29 Lessons I've Learned in my 20's | @halliekwilson

29 Things I’ve Learned in my 20’s

About a week ago, I celebrated my birthday. And I have to say, the last year of my twenties is lookin’ mighty fine (I’m 29, guys — nothing to hide).

heart shaped balloons

Leading up to/since then, I’ve had a few holy-shit-I’m-nearly-30 moments, but I’ve gotten over them quickly. After all, 29 (and 30) is still really young.

More importantly, I’ve felt really, truly, genuinely elated. Birthdays, holidays and new calendar months (December, especially) are like turning to a fresh page of bright white paper in your favorite notebook. And there’s something really empowering about the feeling of a fresh start.

I’ve learned a lot in the last 20-some years — both good and bad — and can’t wait for what’s ahead.

So far, I’m healthier, wiser, and endlessly more self-aware of my mind and body. I’m independent in a way I wasn’t in my early 20’s. Suffice it to say, I’ve finally found my rhythm in life… I think.

As a result, we’re celebrating this week.

That’s right. Celebrating!

Tomorrow, I’m launching a series of giveaways featuring an array of my absolute favorite brands. There will be lots of chances for you to win some cool stuff. I’m excited! I hope you are too.

heart-shaped birthday balloons heart balloons urban outfitters

In the meantime, I wanted to dedicate today’s post to 29 things I’ve learned in my 20’s. It’s another long-tail post for today, but I think you’ll enjoy it… Got your coffee ready?

sequined jacket

I could write a book on “If I knew then what I now know,” (and perhaps I’ll do that in the future). Right now, I’m the happiest that I’ve ever been in my life — and the little life lessons here are a huge part of that.

These are not meant to be groundbreaking nuggets of wisdom, but more relatable thoughts and lessons I’ve collected throughout my life so far. (Please feel free to share your favorite quotes, mantras and motivations in the comments below, too!)

sequin blazer jacket

So here they are, in no particular order:


1. Things happen to people at different times in their lives. I’ve spent a lot of time worrying that I don’t have what others do at my age (a husband, a house, babies, etc), but I’ve worked out that I’m living the unique life I’ve been given and that’s the way it’s meant to be. I wouldn’t have it any other way.

2. Trust the timing of your life. Spoiler alert: Your life will not develop as you expect it to, but just remember that you are exactly where you’re supposed to be.

3. Take care of yourself. You have two assets that you can never get back once you’ve lost them: your body and your mind.

outfit ideas for NYEred pumps style

4. Don’t live the same year 20-some times in a row and call it a life.

5. There are seven days in a week. “Someday” is not one of them. Start (or continue) living the life you want to be living — immediately.

6. Do what’s worth your time, not your money. Time is truly our greatest luxury.

7. Taking time to live your life will only inspire your work.


8. Go the extra mile… It’s never crowded.

9. Build your legacy, not just your empire. (When done correctly, this takes time, patience and persistence.)

10. Trust that when the answer is no, there’s a better yes coming down the road.

11. Don’t let success go to your head — and don’t let failure go to your heart. Sometimes it’s a stumble that prevents a fall.

12. Don’t feel bad about saying “no” to the activities, obligations and people that don’t add genuine value to your life.

13. You can have literally anything you want in life, so as long as you set your mind to it. Seriously. But success isn’t built on dreams and ideas. It’s built on action. Work your ass off and hustle like hell, girl.


14. Learn how to be a good listener. Then be a good listener.

15. Show up for your friends. You matter and your presence matters more than you might know.

16. Seek out mentors for all aspects of your life — respect them, ask them questions and learn from them.

gold sequin jacket

17. Life is easier when you learn to accept an apology you never received. Don’t hold grudges — the only person you’re hurting when you do this is yourself. Forgiveness is power.

18. Adult friendships require constant energy, effort and time.

19. When someone shows you who they are, believe them.

20. Family is everything. My parents have been right about pretty much everything, and now I understand why: They’ve done this before.


21. Grief is a faster teacher than joy.

22. Don’t let other people’s opinions define you – positive or negative. Think of it this way: You can be the juiciest apple in the tree, but there will still be people that hate apples. (Fuck those people!)

new years eve outfits

23. The only person you’re destined to become is the person you decide to be.

24. Don’t compare your behind-the-scenes to someone else’s highlight reel. This is easy to do in the age of social media, but as they say — comparison is the thief of joy. (Also, re-read this when you’re done with today’s post.)

