Secrets I’d Share With My 20-Year-Old Self

Hint: No One Knows WTF They’re Doing.

My little sister turned 20 on Sunday. So I sat down to write her a letter and I realized how many things I wish I knew when I turned 20. 

I wondered whether I should even write her a letter revealing all those mysteries – would I be holding out by not sharing these insights?
Or would I officially be an old person pushing unsolicited advice on her?

Ah, well… I guess we’ll find out, won’t we?

It felt like I’d be robbing her of lessons learned through an entire decade of mistakes and triumphs if I didn’t share some of the lessons I’ve learned. So here they are – just as messy as they felt when I uncovered them. 


“My dear not-so-little bean,

Happy 20th Birthday! 

You made it through two whole decades!

Watching you grow up is truly one of the most beautiful things I’ve ever witnessed – and you’re really just getting started. I cannot wait to see what you continue to uncover and create.

I remember turning twenty so, so well. It’s such a particular time in life. Mom always said, “Your twenties are a new childhood.” And while I always believed her, I definitely didn’t understand what she meant until I went through it myself.  

There are so many things I wish people would’ve told me when I was twenty. So here’s what I wish I knew. 

Will it be annoying unsolicited advice from an older sibling who thinks they know better? I hope not, but I’ll let you decide. 

Maybe you’ll have to learn all these lessons yourself and telling you won’t be the same. But I think I should try, right?

1. Don’t discount your feelings – This. Is. So. Important. 

It doesn’t matter if your life looked pretty good on the outside growing up. You still had things happen to you that hurt, that made you feel small, confused, or lost. Look at each of those square in the eyes and give yourself permission to feel whatever follows. 

It’s essential to your growth. 

Don’t spend years dismissing your feelings as too small to matter. That only makes them bigger and more complex. The faster you let yourself feel all the feels fully, the faster you’ll learn from them and heal.

You’ll feel lighter in your body.

The secret is you’ll be genuinely happy if you look at all this, let it go, and cultivate true happiness within yourself – not because someone tells you, you should be happy. 

2. Remove “should” from your vocabulary – Seriously. Get rid of it.

There’s very little in this life that you really should do in a broad sense (and you’re probably doing it). When someone is using the word should with you, they’re usually (and unknowingly) pushing their beliefs on you. Push back. Think for yourself. 

And when you use should on yourself… it doesn’t usually feel great, does it? It’s usually flanked by guilt and shame, like two thugs. 

When I started paying attention to how I used this word, and how others used it with me, my mind was blown.

Pay attention to this little but powerful word and try to cut it out of your vocabulary. I guarantee you’ll reap benefits from this. 

3. Explore, explore, explore – Do what you can to see the world now (well, maybe not right this second, lol). 

Not only for the experiences you might not get to have later in life, but to build your internal trust.

One of the best things you can do is cultivate a deep sense of trust in yourself – in your ability to figure things out. 

This a profound level of confidence no one can help you with but yourself. 

You have to intentionally choose situations that feel scary time and time again. Each time it gets easier and each time you come out on top, you’ll look back and start to think, “damn, I’ve got this.” And the world becomes less confusing, less scary, and the sense that you can do anything (which you can) will continue to grow.

You’ll figure out that you’re unstoppable.

4. No one knows WTF they’re doing – This was one of the biggest and best realizations of my twenties. Everyone is winging it.

And the world isn’t really run by adults. It’s run by large children riddled with unresolved childhood wounds. Adults are just bigger kids with more responsibility. 

This might not sound like the best realization but I’ll tell you why it really is wonderful. 

First, when you realize this, your empathy grows and you’ll start to take things less personally. You’ll begin to realize most people’s reactions have little to do with you and are reflections of their own experiences.

Second, there is no reason to be intimidated by anyone – they’re just trying fit in, feel loved, and heal their own wounds. (The more I’ve met and worked with prominent people, the more I’ve seen this. No one is immune.) 

Third, very few things are absolute truth, yet, you’ve just spent two whole decades being told things by “adults” as if they are truths.

When you know this, it’s easier to speak up for yourself and create a life that’s best for you. 

