51 Things Not to Do in Your 20's

Michael Loren


Photo by Jamie Street on Unsplash

There is an entire movement in the educational community that champions learning through failure. There are stacks and stacks of books about failure — Failing Forwards, Failing Up, How to Fail, and just plain Fail. And this is all for good reason. One of the most effective ways to learn something is through failure. However, there are also some things I wish people had told me before I screwed them up.

I did a lot of things right in my first full decade as an adult, but I also did a poopload of things wrong. I got married because all of my friends were doing it. I grossly underestimated the importance of my health. I got myself into a ridiculous amount of debt (largely because of aforementioned deadbeat husband). The long and the short of it is that there are a few things that I wish someone had told me.

If you’re reading this right now, you’re a veritable stranger to me (no, not you mom). I know that, for all of my life, if someone I’m close to tells me to do something, I automatically rebel against it. (“Michelle, why don’t you wear stockings to church?” produced bare legs for a good six months).

Strangers, however, have always held a little traction in my life when it comes to advice. Perhaps because I can be assured that strangers don’t have any ulterior motive for offering up suggestions. So, if you would be so obliged, allow me to be your omniscient stranger from the future with a few recommendations on how to live your best life.

Without further ado, let me present to you 51 things that I either royally or slightly screwed up in my 20’s and how to avoid the same mistakes in your own life.

