Why Your Twenties are Terrible/Awesome

Or: Gah I’m turning 27 on Wednesday!

When I was twenty-one years old my mother told me that her twenties were the hardest decade of her life. This kind of puzzled me at the time. After all- I’d just gotten the ability to drink legally; my life was going great! I was getting ready to graduate, my world was full of friends and endless possibilities. If this was what the twenties decade of my life was about, I thought I would be okay.

Me at 21

Now at nearly twenty-seven (my birthday is tomorrow-aack) I’m a bit more circumspect. Every year of my twenties so far has felt like a life time: an individual universe of life lessons, future defining decisions and self-contemplation. There’s been a lot of fun parts and a lot of intense parts but the takeaway is that man, being in my twenties is exhausting.

Our twenties is when most of us make the major life decisions that are going to affect the rest of our years: what kind of person will you be? What will you do for work? Will you get married, and to who? There’s a lot of pressure to choose wisely, to choose as if our lives depended on it. And that is a bitch, because there is just no way to know if you are making the right choice until maybe even years later.

In a way, this is what makes leading a typical, traditional lifestyle so appealing. There is a certain comfort in following the status quo: so many people can’t all be wrong, right? If you do what everybody else is doing your life might not be very spontaneous, but at least you’ll feel secure. You’ll know what comes next because it’s all been done before, a million time, by everyone else.

For some people though, the typical American lifestyle just doesn’t cut it. They want something else, something different, and that in itself is pretty scary. Breaking away from what’s normal can be absolutely terrifying (and exciting) because there is just no way of knowing how it will pay off. It’s higher risk, and hopefully higher reward.

It’s not a better choice, or a worse one, but either way it’s pretty scary to be in your twenties and trying to be the architect of your destiny. I’ve gotten pretty experienced at dealing with the doubts that inevitably creep in. When the doubts creep in there’s only one thing I know how to do. I take a deep breath and I wait it out. Because even if the doubts don’t totally recede the panic does. Then I can actually think clearly about what I’m doing with my life.

I also remind myself that nobody else has it figured out either. Life’s not a race, it’s an evolution. I’m growing and changing and while that’s uncomfortable and leads to late night wine and tears, it’s normal, even preferable.

That’s the thing right? While your twenties are tough and emotionally exhausting, they are also pretty intense, fun and awesome. I’ve done so many things in the last 7 years: I’ve traveled to five continents, I’ve fallen in love multiple times, I’ve learned and experienced so many things. Best of all, I’ve found out so much about who I am as a person. Information that will guide me for years to come.

I'm not a tweeter I just blog a lot

When you come right down to it, that’s the reason I started this website, the reason I’m so keen on people traveling in their twenties. It’s such an intense time, when you learn so much about yourself, and travel just accelerated the process.

The best part is, I don’t feel bad or depressed about getting older at all. I only marginally resemble that twenty-one year old girl and I even kind of miss her sometimes. Or maybe I just miss that simpler time when my biggest decision was what to wear out on Friday night and how long I could get away with procrastinating on my term paper. But I like my life a lot now, I’m grateful for the choices I’ve made that have brought me to having drinks in Bogota with my boyfriend on my twenty-seventh birthday.

I’ve only got a few more years of my twenties left, and I’m excited to see what surprises and revelations they hold!

72 Responses to Why Your Twenties are Terrible/Awesome

  1. janet October 25, 2011 at 9:22 AM #

    yes for lots of life lessons and universes.. the 20s is pretty dynamic. my life is worlds different now than it was 10 years ago.. my college 20s, my long term relationship 20s, my vagabond 20s.. and now my expat 20s.. all SO different!! but i kinda hope the 30s is better because the 20s has been pretty tough for me as a whole, esp. the 20s in a recession :/ and the girl next to you in the first picture totally looks like another traveler i know!! if its her, she would have a name like a beauty product brand. you’ll know it if you get it/know her.. 🙂

    • Steph October 30, 2011 at 1:44 PM #

      ha I don’t think that’s her, but funny!

