I stand on the dock and wearily eye the rubber dinghy bobbing on the water below me. This is my chariot; my commuter vehicle for a life lived on a sailboat anchored in the lagoon. And yet, with many eyes bemusedly fixed on me as I clumsily trip into it with all the grace of an elephant, I wonder just how long it will be before the inevitable happens and I end up in the water instead of the dinghy.

Welcome to daily life on a sailboat in St Martin.

How I Got Started

After a day-sail with some friends in Grenada, I was hooked on the idea of finding out more about sailing, and living on sailboats. I had discovered an entire lifestyle and world that exists on the seas that I hadn’t previously known about; and as a full-time traveler I realized I was amiss not to try my hand at it, since it can be a very financially sustainable way of seeing the world.

So I hopped on Find A Crew (one of a few sites that connects wannabe crew members with captains looking for anything from an extra set of hands to skilled sailors to cooks – and yes, sometimes “female companionship”), to look for a boat I might like to sail on (that didn’t require my “companionship” services).

Lo and behold, I found a couple of fellow Canadians on a boat in St Martin, sailing around the Caribbean and running a few videography businesses (Ambient Real Life and Land and Sea Video). Given my television production experience and social media outreach, we saw a mutual fit of skills, and Captain Rick was unfazed by my lack of sailing experience, saying in some ways it’s better because I don’t have any ingrained bad habits.

The situation got even sweeter when (thanks to Facebook) we realized we had a mutual social circle in Grenada (where he weathers hurricane season each year), so we both had the confidence of solid character references by our friends.

Rick’s boat was in St Martin, so that’s where I headed.

First Impressions of St Martin

After the raw Caribbean flavour and relatively undeveloped landscape of Grenada, St Martin was a shock to my system. Known as the “Las Vegas of the Caribbean”, I was immediately bombarded with lights, casinos, traffic (oh god, the traffic), and people. From the music to the food to the people, I didn’t feel any Caribbean flare in particular; it felt much more American than West Indian to me.

The sheer prevalence of mega-yachts screamed of an over-indulgent life, and money – oh, so much money – being sheltered from taxation in this tax-free haven.

This was certainly not the “Caribbean” I had come to know and fall in love with. (But eventually after a few weeks, I must admit it grew on me, due in large part to my having met a wonderful group of people – which truly, can make or break any destination, no matter how it may seem from the outside).

One Island, Two Countries

St Martin is actually half Dutch (Sint Maarten) and half French (St Martin). (Spell it which ever way you choose). You can drive freely between the two sides, but the currency changes from US Dollars to Euros, the language from English to French, and the culture from American to European.

The Dutch side (despite a European heritage) spoke nothing of Dutch culture to me, and instead is home to the lion’s share of the casinos, luxury shopping, and hopping nightlife. And with an airport in the middle of the action around Simpson Bay, “peace and quiet” is not exactly what you come for (as evidenced by the most dangerous beach in the world).

The French side is a little more subdued, and more authentically French; the perfect place to get a great cup of coffee and a fresh croissant, and go for a beautiful hike or enjoy some outdoor sports.

Misconceptions About Living on a Sailboat

My first misconception about living on a sailboat was that space is limited. In fact, boats make amazing use of space, and can be quite roomy below deck. In addition to a decent living space and galley (kitchen), Rick’s 50ft sailboat had four cabins (bedrooms), each with their own head (bathroom) – complete with shower, toilet, and basin. It’s a little cramped, and certainly not for those who are claustrophobic, but let’s just say in my five years of full-time travel, I’ve made due in smaller spaces with less luxurious accoutrements. (Since then I’ve lived and sailed on a few other boats including a 43ft boat, which has one less bedroom but doesn’t particularly sacrifice on space or comfort).

The "salon" (living room per se), taken from the cockpit

The "Galley" (kitchen)

My "Cabin" (bedroom), which isn't quite as dark/cramped as it looks!

My "Head" (toilet/bathroom), which is a wet room for showering too

Up to the cockpit, from the Salon

The cockpit

My second misconception about living on a sailboat is that anybody who lives on a boat….sails it. To the contrary, I was informed that likely more than half the boats anchored in St Martin don’t go anywhere; they’re simply floating houses for people who live and work in St Martin. This applies to other Caribbean islands as well, but to what degree I’m not sure.