25. If it doesn’t serve you, let it go (or be dragged). As hard as letting go can be, know that there’s something better coming — you run the risk of never finding it if you don’t let go of what’s holding you back.

26. Leaving is just a precursor to arriving.

sequin jacket pencil skirt

27. How to cure a hangover (this is important): Eat before going to bed, take vitamins C and B12, and drink lots of water. If that doesn’t work, get your ass up and into the shower. Or go to SoulCycle.

28. Life is too short for bad: music, beer, wine, coffee, food, people.

29. Lastly, my favorite quote: “A bird sitting on a branch is never afraid of it breaking, because her faith is not in the branch, but in her own wings.”


Life is beautiful — and the world isn’t as bad of a place as the news may lead you to believe. So, celebrate it. Even if that means grabbing a handful of foil balloons, throwing on a sequin blazer and stopping traffic for a photo shoot along Park Avenue.

Honk all you want, bitches — I’m sending off my 20’s in happiness and health. (And a killer pair of shoes, obvi.)

birthday party outfit ideas

A huge, virtual hug to each of you that stops by to read my blog every day. I hope today’s post made you think, smile, nod and remember all of the things you’d like to remind yourself on your next birthday.

Here’s to sending off our 20’s in love, laughter, happiness, health, success and significantly fewer hangovers — together. Let’s make this our best year yet!


outfits for NYE


Sequin blazer: BB Dakota (similar here, here and here)
White tee: Madewell lilen t-shirt (on sale — these are the best)
Pencil skirt: Vince Camuto (on sale)
Red pumps: Alice + Olivia (love this version and this version)
Handbag:3.1 Phillip Lim medium Pashli satchel
Ring: BaubleBar crystal mason ring
Lipstick: NARS matte lip pencil in ‘Dragon Girl’
Nail polish: Essie ‘Jump in my Jumpsuit’
Foil balloons: Urban Outfitters

*Click to shop: sequin jackets | red pumps | casual linen shirts
this post (below):

birthday party outfits

Lydia Hudgens Photography

Join the Convo:

  • Hallie, I am a new reader and this post really made me smile! First of all, turning 30 really isn´t that bad. I am 32 and I enjoy my thirties and yes, feel more mature and comfortable with myself!

    Those life hacks are practically gold – so so true – I just shared them with my lil sis (she´s only 16 but her time will come 🙂

    Rocking sequins and bold red heels in the middle of the day – big thumbs up, you´re basically a rockstar! Hope you´re having a fab birthday party coming up – enjoy every minute of it!

    An early Happy Bday, girl! Nearly 30 never looked better! xo Martie

    • You’re giving me a lot to look forward to! Thanks for the birthday wishes, gal.

  • LOOOVE. Such great advice with the appropriate dosage of humor, as always. Happy happy birthday!!

    • I’m glad — it’s Monday, after all. : ) Have a good week, Monica. x

  • KaraLev

    I’ve been reading your blog for a couple years now and if this post doesn’t perfectly capture you, I don’t know what does! Loved every little nugget! Happy birthday!

  • Happy Birthday, Hallie!

  • First off, HAPPY BIRTHDAY again! And secondly, I want that little jacket…so cute!

    Cathy, your Poor Little It Girl

  • Happiest of birthdays, Hallie! I loved this wisdom-filled list 🙂

  • Happy birthday, Hallie! I love this post, especially the final quote – so cute! Your outfit looks great, obvs. Hope 29 is your best year yet! xo

  • I’m embarrassed to say this, but I just teared up at my desk. This post is perfect. I have the same outlook when it comes to aging, hence 26 and NOT Counting. My late twenties have been the best so far and this gives me the reassurance that the years are only going to get better. I’ve been doing a lot of thinking about #1 lately and my boyfriend and I recently decided to stop the house hunting. We’re actually not even sure why we started..I guess because everyone else was doing it. I’m still learning to trust the timing of my life.

