50 Regrets and the Life Lessons to Learn From Them

After writing the article 6 Ways to Escape Your Regrets, I found myself thinking of the many things that people go through life regretting.  We can all learn great life lessons from each other’s mistakes, so I decided to put together a list.

This list of 50 is by no means a complete list of every mistake you can make in life because nobody can completely avoid screw-ups in life.  It isn’t meant to direct you towards perfection.  However, I believe this list will help sat least one person to dodge at least one regretful choice.

50 Regrets and Life Lessons

1. Saying hurtful words during a heated argument. An argument is usually characterized by two or more people speaking and zero people listening.   Rather than say something that you don’t mean, take the time to cool off so that a productive conversation can replace the emotional outburst.
2. Placing too much value on things. Ina final lecture before cancer took his life, Randy Pausch spoke about how he had his children watch as he poured a can of soda on the seat of his new luxury car. He wanted to let them know that he didn’t worship material things. Things can be fixed or replaced.  If not, we can live without them.  However, there is no replacement when you lose someone you love.  If someone smears chocolate on your new sofa, don’t make them feel bad.  Just clean the sofa and keep moving. If that person died within minutes of the occurrence, you’d regret that you hurt their feelings but you wouldn’t give a hoot about that sofa.
3. Being too committed to a job. No matter what company you work for, you are an expendable resource.  Business will go on with or without you, and if it makes sense for the corporate bottom line—you’ll be thrown out on your ass without notice.  Countless people look back at the end of their career and realize that they missed out on what was really important—because it was not at work.  Don’t wind up bitter and angry because you’ve sacrificed your life to make a living.
4. Focusing so much on the future that you forget to live. Many people have this regret when they become gravely ill, get stricken with a disability, or they reach old age.  Life is always happening right now.  Don’t put off enjoying life until you have more time, more money, the right mate, or a better plan.  Another year, month, day, or even second is not guaranteed.
5. Not showing up when invited. If you knew the Universe had something special in store, you’d show up.  But the fact is that you usually won’t know ahead of time.  Any event may prove to be the opportunity to meet your soul mate, spark up a conversation with an investor in your business idea, or enjoy a final few moments with a loved one before they pass. Nobody can show up for everything, but countless people live with regret for missing a great opportunity when they didn’t have to.
6. Discouraging others from following their dreams. Fred Smith’s teacher gave him a poor score on a paper that he wrote about his idea for starting FedEx. The teacher added that the idea was ridiculous.  That teacher wasn’t the only one to criticize his big dream.  Unlike Fred Smith, many people will give up on their idea if they are discouraged by those whom they trust.  Just because you can’t see how something can work out, doesn’t mean you should push your limited perspective off on another person.  If you can’t offer genuine encouragement, remain silent.
7. Using the word love when you don’t mean it. Careless use of the L word can lead to hurt feelings, misunderstandings, and even fatal attraction-like scenarios.  Remember to truly know a person before claiming to love them.
8. Taking too few pictures of life’s happy moments. Memory begins to fail everyone at some point in life.  Pictures and videos capture those little moments of bliss that we might otherwise forget. Don’t find yourself without visual references that you can share with others as you relive happy times.
9. Not listening during the know-it-all phase. Despite having so little life experience, teenagers and young adults are notorious for thinking that they know it all.  Almost every person over 30 would love to go back and undo some crazy mistake that they made when they were convinced that no older person was worth listening to.
10. Holding a grudge. No matter what the circumstances, it is never worth it to hold a grudge.  Many people spend years being mad at someone who has wronged them, only to realize that the only person hurt by their resentment is them.
11. Being too prideful to say “I’m sorry.” It is hard to forgive yourself when you deprive another person of their right to an apology.  Those 2 simple words, when spoken with sincerity, can heal hearts and mend relationships. If you know you’ve done something that you’re not proud of, don’t hold off on apologizing until it’s too late.
12. Being too afraid to take a chance. Missed opportunities are one of the most common types of regret.  Fear, which never leads to anything desirable, should not be the basis of your decisions.  If that little voice inside says “do it,” you may regret ignoring it.