Life on such a “floating house” is a little more complicated than on land; fresh water has to be brought on-board (or replenished at a water/fuel dock if the boat can get there on its own steam), so water conservation is of prime importance. And many boats rely solely on solar and/or wind generators, which usually generate plenty of power – as long as you’re conscious of what you consume.

Similar to the life I lived off-the-grid in Hawaii, life on a boat makes you keenly aware of many of the things we land-lubbers tend to take for granted.

Dinghy Hopping

My first real adjustment to the nautical life was the use of a dinghy as commuter vehicle. It is your passage between the boat and shore (or other boats), and getting my “sea legs” and sense of balance has taken quite some time. I still struggle to hop gracefully in and out of dinghies like obviously experienced people do; rather I lumber out by practically rolling onto the dock hanging on to anything (or anybody) within reach, and getting back on I usually need to sit down and inch my way on tentatively, ever-nervous of unintentionally ending up in the water. (Knock on wood; it hasn’t happened…yet).

Even more harrowing is the dinghy-hopping experience; if too many dinghies are tied up at the dock, sometimes the only way to get to yours is to hop from one to another. All those years of professional dancing seems to have done nothing for my sense of balance on the water.

But with practice, comes perfection (and the occasional soggy bottom from landing ungracefully on the wet floor of the dinghy).

Life on a Sailboat in St Martin

Very quickly on arrival to St Martin, I fell into a pleasant routine with my crew mates, and adapted to life aboard a boat quite nicely. We didn’t do much sailing (as the videography businesses have required a constant presence in St Martin), but I got my chance to do a day sail aboard another boat, and my next move (to join a charter boat in the BVIs) involved some hefty sailing.

It seems that St Martin was the perfect place to get used to life on a boat, gain my sense of nautical balance, and – literally and figuratively – get my feet wet.

On to the next nautical adventure!

A couple of weeks ago we talked about life insurance and whether it’s necessary for travelers. I also snuck in a mention of estate planning, which is very much linked to our life insurance needs.

I’m not trying to be morbid, but let’s face it: stuff happens. And although it is just as likely to happen while you’re at home as while you’re traveling, it’s infinitely more complicated if you’re out of the country when you get sick, injured, disabled, or even die.

Do yourself – and your loved ones – a favour by being organized before you leave. And that means putting together an estate plan. It’s not difficult, and a good chunk of it is the gathering of information that you should be doing anyway when organizing your official documents prior to traveling.

Check out the article below for some more information on what estate planning is and how to get started on your own estate plan.

Estate Planning: Why Me?

After sailing and cooking in the BVIs for a week, I made my way back to St Martin to rejoin the boat “Sophisticated Lady” – along with Lucky the parrot and the Ambient Real Life video crew.

Then I hopped over to yet another sailboat (living on boats is a lifestyle that evolves very easily with a little networking!) to enjoy the French side of St Martin, along with the wind and waves which are perfect for activities like paragliding, paddle boarding, and kite surfing. Oh yes, and perfecting a rosy sunburn or three.

But my time on boats is quickly coming to an end; terra firma calls in the form of a few friends in Florida I’d like to visit before my inevitable return to Grenada in March.

My month of January – which included time in Grenada, St Martin, and the BVIs – cost me under $600 to live – all in. Want to know my secrets to full-time travel (with loads of resources and links)? Check out my article below on How to Travel Full-Time for $17,000 per Year (or Less).

And if full-time travel is still a pipe dream, check out my article on maintaining the discipline to reach your goals; you’ll get there!

Wise Bread

How to Travel Full-Time for $17,000 per Year (or Less)

For the last five years I’ve been traveling full-time for about $17,000/year, sometimes less. Here’s how I did it, with plenty of resources for you to do it too!

Care One

Having the Discipline to Reach Your Goals

Reaching your goals can be a tiresome slog, but it doesn’t have to be an act of sheer miserable force of will. Here are some tips to help you maintain the discipline to reach your goals – with minimal pain and lots to gain.