  1. Don’t think that you will have only one career in your lifetime. You may want to be an architect and only an architect for the rest of your life, but I guarantee you that you will have another job title (or ten) in your time on this planet. More careers equals more sources of income equals more trips to the Maldives.
  2. If you have not invested money in some sort of account that will compound interest, stop right now, take whatever cash you have (even if it’s $100) and invest it. If you start putting away $100 per month when you’re 20, you’ll have half a million dollars ($506,240.60 to be exact) to play with when you’re 70 (assuming a 7% return). If you start when you’re 40, you’ll only have $117,706.
  3. Don’t make assumptions as to another human’s socioeconomic status based on their current job, appearance, demeanor, or any other factor. More times than not, the most influential people don’t broadcast it. Be kind to EVERYONE. NO HUMAN is unworthy of your time and attention.
  4. Buying shots for everyone at the bar is a small jolt of adrenaline followed by months (perhaps years) of financial regret. Just don’t do it unless you won the lottery.
  5. Your friend’s significant other is forever off-limits romantically. You can try to work your game to win that prize, but you’ll soon find out that if you DO succeed, you’ve won the dummy prize. Because you’ve won over a person that is willing to leave the person they’re currently with. And then don’t think it won’t happen to you in the near future.
  6. Don’t stop talking to your family. If you’re lucky enough to have family that is alive and willing to talk to you, please regularly call your mom/dad/sister/grandma/whomever. Do it while you’re driving or washing dishes or hiking. They won’t care. Just keep in touch. Time flies and they won’t always be around.
  7. Do not wait to travel until you retire. The older you get the less things you are able to do. Have you seen a 70-year-old zipline through the Amazon or climb an alp? Probably not. Travel everywhere. See the world. The sooner you understand the points of view of the many different people on our planet, the sooner you can make it a better place. Also? You’ll look better in a bikini on a Greek island in your 20’s. Which leads me to . . .
  8. Unless you are required to do so, do not feel obligated to dress sensibly. Wear all of the short shorts and midriffs. Bust out your guns at the beach and wear the highest platform shoes you can find. Live your best stylish and risqué life. You never know what life will bring and you will likely never be as hot as you are right now.
  9. When it comes to your opinions, you may change your mind, but the internet is forever. If you have some wildly offensive, rude, or controversial things to say, consider keeping them out of print.
  10. Don’t delay chasing your dreams to get a “real job”. No matter how much your parents or grandparents may say it, there is no such thing as a “real job”. Any job that pays you cash money is a job. You do not need to immediately get a 9 to 5 with benefits to validate yourself as a human. Pursue what you want to pursue. The 9 to 5 can wait.
  11. Do. Not. Live. Off. Credit. Cards. Debt is enemy number one! If you have any debt now, pay it off and never get into debt again. Obviously, student loan and mortgage debt is way better than credit card debt. Credit card debt is the devil! Step away now before you’re drowning under a mound of $40K or $50K in debt and all you can pay is the minimum payments.
  12. Don’t be afraid to ask questions. It’s okay to not know everything. In fact, the people that pretend that they know everything actually know the least. If you don’t understand something, speak up. (It’s also likely that if you don’t get what’s going on, somebody else doesn’t either).
  13. Do not skip the sunscreen. Charred skin was in style in the ’80s and skin cancer is never in style. Sunscreen in your 20’s is significantly cheaper than botox in your 40’s. It takes two minutes. Just do it.
  14. Adventure is everything. If you have an opportunity, take it. Do not think that you’ll get it again. Learn to scuba dive. Go white water rafting. Try unfamiliar cuisines. Anything that you try that doesn’t kill you makes you a more interesting person.
  15. Let all of your family BS go. Let it go. Get yourself a therapist and get rid of that baggage. Whether it’s their expectations of you or their judgment of you or their treatment of you. Let it go. Whatever it is, it’s most likely in the past and you have an exciting future that is of your choosing. The sooner you let that go, the sooner you can move confidently in the direction of your choosing.
  16. Don’t forget to get your teeth cleaned. See #13. Teeth cleaning in your 20’s is less expensive and painful than root canals in your 40’s and 50’s.
  17. Take a chance on love. Put yourself out there 100%. You might get burned, but it is absolutely worth it. Nothing wagered, nothing gained. And, you never know. Someone you don’t end up romantically being with in the long run might turn out to be a lifelong best friend.
  18. If you live in a country that allows you to be a part of choosing their government, DO NOT think that your vote doesn’t count. It does. It matters immensely.
  19. Don’t marry the first person you consider marrying. Marriage is a serious commitment and if you even have a little bit of doubt about it, you should wait a while. Also? If your friends and family don’t like him, her, or them, then you should consider that to be a red flag.
  20. Stop complaining. Do something instead. Complaining not only saps energy that could be more usefully spent on action, but it also spreads negativity. Yes, it’s nice to vent. But if you must complain, put a time limit on it. Say your peace and then take action.
  21. Never ever make an important decision when you’re tired, hungry, or angry. Give yourself 12 hours and then revisit. There are very few decisions (short of life-threatening emergencies) that can’t wait to be made for a half of a day.
  22. Don’t lie. About anything. It just takes up too much energy. You need to remember what you said to whom and when. It’s exhausting. And even if you remember, you might be outed by the internet.
  23. Do not have a friend group that looks just like you. Look around your parties. If you look like you could be related to everyone in attendance, you need to diversify your friend group. Your friends should be different colors, sizes, and ages. And if they aren’t, then that’s on you.
  24. Don’t drive drunk, high, or while texting, shopping, or any other crap you do on your phone. If you’re under the influence, Uber, Lyft, or sleep on a friend’s sofa. It’s not worth it. At all. And, if you’re compelled to do something other than just driving, turn on a podcast or dictate the next great novel into your phone. Just don’t look at it. I know it’s tempting.
