Should I Stay Or Should I Go? A Traveller’s Conflict

by Brenna Holeman
Around the World
I have a secret, something that I’m not very proud of: I’m addicted to travelling.
I do not say this facetiously or sarcastically – I really do have an addiction. Instead of throwing all my money into online gambling, or daydreaming about when I can have my next drink, I’m throwing all my money into travelling, and daydreaming of when I can take my next trip.
Even though I’ve been on the road for over seven years now, devoting my life to seeing as much as I can of the world since graduating university, I’ve always known that I was destined for a life like this; going back through old journals tonight, I found that I had written, “When I grow up I want to travel. That’s all I want to do.” I wrote it in 1994. I was 10.
(I also wrote about how much I loved the movie Death Becomes Her, how I have a crush on Joseph Gordon-Levitt, and how I wish that Kurt Cobain and John Candy weren’t dead, so not many other things have changed, either.)
Every time I’ve tried to settle for a bit, my feet start itching, I start looking up flights to new locations, I buy guidebooks for countries I don’t know when I’ll see. In the summer of 2009, I went to Vietnam for a few weeks on holiday from my job in Japan. Even though I’d only been living in Japan for a year at that point, I wrote,
“This feels so good, meeting interesting people, drinking beer, taking trains and slinging a backpack on my back. I really had forgotten how wonderful it could all be, how easily it could all fall back into place. Maybe I should be doing this instead of staying in one place, maybe I should do this forever.”
I stayed in Japan for another year and a bit after that, even though I managed trips to Sri Lanka, Malaysia, Brunei, and the Philippines in between. I wrote, in September of 2010,
“As much as I love this crazy life I lead, should there be a part of me that also craves a bit of normalcy, a more permanent home, a less transient life? I struggle with this. Will I find that in a city, any city? Will I be content to go back to school at 28 years old, or older? Will I ever shake this wanderlust? When will I have time to go do all those things I want to do – a safari in Africa, studying French in Paris, travelling through India and Nepal, backpacking in South America – if not now?
I often feel very conflicted, as if there are two sides to me: the one who wants a house and a career and kids, and the one who doesn’t want to be tied down, who is free to roam wherever I’d like. Is there a way to have both?”
Recently, I thought I had it all planned out. I had just come back from Brazil after eight months in South America. I knew what the obvious next step was: keep going. I was going to move to London in March, settle there, and hopefully start school in September. It was a way to satiate both the part of me that wants to take it easy for a while as well as the part of me that forever wants to keep moving.
But, as life is wont to do, a few hurdles were thrown my way, and it is no longer possible for me to move to the UK right away. I’m definitely still moving there, just not until the summer. While I’m disappointed, I’m also sane enough to realize that six months in Canada is not the end of the world; in fact, it may just be a blessing in disguise, a much needed respite from adrenaline to catch up on writing, online classes, and to get my health back in order (my body is still recovering from an accident in South America, which I’ll write about another time).
Besides that, I already have trips planned: Arizona and Nevada in March, England, Israel, and perhaps another European country in April and May, and TBEX in Toronto in June.
So even though I’ve been forced to settle for a few months, it’s not as all like it’s a permanent thing. Which leads me back to my quandary: will I ever “settle”? Will I ever have permanency? What if I’m destined to always be inflicted with a need to move on, to see more?
While I have never  succumbed to societal pressures, I’m still a woman nearing 30 with no real job prospects, nor any romantic prospects. I’m, as always, single and unemployed.
I found great comfort in the words of Elisabeth Eaves, who, in her travel memoir Wanderlust, wrote,
“You could say that I forgot to make a life. Forgot to get a steady job, or belongings, or a family of my own. I forgot to choose somewhere to be…I forgot to do the things that, despite decades of feminism, I still feel the niggling weight of, in a way I imagine men don’t…But I created my life.
If you choose one path you can’t choose another. I’ll never wonder what it would be like to sail across an ocean or move to Europe or just take a year off to chill out. I’ll never doubt myself in a strange land, never be scared of languages or funky rooms…I won’t be cynical of human nature, because strangers have helped me out so many times. My ripped suitcase, as it rumbles onto the carousel, is bursting with life.” 
And that’s the thing. Yes, I’m getting close to 30, an age where most of my friends are already well into their careers, are engaged or married, and are set in their lives, whatever they may be. I know that perhaps I should be taking these things more seriously, but I don’t want to.
In the words of Ms. Eaves, I created my life. It’s different, yes, and sometimes it’s difficult, but it’s mine. I’ve done a lot of crazy things, I’ve had my heart broken, I’ve had successes and failures, I’ve learned so much, but above all of that, I’ve been happy. Really happy.
My ten-year-old self knew me better than I could have ever thought: I want to travel. That’s all I want to do. And, come hell or high water, I’ll figure out a life that allows me to do it. My suitcase, my mind, my heart, whatever you want to call it, is bursting with life.
Should I stay or should I go? Well I’ll be damned if I don’t find a way to do both.
Do you ever feel the same way? Do you ever struggle with a need to settle vs. a need to wander? 