    I feel big changes coming in 2015 and this just gave me the kick in the ass to keep working toward what I want. Thanks for always being so easy to relate to 🙂

    • Amen. Timing is *everything,* and that’s a simple yet very difficult concept to comprehend. And speaking from experience, your 20’s will only get better. : )

  • Happy birthday Hallie! I’m turning 29 this year too and this reminds me to think about it in a different way. Lots of good advice to consider and an adorable photo shoot too! You look confident and happy – definitely a good way to start off 29! xoxo

  • I’ve just found your blog and love your musings/photos/observations. You’re wise beyond your years. I’m 34 and still learning (and re-learning) these lessons. Beautiful post! And happy birthday!

  • So first of all, you look amazing. Second, THANK YOU for sharing these amazing lessons. They are beautiful. You are the realest and my abso freaking lute favorite blogger (am I fan girling too much?) but to read this list from someone who isn’t just a fancy dancy contributor to Forbes is refreshing and downright awesome.

    I’d never heard of your #29 quote before…. I just love it. Happy Birthday lady!

    xx Larisa @ weheartbeauty.com

  • Andjela

    Your post almost made me cry, but in a weird happy way (yes, I know). Wishing you a late happy birthday sweetie, you are the kind of person worth stopping traffic for! Cheers to you! <3

  • God, this was THE perfect post to read on a Monday. Thank you for sharing all of these amazing lessons. Whether you believe it or not, you truly are a role model for a 22-year old girl like me. I’ve said it before, but you are THE realest blogger – I love how you tell it like it is. Your free spirit makes me want to go out and enjoy life to the fullest. I love that you’re not afraid to say you’re hungover as shit and then get up the next day ready to work (after coffee and a bagel). You’ve given me so much advice through the years (through posts and personal emails), and I seriously can’t thank you enough! I’m so glad I get to follow you on your blogging journey 🙂 Happy Belated Birthday, Hallie – keep being fabulous!

    Pink Champagne Problems

  • Love all the words of wisdom in this post. So much truth here. Thank you for sharing and for empowering your readers! xo

  • Meagan

    Love this post! Happy Birthday! Cheers to rocking the late twenties! 🙂

  • Happy Birthday Hallie!! I love this list of lessons, sometimes the best gift we can give ourselves is to reflect on what we’ve learned!!

  • Nnenna

    Happy Birthday Hallie! I love your longer posts like this one. I’m thinking about point #13 especially and hoping that next year will bring some positive changes in my life!

  • Whitney

    Love this whole thing. Happy birthday!!! You are gorgeous on the inside and out it seems!

  • Lauren

    Trust the timing of your life…wow, that is powerful!! I love it. Thank you for this post.

  • Happy birthday! I love your list. Keep being awesome. 🙂

  • Tracy

    love love love it!! Happy Birthday girl – you and this blog of yours makes me smile!! (and covet your shoes ;))

  • Yay so excited for this post! I have been waiting for these photos since you gave us a little sneak peek on instagram and that did not disappoint… you. look. FABULOUS! Cheers to all you have learned & all you have accomplished, I am working on #3 right now because juggling definitely takes its tool and sometimes I feel like I’m loosing it … glad to know I’m not the only one 😉 !!! Plus I am really excited for all your giveaways, I never win anything (sand face) but maybe I’ll get lucky!!!
    XO Courtney
    Dress Outside The Lines

    • Aw, thanks gal. I’m so glad we met/that blogging brought us together this year! You definitely aren’t the only one… Often times, I think the best part about having a voice on the Internet (something you can relate to) is being able to share life’s lessons and rally people together behind them. x

  • Courtney

    LOVE. THIS. POST! It was seriously everything I needed to hear on a Monday morning. I’m really glad that I stumbled across your blog this summer. Since then, I’ve been reading it every day 🙂

  • I loved each and every piece of wisdom you just gave and really needed it too. Happy birthday!!! You deserve the best!

  • Ahhh I love this post (Almost as much/if not more so than your fashion week posts)! Perfect timing with the new year coming up, too!

    Happy Birthday!


  • This post is everything!!! I’m for sure enjoying my 30’s waaay better thanks my 20s!! Hope you have a great cumpleanos!!

    Xo Miriam

    • Gracias! And glad to know there’s a lot to look forward to. x

  • Happy Birthday! I also just turned 29 on December 4th. Yay Sagittarius’s! Thank you for sharing your positive energy and outlook. Also, obsessed with the shoes! 🙂

  • Happy birthday – hope it’s even better than the last one!

