The Path NOT Chosen....YET: 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.