Profiles & Shout-Outs

MNN.com featured some creative tips for traveling on a budget, tapping into the experience and advice of myself and Johnny Vagabond. Check it out!

6 Tips for Traveling on a Budget

And the most recent issue of The Caretaker Gazette – one of my favourite resources for finding free accommodation around the world – featured my travel lifestyle, and the various positions I’ve found around the world through them (in Hawaii, Australia, and Grenada). The only way to see the article though – is to subscribe! If you’re thinking of volunteering and traveling around the world, though, I highly recommend it. (And no, I don’t get a commission if you subscribe! I just like it that much.)

Ed Rex is a British RTW Solo Travel Digital Nomad who decided to jack in his corporate job to follow his dreams and recapture his childlike wanderlust whilst blogging his “Rexy Edventures”. He is also deaf and wants to show other deaf people that they too can travel around the world solo. Please enjoy this week-in-the-life of Ed as he embarks on a new chapter in his life.

Day 1 – Sunday 1^st January 2012

Today, my life will change. After keeping it a secret for sooo long, the zip covering my mouth can be unzipped. I will now tell the world of my 2012 travel plans that will be taking place this year! Off to SE Asia, Australia, New Zealand, Fiji and USA! I cannot wait! I announce it to all my family, friends and the travel community over my blog. I’m giddy. I’m excited. I’m awesome! All day I’m bouncing around with a smile from ear to ear and on this day, it’s certainly a NEW YEAR’s DAY!

Day 2 – Monday 2^nd January 2012

I receive my paper copies of my RTW Tickets in my hands. I’m finally going! Everything is real. I check out the coveted flight numbers and stare intently at the destinations.

I relax in a bath reading a guidebook about SE Asia. What I’ve been reading finally makes sense…I will be going to these places. Bangkok! Vang Vieng! Siem Reap! Hoi An! Singapore! Panang! Everywhere!

I make my travel new year resolutions. No alcohol until I go travelling – three full months (sob sob)! Tone my body up to look good for travel photos (ha ha), try to do a photo-a-day challenge to symbolize travelling, backpack around Britain, and ensure my travel planning goes smoothly.

Will I keep to them? Of course I will!

Day 3 – Tuesday 3^rd January 2012

I leave my family home to go back to the daily grind of work. I travel down to Leicester, where I work at my own pace. I think about family. Will they be okay while I’m gone on my travels?

Arriving back, I sort out some of my belongings. I am moving to another place this week to help cut costs and sort out bills before I go. It’s a long arduous process and I throw out or give to charity a huge portion of my belongings. I can’t exactly carry everything in my apartment in one rucksack on my travels can I? (Editor’s note: check out what to pack for full-time travel).

I find my old I love Munich T-Shirt. I thought I lost it! Brings back good memories of beer, sightseeing, a harrowing experience of a concentration camp, a side trip to Salzburg and dancing on the fountain to The Sound of Music in the rain!

I have dinner with my friend and which we discuss where I will be travelling to. This gets me excited again!

Day 4 – Wednesday 4^th January 2012

I move more of my stuff over to my new place. Take my readings. It’s still a long arduous process!

I check out travel visas and figure out which ones I need to sort out before I go. Vietnam, Australia and USA it is!

I practice packing my new rucksack. And again….and again…and again. Hmmm, this needs fine-tuning and also I need to pack less. This makes me write out a packing list. I cut it down by half. Leave it for a while. Add a few more items. Then a couple of hours later, my original packing list has doubled. Damn!

I read more about Australia. Where do I want to go? Everywhere! But Great Barrier Reef to snorkel is number one.

It has been a slow day at work, now I have told everyone outside of work that I am travelling…I want to travel now…it seems like the work days are going ever slower! I’ve yet to hand in my notice…

Day 5 – Thursday 5^th January 2012

I’m bricking it. Today’s the day I’m handing in my notice at work for travels.

I try to catch my manager’s attention all morning. No avail. I try making him stay behind at a meeting that morning but the meeting runs late and we are kicked out of the room. I try catching him at lunch but food calls me. I try catching him all afternoon but computer issues catch him. I try catching him in the kitchen but I spy a Yorkshire Tea. I try catching him when I’m putting on my coat but he wants to discuss future plans.