    Liz @ ShoppingMyCloset.com

  • Happy Birthday, Hallie! This post was just what I needed on Monday—and while so much of your advice hit me in some way, I think this really sums up an awesome philosophy on life to have, “5. There are seven days in a week. “Someday” is not one of them. Start (or continue) living the life you want to be living — immediately.”

    You definitely embody hustle, and I can’t wait to see what’s next for c+c. Keep writing, ’cause I’ll keep reading.

  • A great read to start off the week Hal! Hope you had the most wonderful birthday yet! You’ve got one killer 29-year-old sparkle! Happy Holidays my dear and hope to see you before 2015.

  • Happy Birthday!!

  • Jen

    Happy Birthday Hallie! Those are some amazing wise words. My personal favorite was, “There are seven days in a week. “Someday” is not one of them. Start (or continue) living the life you want to be living — immediately.” SO, SO true! Life is too damn short to wait around for things to change.

    xoxo, Jen

  • Lisa

    Love everything about this post!!!!! I enjoyed reading it on my commute home. Definitely helps get through the BO and bad breath on the CTA.

    Age is definitely on your side – you look gorge. <3 xoxo

  • This post was amazing Hallie and so heartfelt! I’m still working on the learning to say no piece and comparing to someone else’s highlight reel… this post was a great reminder of both those things 🙂
    Happy happy happy birthday!!!!

  • LOVE this list.

  • Meg

    This is such a great list! I love reading your inspirational and positive take on life!

  • Happy belated birthday, and fabulous amazing post. You look amazing, and thanks for sharing some of your words of wisdom. I will be re-reading this post a lot!


  • I first read this post this morning and have been thinking about it all day. This is exactly the kind of post I was hoping you would write after you did your survey – this type of content, combined with fashion (obvs), is exactly what I like to read. And looking at all your comments, I think everyone agrees! 🙂

    Happy belated birthday. I am with you – I turned 29 this Summer and my life is not quite where I thought it would be by now (also, no husband and babies). Yet, I think life works out the way it is supposed to and I know a lot of amazing things are around the corner.

    ~ Christina

  • Jenn

    LOVE this post, and its timing couldn’t be more perfect! I’m turning 32 tomorrow and I’ve never felt more inspired and empowered than I do now. These are great words of wisdom for women of any age!

  • tracy

    love this!!! thank you!!

  • Very inspiring Hallie! Great tips <3

  • This is the best post you have ever written. BRAVO!
    You have an incredible amount of wisdom and perspective; thank you so much for sharing. Also you look FREAKING AMAZING in this outfit!

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  • Jamie

    Happy belated bday! Love the top 3 – those definitely took me until my 30th bday to understand.

  • Libbi

    Happy belated birthday Hallie! Hope it was just as fabulous as you already are! Great post! 🙂

  • Happy Belated Birthday. I have no doubt you celebrated the last year of yours 20s in style and fabulousness.

    I am also glad you shared these tidbits today. I needed to read something like this today, funny how that works out.


  • xo Maggie

    This was a beautiful post!!! Happy Birthday!!

  • HL

    My 30s was the best. Met my husband when I was 34 and had my baby at 37. I’m soo glad I waited to have kids and did all the fun stuff that I wanted to do. I just turned 40 and now on to my next adventure!
    Happy early birthday!

  • #nailedit I’ll be 29 in a month and I am 100% with you on all these (even on how to cure a hangover) haha Great post, babe!


  • Oh I LOVE no #24, really needed to hear all of this right now to be honest. Wonderful post! Xx

  • Kelly

    Hi Hallie! I haven’t seen you since high school. I saw that Mallory had posted on FB about your blog and decided to read it. It was awesome! Completely true! I turned 29 back in August, and I’m loving my late twenties and looking forward to my thirties (I can’t believe we’re this “old”already!) I just got married to my high school sweetheart (I know 11 years!), but it gave us time to grow to who we are today. Now that we’re comfortable with ourselves, we finally tied the knot. We’re looking at finally selling down (we’ve moved a lot – to California to North Carolina) and having kids within the next year or so. I love my job and my husband has decided to return to school to compete his degree doing what he loves. You are 100% correct in that we just need to trust our wings; that’s how we got to where we are today.

    Anyway, you look fabulous and I’m so happy to see that you’re doing so amazingly well! Happy birthday!