  2. Nicole October 25, 2011 at 9:32 AM #

    I love this! And Happy Birthday. I turned 27 this year too. 🙂

  3. Juan October 25, 2011 at 11:19 AM #

    Great post, and happy birthday. Enjoy the Aguila 🙂

  4. Jill October 25, 2011 at 11:41 AM #


    “I also remind myself that nobody else has it figured out either. Life’s not a race, it’s an evolution.”

  5. ehalvey October 25, 2011 at 11:49 AM #

    THIS! I feel like I’ve been in a quarter-life crisis for a few years because a.) I’m in a holding pattern to see where we’re going next b.) I still have no idea what I want to be when I grow up c.) I’ve been jobless since the week after TBEX and d.) my friends are either not married or married with kids so I’m the odd one out by being married with no kids.

    I figured out what I don’t want, so I’m getting there 🙂

    Happy birthday!

    • Steph October 30, 2011 at 1:40 PM #

      Glad that you are at least figuring it out- it’s totally a tough position to be in!

  6. enjirux October 25, 2011 at 12:38 PM #

    a very interesting post – I confess, I never really thought about what it means to be in your twenties (I’m 28) but I found myself nodding along as I read.

    What makes being a 20-something sometimes scary is that the closer the magical 30 gets, the more people expect you to know what you want – because “everybody” at 30 is married, working on their 2.1 kids and have a mortgage….

    but I guess, people will have to deal with the fact that one doesn’t stop leading an interesting life just becausea number is changing 🙂

    have a great birthday and enjoy your twenties – and everything that comes after them 🙂

    • Steph October 30, 2011 at 1:34 PM #

      Thanks. I think that as people’s life paths diverge more there is a lot of pressure and expectations. But whatever, everyone’s gotta do what’s best for them.

  7. Monica October 25, 2011 at 1:02 PM #

    I’m only just 25 myself, but I’ve been thinking so much of the same lately. I would love to be in a position to do what you’re doing. I’ve been in Europe for 2 years and just got back to the States, I feel like it’s time to go again, but I’ve got to sit around and earn some money first!

    Happy Birthday!

    • Steph October 30, 2011 at 1:31 PM #

      Thanks! I’m sure you have many more adventures ahead.

  8. Leslie Forman October 25, 2011 at 1:15 PM #

    Happy Birthday Steph! I am also quite happy with what I’ve been able to do during my 20s. I feel very lucky. I just read this article about the super high expectations of our generation, and I thought you might like it:

    Enjoy Colombia! I might be going there with a friend around Christmas. I hope our paths cross again!!

    • Steph October 30, 2011 at 1:30 PM #

      Thanks! As long as we’re both wandering around South America there is a good chance they will.

  9. Matthew Karsten October 25, 2011 at 1:24 PM #

    Wait until you get to 30! The pressures magnify.

    But a few days later, you´ll relax and wonder why you were worrying so much.

    • Steph October 30, 2011 at 1:26 PM #

      Yeah I guess uncertainty and pressure is a fact of life no matter what your age.

  10. Jarmo October 25, 2011 at 1:52 PM #

    Happy birthday! Yup, nobody else has it figured out either (I think), and besides, it’s just a number. I recently hit the “magical” 30 while traveling. I might have had a bit of a crisis about it as I didn’t tell anyone about it at the time! But in the end, nothing changed. And now I am ok with it 🙂

    • Steph October 30, 2011 at 1:24 PM #

      Happy Birthday and glad you got through it!

  11. Nancy October 25, 2011 at 1:58 PM #

    Happy Birthday. I’m many, many birthdays past yours and I’ve learned that the key is not to worry–about anything, ever. It doesn’t ever help. As the Dalai Lama says, if something is wrong and you can change it, no need to worry. And if you can’t change it, well, no need to worry!

    • Steph October 30, 2011 at 1:20 PM #

      Thank you! I definitely agree- it’s useless to worry about things you can’t control.

