Every now and then my mind drifts back to two Christmases ago on Bottle Beach where I met Jason, a 50-something British man who had lived in the same simple, electricity-free beach bungalow for nine years.
He started traveling the world looking for a new home after his brother passed away, leaving behind Italian sports cars, a big house, and an unused retirement fund. Once he died, all of it went to waste, no longer mattered, and seemed to have been for nothing. It was Jason’s wake-up call. He stopped chasing money and instead chased peace. He found it on Bottle Beach, so he stayed.
I’m no Jason, but I departed a “normal” life in a similar fashion, chasing peace and trying form my own opinions on how I should live. I still don’t have the answers, but maybe that’s because life is really about the questions.
Just about every writer who travels long term eventually puts out a post about things they’ve learned, but for me, there are many more questions than answers.
As much as I’ve traveled outwardly, these past two years have gone inward quite a bit as well, turning my perceptions upside down and challenging everything I thought I knew. Here are 10 key questions I realized we need to ask more, determined from traveling alone for the past two years:
1) Why don’t I realize how rich I am?
Having a roof, real walls, regular meals, clean water, the technology to read this blog, a car (no matter how much of a clunker it is), access to a credit card (or even a bank account), and the ability to obtain a passport that permits entry into most countries in this world are massive luxuries that most people do not have.
It’s easy to get bombarded by rich celebrity worship, obsess over how to be thin or look pretty, feel inadequate because the guy who just passed you on the freeway drives a Maserati, or give too much importance to a Louis Vuitton purse. Every day we’re convinced that who we are and what we have isn’t good enough.
Leaving the Western world and going to places where scores of people live in shacks with dirty water, have no hope of ever leaving their small towns, and do the same back-breaking tasks every day with very little chance of ever knowing what it’s like to worry about gaining weight put this into real perspective. Even the poorest of my circle friends (which is actually probably me now) is rich beyond imagination compared to the majority of people in the world.
2) Why aren’t generosity, openness, and compassion valued more than money and beauty?
I used to think that the most important things a person could possess were money, good looks, and power. Now I realize that so many of those things are fake, fleeting, and so irrelevant and shallow that I shudder at my former definition of success.
The person who selflessly helps another, seeking no recognition or even thanks, and manages to smile and be kind most of the time, plus doesn’t turn up his nose at a new custom, but remains open – he’s the one who I admire and want to spend my time with whether he has money or not.
3) Why do I always think it’s about me?
It’s easy to get frustrated or feel agitated when traveling in a new country where I feel like an outsider because I don’t understand much of anything and can’t comprehend the customs. It’s even easier to get upset when I feel I’ve been cheated or a tout is too aggressive with me. I feel targeted, but that’s silly, because it’s really not about me.
People simply want to pursue happiness instead of suffering. Maybe that means cheating me or waving me away if helping me might be too much of a hassle. Taking it personally is the wrong approach. I do believe that you get out what you put out there, but I also believe how random people treat me is usually not about me.

4) Why do I forget that happiness is a choice?
“I’m captain of this ship,” I often have to tell myself on down days. If I’m going to be sad, it’s because I’m letting myself follow negative thought loops. If I’m going to be at peace, it’s because I’ve mentally put myself there.
It’s important to be careful where one puts his or her energy, because so much of what we subconsciously think or believe shapes our day-to-day lives in ways that we often can’t see until it’s too late.
I thought traveling would cure all, but nothing can, because there are positives and negatives that come along with every choice. Once I realized this and simply pushed out negative thoughts and refused to think of them, life became a lot sweeter.
5) Can less really be more?
Ever since de-complicating my life and possessing fewer things, I’ve realized how much easier it has been to enjoy every moment.
I, for a long time, used to make about 20% of the income I used to as an investment banker. It was miniscule. It means I had to eat street food, stay in cheap countries, and take public transport to make ends meet. It also meant I experienced more local culture, ate better, and loved and laughed more in my daily life.
6) Can love really last forever?
A friend once said to me that all relationships ebb and flow, and I realized how right he was once I started traveling, leaving some of my best friends and could-have-been romantic partners behind. Yet the best friends who have always been there for me from back home still are, and though our friendships have evolved over time, the fact that we continue to put effort in is what makes us close.
The natural state of things is to change. It’s OK if a relationship changes because that’s what life and people do. Accepting this has made life less stressful and put less pressure on my relationships.