Finally, I try catching him when I’m walking through the door; I say ‘Can I have a private word?’ He’s completely surprised by the news but accepts. I feel a sense of trepidation, relief, amazing, very nervous, and excited and also a sense of loss. That happens when you hand in your notice.

I slowly unwind by reading about New Zealand. Milford Sound…here I come!

Day 6 – Friday 6^th January 2012

Everyone now finally knows I’m travelling soon. Family, Friends, Work, Travel Community and everyone!

I check out travel insurance. There are hundreds of deals! Which one is the best? I pour over my computer for ages figuring out the best one. I ask people on Twitter, I ask people on Facebook. Does anyone know what the best deal is? I narrow down some options but I’m still confused.

I get de-stressed by reading about Fiji. Just looking at the photos make me relaxed. Imagine how relaxed I will feel when I’m there! Am I recapturing my wanderlust? My enthusiasm for life? It’s all coming back!

Day 7 – Saturday 7^th January 2012

I finally officially move over to my new place. From this moment on, my living costs are cut 45%. The amount I save will go into the travel pot!

I collapse on the sofa, bring out my laptop and research what to do in USA. Grand Canyon? Vegas? San Francisco? Yellowstone? I’m there!

Finally, I chill out, have a pizza, and wonder what’s to come.

I cannot wait for the travels and my Rexy Edventures. Bring it on!

 
 
At the end of March, Ed will be leaving Heathrow to go to Bangkok to start an eight-month journey around the world going through SE Asia, Australia, New Zealand, Fiji and USA. But that’s not the end; he’s already starting to plan out his 2013 itinerary. Check out his website at Rexy Edventures to follow along his journey, and be sure to follow him on Twitter @rexyedventures and Facebook too!

Along the lines of preparing ourselves for travel with things like travel insurance and life insurance, it’s important to have your official documents in order before you start traveling. This is especially important if you are traveling long-term or full-time.

There are a number of things you can do to prepare, and safeguards you can set in place in order to ensure that everything goes smoothly while you travel – even if everything isn’t going smoothly!

For example, designate a representative at home who can be your go-to person. This person should be a friend or family member who has all your information at hand (banking, insurance policies, copies of passports, etc), so that if you find yourself in a bind, a simple phone call to them can start the wheels in motion of getting you out of your pickle.

Lost your passport – and even your copies of it (because you do travel with copies of your passport, right)? No worries. Your designated representative can help you get sorted. Landed in the hospital and don’t have the capacity to call the travel insurance company to let them know? No problemo. A quick call to your representative and they can advocate for you.

Here’s an article that discusses which documents to travel with and where to keep them, the process of designating a representative at home and what to give them, and lots more.

Preparing for Travel Abroad: Gathering and Traveling with Official Documents

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.

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.

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 five 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?

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. 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 a prominent issue to deal with, since I’m usually quite excited to explore a new horizon by the time I move on.

And although I may eventually set up a “home base” of sorts, I don’t ever think I’ll rid my blood of the travel bug. 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 – will never wane.

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 five years have been, I’m sure it will be one hell of a ride.

I’m regularly asked how I got my start as The Professional Hobo. What was the catalyst for my decision to sell everything in favour of full-time travel? How did I do it? And most importantly – why?

Although I’ve answered many of these questions in one form or another over many interviews for other websites and newspapers, I haven’t properly documented the process on my own site.

Here goes…

Tough Questions

“What are you running away from?” was a question recently asked of me by a friend who was trying to help me through a rough emotional period of confusion about what I wanted to do.

Travel is commonly seen as running away from something or an act of withdrawal, but try as I may to psychoanalyze my actions, I simply can’t see how I’m running away from anything. In fact, it’s quite the opposite.

Best to start from the beginning so I can illustrate my point.

Success in Business – and Life?

In 2006, I was running a busy financial planning practice in Toronto, Canada. I was what you could call a “medium-sized fish in a big pond,” having achieved a certain level of success and a reputation for helping people engineer their finances to enable their life’s dreams. I focused on the emotional issues of personal finance in an effort to transform our vision of money from a taboo hindrance into something that empowers and enables instead.