  12. DTravelsRound October 25, 2011 at 2:11 PM #

    Happy Birthday babe!! I love this post. 🙂

  13. Megan M. October 25, 2011 at 3:16 PM #

    I love this post! As my 26th birthday is coming up, a lot of this really hits close to home. Can’t wait to see where the next few years of my life lead me.

    Happy Birthday!

  14. Alex October 25, 2011 at 5:22 PM #

    Love this post! I’m excited and anxious about my twenties. 🙂

  15. Kelley October 25, 2011 at 5:50 PM #

    Hits very close to home for me too. The Twenties are the best of time and the worst of times, and most of all, VERY pivotal times. Congrats on all the great choices and being in Bogota on your bday!

  16. Jeremy Branham October 25, 2011 at 5:56 PM #

    Woohoo! Happy birthday! Only a few more years until this blog turns into thirty-somethingtravel!! I didn’t even recognize you in that first photo when you were 21! 🙂

    • Steph October 30, 2011 at 1:18 PM #

      Haha people keep saying that- It’s making me worry a bit…

  17. Rebecca October 25, 2011 at 6:17 PM #

    Happy Birthday!! I turned 30 this year and I love posts like this remind me how AWESOME my 20’s were. Like, where was I when I turned 27? Oh yeah, living and working in Australia!!!

    • Steph October 30, 2011 at 1:17 PM #

      That’s the goal, to look back at 30 and think about how awesome everything was.

  18. suki October 25, 2011 at 6:19 PM #

    happy birthday! october babies rock. 🙂 i did a reflection of sorts earlier in the week because i just turned 30. it’s weird. i don’t feel older, but i know i’m much wiser. 😉 maybe.

    • Steph October 30, 2011 at 1:14 PM #

      Happy Birthday and congratulations on being 30!

  19. Christine October 25, 2011 at 6:38 PM #

    Happy Birthday Steph! I’m still in the early half of my twenties, but certainly can relate to a lot of what you’ve said here–as with everything, the greater the risk, the greater the reward!

    • Steph October 30, 2011 at 1:14 PM #


  20. Lisa | LLWorldTour October 25, 2011 at 6:43 PM #

    Happy B-day Steph!! My 30s have been pretty awesome. I think life gets keep getting better the more we learn and see. How are you guys liking Bogota? I liked it!

    • Steph October 30, 2011 at 1:11 PM #

      It’s great but I think I’m ready to go explore the rest of Colombia now!

  21. Gerard ~ GQ trippin October 26, 2011 at 12:33 AM #

    Happy LifeDay Steph! Don’t worry. I’m one year closer to 30 than you. But you know what they say, 30 is the new 20! It’s safe to say you’ve been making the most of your ‘glory years’, but who said those years have to end?

    • Steph October 30, 2011 at 1:11 PM #

      If 30 is the new 20 is 27 the new 17? Not sure I like that htought…..

  22. Ian [EagerExistence] October 26, 2011 at 2:08 AM #

    Happy Birthday!

    I recently turned 29, that means I only have a year left (til I can’t read your blog anymore :-P)!!

    I don’t fear getting older either, but you’re right, some days it sure is a struggle, this growing up thing.

    I love this bit
    “I also remind myself that nobody else has it figured out either. Life’s not a race, it’s an evolution.”

    • Steph October 30, 2011 at 1:08 PM #

      I hope you’ll keep reading anyways!

  23. Beverley | Pack Your Passport October 26, 2011 at 6:34 AM #

    Gaaaah turning 26 in July made me feel exactly the same! It kind of stresses me out that time seems to literally be flying by but I know that, if I was home and married with a house and stuff like a lot of my friends are then I definitely wouldn’t be so ‘ok’ with it.

    Age is only a number Steph 🙂

    • Steph October 30, 2011 at 1:03 PM #

      True that. I’m pretty happy with my choices- or I don’t want the alternative at least.