7) How much of perception is real?
Photoshopped images, only the happy moments that show up on Facebook, and the acquaintances who seem to be hitting every major milestone of the magic three: a master’s degree, marriage, and motherhood, can make me feel like an utter failure at times.
But there’s often so much behind the scenes that gets swept under the rug. Everyone has skeletons in her closet that she hides, no matter how issue-free things appear on the surface. Comparing myself to something that isn’t even real is a recipe for disaster. As Theodore Roosevelt said, “comparison is the thief of joy.”
8) Why don’t I appreciate what I have achieved more?
When I was a kid, I envisioned myself going to the exact university I ended up attending. When I was a teenager, I imagined living in Newport Beach one day and climbing the corporate ladder – something I did exactly six years later. Then, I dreamed of buying a one-way ticket and traveling the world, building a travel blog and having real readership. It has all happened, and yet I still find ways to be dissatisfied with the present moment, always wanting more. More of what, though?
Now I realize, it’s not about, “once I do this, I’ll be happy” (point #4). It’s more about recognizing the triumphs and having pride in my accomplishments while still dreaming and acknowledging that I have and always will have future goals. When I stop and appreciate that I’ve done much of what I’ve set out to do, I feel a lot better about what I haven’t yet achieved.
9) Why am I so afraid of getting older?
Mark Twain said, “Do not complain about getting old, it is a privilege denied to many.”
I can’t help it. I was raised in Southern California and it’s a shallow, Hollywood-impacted culture. We care a lot about our looks and how others perceive us. It has taken a long time for me to finally realize my body is a vessel, and it’s the soul that makes me me. This may seem overly flowery, but appreciating my health, amazing life experiences, and most importantly, freedom, are important and only afforded to me because I have survived for as long as I have.
When I think about all of the things I’ve experienced in my life, I realize that each year is the greatest gift I could ever have been blessed with. Not everyone makes it out of infancy, childhood, or their early 20s.
10) Why do I think everything I do matters so darn much?
I stared up at the stars one night on a boat in Komodo and couldn’t believe how small it made me feel. It was like I couldn’t matter less in this universe. I’m just one small hiccup in millions of years in an endless abyss of particles, ideas, and energy. It was incredibly freeing to realize this. It was like any little mistake I make will never matter, and nobody really cares anyways.
Once I realized how little time anyone else devoted to thinking about me as compared to the amount of time I thought people spent judging me, I realized I was free. I can do anything I want, because every little thing I do, as long as it doesn’t hurt someone else, has almost no impact in the long-term. A few centuries from now, it’ll be as if I didn’t even exist.
This isn’t depressing. Quite the opposite – it’s liberating! The small stuff is not a big deal, and little mistakes are meant to be made.
In closing, there are a lot of things I learned from two years of traveling, like becoming my own boss, and spending most of the year in places completely foreign to me. Chief among them is to never stop asking questions, wondering, and of course, wandering.
Cover photo by Evran Ozturk
Lisa says
Good questions, and great reflections. Thanks for sharing.
Christina T Zchyn says
Great reflection , I adore your courage ! This article is so inspired =) Look forward more upcoming travel share .
Kristin says
Thanks so much, Christina. It appears you’ve had amazing travels as well! I’d love to see Tibet.
Franca says
Once more Kristin you are inspiring others to take the courage of fighting any fear and finally leave the comfort zone. People need to know how enriching travelling can be, but they also need to know everything else that comes with it, nothing is always easy and straight forward. Best wishes and more years of nomadic adventures to come 🙂
Kristin says
Aw thank you, Franca.
Jeremy says
Seriously, AMEN to everything on this list. Looking forward to crossing paths with you someday!
Kristin says
Feels weird to me that we haven’t met IRL because it seems like we have!
KMunoz says
This is my first time on your site and what a post to welcome me! I loved everything about this. Thanks for sharing these beautiful observations.
Kristin says
Welcome! I’m glad you enjoyed it!
Anonymous says
Kristin, you are so inspiring ! Keep writing !!
Evran says
Kristin, how nice you have realised that facts and also shared with us with your beautifully fluent and inspiring writing.