13. Accepting others beliefs as your own. Much dissatisfaction results from trying to live according to what parents, friends, religious leaders, and society believe is best.  It is pointless to be angry with others if following their lead does not work out for you.  Escape that regret by choosing to discover your own path and learn your own personal truths.
14. Crying over spilled milk. Time spent dwelling over things that you cannot change is time wasted. And most people regret wasting time.  The past has passed, so don’t miss out on the present by focusing on what’s already done.
15. Speaking faster than you think. This is often referred to as putting your foot in your mouth.  You’re less likely to regret what you say if you make sure that thought always precedes your words.
16. Overprotecting children. Trials, challenges, and awkward circumstances are necessary to build strong character.  Overprotected children often turn into adults who crumble under the pressure of life.  But overprotective parents usually don’t realize this until it is too late. Be a safety net instead of a straight jacket.
17. Neglecting friends for lovers. If you cling so heavily to romantic relationships that you forget about your friends, the results can be regretful.  You’ll feel pretty bad when you’ve neglected a friend, only to need them desperately when you’re dumped by a lover.
18. Acting based on past hurts and pains. By failing to heal old wounds, we often create new wounds for ourselves and others.  Deal with your feelings so that you don’t let the past keep you from enjoying the present and the future.
19. Gossiping. We all do it sometimes, but it can definitely get you in trouble.  It sucks to find out you’ve been saying something about someone that turns out to be an inaccurate rumor.  Even if the information is true, spreading it can lead to hurt feelings and anger.  Let others choose how, when, and to whom they want to share their personal information.
20. Telling lies. Lying is the easiest way to lose a person’s trust. You may find that you have to tell a lie to cover up the first lie, and then another to cover that one, and another, and another. As it spins out of control, you realize that the first lie wasn’t worth the headache.
21. Doing anything that you have to lie about. If you know you’ll have to lie about it, it’s probably something that you’ll regret doing. 
22. Being an enabler. You may look back and regret that, in a well-intentioned attempt to help someone, you only enabled their demise.  Sometimes the best way to help a person is to step aside while he finds his own inner strength.
23. Tossing out memories of past relationships. In a fit of post-break-up anger, it’s not uncommon for people to destroy everything reminder of their ex-beloved.  Tossing out cards, gifts, souvenirs, and pictures often brings temporary relief from hurt and anger.  It feels right in the moment, but you may find yourself wishing that you had just put everything away until you were rational enough to decide what you’d like to hold onto.
24. Choosing a job or career for the wrong reasons. Because most people spend more waking hours at work than at home, life feels miserable when you don’t like the way you’re making a living. You’ve set yourself up for regret if you choose a career solely based on money, influence from parents, or any reason other than that you’ll enjoy it.  Doing what you love and it won’t feel like work.
25. Neglecting your body. The body will slowly fall apart if you don’t give it proper care.  Ensure a better quality of life by eating right, exercising, visiting the dentist regularly, and getting annual medical check-ups.
26. Not speaking up. There are times when keeping your mouth closed is for the Highest good, but there are times when speaking up is difficult yet necessary.  You’ll regret pretending not to know the difference.
27. Losing sight of the fact that life is supposed to be fun. All work and no play creates a boring life with very few, if any, amazing memories that make it all worth it.
28. Not expressing your feelings to loved ones. It’s not fun to be the person speaking through guilt while expressing their feelings at a loved one’s funeral.  Let people know how you feel before it’s too late.
29. Holding back the tears. Some people are so opposed to crying that they will hold tears and pain inside until it surfaces as physical illness, violent anger, or deep depression.
30. Saying yes when you want to say no. Being a yes girl or a yes guy can lead to feelings of overwhelment and resentment.  
31. Borrowing things that you can’t pay back. Ruining your reputation as a trustworthy person is always regrettable.  This can damage friendships, family bonds, and your credit score. Find a way to do without those things that you can’t really afford.
32. Not caring for your elderly parents the same way they cared for you. Some people experience this regret when they are neck-deep in guilt after a parent’s death.  Others don’t realize this regrettable life choice until they become the elderly person who needs care. You were born unable to care for yourself, so remember who was there.
33. Following all the rules. Following rules is a part of everyone’s life.  Rules make it easier for us to live and work together as a society, but you have to know when to break them.  If you don’t do what you feel is right simply because it is against some rule, you’re likely to look back with a heart full of regret.  The same is true if you do something that you know is wrong simply because it falls within the rules.
