How I Became the Professional Hobo (Part II: The Logistics)

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After growing up with a dream of travel, and eventually making the decision to leave everything behind to chase down the dream, I had to start to walk the talk. Here are the nuts and bolts of how I Became The Professional Hobo.

This post was originally published in 2012. It has since been updated for accuracy of links. 

In Part I of this series, I discuss how adversity forced me to celebrate the present moment and seize my dreams of traveling the world slowly. Now it was go-time.

After deciding to leave everything to chase my dream of travel, I had to walk the talk. Here are the nuts&bolts of how I Became The Professional Hobo. #WhereToGo #ChasingTheDream #ChaseYourDreams #FullTimeTravel #TravelBlogger #TravelTips #TravelLogistics #TheProfessionalHobo
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Telling my Boss, and Selling the Business

I’ll never forget the day I walked into the office to meet with my divisional and regional directors. Although I’m not an egotistical person, it is safe to say I had garnered some attention in the financial planning industry, and specifically the company I worked for. In addition to my media appearances, I mentored new financial planners starting out in their businesses, was featured in training videos, and addressed groups as large as 3,000 people representing the company as a whole – the largest financial planning company in Canada.

So I wasn’t particularly surprised when my announcement of plans to sell my practice and go off to “play” in Costa Rica (an arbitrarily-chosen first destination) was met with open mouths and wide eyes.

“See, I told you,” said Bill the regional director, to my division director when he recovered from the initial shock. “I knew something was up.” Bill had seen my downward spiral of both health and happiness over the last few months. In the weeks leading up to my announcement, I was hardly in the office at all. My division director, however, continued to sit in shocked silence, opening and closing his mouth like a fish out of water.

“Tell you what we’re going to do,” chimed in Bill, who seemed even more prepared for this announcement than I had anticipated. “We’re going to manage your business for you. Go do what you need to do, for six months, a year, whatever. When you get it out of your system, you can come back and step right back into your life here. There’s another consultant I know who does this; he builds mud huts or something for four months out of every year in a developing country and has somebody hold down the fort while he’s gone.”

This was a tempting offer. After six long hard years of work, I was earning six figures, and had reached the point in my business where I could follow a trend of working less and earning more. In many ways I had done all the hard work of building up a business without fully reaping the rewards. If all I had to do was “get something out of my system”, then this arrangement would have been ideal. Traveling with the security of knowing there is something to come home to can be a wonderful safety net, especially if you’re not sure what you’re looking for or what you’ll find.

However, instead of seeing this offer as a “safety net”, I saw it as a limiter. A hindrance. How could I embrace whatever was on the road for me to discover if I knew I had to come back to a life so stressful for me that I burnt out mentally and physically from it? And how did I know that when I came back, I’d even want to live in the same city? I was drawn to western Canada’s vast landscapes and giant mountains, and having a business waiting for me in Toronto seemed to complicate things more than simplify them.

I was also looking for a truly fresh start. Having anything tying me to “home” was difficult to comprehend; everything had to go. The business, the car, the motorcycle, the skydiving gear, the chic urban loft on the beach (I do miss that loft), and all the “stuff” that was inside of it. In so doing, I was letting go of the traditional definition of “home” in its entirety, knowing that letting go would reveal a new definition of “home” and a new way of life.

So I kindly declined the offer and proceeded to sell my business outright. But despite my confidence in this move, I still wasn’t looking forward to the next three months of transition.

Selling Everything Else

Not only was I selling my business in as responsible a way as possible (in fairness to my clients who I had emotionally invested in – often waking up in the middle of the night in a cold sweat wondering how they’d react), but I was also selling everything else I owned.

There was no family home with lots of space to store my things, and I wasn’t prepared to pay for monthly storage. And as with my business, in the name of transitioning to a new definition of “home” and freedom, I needed to divest myself of everything; not put it on hold.

So I sold all my crap over the next few months, deciding to store only the absolute “necessities”: those things I deemed priceless or irreplaceable, as well as official paperwork and files I had to keep. In total, I had five boxes that I reverently stored in a friend’s garage.

