Don’t you sometimes wish you knew then what you know now? Here’s a letter full of career advice from my 42-year-old self to my 22-year-old self.

Dear 22-Year-Old Self: Hi! How are you? I’m fine, except that I haven’t gotten much sleep lately. I’m pretty busy these days, at 42. I have a kid (You won’t believe me but it’s true. Suffice to say you will actually meet someone you like enough to have one with) and am working full-time, in an office, during the daylight hours. So, no, you won’t be working in bars and freelance writing forever. You will get up before 7 a.m. on the regular (in winter that’s before the sun comes up!). I know your mind is officially blown right now, so I’ll give you a second to gather yourself.

Right then, moving on…

I’m writing this letter on the off-chance that time travel is ever invented — in which case it already exists, of course – because, now that I’ve got 20 years of hindsight and experience, I’d like to share some career advice that could give you hope and save you some frustration and disappointment.

So, here it is, even though I know you won’t listen.

1. Listen. You’re not as smart as you think you are. Right now you think you know everything but when you get older, you’ll realize how much you have to learn. Save yourself some time and start listening now.

2. Ask questions. Don’t be afraid to admit you don’t know something. Allowing others to teach you isn’t the same as admitting you’re stupid.

3. Pick your battles. Not everything is worth fighting for, even if it feels important at the time. If no one will be hurt and you won’t lose anything major, consider letting it go. This isn’t the same as letting people walk all over you.

4. Say “Thank you.” A lot of people are going to help you out over the years. Be sure to be appreciative and never let the opportunity to say a heartfelt “Thank you” pass you by.

5. Say “I’m sorry.” If you fly off the handle or say something you shouldn’t, apologize. People will respect you a lot more for admitting you were wrong than for pretending you weren’t.

6. Your grumpy, nasty boss is a normal person trying to get through life, just like you. If someone is treating you badly, remember that they have their own thing going on, their own worries, their own job that they are just trying to get done, and that they’re doing the best they can with the resources they have available. Be nice. Do your best. If it’s not enough, there’s nothing you can do about it.

7. Don’t talk about people behind their backs. Like a lot of people, you join in the workplace gossip and trash talk because it makes you feel like you fit in. But this is the worst way to fit in. If the realization that you’re unfairly maligning someone who is not around to defend themselves isn’t enough to stop you, then the realization that higher ups who don’t approve of this type of behavior might be listening should be.

8. Because someone doesn’t like you is not a reason not to like them. Likeability is one of the most important traits you need to get ahead in your career, and it takes work. If you don’t dislike people because they dislike you, they won’t dislike you because you dislike them, and this whole stupid cycle will end. These days, I dislike hardly anyone, and I don’t care who doesn’t like me.

9. Everything is worth doing well. Even if the work sucks, do it with enthusiasm and with a smile, and do your best. It will go faster and be more enjoyable for everyone.

10. Don’t let failure discourage you. You will fail more than you can possibly imagine. You will fail so much you will wonder if you will ever succeed. Keep trying, even when you want to curl up into a ball and give up forever. You won’t succeed in the way you imagine, but you will have many opportunities to redefine your definitions of failure and success.

11. Be available. Reply to emails. Follow up when you say you will. Say “Yes” whenever you can. Do people favours. If you can be helpful, be helpful. People will be grateful if you go out of your way for them and will be more willing to go out of their way for you. Not always, but sometimes. And the thing is, they might not always remember every time you said “yes” but they will never forget the time you said “no.”

12. Keep promises. Keep your word. Meet your deadlines. Again, people won’t always remember when you keep your promises but they will never forget that you broke one.

13. You’re not above having to prove yourself. And you will have to do it again and again. You’re not above working for free to do this. It’s OK to swallow your pride. You’ve got too much of it anyway.

14. Count to ten. OK, count to five, before you react. This will save you a lot of later embarrassment. You will meet a lot of people over the course of your career who you will think are colossally stupid and you will not hide it well. Hide it, because you will later realize maybe it wasn’t them who were stupid. Also, it’s just generally a good idea to think before you speak.

15. Stop worrying. Work is a stupid thing to stress over. Actually, everything is a stupid thing to stress over. Things will go wrong and yes, sometimes it will be your fault. Worrying about this won’t stop it. So, you might as well relax.

That’s all the advice I have for now, Younger Me. (Oh, on an unrelated note: don’t shave your head that second time, and don’t date the tattoo artist. He’s a jerk.)

Write back if you have time. Take care!


What career advice would you give your younger self? Share it with us in the comments.