(Most of) My Twenties: Failures, Successes, Mistakes & Lessons Learned

I turn 29 in a little less than a week. Age is just a number, birthdays aren’t that big of a deal, and [insert anything else I can say to seem super chill and nonchalant about not needing attention on my birthday].

I have to say though, when I finally processed that I was entering the last year of my twenties the other day, when I really internalized it — it did seem like a big deal. 

It seemed like a big deal because of the stories I used to tell myself (for better or worse) about where I’d be by the time I hit 30. It seemed like a big deal because of all of the things I had accomplished in my twenties. It seemed like a big deal because of all the things I hadn’t.

It seemed like a big deal, because it seemed like a good time to reflect on the wisdom I had acquired the past 9 years — through failures, successes, mistakes, and lessons learned — and to make sure that I applied that wisdom moving forward. 

To make sure that I went into the last year of my twenties, armed with the wisdom of my experiences, and ready to learn even more.

Over the past few days or so, I’ve been thinking about different things I’ve learned in my twenties. When I woke up last night at 3:36AM with a sentence in my head for this essay, I knew I had to quit thinking and start writing (thanks for the creative burst, but I’m not 25 anymore — I need my sleep.)

I’m writing this so that I can look back on it when I feel lost or forget or fall back into old patterns (because I will). I’m writing this so I can possibly help someone else in their twenties or nearing their twenties or reflecting on their twenties.

I’m writing this because I want to, because I feel like I, personally, need to.

So, if you’re still there, let’s dive into my (many) failures, successes, mistakes & lessons learned during (most of) my twenties (in no order).

Lesson 1: The Secret to Self-Love

For the majority of my twenties (and sometimes still to this day), I struggled with loving myself. I went through seasons of speaking my own language that I call “self-deprecation”. I beat myself to a pulp daily, sabotaging myself through food, spending and relationships. No matter how much others loved me, I never was enough for myself. If I moved to Boston, I “needed” to move to New York. If I got a promotion, I “needed” the next one. 

I searched for this love to fill a hole within me through clothing, food, Instagram likes, and resume boosters. What I didn’t realize until I was 28, was that the hole I was trying to fill with these items could only be filled by me, and that the things I was trying to fill them with — the spending and the “perfect” social media presence and the diets and binges and the attempts at the perfect workout routines — those things were only taking me further and further away from filling that hole. They were only taking me further and further away from loving myself — from being the best version of me.

I found, through trial and error, that by simply doing things to take care of myself such as moving my body, eating good food, having fun weekends, reviewing my very attainable and flexible goals, and being kind to myself when I got off course because I was living balanced — I was able to find the love for myself that I never knew I was missing.

Because I was making promises to myself, and I was keeping them (even promises such as “not beating myself up if I miss a couple of workouts”.) And in doing so, I built confidence in myself. I built trust in myself. I learned to take care and nurture myself. 

I, without meaning to, started loving myself.

Lesson 2: Dating (and Life) — Learn Your Value, and Learn to Let Go

Confession time. I didn’t date for a majority of my early to mid-twenties. I didn’t date because I didn’t love or like myself, in fact, I kind of hated myself. And so, I closed myself off from this area of my life due to a lack of confidence, probably a fear of rejection, dealing with my inner demons of anxiety and body dysmorphia, and as a defense mechanism I suppose. It was easier to just “not” than it was to risk it. 

But alas, in my later twenties I started “dating”. And wow did I make every mistake in the book (okay, not every mistake but like… a few). 

I often pretend to not care, and try to show that I have a “hard” exterior through my black coffee and career. But I’ve been a few people. I’ve been the girl that won’t let go. I’ve been the girl that tries to convince someone of why they should stay. I’ve been the girl that waits for a text. I’ve been the girl that believes talk when there is no action.

I’ve been the girl that can’t let go, because I’ve been the girl that doesn’t believe she’s worthy of more.

