9 Things I Wish Someone Had Told Me In My Early 20s

Want to hear a crazy fact? One that I can’t quite seem to really wrap my head around yet?

I’m turning 29 next week.

I know what you’re thinking: you’re not THAT old... Lot’s of people have turned 29 and continue to do so every day.

Yes, that’s totally true. And honestly, it’s not even that I think I’m super old. What I’m most perplexed by is how quickly my 20s seem to have gone.

I remember one of the several nights I spent celebrating my 21st birthday (hey you’re only 21 once, right? Gotta do it up!) while I was studying abroad in Paris. My friends and I went to this divey Irish bar that we loved: the type where after a certain hour they pushed aside the tables and the whole place turns into a dance floor, complete with tequila shots and beer sticking to the bottom of your shoes. Super classy, I know.

That night I danced with a guy and told him I was celebrating my birthday. He asked me how old I was and I excitedly shouted “21!!!!!” Being polite, and slightly inebriated, I returned the question and he told me he was 29. I’m pretty sure the next words out of my mouth were “Damn you’re old!”

Back then, 29 seemed like eons away. I really couldn’t picture myself at that age. I mean, I guess if you had forced me to tell you where I’d be, I would probably have told you that I’d be married, thinking of having kids soon, and living in a house that I owned. You know, all of those things that our society tells us will magically fall into place as we approach 30. But I didn’t really have a true picture of it. It was so far off. I’d worry about that later.

Of course, I never could have truly predicted where I’d be now. None of us can - we don’t have a crystal ball. Never in a million years would I have guessed that I’d own my own business before 30. I mean, I didn’t even know what coaching was at that point in my life.

I also couldn’t have predicted the weird time warp your 20s becomes: feeling like it’s lasting forever, while flying faster than the speed of light at the same time.

What I can tell you now are some important lessons that I’ve learned along the way.

Lessons that had I known them at the time may have saved me a few tears and helped me to live in the moment. They are things I wish someone had told me so that I could have had a bit more perspective when the going inevitably got rough and I felt alone with my struggles.

No matter where you are in your 20s, you have your own lessons to learn and by no means is this list meant to be a replacement for the experiences that will teach you them. In fact, it can’t be because to truly internalize these, we all have to learn them in our own way.

My hope in sharing this list with you is that as you’re learning these lessons, it might help you remember to look for the lesson in every experience and make decisions that are true to YOU, not what the outside world tells you that you should value. 

I hope that it will help you feel a little bit better about where you are right now and what you’ve been through. 

I hope that it will help you get out of your own damn head and realize just how far you’ve come.

Okay, here goes...


1. You don’t have to settle

Not for a job, a romantic relationship, a friendship, or a city - none of it.

Whatever you’re unhappy with in your life right now doesn’t have to stay that way. You ALWAYS have a choice to change things. While making that change might feel scary in this moment, letting go of what’s holding you back and keeping you stuck can be extremely liberating.

Deep down you know what gets you excited and what keeps you stagnant.

If it’s not lighting you up, go find what will.

2. Heartbreak doesn’t last forever

As someone who went through a bad breakup at 24, I know that heartbreak can feel like it’s never going to end. I know what it feels like to wake up each morning crying and then cry yourself to sleep again that night. I know what it’s like to feel like you’re in a dark hole that you can’t seem to find your way out of.

But, at 29, I also know what it’s like to climb out of that hole. I know what it’s like to feel the weight of heartbreak finally slip off your shoulders. I know what it’s like to take that first gasp of real air again.

I promise you, you will get through the heartbreak. It doesn’t mean it won’t be painful - it will - but you will eventually move on. Whether you spend time being single afterward or discover someone who is an even better fit for you, there will be a day where it doesn't all hurt so damn much anymore. And I'm willing to bet that you'll grow in the healing process and learn a lot of things about yourself along the way.

3. Live in the moment

To this day, I struggle with this lesson a lot. I like to set goals, hit milestones and keep going. Sometimes I forget to slow down and take in the scenery.

But it’s those little moments that come back to me when I’m least expecting it. Like when I’m reading a book and all of a sudden I’m transported back to my first couple of summers out of college living in NYC, dripping sweat in my terribly ventilated apartment. Or when Facebook Memories reminds me that I moved to Boston almost 4 years ago and I’m overcome with the feelings I had at 25, when the newness of the city made everything feel so ripe with possibility.

Some of the experiences you have in your early 20s will seem unimportant. There will be other moments where you wish you could just fast forward time. But years later, those moments, the ones you gave so little thought, will come back in vivid memories. Sometimes seemingly out of nowhere.

Yes some memories will involve battle wounds, while others will be pure fun. But amidst all of your planning for your future and your busy schedule, take a moment to appreciate where you are now.