  25. Discipline is a skill that crosses all boundaries. If you learn to delay gratification in order to reap larger rewards in the future, you will be more successful than your immediate gratification-craving contemporaries.
  26. Don’t live like you’re camping out. Your environment is such an important part of your emotional well-being. If you need to save money, bust a move. Sleep on an air mattress. But, after a few months, you need to buy some grown-up furniture.
  27. Don’t skip out on the journal. You can chronicle your exciting adventures as well as reflect on the present and your present state of mind. Journaling is meditative but it also serves to solidify the seemingly intangible thoughts in your head.
  28. Refrain from pulling out your phone to chronicle that last shot of the evening. Instagram and Facebook stories don’t magically disappear in 24 hours if your “friends” film them with their phones.
  29. Don’t be afraid of any kind of love. Explore loving whomever you want and graciously receive love from anyone willing to give it. Love is love is love. And there are a lot of people without it, so give it and receive it while you can and in every way that you can.
  30. Don’t forget to say thank you. We all hasten to post the terrible review when we have a bad experience, but how often do we write positive reviews? How often do we tell our postal workers, our bus drivers, our friends, our neighbors, our teachers, and our coworkers how much we appreciate them? Gratitude is a gift that not only benefits the recipient. It also benefits the giver.
  31. Bridges are not meant to be burned. Inevitably, you’ve spent some time building said bridge. And, in some way, shape, or form, that bridge connects to a human being (or an organization run by human beings). Human beings are fallible. There are very few things that cannot be worked out. And you never know where you’ll go in the future. You might need a bridge to get there.
  32. Don’t neglect your ten-year plan. If you don’t have one, get one. You must know where you’re going in order to get there. You might have some detours along the way, but, as Seneca said, “If one does not know to which port one is sailing, no wind is favorable”.
  33. Don’t be a mean girl. Or a mean guy. It feels good to belong to a group of people, but making fun of any other person erodes your soul from the inside out. And that includes anything you put on social media. Even if you don’t know the other person.
  34. Don’t go through life without seeing the big picture. Every action has a consequence. Every day is a part of a larger arc that is your life. Look down the road. Look around yourself. And connect the dots.
  35. Don’t ignore physical injuries. Do the dumb physical therapy even if it takes a huge chunk out of your day and you think that it will heal anyway. It might not. In fact, it probably won’t. And you won’t notice it until twenty years down the road when your right knee is only useful to tell you if it’s raining or not.
  36. Do. Not. Give. Any. Craps. About. What. Other. People. Think. I have spent my entire life as a people pleaser. It’s exhausting. And guess what? Chances are, they’re not thinking about you anyway. Why? Because they’re too worried about what you’re thinking about them.
  37. Don’t ignore your elders. They know stuff. If you can shove your ego to the side for a hot second and listen to folks that are older than you, you might learn something that will help you in the future. Worst case scenario, you learn nothing, but you have given another human the opportunity to feel heard and valued.
  38. Don’t say “yes”, “maybe”, or “I don’t know” when you really want to say no.
  39. Whatever you do, do not let another human determine your future or deter you from pursuing your dreams. And yes, that applies to the hot boy/girlfriend whom you believe is way out of your league who wants you to put off going to the college of your dreams because he/she/they want to rent an RV and pursue their music career while driving around the country using you as groupie bait. Wait. Just me? Okay.
  40. Along those lines, do not follow another person on their pursuit of a dream unless you are positive that they will reciprocate in the not-so-distant future.
  41. Don’t settle. Ever. For anything. Unless it’s for good cheese. Settle for all the good cheese.
  42. Never assume that anything is too hard to learn. It may take you more time than other people, but you can literally learn anything. Bitcoin, aerospace engineering, tightrope walking, or Swahili.
  43. Don’t act like you’re in your 30’s, 40’s, 50’s, or 60’s. Do you know why? Most of them wish they were in their 20’s. Your 20’s are a time to explore and screw up and everyone is okay with that. You have time to be curmudgeonly when you’re older.
  44. Don’t hook up with your college professor, TA, director, boss, or manager. I don’t need to tell you why. You know why.
  45. Never ever turn down an opportunity because you don’t think you’re “ready”. If you are being offered an opportunity, then you’re ready. Nothing is ever perfect. You will figure it out along the way.
  46. Don’t be afraid to listen to opinions that are different from yours. Listening to the other side of any issue can only inform you more. Sure, some people’s information is faulty (always fact check), but knowledge is power in every way.
  47. Don’t assume that you can change another person. The only person that can change another person is that person. And, if you try to change another person and they don’t change, it’s not your fault. The only thing you can control is yourself and your reaction to the world.
  48. Be present. Always. Yes, you should remember the past and plan for the future, but if either of those ever becomes more important to you than the present, you’re doing something wrong.
  49. Don’t assume that you will make it to your 30’s. You probably will, but the fact of the matter is that you should live every day as if it is your last.
  50. Drink water and eat things that are good for you. This doesn’t mean that you can’t ever eat McDonald’s and drink tequila. But, overall, you should be doing more of the former and less of the latter.
  51. Don’t do what everyone tells you. And that includes this list of things. You are your own special and unique person who was put on this planet for a specific and important purpose. Live your own life. Carve your own path. And squeeze every little bit of life out of this decade.

At the end of the day, your 20’s is the time to live your best life. YOUR life. Not anybody else’s. And if you’re going to fail, fail brilliantly.

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Professional writer and journalist with concentration in data analysis. I specialize in interpreting data to give you unbiased, understandable information related to the state of California.

Los Angeles, CA

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