On Turning 29 and Being a Travel Failure

Travel in your 30s

Photo: ThunderKiss Photography, Flickr

Last month, I turned 29 on my second glass of wine at San Francisco International Airport, waiting for my red eye flight to Nicaragua. OK, maybe it was my third glass of wine (is that OK, or am I too old for that now?).

I was en route to a destination that had been on my to-do list for years, and I was super excited about it. But I couldn’t quell a nagging feeling: I was slightly freaking out about the fact that I’m now really close to being almost 30.

A lot of women my age associate 30 with life milestone deadlines: you should probably be married, own a home and have already popped out a kid. None of those things stress me out, though (I live in the Bay Area, and since my parents’ last names aren’t Gates, Buffet or Bezos, I’m aware that property ownership is still in the distant future). Nope, what stresses me out is that I’m a travel failure.

Many of my friends and family consider me an avid traveler. I mean, I have a travel blog after all! But they don’t know the truth: that I’m way behind other travelers – many of whom are much younger than me.

I’ve never backpacked through Thailand. In fact, I’ve never even owned a “backpacking backpack.” I didn’t take a gap year to travel across Europe. I haven’t found myself on a spiritual journey to India. I haven’t been to all 20 of the countries in The New York Times article, 20 places to travel in your 20s. I’ve only been to a measly 12 of them, and with all the weddings in my near-future it’s doubtful that I’ll make it to 8 more before I hit the dreaded three-zero.

Great Wall of China

The Great Wall of China, a place I have not been. Photo: Güldem Üstün, Flickr

Things look even rougher when I consider Travel + Leisure’s 20 trips to take in your 20s – I’ve only had 6 of these experiences. And according to Smarter Travel’s 30 Places To See Before You’re 30, I should have already traveled to Mumbai, South Africa, Ibiza, Brazil, the Great Wall of China, Macchu Picchu, Cuba, Egypt, New Zealand, Vietnam, Portugal, Zimbabwe, Greece and even Samoa before I reach that dreadful age where fun no longer exists.

I’ve only been to a measly 25 countries (and that includes the Vatican, which I’m not sure really counts). There’s no opportunity in sight for me to hit 30 countries before I reach 30 — I don’t have enough vacation days or money to travel to 5 new countries in the next 11 months.


Good thing I’m not particularly interested in summiting Kilimanjaro, because it’s too late. Photo: Ninara, Flickr 

The trend continues. According to Thrillist’s 15 Countries You Should Visit Before You Turn 30, I should have already hit up Tanzania, because in order climb Kilimanjaro, “you need a good set of lungs on you.” Obviously, Canadian-Swiss couple Martin and Esther Kafer, who reached the summit of Kilimanjaro in 2012 at ages 85 and 84, respectively, didn’t read that article before they went. The article shares a similar reason for why I already should have hiked Macchu Picchu (it’s “damn difficult,” clearly only a 22-year-old can handle it) and visited Vietnam (its terrain “isn’t for the delicate,” so basically, when my bones turn to dust the day after my 30th birthday I probably can’t hang).

Hotel room

On the plus side, I hear there are a lot of king-size beds in my future. Photo: KB Collection, Flickr

According to Elite Daily though, things are really going to turn around when I hit 30. Their article on the differences between traveling in your 20s and 30s reveals that I’m no longer going to have to worry about budget. Nope, I’ll “be able to travel to lavish destinations” on my bucket list (perhaps I’ll still have the chance to explore some of those destinations that The New York Times asserts I should have visited before I reached old age). The article also notes that instead of getting dropped off at the airport, in my 30s I’m going to be “taking a limo in style.”  I’m personally really excited about this, even though I don’t know how it’s going to play out. Do you automatically get a huge raise when you hit 30? Does the government send you a check? All I know, is that I’m excited to join the club!

Elite Daily does outline some negatives to hitting 30, though – the article goes on to say that in your 20s, you’re all about adventure (skydiving, cliff jumping and jet skiing) while in your 30s, you’re more about basking in the sun on the beach. I’m a little concerned about that, as I get bored pretty easily on the beach after a couple hours and don’t know how I’ll adapt.