I regularly appeared on television, gave interviews in newspapers opposite financial “celebrities”, and I spoke in front of audiences as large as 3,000 people.

But something wasn’t right.

There was a little voice inside of me – a voice that has been a lifelong friend or pest, depending on how you look at it – that said “Nora…you’re not doing what you’re supposed to be doing. There’s something else out there for you.”

Those dastardly words. I’d heard them so many times before, and in the past when the voice kicked in I changed careers. I’d been a television producer and host, stage manager, professional actor/singer/dancer, operations assistant, assistant property manager, I started an administrative business, and – most recently – I ran a financial planning practice.

Not this time

But this time when “the voice” chimed in, I refused to listen. I’d put way too much blood, sweat, and tears into my business to leave it callously for yet another career. So instead, I filled my life with other things that I hoped would satisfy the ever-growing void in me. I became a Toastmaster, an active Rotarian, I sat on boards of directors for large charities, I got back into film & television acting, and I performed in numerous stage musicals.

Soon enough, I was busy 18 hours a day, and the voice was getting louder, not quieter.

In January of 2006, I was in two car accidents in one week. People said “the universe is trying to tell you something,” but I was only annoyed at this diagnosis. “What is the universe trying to tell me, for goodness sake? That I shouldn’t drive in the snow?! Get outta my way; I’ve got work to do”.

Forced contemplation

It wasn’t until a few months later when two bouts of bronchitis devolved into walking pneumonia that I was forced to stop everything for a spell. Shortly thereafter, the ball dropped. I was in absolute tears about having to go into the office to do some work that I’d been avoiding for weeks.

“What do you want to do?” was the poignant question asked of me when I had my head in my hands, at wit’s end.

“I just want to…retire!” I wailed dramatically. Shortly thereafter though, I considered what retirement meant to me. What was the retirement vision I had for my golden years? I counseled my clients to describe a day in the life of their retirement so we could plan towards it, and I’d neglected to do the same for myself.

Retirement….meant traveling around the world, slowly. Meaningfully. But not just passing through; rather, living around the world.

Rewind: Some history about my view of travel

Before I go further, there’s some back-story required.

When I was 8 years old…

I was sitting in class when the teacher showed us a documentary about Europe. I was fascinated. I saw people, but I didn’t recognize their garb, the language they spoke, the food they ate, the markets they shopped at, or any part of the architecture or scenery. It was so completely foreign to me. And I desperately wanted to know how the children my age played, and what daily life was like inside their homes.

This is the very root of my literal life-long dream of travel.

As the years passed….

Travel being important to me, not a year passed in my adult life when I didn’t go away for at least one vacation each year. But with a paltry vacation allowance and limited funds, most trips were only a week long, and were often superficial attempts to escape Canada’s long winters rather than culturally immersive experiences.

Then, in South Africa….

I took the month of December 2005 to go to South Africa. People at home thought I was nuts.

“You’re going away for a whole month?!” They said incredulously, implying that I was somehow irresponsible.

And the ultimate disconnect: when I was in South Africa, the heavily European-influenced locals asked “And how many months are you here for?”

“Months?!” I’d reply in disbelief. “I’ve only got days – no, hours – here! What do you mean?”

And at the end of my month, as I flew out over low-lying South African fields, watching the farmers tend to their livelihoods, I realized that I still had absolutely no idea how they lived. I’d thought that a month would be long enough to crack the code of the South African mentality; long enough to gain even a faint understanding of the people, their way of life, and their own dreams and ambitions.

Instead, a month of travel throughout this large and convoluted country left me with more questions than answers.

…Back to my breakdown…

So here I was, bed-ridden, considering what retirement meant to me.

I wanted to climb the mountains of the world.

I wanted to break bread around dinner tables round the world.

I wanted to shop at markets around the world.

I wanted to understand daily life in remote corners of the world.

I wanted to volunteer my services to help people around the world.

I knew I couldn’t achieve these goals in the way I truly wanted with week-long – or even month-long – vacations. I had to go much deeper than that. It had to be a lifestyle.

