29 Life Lessons I Learned In My 20s

Imagine you have the chance to meet your younger self for coffee. You wait for her to show up at a Starbucks (because in 2002 they're literally on every corner in Chicago). You raise an eyebrow as she pours a packet of Sweet‘N Low into her Vanilla Latte, then glances at your left ring finger. The two of you shoot the breeze for a while before things get real. And when they do, maybe this is what you'd say...

1. You're not fat. 

Let's get this out of the way first. I know everyone says this to young people, but that's because it needs to be heard. If you can find a way to save yourself the hours you'll spend judging yourself for various things that don't matter, just imagine what you'll be able to accomplish with all that extra energy.

2. People won't like you better if you're skinny. 

Or maybe some will, but in the end, trust me, they aren't the people you will like. (By the way, I'm talking about both the men and women in your life.)

3. There will always be someone more attractive, more accomplished, and more interesting than you. 

But …. very few people will rock your Kentucky accent with an occasional stutter. Rely on what's real and go for others who do the same. Your social life will turn out just fine.

4. Stop worrying. Just stop. 

Your life is moving in the right direction and even if you fall behind all your friends and screw up big time, you may one day be more grateful for the screwups and setbacks than for the accomplishments. You'll doubt this a lot, and it will always be true.

5. Just because you doubt something doesn't mean it's untrue. 

Sometimes the truth is complicated.

6. When a 9-year-old girl (who you’ll babysit in a few years to help pay for grad school) emails you a poem she wrote, save it.

Once day you'll wish you still had it to send that back to her when she's 19 and worried about the direction of her life.

7. In fact, when anyone sends you a poem, a story, a song, or a drawing, save it. 

Send it back to them one day. Note: this does not apply to love letters. Never send those back.

8. Although it may seem counterintuitive now, fat-free does not mean healthy. 

In fact, calorie-free is probably even worse, and in a few years, everyone will realize that Olestra is the worst invention of all time. And spray butter is a close second (maybe tied with Sweet‘N Low).

9. It's a really good thing you won't get that ad agency job in Chicago. 

You're confused and trying to get into media through the wrong door. Don't take this too hard, it's just not for you. And let's be honest: it's a really good thing you don't get every job you don't get.

10. And while we're on this topic, maybe you shouldn't take that random sales job at Banana Republic. 

It's just not your thing. You'll have no reason to buy all those business casual clothes they’ll make you wear, and eventually the manager will kindly ask you to resign because it'll be obvious you feel guilty asking people to sign up for a store credit card. You'll also be really terrible at giving enthusiastic feedback in the dressing rooms. Like I said, it just isn't your thing.

11. When your instincts tell you to follow someone, do it. 

One day, you'll show up for an interview at a progressive little magazine in Chicago and that will be your thing (it will also be the thing that leads you to MindBodyGreen). And when a 60-year-old woman in torn jeans laughs at you for being "too dressed up" (you’ll be wearing a discounted skirt suit from Banana Republic), laugh with her. She’ll become a dear friend who will try to persuade you again and again for the next three years to leave work in the middle of the day to eat sushi and go to the movies. Go with her. This will never get you fired and, one day, she will put you in her will.

At that same job, you will also meet a girl who listens to Cat Power at her desk all day. One day, she’ll ask you to drive with her across the country, to San Francisco. And as crazy as this will seem to everyone you know, trust yourself and go with her.

12. Trust yourself. 

Knowing when to trust yourself will be the hardest and somehow simplest thing you learn.

13. Pick a passion. 

When you get to San Francisco, people will immediately want to know what you're passionate about, and anything relating to "your career" will not be an acceptable answer. You may find yourself saying various things off the cuff like "writing!" and "literature!" and "travel!" just to have an answer, but one day it will all be true. Funny how that works...

14. People who proclaim to be the most spiritual will probably have the most work to do. 

This is OK, and it’s OK if you aren’t that spiritual.

15. There's no need to preach what you're learning, just live it. 

Because I once heard a meditation teacher say this about spirituality and family: "They hated me when I came home as a Buddhist, but loved me when I came home as the Buddha."

16. People who judge the most are usually the most afraid. 

Folks with the strongest opinions usually have something to hide. Don't take these things personally; some days it might be you, too. Let intense emotions be your guide.

17. It's OK if you get back together with your ex-boyfriend again and again and again. 

You aren't wrong. He's wonderful, but some mistakes need to be repeated until they're truly learned. You won't know until you know, and nothing will convince you otherwise. Not even opinionated sisters or 10 girlfriends with multiple bottles of wine.

18. Be wary of drama. 

Intense passion does not automatically mean you're soul mates. Just that you'll be exhausted in the morning.

19. You will always feel better after a yoga class. 

Trust me on this one.

20. Do not go on that one yoga retreat in India. 

But do go on that other yoga retreat in India.

21. Travel to foreign countries whenever you get the chance. 

For one day your curiosity may become overshadowed by a simple disinterest in things like crowded hostels and sleeping in the smoking car of an overnight train through Kerala. This shouldn't depress you. It just means you'll take a different kind of journey, a little less often.

22. Say what you mean. 

This will be good advice after six years of living in Northern California where really important words like gratitude and vulnerability and openness and will be used so frequently their meanings become diluted. So don't subscribe to a way of speaking just because it works for others. Be specific and real.

23. When someone describes you as a feminist, don't assume you’re being insulted. Same goes for: reserved, direct, or hard-to-read. Years later, you may understand these words as compliments.

24. Facebook is going to be huge. 

Right now you don’t really know what that is...you think it’s a "college thing." It will redefine everyone's ideas of connection and self-promotion (and inspire funny little narcissistic words like selfie). But you should never view it as a place for comparing your accomplishments (or lack thereof) with someone else's. See it for what it really is: a giant well of aspirations, not anxiety. Maybe it's just a billion people posting snippets of a life they're hoping for.

25. Moderation is not boring. 

Some of the wildest and craziest people you know will later find themselves in rehab or teaching yoga. (Which is partly why they'll be some of the best teachers!)

26. Be curious about yourself. 

For as impossible as it seems, it’s actually possible to hold onto grief (and a plethora of other uncomfortable emotions) for a decade without knowing it's there. Not a clue.

27. Therapy isn't just for crazy people and unhappy married couples. 

Everyone could use a little of it. When a woman offers to crack you open for $100 an hour, say yes. Some days it will be incredibly unpleasant and most days you'll be broke because of it, but in the end, trust me, you will be the luckiest person.

28. Risk a lot for love. 

Although it may seem counterintuitive now, avoiding a broken heart is not a victory. (The walls you'll have to build to protect yourself from this would need to be impossibly thick and isolating). So figure out how to make that happen.

29. But seriously, don't think too hard or worry too much about any of this advice. 

You won't know until you know and nothing will convince you otherwise, not even me, who is actually you. That's the thing about your 20s...

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