Deciding Where to Go

I’d arbitrarily chosen Costa Rica as a starting point, having heard of an Outward Bound instructor course that sounded ideal. I could enjoy nature and train to be an outdoor education instructor, which would be a skill I could travel with and enjoy using around the world. It was also a ticket to potential income for sustaining my travels, since I had no idea how to make the finances of full-time travel work (yet).

But for some reason I couldn’t book the ticket.

Then my boyfriend at the time got a call from his brother who was getting married in western Canada and wanted him to be in the wedding party. So, west we went instead.

(You may note that in this tale so far, Kelly is only now being introduced, despite his role in the first few years of my travels. This is because I believe that my process to becoming The Professional Hobo was very much an individual one, as can be evidenced in this post. Although I treasure our relationship for what it was and what we learned from each other, I don’t believe the dream of travel was a shared one. This is my story.)

And with our last-minute decision to spend the first summer “abroad” in western Canada, also came the faith and understanding that the next travel move will always reveal itself when the time is right. And so it did (and does)…every time.

Writing…for Pleasure, and Money

Barely being able to define a blog, and with no idea that anybody else in the world was doing what I was, I started a travel blog as a way to stay in touch with family and friends while I was gone and to chronicle my travels online without needing reams of paper.

But as I did more research, I found people making money online with writing and blogs. I still didn’t see a market for my blog in particular, but I found a few others that invited me to write for them, including Wise Bread and Vagabondish; two fledgling websites at the time who were willing to give me a chance.

“Hey, wait a minute!” I said. “If I can write and making a living with nothing more than an internet connection, I’ve got it made for full-time traveling!”

What a revelation.

I had no delusions of this being an easy or quick way to riches; in fact I expected it would take years of relatively full-time work to build up a portfolio and reputation to crack into the industry. Luckily I had an income from the sale of my financial planning practice to cover me for 2.5 years; hopefully long enough to generate a new stream of income from writing.

Niche Writing

I also had the advantage of a niche expertise in personal finance to combine with travel that differentiated me from the masses of people trying to be travel writers.

So I wrote about travel for various financial publications, and I wrote about finance for travel publications. The two topics married quite nicely (since you need money to travel!), and soon thereafter I identified another niche in lifestyle design and location independent career management – since that was the life and career I was hacking into, one steep learning curve at a time.

So after a couple of years (and a lot of hard work with very little income), learning the ins and outs of traveling inexpensively using various tips and techniques, I eventually found the perfect balance; I had figured out how to make full-time travel financially sustainable.

The Professional Hobo” is Born

Along this journey, I was often asked by people I met what I do, where I’m going, and how long I’m traveling. (This is standard “cocktail party” conversation on the road). Without having firm answers for any of these questions, I self-deprecatingly dubbed myself a “Professional Hobo” to get a laugh (which it often did).

But after a while it stuck. A “hobo” in its early definition was a migrant worker without a home who hopped on a train and rolled into a new town, found temporary work, then moved on to a new town when the time was right.

I was certainly a “hobo” – without a home I was rolling from one place to the next, often finding volunteer jobs that covered my accommodation expenses (allowing me to delve deeper into the local culture than I could as a tourist), before moving on to a new destination and volunteer gig.

But I also had a “professional” edge to my hobo-ness, with a fledgling writing career and finance background. I was putting a science to the hobo-lifestyle.

Eventually when it became apparent that I’d outgrown my blogspot blog and needed to upgrade, I embodied the “The Professional Hobo” through and through.

It has now been five years since I walked into my regional director’s office to announce my decision to sell everything for a life of travel, unknowns, and the stuff (my) dreams are made of. Over 12 years of full-time travel later, I’ve found a way to make full-time travel financially sustainable and I’m still going strong.

When Will I Stop? (2021 update)

This is one of the most common questions I get; my lifestyle couldn’t possibly be soul-satisfying for ever onwards, could it? Surely I’ll want to “settle down” and adopt some sort of normality to my life.

Right?

Well….maybe. Maybe not. Prior to 2017, I’d have said I’ll never “settle down” in any conventional sense. Since then I have, and haven’t, at the same time.

Since my dream of travel is much more about living around the world rather than merely passing through it, I travel slowly, spending months – if not years – in a given destination. So travel fatigue is no longer as prominent issue as it once was to deal with, since I’m usually quite excited to explore a new horizon by the time I move on.