34. Sticking to the plan. Some people enjoy planning out every detail of their life.  There is nothing wrong with this if it works for you.  However, you may feel like kicking yourself if you miss out on a marvelous opportunity because you were too afraid to stray a bit off course.
35. Not saying thank you. If you overlook the need to show appreciation, you may find that people are less willing to offer you something to appreciate in the future.
36. Taking for granted those dearest to your heart. It can be unbearable to look back at your neglectful behavior when your spouse or partner leaves you, your children resent you, or one of these loved ones dies. The assumption that certain people will always be there for you is not an excuse to be lazy in showing appreciation. Don’t wait until your family falls apart to show them what they mean to you.
37. Impulse shopping. Unless you’re rich, you’ll likely have a time in your life where you buy something you don’t need or can’t afford.  Writing lists and setting budgets may take some of the fun out of shopping, but it can also save you from financial regrets.
38. Trying to do it all. When you end up with 10 sloppy or mediocre project results, you’ll usually wish you’d said no to half of them so you’d have 5 that made you feel really proud.
39. Worrying too much. Every moment spent thinking of what could go wrong is a complete waste of time.  Most issues work themselves out just fine, thus you look back and shake your head at all of the time you spent worrying about it.  Even if a problem doesn’t’ work out the way you’d like, you’ll regret adding an additional layer of unhealthy stress by worrying about it.
40. Remaining in a relationship for the kids (or for money, security, etc). One great way to make life miserable is to stay in miserable situations.   If you’re in an unhappy marriage just for the kids, chances are the kids are unhappy and they are learning a sad lesson about what is normal for relationships.  If you’re with someone just for money, you have put a price tag on your happiness.  And you can’t learn to be truly secure if you’re relying on another person to give you the illusion of security. End dead-end relationships.
41. Knowingly causing harm to another person (emotionally or physically). Any person with a conscience will feel bad about taking actions that they knew would hurt an undeserving person.
42. Forgetting to take care of your inner self. Although many people neglect their body, even more people neglect their inner self.  This allows unnecessary problems that result from allowing stress, confusion, anger, fear, and anxiety to fester.
43. Giving up. If you have not yet experienced watching someone else accomplish something that you gave up on, intend to avoid this.  There is no reason to give up as long as you are still breathing.
44. Leaving (jobs, relationships, family) on bad terms. There is a saying that the hand you bite today may be connected to the ass you need to kiss tomorrow.  In other words, always leave on the best possible terms because there is no way to know if you’ll need that person for something in the future.
45. Teaching children what to think instead of teaching them how to think. This is usually done with great intentions, but the result is a sad one.  There won’t always be a parent, teacher, or other guide there with the right answer at the right time. Young people need to know how to think for themselves in order to make important decisions as they get older.
46. Jumping into a relationship because of everything you like about a person. Everyone has some likeable qualities, but commitments are about dealing with both the good and the bad.  If you don’t know what irks you about a person, you don’t yet know them well enough.  Avoid regretful romances by taking the time to discover what you do not like about a person—and then deciding if you can live with it.
47. Sheltering your heart too much after it has been broken. If you fail to properly heal after heartache, you may destroy the next relationship with your inability to “let go.”  Losing a great love by your own fault is deeply regrettable.
48. Only doing what seems rational. If people didn’t use their imaginations to dream the big dreams, there would never have been an industrial revolution.  We wouldn’t have cars, braille and hearing aids, computers, airplanes, or heart transplants if it wasn’t for thinking outside of what seems rational.  By always following what makes logical sense, you may miss out on your chance for greatness. Dream big!
49. Betraying a friend. True friendship is one of the most valuable gifts one can ever receive.  Those who make choices that lead to the loss of a friend, find themselves living with the pain of regret. Honor your friends and follow the golden rule.
50. Making promises that you cannot, or will not, keep. Although there may be hurt feelings, people will easily forgive an outright refusal.  However, the scar runs a lot deeper when you say yes and then break your word.

If you are having trouble dealing with regret, please take the time to read the self improvement blog post, 6 Ways to Escape Your Regrets.

Tagged as: Emotions, Life lessons, Regrets