The Top 10 Lessons I Learned In My Twenties

The Top Ten Lessons I Learned While Navigating Through My Twenties - Cassandra Photo

Real talk: It’s pretty surreal to no longer be in my twenties. I never gave much thought to the matter, but now that it’s my reality I have to be honest: sometimes, it’s sort of trips me out. It’s not that I fear aging – I don’t. My dad always said “it’s not about the age, it’s about the heart,” so I’ve always tried to pay more attention to how I feel and what I’m accomplishing as opposed to the number at hand.  Yet still, here I am, writing a post on turning 30. ;)

About a week ago, I was lucky enough to meet a really awesome girl who just embarked the magical 30 as well. We reached over our margaritas to meet in high fives as if to say “I feel you” and from there, talked about the things we thought had shifted the most. Both of us agreed that we gained this new found form of confidence. Not the kind that makes you strut your stuff (well, kind of) but more so along the lines of, “This is me. This is who I am and who I worked hard to become. I love myself, so I might as well own it.” That’s not to say I don’t still have things I want to fix – I do! But it’s just different now. I’m more forgiving towards myself, more understanding – and most importantly, more accepting. I don’t need the validation of others, and that in itself feels like I’ve broken free of a prison I didn’t even realize I was in during my 20’s.

A couple of days ago, the aforementioned friend (Jen) sent me this article which got my wheels turning. I started thinking about not only the things I’d tell my 20 year old self, but what I really took away from that phase of my life, and the lessons I hope to continue to implement into my years as a 30-something (and beyond).  It’s true what they say – your 20’s are for messing up and making mistakes. Your 30’s, I’m hoping, are about living from the valued lessons of those mistakes, and embracing the possibilities that lay ahead.  It’s a lot more pressure, because you’ve entered the era of “you know better” – so while I’m still open to making mistakes, and lord knows there will be plenty, I’m more excited about being patient with myself and others, being less impulsive, and living a life that has intense value and meaning.

So with that being said, I compiled my top 10 lessons I learned in my years as a 20-something:

1. Find your balance.

My early 20’s were all about high-leveled emotions and impulse purchases and commitments.  I tried to justify anything and everything with emotion, and as we all know, that can be a destructive path. I also committed to things way too quickly, often leaving me to feel burnt out and resentful. As I made my way into my late 20’s, I began  to learn how to balance emotional decisions with some logic, and to take a beat before accepting an invitation (to anything)

2. Give and take.

This is what relationships are all about. Some people aren’t willing to honor the “give” part, and that’s okay. I began making mental notes of relationships in my life that felt draining and over all unfair.  Plus it’s a good thing to remember and to be able to accept that not all relationships are meant to be forever.

3. Save your money.

This is always a work in progress, but towards my mid-twenties I had never thought I’d save as much money as I did.  It’s addicting to watch your finances grow and to take the time to learn about your personal finances. Now don’t get me wrong. I’m no where near perfect. I over-spend and always say yes to travel, but I make sure to have a cushion to fall back on ;) If you’re a visual person like me, you can track your finances on

4. Communicate your feelings. (this one is a long one)

Learning how to properly handle communication has been such a lifesaver, and one that I wish I would have perfected long ago.  My early-mid 20’s were all about high strung emotion and acting in the present with fire. I’m a passionate person, so when I feel something, I feel it hard. Love? I’m melting and will shower you with affection and TLC. Anger?  I get shaky and almost immediately start crying. Heartbreak? I’m broken and stuck in the fetal position again, crying. With zero appetite. I’m not a yeller and I never really have been. But crying was my jam. It’s how I would handle any argument if I’m being honest. The moment someone began to communicate an issue with me, I’d cry. I wouldn’t even be able to hear them out because I’d feel so devastated that they were upset, or feel so embarrassed and defensive of myself that the passion would bubble over and tears would flood out. It was a mess.