US News also notes that “when you hit the 30-year mark, suddenly your tastes, time constraints and career demands can get in the way” of seeing the world. This is thoroughly stressful for me. I worked about 60 hours last week, and they’re saying my career is only going to get more demanding? And my tastes are going to change? Does that mean suddenly I’m not going to enjoy the views on a tropical beach, or that the wine I order with my pasta in Italy will be less delicious?


If you didn’t take a safari in your 20s, you might as well not even bother. Photo: nijaba, Flickr

Similarly, The Independent highlights no less than FORTY trips I should have taken before 30, “while I can still handle the thrill.” Aka, before my heart just gives out at the thought of anything exciting. According to this list, not only should I have hiked the 2,650-mile Pacific Crest Trail, I should also have trekked on a glacier in Patagonia, skied the Swiss alps, flown to a place called  Ittoqqortoormiit in Greenland that can only ben reached by helicopter, gone on safari in Kenya, paraglided over the mountains in New Zealand, surfed 120-foot waves in Maui and skydived in Dubai. And here I am with two surf lessons under my belt thinking I’m pretty cool. Apparently not!

Business Insider also warns ominously: “you’re not young and free forever” while USA Today claims that travelers in their 20s “have opportunities that aren’t available to older travelers.” And according to the HuffPost, I’ve missed out on key “formative” experiences in Namibia, didn’t know how to go Bhutan and even Antarctica that would have prepared me to take on “real, adult existence.”

Antarctica: a prerequisite to adulthood. Photo: Andreas Kambanis, Flickr

So while I’m partially looking forward to 30, and being a “real adult” who frequents luxurious hotels and rolls into bed around 9pm after an exhausting day of laying on the beach, I’m also realizing how sad it will be that I’m no longer allowed to make friends on the road, have crazy adventures, or even hike, since my knees will probably buckle and collapse under my frail body.

In reality, I’m pretty confident that I’ll feel exactly the same on Feb 3, 2019 (my 30th birthday) as I did on Feb 2, 2019. And while I’d love to wake up on my birthday and cash that big fat check that will open the door to the fancy pants hotels, I think I’ll be just A-OK being a 30-year-old who continues to struggle to balance travel with relationships and a demanding-yet-normal-paying career – just like I was in my 20s.

But most of all, I hope you guys will continue to follow along as I plan to keep traveling until they throw me in the nursing home! 🙂

(Because it’s 2018 and people have a tendency to react strongly, I feel like I should clarify that this article was intended to be sarcastic. I understand that I’m truly lucky to have been able to travel to so many amazing places – even if I haven’t made it to an arbitrary number of them before I reach an arbitrary age!)

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9 Comments on "On Turning 29 and Being a Travel Failure"

  1. Hi Anna, I find this post of yours interesting, since we were born in the same year (’89) and to be honest I was obsessed with number of countries – all this time. I did manage to travel to 30 countries before 30, but I haven’t achieved a lot of other things I wanted to achieve – like getting a master degree or even settling down in one track of career. I used to feel like of down about this, but then I realized that different people have different time zones, and putting limitations on the things we should do before certain age just feels kind of useless in the end! I guess we should just cherish all the accomplishments we had so far and just keep working hard to make our other dreams come true, no matter what age we are 🙂

  2. On Kilimanjaro we went a week without a shower and that was way to much for me!

  3. I think for every travel will come your time! Don’t worry about count!

  4. Love it. I went nomadic at 35 after graduating from law school in my 4th career. It’s never too late and your 30s will be better than your 20s (mine sure were!). Good luck, and I look forward to more posts from you!

  5. What inspired you to start travelling?

    • theweekendjetsetter | August 12, 2018 at 3:42 pm |

      Well that’s easy… traveling did! After my first trip, I was sold and needed more 🙂

  6. I hate being told that I’m too old and therefore not suitable for adventure or excitement. Life isn’t about ticking boxes either. Sounds cliché but it’s not about the destination it’s about the journey!

  7. Great post.
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  8. Nice post!
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