Which leads us to…

5. Question everything – And I mean, EVERYTHING. 

  • Every belief you have about yourself
  • Every sensation in your body you’ve been calling some emotion like anxiety, etc.
  • Every path you’ve been lead to believe is noble or worthy
  • Everything.

So many things you’ve been told are not necessarily true. They’re just things the generation before you have come to believe to be true. They pass these on and without taking the time to examine them, you end up adopting beliefs that aren’t really yours. 

6. Traditional 9 to 5s are no longer the safest bet, so build a life you truly love – You’ve heard me go on and on about this one (lol) so I’ll spare you the details. 

Just do what you love. Follow inspirations. Make changes that don’t make sense to other people.

Also, keep in mind careers with high prestige often aren’t the ones that fill up your soul.

Life is too short to build a life around the opinions of others.

Build whatever the hell you want and people will come around. They’ll see that you’re sparkling and wonder what secrets you’ve figured out. 

7. Know that you can *literally* do anything – Think bigger, right now. 

Every dream you have is totally possible. And I’m willing to bet you aren’t dreaming big enough. 

Write down your dreams. Say them out loud every day. Take baby steps in the right direction – and you’ll be amazed at what happens in your life. It’s not big changes that shape your life, it’s little daily actions compounded over time. 

Your life will literally change around you. And one day you’ll wake up and have to remind yourself that your current day-to-day life was once your dream. 

8. Know that your body listens to your thoughts – I’m going to be that annoying older sibling for a second and call out the people in your generation a bit (cue eye roll, lol). But this is important. 

The words you choose matter. Saying things like, “I hate you” jokingly to friends or “I’m dead” when something is hilarious, it’s all taken in by your subconscious. 

It may have been funny as a teenager but it’s time to pay closer attention because no matter the tone of voice, it plays a role in your subconscious. I’m not saying get rid of all sarcasm, I’m just saying pay close attention and get rid of anything that’s unintentionally weighing you down. 

9. Be ok with outgrowing friends – Up until now, most of your friends were picked for you. Not necessarily intentionally but they were usually the closest people –  in the neighborhood, in class, or in the dorms. But they aren’t necessarily the people who are doing the same internal work, asking the same questions, and encouraging you to grow. 

It’s really ok to outgrow your friends.

Look for people who really love you for you. And there’s a lot to love, my dear. 

Look for the ones who are constantly trying to better themselves – those people are precious beyond words.

10. It’s ok to be messy – There were times when I ignored my intuition solely for the sake of maintaining my appearance. This was a mistake. Being a perfectionist isn’t nearly as beautiful as being raw and true. 

11. You can contradict yourself – You can be it all. 

Science-nerdy and creative. Soft and fierce. Hilarious and serious. 

Stretch into the limitless potential of human personality.

12. You can completely change your mind – At any point. Seriously. 

Even if you’ve been saying something adamantly for a while, even if it became part of your identity, and even if you’re about to walk down the aisle. You can always change your mind and follow your new path. 

Each time you listen to your own inner knowledge and choose what’s right for you, magic happens. 

13. Ultimately, listen to yourself more – Starting with this letter. These are truths for me but they may not be truths for you. 

If there’s anything I wish for you, it’s that you take your 20’s for yourself. 

To heal wounds, to challenge yourself, grow your sense of self-worth, and return to who you were as a child before all the conditioning took hold. 

I was so mesmerized by your last few years of high school. 

Remember, how I always teased you about your teenage angst? 

It was because I sooo related to you. I remember feeling that way myself so well. I’ve come to believe those angst-filled years are when we start choosing which parts of ourselves we hide and which parts we share. It’s exhausting. 

Your 20’s are a time to return to your full expression of yourself. To feel calm, sure, and light in your body. 

Hopefully, armed with this insight, it won’t take you all the way until your 30’s to do so. 😉

So go create wonderful, magical things. And continue to amaze yourself at what you can do and how you can grow.

Onward and upward.

It truly gets better and better every year. 


One Comment

  • Trevor Smith

    Wow! I was recommended to you by a friend of mine that desperately wants me to start writing for myself. After reading this and becoming ever so emotional, I realized you have incredible talent as a writer, and that I am so ecstatic to be able to read your work. I look forward to reading so much more!

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