  24. Camden October 26, 2011 at 9:30 AM #

    Thanks for posting! I’m 25 and living in Shanghai. It’s awesome to know other people are living their lives in a similar way!

    • Steph October 30, 2011 at 1:03 PM #

      Thanks! It definitely helps that there’s more of us.

  25. Carmen October 26, 2011 at 1:22 PM #

    Happy Birthday!!!!
    Thanks for writing this wonderful post. I stumbled upon your blog while my great friend and I are planning our first girlfriends trip this December. We’re both in our mid-twenties and have decided to take a risk and pursue second degrees in another field (from our undergrads)…. Our twenties has definitely been a challenging and wonderful experience!
    Best wishes on your day!

    • Steph October 30, 2011 at 1:02 PM #

      Great, glad it was helpful for you!

  26. Audrey October 26, 2011 at 2:02 PM #

    Happy 27th! I can definitely relate to this post! I’m in my 20s and I’m definitely familiar with that ‘place’ full of decisions that will affect which way your life will go – conform or take the leap of faith! 😉 Wishing you all the best in this coming year!

    • Steph October 30, 2011 at 12:57 PM #

      Thanks! I think it helps that so many people feel the sames things.

  27. Alouise October 26, 2011 at 7:10 PM #

    Happy Birthday.

    “Life’s not a race, it’s an evolution.”

    I love this philosophy. We put so much pressure on ourselves to get our lives figured out in our 20s, but no one has their whole life figured out. I’m 27 too and as much fun as I had in my early 20s I wouldn’t want to go back. I like who I am now, and I wouldn’t want to have to relearn everything that I learned in my early 20s. Age really is just a number and I’m sure the best for you is still to come.

    • Steph October 30, 2011 at 12:55 PM #

      Very true- my early twenties were fun but I definitely wouldn’t want to go back!

  28. Juno October 26, 2011 at 9:55 PM #

    Happy birthday Stephanie 🙂 Great post. Yes, Twenties… it was awful and awesome at the same time but I gotta say, it’s getting better in time. Now is way better than few months before, and than few years back.
    Glad you are enjoying life 🙂 Cheers to twenties!

    • Steph October 30, 2011 at 12:54 PM #

      Yup, there are ups and downs but I always feel like I’m moving in the right direction.

  29. Claire October 27, 2011 at 6:01 PM #

    Happy belated birthday and that is a fantastic way to celebrate (beverages, boyfriend, Bogota). My twenties were mostly awesome, with a few terrible parts thrown in, which just made the complete package of the 20’s all that more awesome! I turned 31 a few months ago and it’s a little……..different than your 20’s!

    • Steph October 30, 2011 at 12:40 PM #

      I’m sure that thirties are a whole adventure in their own right.

  30. Kelsey October 27, 2011 at 11:01 PM #

    I really love seeing more personal posts like this from you. They’re some of your best.

  31. Lauren F. October 28, 2011 at 1:41 AM #

    So this first picture I thought was a recent one. Maybe you don’t marginally resemble your 21-year-old self emotionally, but you sure do physically. Good genes!

    I’ve been thinking a lot of doing a similar post as I’m turning 30 in about five weeks. I can’t believe how different I am at 29 compared to how I was at 20. It really is amazing the changes you go through in this decade of life.

    Happy Birthday, Steph.

    • Steph October 30, 2011 at 12:38 PM #

      Thank you for that! I was starting to feel a little insecure…

  32. Joya October 29, 2011 at 8:46 PM #

    Happy Birthday Steph! I completely agree with you. I’m 26 and while I’ve done so many amazing things in the past five years, I feel like I still have so many things to figure out and it can get overwhelming. Thanks for writing this and if anybody wants a good laugh about being in their twenties, the tumblr F*ck! I’m in My Twenties is hilarious.

    • Steph October 30, 2011 at 12:34 PM #

      Oh man, thank you for that!