Could I wait another 30 years for a conventional retirement to live out this life-long dream? What if I did, then come retirement age, I wasn’t willing or able to do these things any more? How would I view my life as I lay on my deathbed? I already had a few close calls with the car accidents and my illnesses…what would I feel about my life if it ended right then and there? Would I have regrets?

Early Retirement

After considering these things, it became obvious to me that with only one shot at this life, I had to make the most of it. I had to “retire”. Putting in time for another 30 years was not possible; time wasn’t to be wasted or bided – it was for living.

Finances

I had the good fortune to have saved and invested for my future from a very young age, and had a good nest egg socked away for later years when I can’t work and need income. And in selling my financial planning business I was granted a small income for 2.5 years; long enough to figure out what form my travels would take – or even just to play out whatever dreams I had of long-term travel and return to the “working world” re-energized and enthused.

Ultimately I had no idea what form my travels would take or how long they would last when I made the decision to go. I just knew I had to go. And for once – the voice agreed. Despite the counter-intuitive move of selling a business I’d just built to the point where it could run itself and generate increasingly larger amounts of income, my inner voice actually applauded this decision to break out of the mold and chase down my dreams.

And so it was with a good financial footing and a large dose of faith that I put the wheels in motion for a life of travel.

Stay tuned for Part II, where I discuss some of the logistics of how I became The Professional Hobo; from quitting my job, to selling everything, to deciding where to go and what to do, to developing a location independent career as The Professional Hobo.

A while ago we talked about travel insurance with its pros and cons. Some aspects you need, while others you can omit and save your money.

But do you need life insurance when you travel?

I believe the answer to this would be the same regardless of whether you are traveling or not: it depends.

Some of the factors that affect whether or not you need life insurance (and in turn what kind of life insurance you need) include your current financial situation, whether or not you have dependents and/or a partner, and your estate planning needs. (Don’t know what an estate plan is? Stay tuned for next week’s tip!)

I believe in insurance, but I also believe it’s possible to over-insure ourselves, thus spending too much money on insurance premiums and not having as much in the budget for the things we like to do while traveling. With the right knowledge about what our needs are and what insurance plans can satisfy those needs, we can get just the right amount to protect ourselves (and our loved ones) from financial ruin in the event of “life happening while we’re busy making plans”.

Want to test your knowledge of life insurance and determine your needs? Check out this Financial IQ Test to see how you measure up.

Financial IQ Test: Life Insurance

Greetings from the British Virgin Islands! After trying my hand at sailing a 32ft sailboat for a day in St Martin (as seen above), I was offered an opportunity to join a charter on a 43ft sailboat for a week in the BVIs. My job: one that I love – cooking! There are four of us on the boat (the captain, myself, and a couple who are friends of the captain), and although it’s cozy, it really is amazing how ingenious the use of space is on these boats.

The 12 hour sail from St Martin to the BVIs was not without its grief, however, as I was seasick from about the three hour mark onwards, and my only relief was to be unconscious. But my spirits remained undeterred, and since then I haven’t felt any pangs of nausea as we hop around this tightly knit group of islands in the northern Caribbean; the sailing capital of the world.

I’m not sure what my future holds in store (as early as next week), but I’m fairly sure I won’t attempt the sail back down/over to St Martin; it’s officially called the Anegada passage, but unofficially known as the “Ohmygodda” passage – and for a reason. The wind was at our backs enroute, but I can only imagine how relentless it would be with the big swells going the other way. Although I’m feeling somewhat confident that I might have gained my sea legs, I’m not entirely willing to test that theory.

All this time on sailboats (something I would never have imagined myself doing a few mere months ago), it gives me pause to consider some of the amazing opportunities I’ve had in life so far….and some that are yet to come. Check out my article below on Reverse Bucket Lists for more about this. While you’re voraciously reading, check out my Flaskpacking article; are you a flashpacker?

Wise Bread

Reverse Bucket List: Look Back Before Looking Forward

Before you make a “bucket list” of things you want to do in life, don’t skip this vital first step ― it could be the key to happiness.

Care One

An Introduction to Flashpacking

Are you not quite a backpacker, but not quite a tourist? Do you like to travel with certain comforts and style? Are you on a budget but not willing to sacrifice experiences because of it? Then read on; you just might be a Flashpacker.