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  • Love this post! I have learned so much in my mid twenties & I feel like I have found what matters to me. I especially agree that finding the right people is so IMPORTANT. I also share your views on not wasting time on bad coffee, food. wine or beer :)!

  • Happy belated birthday! Fabulous outfit! Your list of 29 things you learned is great – I can definitely relate to most of them. It is definitely hard to live up to them every day, because our minds/self esteem/moods are a constant upkeep. But hey, self realization is the first step to achieving happiness and self fulfillment. Keep on rocking on!


  • Teresa Sturdy

    Happy belated birthday! Jessica is so fortunate to have you for a best friend. Your paths were meant to cross back in Chicago! I remember when she first met you. She told me that you were like a sister that she never had and that it was like she had known you her whole life. I believe everything happens for a reason! It was good to see you Tuesday night. Hope you two have a great time in Pasadena with all the Rose Bowl festivities!

    Mother Teresa

  • Suzanne

    I’m a long time reader but have never commented. I love this post! Thanks for constantly making me laugh. Happy birthday!!

  • Amy

    Hallie, happy birthday. Better late than never. I really appreciated this post. I’m in my mid-twenties and am nowhere near where I thought I’d by now. But you know what? I don’t care. I’m happy, healthy and excited to see where I’ll go next. Thanks for this post – it is a perfect reminder that life takes us different places at different times, so we should just go with it and make the most of it.

    Here’s to caring for our minds and bodies, wearing whatever we damn well please, being lucky enough to have the friends, time and means to cause hangovers, curing said hangovers, making the best friendships and generally revelling in whatever is thrown at us.


    Girl for Granted

  • Happy Birthday! I love your post and it rings so true with me. I’m i my thirties and have never felt better. I know who I am, my confidence grew and finally all that work I’ve put in in my twenties is paying off. Fabulous decade!

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  • LOVE this post, Hallie! Wise and oh-so-true. Hope you had an awesome birthday!

  • SO well written – you have a gift with words & a beautiful perspective on life – you continue to inspire me and so glad to have you in my life!

  • Found this through Mackenzie’s blog and so glad I did! This is amazing and at 24, I’m really happy I got to read it. A lot’s been happening at this age and so much change has taken place, and it hasn’t been easy! Your list is so inspiring and makes me feel a bit better about how life is unfolding 🙂

  • Maria Fernanda

    Great post! First time reading your blog. Will swing by everyday, from now on. Also found it through Design Darling. Happy Belated Birthday!

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  • This post is incredible, Hallie! Wonderful words of wisdom, and you look fab as always. Cheers and happy belated birthday! xo

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  • I’m a little bit late to the party, but this post was amazing! Hallie, you truly are an inspiration and I love following you along your journey. Thanks for sharing!

  • This is a wonderful list and one that I relate to greatly. I too am in the midst of my final year of being a 20-something and this post and your outlook has spoken to my internal voice. I love reading your posts and knowing that you and I are close in age. I only have 6-months to live it up in my 20’s! Here’s hoping I round them out with grace, charm and class!

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  • I came over from bows & sequins. I love this post! I’m 32 and I can honestly say that even though I’ve only been in my 30’s for a short time, it is the best. Annnd I love number 22!!!

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  • Olivia

    I wouldn’t have gotten a chance to read this post had you not mentioned it in your post today! I was so busy in December but i’m glad i didn’t miss this. So worth the read. – a 24 year old 🙂

  • Maggie

    Hey Lady, thank you so much for this article! I’m turning 29 in August and am already feeling the pain. I wrote down a quote from you that comparison is a thief of joy and I’m going to remind myself a few more times. I will definitely be rereading this post to get even more from it. Really, thank you.

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  • I’m a new reader (via Hitha’s blog!) and I’m printing out this post and keeping it in my office- I LOVE IT! Thanks so much for sharing!

  • Mechelle

    Hi Hallie,

    Just saw this post via Pinterest- could not be more grateful (insert hands in the air emoji here!) to have read this today. I am 26 going on 27 (young, I know) but recently broke up with my fiance because it just wasn’t as “right” as it should be and in my gut I knew something was wrong. Anyways, just so happy to have read these life lessons. Thank you for posting! Definitely printing out as a little reminder 🙂


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