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Steph Lloyd February 1, 2013 - 4:19 am

i feel it too! i am married, but have no children. i feel the need to go. sooner than later. it’s compulsive. i haven’t seen as much as you yet but my best memories are abroad. thanks for sharing and getting me to think more about it. i need to get a copy of wanderlust.

Andi of My Beautiful Adventures February 1, 2013 - 4:29 am

I found a way to do both!!!!! As long as you’re happy, that’s all that matters. Sorry your UK plans have been delayed.

This Battered Suitcase February 1, 2013 - 4:32 am

Steph – It definitely is compulsive! I hope you buy the book soon, I really enjoyed it.

Andi – You did, and congratulations to you for it! You’re an inspiration for all of us travellers.

liveletlive February 1, 2013 - 4:51 am

I dont think you should force yourself to do anything, just because you feel like you’re at an age milestone, but I’m a HUGE fan of balance.

I do eventually want to be a long term traveller, but the thing that would worry me the most would be retirement. There would have to be some ratio for travel to savings. And a lot has to go into savings because I want to retire early. 🙂

My dream retirement age is 35

Lorra Fae February 1, 2013 - 5:07 am

totally awesome post. i TOTALLY struggle with these feelings, all the time.

Spencer February 1, 2013 - 6:48 am

I feel your words so deeply in this particular post. Keep on keeping on and you will never be disappointed.

They say the only things we regret in life are the things we decide NOT to do. So just do it! Haha, (sorry Nike).

This Battered Suitcase February 1, 2013 - 7:09 am

liveletlive – I agree, age should never dictate what we can and can’t do (physicality aside). I also want balance in my life, which is what I hope to find in the next few years. What can I say, I want to have my cake and eat it, too!

Lorra – Glad to know I’m not alone…

Spencer – Thank you so much! And I completely agree with your last statements, whether they are influenced by Nike or not. I feel a little Mark Twain in there, too.

Caitlin Oliver-Olsen February 1, 2013 - 7:56 am

Hey Brenna!
I’m very much the same–nearing thirty, single, unemployed, and still picking up my bags and moving every 6 months or so. I feel the same conflict–the desire to travel and see the world, to live in different countries and cultures, and to be on a continuous, wild adventure; and on the other side of things, I do have a desire to settle somewhere, chill out, have a stable community of friends, have a steady boyfriend, etc. I keep believing that when I find the “right” place in which to slow down and stay a while, I will. But sometimes I wonder–maybe it’s just not in me. Maybe I”ll always get itchy feet. I don’t know. Either way, I’ll figure it out and live my life as my heart tells me to. Think you’ll do the same 🙂