Pia is a mother, travel addict, journalist, and troublemaker. She and her son Paul have been traveling the world since Paul was two years old, and together they’ve crossed a few countries and continents. Please enjoy this week-in-the-life of Pia and Paul as they travel through Israel.

I have always travelled off the beaten path with my backpack and when I turned mum I continued, except that I had some extra luggage named Paul then. Usually we backpack. But this day we decided to took a guided tour through Israel. Not because I was to scared to go on my own but because I need to have someone who teaches Paul all the stories about Jesus and his mates.

Day One

“What are all these police officers doing here?” asks my seven year old son Paul when we arrive at the counter of El-Al, the Israeli airline. We are on our way from Frankfurt, Germany to Tel Aviv, Israel where we will start our tour around the country. The police officer explains to Paul that the German and the Israeli government have an agreement about security measurements. The officers are here to help prevent any attacks. Israel must be a very scared nation.

Really, as soon as you are in the queue in front of the El-Al counter you feel like you have already left Germany; so many checks and questions! It is unbelievable: a question before you get to the counter, another one at the counter, you get directed to a special gate where there is a security check right before you board the plane and everyone gets a body-check – everyone head to toe. It is impossible to make it in less than three hours and I am glad someone told me before because I am one of those who comes when the “Last Call” announcement is made.

Day Two

Paul is dead tired. We arrived late yesterday and had to get up way too early for us. What the heck is a holiday when you’re scheduled to be at brekkie at 7am? And for those of you who read this and don’t have kids: No, they don’t get up a 6am by themselves and start to stress you out unless you force them to go to bed at 7pm. Paul gets tired around 10pm and I am happy with that.

Usually we backpack on our own pace but this time we joined a tour group. Paul wanted to learn about Jesus and his life and I know nothing about him – I deleted most of my religious knowledge at some point. Therefore someone else has to teach Paul: The tour guide and the parents of the other kids (there are another five with us).

I thought traveling with a tour group could be nice. When you are a parent on holiday with your kids you never have a proper holiday. Before you go you dream of relaxing and one day into the trip you realise how delusional you were. You are always on duty. It might be okay if you have two of the little ratbags and they keep each other busy, but if you have only one you feel like a human game center. Play this, say that, make this tune. I hoped to get somehow away from that by joining a group with a few other kids. I didn’t take into account that other parents actually put their kids to sleep at 7pm…

Day Three

Do you believe in miracles? Can you turn water into wine? Can you walk on water? “Mum, I think it isn’t possible”, Paul says.

We are exploring the area around Lake Khalid where Jesus did most of his stuff. I am already getting sick off this getting on the bus, getting off the bus, listening to a story, get on again and start all over again. I’d rather talk to people than just listen to one who knows it all.

I get confused by all the names. All girls Jesus was close to were called Mary. If Jesus would live today he would be one-of-a-kind casanova with smartphone and he would have all those Marys in his address book. Maybe he would put notes in brackets behind their names. Like Mary (mom), Mary (sis of Lazareth), Mary (gal from Migdal). It is sort of what the Bible does too.

I am not really familiar with all those Marys in detail so I am getting really confused every now and then. Paul has already zoomed put. He is sitting in the bus and playing Nintendo. “Another church?” he asks when we get off on our second stop. And this is only our third day! Plenty more churches to come. I begin to think that a mono-thematical holiday isn’t the best for kids. There should be some animals and splash-pool fun involved at some stage.

We stay in a Kibbuz-Hotel at the shore of the lake. A Kibbuz is a little village with a few hundred people that is self-sustained. That is a neutral definition. You could also say: It is the old socialist idea of community realised in Israel. I love it. Everyone has their own house but they have a shared laundry, a place where old people can go, a kindergarten, common rooms – and bunkers. Bunkers and soldiers are everywhere.

Day Four

This is Israel. Everything is complicated. There are Israeli Jews and Israeli Muslims and Palestinian Christians and Muslims. It is not even that there is just Christianity; there are Russian-Orthodox, Druids, Catholics, Protestants, and so on.