I’ve learned through my experiences (and each experience has taught me something new) that if something or someone in my life doesn’t want to be a part of it as much as I want to be a part of theirs — it’s not worth my time. I learned that you have to learn to let go of things and people that want to leave, so that you can make room for things and people that don’t.

I’d rather be on my own than with a relationship or friends or anything else that half wants me. If it’s meant to be it will be, and if it’s not, there’s a reason, whether that is because there is something or someone else, or because you still have more lessons to learn.

Lesson 3: Want Clarity? Sit with Uncomfortable Thoughts & Often, Take Your Time with Decisions

I heard this TikTok (ugh I know I’m almost 29 OK) about how if you keep getting abandoned in dating and relationships, it’s because you might be abandoning yourself. I’m not sure how much I believe that, but it did get me to thinking about where in my life I abandon myself, or used to. 

It got me thinking about the times I numbed out anxiety or loneliness or fear with food or writing perfect goals and plans or buying a new jacket. It got me thinking about the times I was feeling lost, and so I immediately started planning my next big life change and telling others about my plan to move or to uproot or whatever else. 

But you see I was recently (like literally a month ago) feeling lost, probably the most lost I had felt since my early and mid-twenties when I was very much on the struggle bus with anxiety and body image issues. And of course, I freaked. I started working hard to figure out what was next for me and what my direction was. I lay in bed at night grilling myself and beating myself up trying to figure it out. 

What I realized amid doing this was that what I really needed was some time to be in this place of confusion and a bit of sadness, in order to practice the small things that make me happy such as working out and cooking and killing it at work, so that I could learn to just “be” rather than searching for the next big thing that would give me external validation and make me feel whole/good for a little bit.

You see on the other side of your most uncomfortable times, are usually your greatest moments of clarity. And, learning to live with those feelings for a little bit without distracting yourself with a big decision can be a good thing (not to mention, making decisions from a good place rather than a desperate one is a best practice when possible).

Lesson 4: Listen to Your Gut & Quit Giving a dang What Others Think About It — It’s Yours

You want to do something? Do it. Quit being afraid of what people think about it and quit being afraid to fail. Life’s too short to watch others live the dream you always knew you could live, but never did.

Also, stay in your lane — no one cares what you’re doing anyway.

Lesson 5: Beating Yourself Up Will NEVER Help (But My Gosh Take Accountability) 

A few years ago I went through a “breakup” with someone I was never actually dating (the worst, amiright?.) I was on the phone with my mom bashing myself over all the things I did wrong or could have done differently. She asked me a simple question “Why are you so dead set on this being your fault?”

I realized in that moment that when anything would go astray in my life I felt the need to take all the blame. And more so, I felt the need to have a boxing match with myself about it until there was nothing left. You see I like to take accountability for my actions, always have and always will. But the thing is, beating yourself up and taking accountability for your actions are two very separate things. 

And beating yourself up will never help you to move forward, in fact, it will make you sabotage and make you move backward.

Take accountability for your actions, make the necessary changes, and move ahead.

Lesson 6: be A Little Talk, All Action

I spent a lot of my twenties talking about things I wanted to do (writing/blogging) instead of doing them. I spent a lot of my twenties complaining about my finances or body or love life or whatever else, instead of doing anything about them.

Quit talking, and start doing.

Lesson 7: Recognize Your Patterns — Nothing Changes if Nothing Changes 

I spent YEARS trying to put myself on perfect schedules and diets and workout routines and plans to reach different goals. Only to crash and burn harder and harder each time. The universe will teach you the lesson you need to learn as many times as it needs to until you learn it.

If something hasn’t worked for you four times, try something different. Nothing changes if nothing changes. 

Lesson 8: Relationships are Important, But Don’t Forget About the One You Have With Yourself

I pride myself on my friendships and relationships. What I’ve learned over the past year however, is that I also have to make sure I am giving time and attention to my relationship with myself. You can’t only put others first and expect to live the life YOU want. 