Antastesia. February 1, 2013 - 11:18 am

Eventhough i’m only 21(it seems way too old to me anyway) I probably think about that matter everyday.
My friends all have career ambitions, or want to create a family, or just enjoy their steady lives, pretty much knowing they’ll stay where they are now forever, and they’re content with what they have now.
But I feel this need to diseapper, to go away, to leave everyday. I love Paris, and I miss it when I’m away, but I equally( well apparently more) love being abroad. People ask me why I don’t have a boyfriend, simply because I feel like it would take too much of my time, and I wouldn’t feel as free as I am now, and eventhough I do like the job I’m studying for, it is only a way for me to be able to travel while working.
The thing is my friends don’t feel this way. And I love my friends, a lot. I’m always wishing to be somewhere else, but with all my friends, family and home at the same time. Thing is, it’s not possible. But probably, any life you choose to live or to create, you’ll let some things along the way?
Since I’m still pretty young, I’m trying to enjoy as much as I can this life in Paris, while travelling everytime I can. Because I know that as soon as I’m done with university, I’ll have to really face this “should i leave or should i stay” dilemma.
Thank you for writing always such interesting posts, and also commenting on my blog 🙂

Georgie October 23, 2013 - 4:07 am

You are exactly like me! I am just about to finish me design degree, all of my class mates are focusing on finding jobs in Australia, I’m looking all over the world. I’m moving to Europe on March job or no job. I just want to travel and be free.
I’m glad other people think like me sometimes I think I’m a bit weird for not wanting to be tied down.

Brenna Holeman October 24, 2013 - 10:20 am

There’s an amazing community of travellers who think just the same way. We’re not weird – we just want something different!

[Ali] To Be Continued... February 1, 2013 - 2:11 pm

Darling it sounds like your heart knows exactly what it wants and needs but the little niggle in the rational brain sometimes tugs you to fall in line to conform with the majority of western society and settle down. Not necessarily because you want to but that’s because what is deemed the thing to do [I think we all feel this if we’re honest!].
Well stuff it I say! Life is for LIVING, experiencing and loving with our arms, eyes and hearts wide open, all guns blazing!
You’re writing your own unique book of life my dear and boy is it going to be an interesting one!
Besides who’s to say you wont eventually find somewhere and someone worth staying in one place for a while… nothing is permanent after all [all of this coming from a single 32y/o, on The Road! haha!]. xxx

This Battered Suitcase February 1, 2013 - 8:11 pm

Caitlin – So nice to hear from you! I was just talking about a few weeks ago, telling someone how small the world is and how we bumped into each other twice in Europe. I completely agree with your comment, especially the last two lines. I’m sure that we’ll keep in touch over the years and find that we’re both off adventuring. xx

Antastesia – Thank you for always writing such thoughtful comments on my blog! 21 is young, of course, but so is 28 – I don’t think it matters what age we are, we’re always going to think about our futures and think about what we really want. I think it’s great that you are considering all your options, and, you’re right, sometimes we need to let a few things go. We can’t have it all, of course…but I struggle with that all the time!

Ali – Wise words as always my dear. I feel that you and I have so much in common! I once read in a book (Zeitoun, by Dave Eggers) that the man, a sailor, would decide to settle once he found either a port to love or a woman to love. I think we’ll be the same.

'Lara February 2, 2013 - 10:04 pm

OMG, this post reads my state of mind at the moment…I have not travelled as much as you have but then I am not settled and the only thing I think about nowadays is to travel or do something random.

This Battered Suitcase February 2, 2013 - 10:28 pm

I’m glad you can relate, Lara! It seems as though all I think about is travel, too…

Ms.Magpie February 3, 2013 - 12:49 pm

The timing of this post was perfect for me. Since I graduated from college in 2009, I’ve either been saving up to travel or on the road.

In just under 6 weeks, I’ll be heading off on a 6 month trip across South America and the US with my boyfriend and while I couldn’t be more excited, there’s this small part of me which is conflicted. All I’ve ever wanted is to see the world but despite decades of feminism, I still feel the desire to settle down and raise a family.