Now? I truly feel like I have a real handle on this subject of communication. I’m almost never accusatory, and am sure to always begin sentences with, “I feel like” rather than “you do this and I don’t dig it” ;)  Sharing your feelings as apposed to picking someone apart is not only the most effective way to a solution, but it’s the kinder, healthier way.  When you respect someone, you never (ever, ever) want to make them feel less than they really are, or cover them in foul names that you don’t really mean. Another example: on the (very, very) rare occasion that my sister and I need to talk it out, we never raise our voices. Keeping your feelings, as valid as they are, at an even keeled level is a surefire way to quickly bring a resolution to the table. Try it. You’ll never “fight” the same way again.

* Also, lets be real. I still cry sometimes, but its generally targeted towards my grieving process. And I do yell but it’s next to never.  We all have emotions and hormones running wild that make us act ridiculous from time to time. But even after those lashed out rare moments, the aforementioned saves the day. Just be ready to own where you were wrong ;) 

5. Say no.

I used to think that success was based on how full my calendar was.  That was a disaster. I was so over committed, exhausted and worst of all – resentful to all of the wrong people. It was 100% my fault for never saying no to things. Now, I say no to about half, if not more, of the things that come my way. It has to really get me excited or fuel my fire.

6. Figure out your passion.

And don’t ignore it. I was so lucky to find mine so early on in life – and the cool thing is.. I’m still discovering more passions as I get older.  In my twenties, I was impulsive to no end like I mentioned earlier. Now I take things a bit more seriously and give them more thought.  I swear if I didn’t do this, I would have 20 random businesses most likely failing left and right and disappearing into thin air after only a couple of weeks.  Now, business plans and product development and investing in learning about my passions are things I take really seriously.

7. Don’t pay attention to negativity.

In my 20’s I was overcome with negative energy. Whether it was my own or coming from other people, it was something I couldn’t seem to ignore.  I soaked it right up, and anyone else’s issues or problems suddenly became my own. It was truly awful.  Now? That just doesn’t happen.  I know that a lot of it has to do with this new found perspective after losing my dad so quickly and just feeling like I  a) truly didn’t have the room for negative energy and b) understanding what true pain feels like along with the shittiest day of your life, so it’s pretty tough these days to knock me over.

8. Forgive quickly.

No one said that you have to forget. But forgive and be gentle with others and yourself. You’ll be lighter because of it.  Remember #7? That negative energy will only drag you down.  Forgive and move on, or forgive and repair.

9. Put yourself first.

Making time for YOU is so crucial and something that I 100% swept under the rug all throughout my 20’s. Everyone else came first, and I thought that made me this epic human being. In reality? It made me a tired one. Over the past few months, I’ve found that I am truly so happy when I carve time out to go to the gym in the morning, or stop checking emails to make myself a good breakfast, or when I’m able to take a long shower with a candle burning and Adele blaring in the background without worrying about what I “should” be doing.  I work harder and more efficiently when I’ve given myself a break (or three). Plus, I have so much more energy to lend to others throughout the day, and I feel like the best version of myself at the end of it.  Isn’t that what we’re all striving for?

10. Keep moving. 

This can mean so many things. Exercise, travel, failures, etc. Just keep moving. In my early 20’s I always felt like I was stuck between a rock and a hard place. I wanted to be healthy, but I didn’t feel like making the time to get there. I stayed put.  It was the same with traveling. I was almost afraid of it because of my fear of flying.  I wish I would have known then that you only conquer a fear by staring it right in the face. So I put myself on a plane, and just kept doing it again and again. Traveling further and further each time. Now? Flying is like second nature (even though I still don’t love it!) but I just kept at it.

The hardest lesson I learned in my 20’s by far, is to keep moving through failures. It feels like such a crutch when you’ve learned that all of your hard earned work and dedication just fell through the cracks. It’s embarrassing, devastating, and exhausting.  But what I took away from this saved me: you can’t succeed without failure. These failures are crucial to the learning process – figuring out what works and what doesn’t. If you keep moving through them, you’ll not only succeed, you’ll thrive.



Things I Learned in my Twenties - Cassandra Photo



  1. Kelly
    November 13, 2015 / 12:14 AM

    Cassandra, I LOVED this post!! Really resonated with me. You’re an amazing person, and you’re so missed in Chicago!


    Kelly | Kelly in the City

  2. Cassandra
    November 17, 2015 / 12:26 PM

    Oh man, thank you so much for posting this! I’m so glad it resonated with you. I miss you, too!

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