it until your graduation. So when you end up not liking it, you just had to swallow that pill and continue with learning the language.

I do have to say it's pretty cool that in a lot of languages you can find words and sayings that are based on Latin and may makes it easier learning other languages. But then again, Italian and Spanish are very closely related to Latin as well and have these words and sayings in a similar fashion too.

I would advise people to learn it when they are a big fan of the culture and the Latin history and maybe want to do something with that as a career choice.

For me it's not beneficial for my career choices and hobbies and it never happened that I got the opportunity to use my knowledge of it. Except maybe when going to a museum. But I still wish I could've taken back all these hours of hard work learning Latin and using the time to learn Spanish or something else instead.

Guest's picture

So many people fall victim to telling off their boss once they quit. Its just so foolish because you are likely to need their help in the form of a reference, or maybe even a change in plans and a need for your old job. Even if you were unhappy with your boss, its always best to be professional.

Joe Epstein's picture

Couldn't agree more. It's so tempting, and so ill-advised.

Guest's picture

I TEACH Latin, and I really, really resent this article. Latin improves students' thinking skills and helps them to easily make connections with all the other Romance languages. I never studied a word of Italian but I understand a fair amount of it when I read it or even hear it, because I am proficient in Latin. And it definitely expands people's English vocabulary. Seriously, I usually like the articles on here, but I am angry enough right now to never read one again. You are contributing to the downfall of classical studies and it doesn't need any help because so many people like you have that attitude.

Joe Epstein's picture

Well I hope you're not Mr. Edbrook, my wonderful high-school Latin teacher, because that would be awkward.

Guest's picture

I think I can agree fully with all of these, EXCEPT #16.
Granted, I've never tackled Latin myself, but for anyone interested in linguistics or classics, I cannot believe that it would be a waste of time.

As to living languages- who said it's either/or?

Joe Epstein's picture

A waste of time? Definitely not. There's value in Latin.

But in the majority of pre-collegiate American school systems, it IS either/or: scarce resources means students aren't taking multiple languages.

So my point is only that there's MORE value in some other language options, if you're forced to choose.

Guest's picture

Another former Latin student here who has no regrets about 4 years of Latin in high school and 2 semesters in college. I was a lousy student but had great teachers, whose enthusiasm and education had a good effect on me. The vocabulary boost extended beyond English to Spanish and German; the cultural background (incl. ancient Greek history and literature in translation) and interaction with other classics students lifted me a notch or two intellectually. It's not for everyone, but knocking Latin does not belong on this list. As a substitute, I'd suggest "Not learning a second language" (especially when you're young).