So, ask yourself, what would you be doing if you were truly living life for you? 

Lesson 9: Hard Work Pays Off

When I was in my mid-twenties I had multiple breakdowns about what I was doing with my life each week. I thought I was meant to own my own business and be famous and live in NYC but it seemed so far away or not possible (also I wanted it for the wrong reasons, but that’s another lesson). On top of this, I had major anxiety and was trapped in my own mind for quite some time.

Amid one of my freakouts, my dad walked into the room. He said something to me in the middle of a solid scream-cry (I’m honestly impressed by my performance), “You are the only thing holding you back. Work hard, do what you want to do but be smart about it, and be a good person — and life will work out for you.”

This quote is now how I try to live my life. And, I can truly say, after years of hard work, I was able to move across the country to my dream city and work in a career I had been going after for years (and progress in said career). No shortcuts, no excuses — just work.

Working hard for what you want makes it that much more rewarding when you get it, and doing things the smart way instead of through impulse because you think you need it “now” will help you in the long term.

Lesson 10: Why Not (Why Not) Take a Crazy Chance?

Take the job, move to the city — do the things. Make sure you have enough experience or money or whatever you need to do this, but ultimately, you have to say “yes” before you’re “ready”, because I’m not sure that “ready” truly exists (hint: I was not ready to move to Boston, but moving here gave me everything I needed to be who I am today).

Lesson 11: Your Struggles Will Lead You Into Who You Are Meant To Be

Every hard time you go through is growing you into a better, stronger version of yourself. Read that again.

Lesson 13: Quit Waiting to be Happy — The Grass Isn’t Always Greener

I spent the first part of my twenties being bummed because I didn’t live in the city. When I got to the city, I spent the first few years being bummed because I wanted to figure out what was “next”.

This is your life. Quit making excuses about why you can’t be happy. You will never be happy if you are not happy right now, today. Slowly work for what you want and let it go if you don’t know what that is yet. Embrace who you are.

And remember, the grass isn’t always greener. So always, always, always, be grateful for where you are today.

Lesson 14: Why Would You Want to Feel Like Sh**?

I asked my brother how he stays on track with wellness and fitness. He said, “it’s pretty simple. Why would I want to feel like sh**?” (gotta love the male brain.)

But it’s true. Why would you want to do things that make you feel worse, and not better (in all areas of life)?

Lesson 15: Comparison Will Kill You (Or At Least Your Soul)

You get it. 

Lesson 16: Do Things Because They’re Fun 

I used to box myself into a perfect personal brand, or only do things if I was pursuing it perfectly. Turns out, I can still do ballet sometimes just because it’s a part of who I am even if I’m not pursuing it anymore. Turns out I can do things just to do them. 

Don’t fall into the trap of making everything in your life “optimal” and to “better” yourself. Joy does just that. 

Lesson 17: Each Season of Life is Meant For You — Figure Out Why

I think that everything happens for a reason, but I think this because I think that everything happens for a reason if you choose to find a reason. If you choose to find the lesson, the growth, and the value. That part is up to you.

I also think that we can miss out on beautiful seasons of our life because they might not “look” the way we thought they would. Newsflash: nothing looks the way you thought it would. Embrace what you have and remember that it was once all you ever wanted and exactly where you wanted to be.

Lesson 18: Do Things for The Right Reasons (And Allow Your Dreams to Change)

I spent a long time doing things for approval and praise. I want to show off what I had and had done. But my sister reminded me that people will not remember what you have, but they will remember how you make them feel — and I try to remember this when I think about “why” I want things.

It wasn’t until I realized this and worked to change it that I realized that some of the things I thought I had always wanted, well I didn’t want them for me, because I wanted them for them.

And so I pivoted. I let go. 

I embraced a new, evolved direction, and I enjoyed each step of the way.


If you’re still there please slide into my DM’s to tell me what you think for my external validation thanks!

Anastasia Warren