  33. Emily @Travelated November 1, 2011 at 11:03 PM #

    I couldn’t agree with this post more. I just turned 28, and I have to say that my 20s have been pretty tough, but very important. I’ve learned a lot about who I am, what I want, and what I believe. I am so looking forward to my 30s, because I know I will have more of life figured out and I will be more confident in myself as a woman.

    Here’s to the next few years! Let’s enjoy it while we can!

    • Steph November 6, 2011 at 7:27 PM #

      Yeah I’m definitely looking forward to being even more confident and self assured in the future.

  34. rob November 6, 2011 at 9:17 PM #

    I turned thirty while living in Sweden and it took me a year to get over the depression of not being in my 20s. I guess I wasn’t like many of your commenters – I loved my 20s, and after getting my act together my 30s were pretty great too. But do be sure to wallow in every moment of your 20s. After that people expect you to settle down a bit, and it’s annoying.

    • Steph November 15, 2011 at 11:09 PM #

      Yeah I’m trying to enjoy every little bit!

  35. Tonya Keitt Kalule November 10, 2011 at 12:11 PM #

    Hi there sweetie. I am with your mom, it was the hardest decade of my life, and I would not go back to it. No nothing tragic, just the pressure, and not having enough sense to take the time to figure out who I was and what I really wanted, because everyone was telling me who and what I was. I know they meant well, but I spent most of my life trying to be someone else, and you have probably heard how stressful that it.
    I love that you are figuring it all out and are not propelled by any of it. I am 50 and my daughter is 25, so she is about where you are. I have always told her the same thing that you mom told you.

    Thanks for sharing.

    • Steph November 15, 2011 at 10:46 PM #

      Thank you for the thoughtful comment! I really appreciate it, and I think your daughter is lucky to get the same advice 🙂

  36. Anthony November 23, 2011 at 8:04 AM #

    I couldn’t agree any more, Steph! The twenties are emotionally intense, but you seem to have reacted pretty well 🙂

    Here’s to more awesome years in the twenties (I have two more years left) and have a lovely birthday.

    • Steph November 23, 2011 at 5:49 PM #

      Thanks Anthony!

  37. Nicky November 28, 2011 at 10:46 AM #

    I’m slightly late, but my word, am I glad I found this post! I needed it! I’m not in exactly the same position you are – I’m 27 in a week and haven’t really travelled at all. But I feel the same way about the pressure and decisions and changes, and am just going through a realy crazy time at the moment. And it’s so good to hear that not everyone has it figured out at my age. Thank you.

    • Steph December 4, 2011 at 5:05 PM #

      Aww, glad it resonated with you!

  38. Allison January 14, 2012 at 11:00 AM #

    This was very well-written! I’ll be 27 this year and I’ve never traveled due to more pressing concerns. I have to admit that I’m envious of your life and the life of other 20-somethings. I can’t help but feel I’m missing out on the almost-carefree lifestyle that many 20-somethings experience.

    I’ve been working to support myself since I was a young teen in order to survive. My 20s have been nothing but stressful and miserable. Although I’ve experienced a lot of adversity and managed to overcome it, I still feel like I know absolutely nothing about life. I feel like I don’t know much more than I did at 17, which is a scary thought since I’ll be 30 in a few short years.

  39. Jenny May 3, 2012 at 9:09 AM #

    I’m turning 24 soon and all of a sudden have realised I don’t have a clue what to do or where to go next. It’s nice to know that that’s ok, and maybe a good thing.
    I’m exited for the rest of my twenties now so thank you xx

  40. Lauren December 3, 2012 at 10:12 AM #

    I turned 27 in October and this is pretty much spot on for me. It seems like there are so many life-changing decisions to make in our twenties, I wonder if it ever slows down. I try to remember that no one knows what they’re doing, really, everyone is just “winging” life. I have taken my passions–backpacking abroad and working with college students–and parlayed them into a job where I run a study abroad office at a college! While my life doesn’t always match up with other people’s expectations or ideas about what I should be doing (for instance, marriage, family, etc), I love what I’m doing and I’m happy figuring out my life as I go along. For me, that’s what is important!

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