You won’t be here again and this moment might bring a smile to your face years from now. You never know!

4. Everything happens for a reason

I know it might sound cliché, but I truly believe it. 

All of the things you are experiencing right now - the good, the bad, the ugly - are teaching you something. It may not be clear right now, especially if you’re reading this in a state of confusion or heartbreak, but I promise you there is a lesson in everything you are experiencing.

And when it becomes apparent, it will finally all click and you'll get the reason you had to experience it in the first place.

5. Sometimes you have to go through some shitty stuff to get to the really good stuff

Not gonna lie, there are times in life when things feel really shitty. We all go through it. It’s a natural part of human life. No matter how good your karma is, there are going to be times when you are tested, when things don’t go your way, when you want to scream “THIS FUCKING SUCKS!”

But on the other side of that shitty stuff, there is often some really awesome stuff waiting for you. In each of those bad moments, you learn something about yourself or the world and this learning often leads to some great (dare I say joyful) discoveries.

Remember, the good stuff wouldn’t feel so freaking good if everything in our lives was at that level all of the time.

6. Take initiative and make decisions

Despite what our culture tells us, our lives don’t magically come together at age 30. The decisions we make throughout our 20s affect our lives. So does lack of decision making.

Yes, some decisions can be tough, but they are necessary. You don’t want to wake up at 29 and be in the same job you’ve hated since you got out of college just because you were afraid to make a decision.

Do the necessary work to create the life and career that you want for yourself. Only YOU can make your dreams happen!

7. You don’t have to be BFFs with all of your colleagues

If you really click with people at work and want to spend your nights/weekends out with them, great! But if that’s not the case for you, it’s totally okay to have a separate life outside of work.

When I started my first job out of college, I thought I was immediately going to have a new crew of friends through work. Doesn’t every TV show ever tell us that this will happen? Well that was not my experience at all.

Honestly, the first time I had a #workwife was when I was 27 and by that time, I wasn’t particularly looking for one - it just happened.

It is okay if you choose to keep your social life and your work life distinct from one another. You can have good relationships at the office without going out and getting drunk together at night. Yes, taking part in company team building events can definitely be beneficial, but you don’t have to become best friends with everyone simply because you work in the same office.

In fact, it’s entirely unrealistic to think that you’re going to want to be BFFs with everyone at work. Do you want to be besties with every single person you meet? Didn’t think so. So why put that pressure on your work relationships?

8. Don't compare yourself to everyone else

It's so easy to fall into the trap of believing that everyone you're friends with on Facebook or following on Instagram has their shit together and is years ahead of you at whatever goal it is you want to achieve. The trouble is, when we do this, we are comparing ourselves to a semi-reality. Our social media accounts are just the highlights, not the full picture. 

When you're only insight into someone's life is highly edited highlight photos, it's no wonder that playing the comparison game only makes you feel shitty and not "enough" - whatever that actually means. So cut it out! Because the truth is... NO ONE has it totally figured out! 

Every single person you meet, no matter how perfect their life seems, is struggling with something, whether they make it known to you or not. You never know what's going on behind those shiny, smiley photos, so what good is it doing you to compare yourself to that?

Celebrate your friends' successes, be their biggest supporters, but DON'T compare their life path to your own. Their success doesn't make you any less successful and I guarantee you've got something that they wish they had too. 

*Full disclosure, this is another one that I struggle with to this day, especially as I'm building out my business. But when I can let go of comparisons and appreciate where I am in my own journey, that's when I'm at my happiest and most confident.

9. Prioritize your spending on experiences, not objects

That gorgeous bag you are drooling over isn’t going to last as long as the memory of going on that crazy road trip with your best friends.

Don’t get me wrong, I love a new purse or dress as much as the next girl and I’ve been known to shop a good amount (my boyfriend would probably argue that I like to shop A LOT).

But when I think back on the things that have made me happiest over the past 10 years, they haven’t been those new clothes that I bought. Actually those clothes have often turned into a source of guilt, rather than the happiness I thought they were providing.

The moments of pure bliss in my life have always involved doing something memorable with my friends, family, or boyfriend (or even with just myself), whether that’s been indulging in an amazing meal, wandering around the streets of a new city, going to a concert or experiencing nature.

So contribute to that entertainment fund. Book that flight to Europe. Say yes to that once in a lifetime dining experience. Visit your family. Go see the world! It will make you a more informed, engaged and arguably happier person than any new outfit ever will.


And that, my friends, is my list. I hope it helps you on your own journey of learning these lessons too. While I can't wave a magic wand and help you skip past all of the experiences you need to have to truly internalize these for yourself, sometimes just having a little seed of these in the back of your mind can provide a bit of clarity in the moment.

What do you think? Have other lessons you’ve learned in your 20s? I’d love to hear about them in the comments! 

Be well,