Kristin says
Haha, beautifully fluent. German is next! 😉
Kaleena's Kaleidoscope says
Great questions! I particularly relate to #8. I think it’s a trap that people like us with ambitious, perfectionistic tendencies tend to fall into. I have to constantly remind myself that by living abroad, I AM living what I used to dream of, even though right now I catch myself feeling like I’m not accomplishing much. And it’s true–I’m totally afraid of aging now when I know I shouldn’t. But these wrinkles–they’re really setting in! haha. Lovely post. 🙂
Kristin says
It’s definitely a trap but also part of our culture, so it’s a hard thing to shake. I agree with the wrinkles and every time I see a new one I’m like, “noooo!” but it’s inevitable so the two choices are to embrace it or fight it and the latter battle isn’t one I want to wage.
Rika | Cubicle Throwdown says
Wonderful post Kristin! Love how you framed it with questions. Very insightful!
Rachel of Hippie in Heels says
I really enjoyed reading this. Number 7 is one I struggle with. Actually, I think in blogging it becomes a competition sometimes, so adding that on top of personal life is a lot of comparison that I can’t help making. Before I travel blogged and worked as a nurse, I wasn’t ever wondering if someone was a better nurse than me- but choosing a job of writing in a public space has changed a lot.
Kristin says
I agree that in that regard I always feel inferior, but then I look at the people who have larger readerships and they have definitely been around for longer, and longevity has a lot to do with success. Working more and more and more are what lead to success in just about any field I can think of. Experience is what you need. Isn’t easy but it’s a journey and a great one once you start to see it paying dividends.
Katie Featherstone says
The main thing I take away from travelling is that life is just whatever you make it. Travel just means we can leave all the mundane behind and try and find something new and exciting- like you said, you make your own happiness. Thought provoking post, thank-you.
Kristin says
Very true.
Kristin says
Gratitude is huge, and compassion. Those two are major for me.
Silvia says
This are such great questions to raise! I tell myself that I’ve broken free by deciding to travel and write instead of pursuing a “normal” career, but in many ways I’ve just attached myself to a new set of standards set by travelers and travel bloggers. It’s important to step back sometimes and reassess my priorities.
Kristin says
That’s such a good point. You leave one routine but inevitably pick up another. Just has to be all well in your heart.
Chris A Sharpe says
A touching analysis of the things we all think when travelling a long time, but are too afraid to talk about. The questions you ask are tough, and can only really be understood through experience. Everyone at one point in their life will have been guilty having these thoughts, doubts and fears, opening up and breaking down these misconceptions is something to be applauded. Excellent use of a Mark Twain quote as well (a personal fave) “Do not complain about getting old, it is a privilege denied to many.”
Kristin says
That quote was big for me once I discovered it, and really put things into perspective. Why are we so afraid of getting old? I guess for most it feels closer to death but that could happen any time.
Abi says
So glad you pointed out number one…If only more people could realise!
Kristin says
I think it takes traveling to realize. Leaving your bubble is so important and most people never do.
Ayngelina says
I don’t think travel ever solves these questions but maybe makes us feel more comfortable that we don’t know the answers. Or maybe the older I get the less I need to feel like I have everything under control. Don’t fear age, I’m happier each year.
Kristin says
I also wonder if it’s just maturity or travel that has helped me feel less worried about not having the answers. I’m sure it’s a combination of both but traveling was definitely a catalyst.
Abby says
Our society almost makes us feel guilty for being content: “I know I should be happy, but…” Beautiful, beautiful post.
Kristin says
So very true. It’s like saying “I don’t want anything more and I’m happy with this,” feels arrogant, but why should it be?
Thank you Abby 🙂
Alana - Paper Planes says
I loved reading this, Kristin, and have many of the same nagging questions. While traveling has opened up my world in wonderful ways and made me more comfortable in some truths, in reality it’s made me question things more and become even less sure of things than I was before I left home…
Kristin says
So true. I question a lot more, but I think that’s a good thing.
Alex says
Wow, Kristin, I can’t tell you how much I love this post. I’ve come back to it and reread it a few times now! I’m going to keep a lot of these questions in mind for my own self reflection. I found myself saying, “I am the captain of this ship” when I woke up to some unpleasant thoughts this morning! Love, love, love.
Kristin says
That’s wonderful! I’m so glad it made a positive impact. Thanks for the amazing comment <3
Angie Away says
Awesome post! Thought-provoking! Traveling has certainly made me ask a lot of these same questions — and even though I continually come back to the same answers, I find myself getting caught up in the non-important stuff over and over. It’s great to be reminded of the big lessons I learned while on the road full time, so thank you!