Reading this post has helped me to realize that it’s okay to feel both the need to settle and to wander. I’m still going to carry on having adventures for as long as I’m able to and I will find a way to make it work.

I’m sorry your plans to move to London haven’t worked out exactly as planned but – and I know its cliche, sorry! – sometimes these things happen for a reason. London will still be there when you’re ready and your plans for the next few months sound incredibly exciting!

Morgan x

This Battered Suitcase February 4, 2013 - 7:22 am

Hi Ms. Magpie! I think that so many of us travellers (especially women) feel this conflict from time to time. It is definitely comforting to know that we are not alone, though!

And yes, I’m sad that my plans for London didn’t work out, but I’m still going to be there in a few months, so I can’t stay sad for long!

Reply February 5, 2013 - 6:41 am

I just want to start off by saying that I absolutely love your blog and have since I first discovered it about a year ago, it’s amazing! 🙂

I am still relatively young (18 and a college freshman!) so I can only imagine what this must feel like! But if I know anything for sure it’s that I want to live this lifestyle and nothing is going to stop me from it as soon as I graduate, so chances are I will also eventually face this dilemma. I have such a restless, adventurous heart and am always trying to travel whenever I can or making plans to.

I’m sorry your plans for London didn’t work out, and I hope everything falls into place for you! Speaking of travel plans…I will also be in Arizona in March. I am roadtripping there with some friends for spring break! I may just run into you haha 🙂

– Anne the Adventurer

This Battered Suitcase February 5, 2013 - 9:31 am

Thank you so much, Anne! That is a really nice thing to say.

I think you have a great attitude – having that insatiable wanderlust is the first step to accomplishing your dream to travel. I can only imagine where you’ll go!

London didn’t work out for now, but I’ll be there full-time in the autumn, so I can’t really complain. And hey, yes, we might see each other in Arizona!!

Katie February 5, 2013 - 9:42 pm

My boyfriend and I are currently saving for a year-long RTW trip. We have been letting friends know that we are saving money, and going out less, and one friend asked, “Oh, are you saving to buy a house?” It was hard not to laugh out loud when I answered, “No! For long-term travel!” I am the same age as you, and there are many societal pressures of what we “should” be doing at this time in our lives. While I have a steady day job right now, I can’t imagine it becoming a career…and I haven’t been able to imagine that in any of the other various jobs I’ve held. I guess that is my way of not feeling tied down to a place.

I know it is sometimes hard to not do what everyone else your age seems to be doing – I have felt that many times – but as long as you do what makes you happy, you will have lived a true and fulfilling life. That is why I love reading your blog – you always seem to be exemplifying this attitude throughout your travels.

Enjoy your extra time in Canada. Waiting for and anticipating a new trip or adventure is the hardest thing for me! But it sounds like you have a lot of great trips planned in the meantime. I can’t wait to read about them.

This Battered Suitcase February 8, 2013 - 8:36 pm

Aw, thank you so much for your comment, I really connected to your words. I have never followed what I “should” be doing, and I hope I never do. It sounds like you and I are very similar!

Good luck on your upcoming adventure! It is going to be amazing.

usaabroad February 8, 2013 - 12:24 pm

I literally just wrote a post about this idea and having just turned a year older i often struggle between the pressure to settle and the desire to “do my own thing”. It’s amazing and makes me smile to read about someone struggling with the same things and still coming out with the same outcome. well done us!

This Battered Suitcase February 8, 2013 - 8:34 pm

Yes, it seems that there are a whole group of us 20 or 30-something women who have bucked the system! I agree with you – if we’re able to, we should do what makes us happy. That’s what counts in the long run.

Erika from Chimerikal August 4, 2013 - 9:45 am

These are thoughts that have been on my mind lately… and I just love the way you put this! I also love the quote, too.