That said, in late 2018 I returned to my home town of Toronto to set up a home base – something I honestly never thought I’d do. In the years since, I have traveled several times a year for weeks to months at at time. My inner travel bug lives on.

My thirst for exploration, breaking bread around dinner tables around the world, climbing the mountains of the world, shopping the markets around the world, volunteering around the world, and – most of all – celebrating the human connection – hasn’t waned.

The mechanics of what I do and where I go will continue to evolve with me and my lifestyle, as it should. So please stay tuned to The Professional Hobo to see what the next curve will be; if it’s anything like the first 15 years have been, I’m sure it will be one hell of a ride.

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52 thoughts on “How I Became the Professional Hobo (Part II: The Logistics)”

  1. Love your blog .. it’s so inspiring! We’re working on getting rid of “all the crap” this year to travel on our sailboat on a very small budget. I yearn to travel, and can’t wait to get out there. Blogs like yours confirm that we can (and will) make it happen too!

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  2. Nora, I loved reading your story and am so inspired to live the life I’ve been dreaming about. I know it’ll be a long and probably challenging road, but as you say, you only have one life to live so you better make it a good one. Thanks for sharing!

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  3. “builds mud huts or something”…lol!
    I remember when you first announced to me your plans, I thought you were crazy too. Me going from Toronto to Florida seemed like moving across the street compared to what you were planning. But you proved to everyone how capable and brave you are and you deserve everything that you have acheived. Can’t wait for your next visit!
    Great post!

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  4. Very inspiring and lovely writing. What fascinate me the most, other than you traveling the world, is the financial aspect of how you make it happen, stuff you hold in your portfolio, how much you obtained when you sell your business, you have make enough money to reinvest in your portfolio, etc. All sort of very private information that you probably don’t feel like sharing or could be inappropriate to ask you. See what I mean?

    🙂

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  5. Nora, you are an inspiration. I don’t know if this gypsygal can become a professional hobo but I do like to be location independent and working on it now. 🙂

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  6. Very inspiring story. Actually, we have a lot in common (not life experience, more like attitude) and it is always great to hear your own story re-affirmed in someone else more successful that you.

    I mean, I know my own life is worthwhile, but it is hard to ignore the pressure from people and society to “settle down” and begin your “real life” so it’s important for us to know there are other strong, independent women out there with a great life doing what they want to do.

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  7. inspirational it is indeed..well written and narrated I wonder if any of it is fictional though…seems too cooked up to be entirely true…but I love it, love your guts and courage and wish I could do the same….keep up the good work

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  8. @Mid-Life Cruising – Getting rid of your stuff can be a very cathartic process. I found it very difficult – but ultimately very cleansing too. Enjoy!

    @Kim – Life without challenges would be boring! Let’s get into it! 🙂

    @Miki – I remember the cautious optimism in your voice when I announced my plans! Like “Okay…I guess you know what you’re doing…..” sort of caution…..LOL!

    @Sunny – I actually shared some of these details for a profile that Canadian Business Online/The Globe & Mail did on me….but it’s a little detailed for this forum right now! Maybe I’ll write a post about the specifics of my finances one day.

    @Prime – Location independence is the way to go!

    @Becky – I’m asked all the time when I’ll “settle down”, to the point where I tend to answer the question preemptively now! It’s not judgemental though; more out of curiosity than anything else. Travel can mean lots of different things and take on many forms; but not everybody sees it that way I guess.

    @Baron’s – Every word of it is true! C’mon; it’s too far-fetched to be a lie! 🙂

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  9. That happens to be our most FAQ as well – “When are you stopping?” – like people can’t believe that it can be a perpetual lifestyle, and that there MUST be an end to it. Not saying that we will never stop as we have no idea what the future holds, but I can’t see that happening for a long time. Like you, the slow travel allows us to keep going. I can’t imagine being tied to one place and not being able to constantly explore new places.

    Love this glimpse into what got you here. 🙂

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  10. So inspiring. We get asked that all the time… when will we come home and settle down? I told my grandmother on the phone yesterday that after our visit home in late 2012 we will head to Central America. ‘Oh. So you’re not stopping then?’ I haven’t commented much before, but I always enjoy your posts and your writing style. A great glimpse at how your hobo life started!