Rekha Devarapalli says
Beautifully written Kristin!!
Jess says
Wow – you have just summarised everything I’ve been thinking and feeling for the past 6 months. That’s why I so love reading these blogs. I’ve just moved to Thailand for two years, it’s been my plan for 5 years. Now I’m so happy but the first few weeks I was like – ok what next?! Enjoy the moment is the best advice I’ve given myself 🙂
Kristin says
Good for you! Thailand is awesome.
Laura says
Very though-provoking. Number 4 is a big one for me, especially when getting pulled into the sometimes drama of daily (read: work) concerns.
Kristin says
It’s hard to remember to just push bad thoughts out but when I can do so effectively it’s a big help.
Simone says
This has to be one of my favourite and most thought provoking posts of yours! You’ve given me a lot of food for thought 🙂
Kristin says
Yay! The good response on this has led me to write more similar posts.
Camels & Chocolate says
YES to all of these, but especially NUMBERS THREE and TEN. This is so thought-provoking and lovely. Enjoyed reading it!
Kristin says
I’m glad you enjoyed!
Joyce says
I love how travel changed your perspective. Thanks for sharing, I always love to hear other people’s stories and lessons learned.
Kristin says
I do as well. I always find those kinds of posts to be very uplifting.
Mary says
Bravo! What a brilliant philosophy you have developed through your travelling. Mine is similar! As a 75 year old wrinkley, who still loves solo travel, let me reassure you that wrinkles don’t matter a jot. In fact I believe they have become an advantage while I am travelling the world! Thank you for a great read. I found your site through Nomadic Matt. May your journey throughout the world continue to bring you many more joys with no troubles. Mary.
Kristin says
Thanks Mary! Really nice to have your thoughts on the beauty of aging and traveling solo at 75! My grandmother traveled a lot as well and I always looked up to her for that, among many other reasons.
Anne says
Beautifully stated. Everything! We have just been (“just”) on the road for 10 months and I can genuinely relate to these questions. And to your point about how much of perception is real. It goes both ways. I post pictures and send my friends and family pictures of all the FUN things we do… but there are also the very REAL moments of long term travel like this that aren’t so glamorous, that don’t often get told. 🙂 I know you can relate to that, too!
Keep doing what you’re doing… I think you’re amazing!
Kristin says
Thanks Anne 🙂 I’ve written posts from time to time about the non glamorous side, but it’s hard to understand until you go, right? Otherwise it just sounds like griping about an otherwise awesome lifestyle. Lots of REAL moments traveling, that’s for sure.
ChasinJason13 says
#11- Why in the hell did I think that what I wanted, or even thought I wanted before I went to would be the same things I wanted when I returned? What, did I think going on adventures of a lifetime would just cement in me that everything I was doing before was right on the money?
You know, it’s cliche these days to say that you’re going traveling to “find yourself” but I for one have found much more of myself out there -wherever “there” may be- than I ever have at home.
Kristin says
I have as well and honestly I think traveling does help you find your true self – without the influences, values, and judgements affecting your decisions like they did when surrounded by a certain type of society, friends, and family. No matter how well-meaning, we affect each other’s decisions. Once you’re on your own exploring the world you start to realize how capable you were all along of making your choices on your own. It’s pretty cool.
Alex B says
I love this so much! I’m bookmarking this under my “Inspiration for when I get down on the road” folder 😉
Kristin says
Aw thanks and that’s a really good idea to keep something like that. I think this one is really good to stick in there too: http://zenpencils.com/comic/98-alan-watts-what-if-money-was-no-object/
Martina Donkers says
Hey Kristin 🙂
This is such a beautiful post, and an affirmation to life.
It’s so important to remember what we have, how privileged we are in our travels, and how much of the world there is to explore.
Martina 🙂
Kristin says
Thanks Martina. Agreed 🙂
Navraj says
You get a perfect ten for your thoughts! But like you said about relationships, it’s true of ourselves too. Feelings and emotions also keep ebbing and flowing. The key is to remain centered by being in harmony & balance with all our surroundings and most importantly with ourselves.
Happiness is our choice, our responsibility to ourselves. I have observed that it’s not bad that relationships change. Those which help each other grow and experience life in a much deeper & more meaningful way tend to flourish.
Life is beautiful and we need to disconnect the thought that happiness depends on getting something or someone.
Keep on! God speed!