I’m a “grass is greener” person but what I am learning is that wondering is so normal. Wondering what if. And I think it just happens — it’s not necessarily an indication of a wrong choice, or unhappiness, or whatever. It’s just natural curiosity. I think it’s realistic to understand that there is more than one way to be happy, even if there are things that make us happier. And I think it’s also natural to long for some of the creature comforts of a stationary life. And I also think the opposite is true, too… even people staying wonder about going, wonder what things would be like if they set out. I don’t think the wonder = regret straight off. But I do think if people feel like they are disappointed or would be disappointed with their choices, well then, something needs to change.

I think this is the thing they don’t tell you about “dream jobs” or “dream lives” — there’s still reality mixed in there. And doubt sometimes and longing. And even if you’re doing what you always loved and dreamed of, there will be moments when you’ll wonder, when you’ll second-guess, when you’ll worry. And especially when you take the non-conventional path and can’t “check off” the same things that most people your age can. But then again, those same people can’t check off the same things that you would, too.

I’m happy to hear that you are living your passion. That’s so beautiful. And I’m also happy to read that I’m not alone in these kinds of ponderings. Thanks for sharing.


This Battered Suitcase August 6, 2013 - 7:46 pm

Oh yes, the grass is always greener! Sometimes people write to me and say, I want your life. I always write back and say, well, my life has just as much crap in it as the next person!

I totally agree that there is more than one way to be happy, and I’m thankful that I have found my personal way. Here’s hoping you’ve found yours!

Rebekka October 19, 2013 - 10:02 am

That’s exactly how I feel. I study in two different cities, which are more than 500 kilometers apart just that I don’t have to stay in one place for more than a few days. I love trains. I spend all the money I have to get somewhere, some city or country, I haven’t been, and when I can’t I at least visit someone on the weekends so I don’t have to stay.
I really get kind of desperate if I have to stay in one place for longer than two weeks. It’s like being in a cage.
In my case, the reason may be, that I have never lived in one place very long even as a child, so I was always at home on the road. The funny thing is I feel at home about everywhere, it’s not that I don’t have a home. But I feel in the forest behind my parent’s house just as much at home as on some beach somewhere or at some beautiful place in a city I barely know.

Brenna Holeman October 20, 2013 - 11:31 pm

That’s really interesting, but it makes perfect sense given your history. I love that you feel at home everywhere, I think that I’ve gotten to that stage, too. It’s amazing how quickly we can feel safe and comfortable in one place.

Thank you for your comment, your last lines really resonated with me.

Brigitte May 2, 2014 - 12:55 am

Hello Brenna,
I love reading your blog. I love all the articles you wrote. But this one is the one in which i identify myself the most. I’m 24, and i still don’t know! Should I start my master, or just buy that one way ticket i’m thinking about for a year now! So this article just confirm me that I have to do what my whole body is telling me to, instead of over thinking it. Then i won’t regret because it’s my decision, and i have that chance to choose!

You’re an amazing writer, so please keep telling us about your adventures, your struggles and feelings.

(sorry for the mistakes, french is my mother language :P)

Thanks again for sharing!

On Being Happy With Being Content - This Battered Suitcase January 9, 2015 - 3:39 am

[…] road is nearly always exhilarating, challenging, and fulfilling. I’ve mentioned before that I’m addicted to travelling, obsessed with it; it’s not a joke. What I believe I’m feeling when I get those pangs […]

Anna April 16, 2016 - 6:58 pm

I know this post is old, but my thoughts have been obsessive over this subject. I started travelling young, then I went full force into a career in my mid-late 20s, found the love of my life, bought a house. I’m 32 and craving to go travel again but terrified to do so. I think about retirement, I think about how I don’t want to keep jumping from one job to the next all the time, I think about having kids and saving up for unexpected expenses. And the more I stay put and worry, the more I want to break away, put a backpack on my back and go back to living my life day to day as I did when I was on the road. It is hard to make those decisions sometime.

Brenna Holeman April 18, 2016 - 4:37 pm

I totally get it, Anna. I feel like that all the time! I know I’ll be in London for at least another year but then I have no idea what’s going to happen… best of luck, and thanks for sharing your story.


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