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  11. @Dalene and @Dayna – I’m just reading Chris Guillebeau’s book about Non-Conformity, and he concurs that you most people simply don’t understand that living an international life is possible (which is why they always ask when we’re stopping). Let’s show ’em international living IS possible! 🙂

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  12. hey.. come across ur website via Rolf Potts. i like it!!!
    ok.. one question…do u cut all links to back up…..? tell me how u manage ur money…i am in the UK.. bank cards are only valid for 3 years , after that, assuming one does not get robbed, how do u over come this ‘issue’ as banks only send bank cards to a ‘home’ address.. i am planing on hitting the road forever soon….

    thank u….

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  13. Thank you @Steven and @Carmel (sorry for the delay in responding to your comments….)

    And @frugal expat – I’m grateful for your loyalty to my site! You’re on quite the adventure yourself in Abu Dhabi – how long have you been there?

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  14. Hi Nora,
    I recently discovered your blog and I have completely fallen in love with it.
    I have belonged to the “naysayers” as you call it, doing something my heart wasn’t really into just because it was expected of me.
    A couple of months ago I realized that this kind of life is never going to satisfy me or make me grow in the ways I wanted to. But everybody kept telling me that it just wasn’t responsible to follow my real passion: traveling the world and seeing different cultures.
    You need tons of money to travel, why don’t you do something save first? And: this can’t be something you want to do forever, were the kind of comments that let me postpone the decision I finally took: Basically, NOT to listen to people who just want to bring me down, because they had given up dreaming long ago.
    I got together with my boyfriend and we took a leap of faith, gave up our apartments, jobs and left most of our worldy belongings behind and started going out into the world.

    We are at the very beginning of our full-time travelling “career” and we have a lot yet to figure out, but so far it has been a wonderful experience. We keep our expenses low by workawaying (it’s basically like HelpEx), but we would also like to be able to make money on the road. We started a travel blog just because we love writing, but ever since I read this article I have been asking myself: Could we actually earn a little something doing what we like?
    Do you have any tipps for us as to how we could get started? And I was wondering how you got invited to write for Wisebread and Vagabondish?

    Lots of love and thank you for this wonderful blog

    Sandra

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  15. Hi Nora,

    thank you so much for your swift reply! The links you provided helped me a lot and once I started researching I came across all kinds of articles you wrote for wisebread; one of which included the wonderful ebooks you reviewed for setting up ones own business:
    http://www.wisebread.com/three-e-books-to-help-you-make-money-travel-and-change-your-life
    I am really enthusiastic right now and can hardly wait to get my hands on these books and start learning everything I need to know to support my full-time travel lifestyle.
    So far we have been in Germany helping to build a wooden catamaran, in France renovating an old sailboat and are currently working on a self-sustainable farm in Portugal.

    I signed up for the newsletter right away. Sounds like it could supply me with a lot of valuable information.

    Thank you again for everything. You’re the one who got me started on finding solutions for earning money in a location independent way.

    Sandra

    Reply
    • Hey Sandra – That’s awesome! I’m so glad the links were useful, and it sounds like you’ve done some very cool work-trade gigs so far! Good luck in creating some location independent income, and happy travels!

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  16. Hi Nora!

    I found your blog via Wise Bread, which I found by searching travelling advice on the internet. I’m 20 and a junior in college about to embark on my second semester studying abroad, the first time in Rouen, France and this time in Shanghai. I’ve know for the last decade that travel is in my blood. Whenever anyone asks me what I plan to do with my major or after graduation (yikes!), all I have ever been certain is, “I want to travel.” I yearn to see more, challenge the boundaries of what I know; these are the experiences that have truly made me feel alive.

    I just read your story posts and although you had a tumultuous struggle between career and your heart’s calling, you clearly have the advantage of experience and wisdom (financial and otherwise)! I know I need to repay loans, that’s definitely first. But after that– I want to be able to do what you do! Yet I also struggle with cutting lose; people, places, things… let’s just say that I do NOT have minimalist tendencies. I also become overwhelmed with goodbyes and nostalgia, which is natural I suppose.

    Anyway, that’s my story. I’ve bookmarked your blog because you impart wonderful advice and I really enjoy the voice of your writing to connect with readers. You are an inspiration and I hope one day that my life falls in place (or out, I should say!) as yours has!