Our bus driver is a male Israeli Muslim, our guide a female Israeli Jew. We say “Boker Torf “ (Hebrew) to one and “Merhaba” (Arabic) to the other. We are still at Lake Khalid which is also where Israel borders Syria and Jordan. Israel occupied the Golan heights about forty years ago. This is an area where tourists don’t go.

Our bus is the only one on the road. No other pilgrims around. The streets are tiny and the turns are scary. A wide endless hilly beige-coloured landscape lies in front of us. An area of war. There are bunches of big rocks in bends that could be blown up in case the Syrians attack. There are tanks and bombed houses along the streets. There are bomb shelters everywhere. The land is empty, lonely, lost. Israel is such a small country! Everything is squashed next to each other.

Paul and the other boys on the bus like it. To them, war is a game they know from their Nintendo games – it is far off reality. Their little minds can’t grasp what it means when thousands of people are dying. So they keep on playing Star Wars while we gaze at a landscape of real war.

Day Five

Change of scenery: We are at the Dead Sea. One majesty of a lake. It is like a mirror. A sunset couldn’t be more kitschy. On the other side the mountains of Jordan rise.

“Why is it called Dead Sea?” Paul asks and adds “Is it because this is a war country and there are so many dead?” He learned his lesson yesterday. So I explain to him about the impossibility of living in salty water.

The children go together down to the beach with just one parent. We others have time off. Great! Exactly what I was looking for. I head to the sauna and Spa. I didn’t know that Israelis are so into saunas but they seem to be everywhere. I try to talk to a bunch of Russians while I am floating in the water. The Jacuzzi is filled with water from the Dead Sea – it’s just not as cold as the Dead Sea.

There is no late night entertainment. This is very unusual for us. We tend to have dinner on the streets wherever we stay and then hang around and watch people for a little while. Yes, me and my seven year old son! I don’t drag him to bars or clubs – don’t worry. But life isn’t just the thing we experience when the sun is up.

The children have sat in the bus for too long for too many days. They are running wild in the lobby but none of us parents feels responsible.

Day Six

We are allowed to sleep in! I can’t believe it. We don’t depart until 9.30 am. That is as late as it gets.

Not far from our hotel is En Gedi, a waterfall – in the desert. We have to walk and climb a bit to get there. We are allowed to walk, I should say. I feel like have never moved so little on a holiday.

Here is something other than a church but Paul is still not impressed. The kids can’t grasp the contrast between this dead dry landscape and the running water. They don’t care either. Instead, they look for sticks and stones and play around. At the end of the day I have a huge collection of sticks in my suitcase that I am not allowed to throw out.

On this tour, there is just too little to do for children. They have much more energy than we adults have and can’t get rid of it. And it won’t get better today because we’re on the bus and heading for Jerusalem.

Day Seven

Jerusalem, the middle of the world. This place is amazing. There are so many layers of history that you have to dig into. It seems like any civilisation that has ever been megalomaniac made it to the Holy City: The Romans, the Byzantines, the Ottomans, and so on.

Temples have been built and destroyed and with the same stones something else has been built. I guess you could tell the story of this city by just telling the story of one stone of the Western Wall – the wailing wall as it is called. There is a high speed connection to God here, our guide tells us, and we could write a wish on a piece of paper and stick it in the wall. Paul asks if it works like Santa Claus. Sort of, I tell him, just without the elves.

We walk along the Via Dolorosa, the path Jesus took to get to Golgatha, the place where he died. The children have all sorts of funny questions: The alleyway is narrow and they wonder how Jesus could walk here with the big cross behind him without hitting the walls all the time. They wonder how heavy the cross was and how long it took him for the walk. They wonder if the streets were as busy with vendors in former times. They wonder about all the normal things and not the miracles and pain. I want to buy them each a crown of thorns but they laugh at me.

“So, what do you think of God?”, I ask Paul at the end of the day.

“God was only Jesus’ dad and dads aren’t that important”, Paul says.

There you go: The decline of belief through single mothers.

Pia is planning to go to Sweden at the start of February (without Paul) to a Hot Air Ballon Festival, then Panama just after Easter, and on a Mediterranean cruise at the end of April. You can read about her adventures at Are We There Yet.