    Thank you for reading my rambles. I can’t wait to read what comes next for you!

    All the best,
    Nicole

    p.s. When I returned from France last year, I deleted my Facebook because it reminded me too much of home, and what everyone else was doing, without me. Do you have a personal Facebook? What do you do to overcome missing people? I’m curious on your thoughts, because I realized that I needed to remove that distraction to focus my energy on the present experience. But I still have my personal blog for stories and photos.

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    • Hi Nicole – Thanks for introducing yourself and sharing your story! You’ve got the right idea in needing to get your financial house in order before you embrace long-term/full-time travel, and it looks like you’ve got the gumption and passion to make a travel-related career happen!

      As for missing people, yes I do miss them, but going away doesn’t necessarily mean losing the friendship or losing touch (although admittedly, both are risks). But there are always some good friends who, even if you lose touch while traveling, you can always pick up exactly from where you left off.
      And I actually find Facebook useful as a traveler as a way of staying (loosely) in the lives of friends – old and new. Then again, I don’t get distracted by the day-to-day stuff on Facebook the way many people can.

      The blog and photos are a better way than Facebook (in my opinion) of logging your travels and reflecting on your experiences. So it’s good that you kept that going.

      And don’t worry about the small stuff! Like you said, do what you need to do to remain present in the experience you’re having (no matter what you’re doing)!

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  17. Hi Nora,

    This post, and yourself, are so inspirational! I know that Michael and I are FAR from the point of making money from our nomadic life but reading this gives me hope and motivation to make it work. Ive only been living this “hobo” life for 12 months but I can’t see us getting sick of it and ever wanting to stop!

    Thank you for continuing to be an inspiration for us (we’ve been fans for a couple of years) and to many others out there!

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    • Hey Nicole – Aw…I’m blushing! Thank you.
      I think that if travel is in our blood we don’t ever want to stop doing it. And we won’t! The only thing that will change is our travel style – which for me, has evolved many times over since I started traveling full-time.

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  18. Thank you for writing all of this. I am ready to start now, however, my finances are not. I keep finding myself in the same old place, wondering, and wondering, what is missing? What is my hearts desire? I have never had much and there is not much I want, except to see and experience other cultures. It may take a bit, but I have a new goal to work for. I think my sister is feeling the same way. I may talk her into joining me. She already travels as an RN. Happy traveling to you.

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    • Hi Terri – It’s a difficult thing to have the wanderlust but to have to wait until your financial house is in order. But at least you can use this time to clarify your travel dreams and wishes. During this time you can do some research, look for opportunities, and read lots. (That’s what I did).
      And to travel with your sister could be great fun! Happy travels to you as well!

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  19. Every day I come to work feeling stuck in this corporate jail! I can relate to how you feel and I deeply respect and commend you for taking that leap of faith. Kudos!

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  20. I’m loving your blog, and finding your posts inspirational. Now I’m seeing a bit more possibilities to travel and financially support myself. I’m sure there’s a way I can combine my marketing background with travel. Thanks again!

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    • Kris – Marketing expertise can translate very well to a location independent career.
      I see you just signed up for my free e-series/newsletter; over the next couple of weeks I’ll inundate you with ideas! Have fun! 😉

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  21. So inspired! I read your description of your early love of travel like I was reading my own story! I used to think I would outgrow it or want to settle down but it’s only gotten worse! I’m in my 40’s, not married, no kids and happy about that! I’m self employed as an event planner and am lucky enough to take 4 week – 3 month trips as often as I can afford them. But like you, it never seems like enough. People always assume I know a country because I was there for a month – but I always feel like a fraud – like I only touched the surface. I dream of doing what you are doing. I know the only thing stopping me is fear – I am devouring your website and can’t wait to receive your newsletters! Thanks for being an inspiration!
    Liane

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    • Thank you Liane! Hopefully you can take your business on the road and travel full-time! You’ll get lots of ideas from the newsletter series. Enjoy!

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  22. Wow! Your story is amazing!! I’m a 24 yr old that has been a traveling nurse for going on 3 yrs now. So many people look at me like i’m so strange for moving every 3 months. I get asked all the same quesions like “Are you going to settle down?” I love travelling the USA (and doing my short trips to other countries) but like you, I want more! I want to see this entire world!! Its so amazing to know there are other people like me in this world! I do plan to try and read all your aticles. I want to learn how to do what you do (except i’m a horrible writter)! To travel the world at your own pace and speed, while making a living. I wish i could sit you down and pick your brain!! I feel the hardest thing to travelling is the legalities of it. If you make money, someone or some place is going to try and tax it. I wonder if you have troubles with Visas and such. Anyways, your my inspiration that all my dreams are reachable!

    Reply
    • Hi Valerie – Oh, as a nurse you have TONS of opportunities to live and work around the world! You’ve chosen a great career for it. I’m not entirely sure of the legalities of getting jobs as a nurse abroad, but I know others who have done it, so I don’t think it’s too difficult.

      And, because you’re under 30 years of age, you have an even easier option to entering a country with the ability to work (then all you have to do is find a job, which again as a nurse won’t be tricky): working holiday visas!
      Here’s more info:
      https://www.theprofessionalhobo.com/2013/01/financial-travel-tip-65-earning-money-with-a-working-holiday-visa/

      Reply
  23. Oh my goodness! I just read part 1 and 2 of your story and it was like you wrote my exact story (except more eloquently than I ever could’ve). I am 2 months into my open ended RTW and loving every minute of it. I didn’t plan on spending the first four months travelling the US, but I am just doing what feels right. One way ticket to Colombia is booked for August, and the international portion of the trip begins. I am looking forward to cracking a bottle of wine and reading your entire catalog for inspiration and advice. Thank you for sharing.

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  24. Thank you for your website. I was surfing the internet trying to find a backpack and came across your link.

    I have just quit my job, with some very abstract plans to go to South America, and was having a bit of a wobble-having been asked questions all day by well meaning people about what I am doing. So, thank you for having written about all of this. I am not sure either why I need to travel, I just know, that again I am ‘escaping’ while others worry about what that means and try and break it down into something that makes more sense to them-and less to me.

    I dont really have the words for others at the moment to explain why I feel choked having to go to work every day, I just know that I have ignored that feeling for long enough, and any longer and it would be a big problem. I think that is probably why I appreciated your abilty to explain why you left so well.

    I wish you all of the best.

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  25. Nora,

    You are a dream merchant and nothing more…. Most of your readers just enjoy the escape of reading and fantasizing about your life.

    But hey that ain’t all that bad eh?

    I share your profession, I write for Escape From America Magazine

    feliz viaje!

    Reply
  26. Hi Nora,

    By some magic I came across your blog, and I’m certain it is soon to be my bible. I’m an Australian who won what is deemed the ‘Green Card Lottery’ to the States and I have every intention of being a hobo the day I arrive. After months of telling people I intend to set off alone with the sole intention of living state to state, taking any job that will fund my way, and being met with stares of confusion, it is refreshing to read the words of a kindred spirit.

    Your Newest Fan

    Brooklin

    Reply
    • Hi Brooklin,
      Congrats on the green card lottery! What a boon. Enjoy your hobo-life in the States….there’s a few of us “hobos” around, so you’re not alone! 🙂

      Reply
  27. That really does take a lot of nerve to give up everything we know, everything we have geared ourselves to, and set out on a new chapter. On one side there is the fear, like, “Oh gosh, am I making the right decision? Here is security and knowing the way, being familiar with everything, I’ve always done it this way.” and then, “But here is the unknown, and if I don’t try it I will always wish I did and wonder what would have happened if I did.” So I really admire your fortitude and willingness to dive into the unknown, and look how it worked out! Your life is enviable and magical, and you sure have a lot of great stories to share now! Thank you for being the daring adventuress you are!

    Reply
    • Hey Christine!
      I’m lucky in that my sense of adventure (and thrill of the unknown) is innate. Prior to traveling full-time, I was a competitive skydiver, motorcycle racer, avid climber, caver, etc. I’ve always enjoyed pushing myself. So this leap into full-time travel was like making another leap, of a slightly different kind. No less terrifying, and in fact I guess I kind of like it that way. I guess that’s why I’ve also been well-suited to working with plant medicine! 😉

      Reply

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