How to Become a Nomad: It Takes a Lot of Planning to Be Carefree

Contrary to popular belief, I don’t just flit around the world on a whim, landing wherever the wind blows me, whenever I get there. My nomadic lifestyle, exciting as it is (at least to me), doesn’t just happen by chance.

It takes a lot of planning to be carefree.

Maybe carefree isn’t the right word. Maybe just “free” is. Or maybe “happy”, or “not worried” or “at peace with whatever the future holds”. Because for me, carefree encompasses all of these things. Some days the mix isn’t quite right, and I’m less happy or less sure or more worried, but in general, this is how it goes for me.

But how is it possible to go through life running around the world, going from job to job and not worry too much about things? Or how is it even possible to do it at all, worried or not?

You’ve got to:

1. Embrace uncertainty. (Don’t worry, be happy!)

Read here if you’re not sure what I’m talking about. In short, start being OK with not knowing what’s going to happen to you or how a certain situation will turn out.

2. Learn all you can about the things that matter. (Knowledge is power.)

You want to live in Lisbon for a month and not worry while you’re there? Figure out what it takes to live in Lisbon for a month. Get on your Google machine and find housing costs, transportation costs, restaurant costs, etc. In this day and age, it’s all out there. This way, you’ll reduce the number of unhappy surprises you encounter.

You want to hop from contract job to contract job? Learn the system. Learn when certain jobs start and finish, in general what they pay, and when you have to apply and be hired for them. I teach ESL in Toronto. I know which schools generally hire when, what they pay, and when the start dates are for their terms. I know which credentials I have to have to be hired. I know when I should expect to hear about my summer employment leading student groups around Europe. I know how much I’ll make, and which of my costs will be covered.

I understand how the system works for the things I like to do, so I can plan for various situations.

3. Don’t grab onto the first shiny thing you see. (Be realistic!)

Just because you do your research and find that there ARE apartments in Lisbon for 200 euros a month, doesn’t mean you’ll want to live in one, and it doesn’t mean one will be available to you. This shouldn’t be what you bank on. Don’t stop your search about the cost of living in Lisbon because you’ve found an answer that suits your budget and feeds your over-optimism. Think about the probability of being able to find a decent apartment for 200 euros a month. Are there many listed? How do they look? If 200E is the middle of the road, chances are good you’ll be able to find something. If you see one hole-in-the-wall apartment listed for 200E, chances are that shouldn’t be what you budget for.

This also applies to the employment system. Just because you apply for a job, doesn’t mean you’ll get it. Just because you know when start dates are, doesn’t mean that’ll help you get hired. However, think about things like this: Have you done this job before? Do you have experience? Do you have relationships with anyone hiring or currently doing that job?  Are they hiring many people, or just one? Have you applied many places (good), or are you putting all your eggs in one basket (bad)?

4. Know your options. (Know your options.)

You’ve embraced uncertainty. You’ve learned all you can about things that matter in your life plan. You’ve put on your realistic glasses and assessed the situation. Now, flesh out as many possible scenarios as you can. Not in a manic, worried way. In a calm, cool, collected and objective way.

This was my thought process in late August. I had just come back from Europe travelling and working for 3 and a half months. I knew I had to attend my best friend’s wedding in New Zealand in December.

I want to go back to teaching at the college where I taught before. I want to save as much money as I can, and I want to leave for my trip across the world in November/December, hitting a few countries. I don’t want to use up my savings. 

Scenario 1: I get the teaching job, save all sorts of money, and everything goes according to plan. Leave for trip in November/December.

Scenario 2: I get a job, but not with the amount of hours I want, which means less money. I save all the money I can and still leave in November/December. I re-evaulate the length of the trip but still go.

Scenario 3: No teaching job for me. I find something else short-term, otherwise I freelance as much as I can and live off of canned beans. I pare down the travel dream, but I still go at least to New Zealand.

Luckily, I landed with scenario 1. However, I had a plan for the three different realities I may have come up against. And if I had ended up with scenario 3, that would have been OK too, because of step number #5.

5. Prepare for your worst-case scenario. (Cushion the fall.)

I’m not saying to always expect your worst-case scenario. You wouldn’t be too happy and carefree then, would you? What I’m saying is to be prepared so that your worst-case scenario  isn’t actually a terrible scenario, just a less-than-ideal one.

For example, if I had ended up jobless and eating canned beans right now, I’ll admit that it wouldn’t have been the highlight of my life. But I still would have been able to see friends and family, be constructive by writing, and stand by my best friend at her wedding across the world.

Why? Because I had money saved up from before, and I have parents who love to have me at home. (Right, Mom?) I wasn’t starting from zero. I know there’s always the possibility that I won’t come back to an open teaching position, or that a surprise expense will launch a sneak attack. I didn’t want to delve into my savings to live off of from September to December and to pay for the NZ trip, but I would have if I had had to, and it wouldn’t have been the end of the world.

Not bad for a worst-case scenario, right?

In this How to Become a Nomad series, many of the things I recommend doing build on one another. Changing your attitude, planning, and having the right outlook are all interrelated, and the success of one of these pursuits affects the success of the others.

How I Became A Nomad

“Oh yeah? Well you’re a nomadic Gypsy!” is a wannabe insult my brother often hurls at me. I say “wannabe” because it’s not really an insult to me, but I know he means it to be a little more derogatory than I take it. I like changing things up, moving around, seeing new things, breaking the routine. I like being a nomad.

I don’t want to cast my dear brother in a bad light here. No, not at all. We get along (pretty) well and have a loving, teasing, bickering older sister – younger brother relationship. (If only he would listen to me more!) But with me at twentysomething and him, still at twentysomething but three years younger, and our being different people and all, we have different ideas about the paths our lives should take.

Recent sibling selfie.

Having recently graduated from college, my brother moved home, bought his dream car (a bright orange, ’69 Chevelle) and took a full time job working in the family business. He’s happy. He’s good at it. He’s needed. He’s got a plan to save for a down payment on a house and wants to buy one when he’s 25 or 26. I’m proud of him.

Now, we’ll take a look at me at his age. I finished school, started this blog and fled to Italy. I came back to Canada with no idea of what I’d do, but with the notion that I needed to find a job. So I found one, in an office. The job was stressless, the pay was decent for entry-level and it had the added bonus of being right across the street from my parents’ house. Ottimo. Great.

So I did that for a year, reading blogs by travel gurus like Nomadic Matt and Chris Guillebeau  when work was slow, slowly becoming bored and feeling trapped behind my desk. Luckily, the universe was on my side. The company downsized and let me go, which I documented here. Around that time, my first magazine article was published here, and I received my first cheque for writing. I took a month off, enjoyed Christmas and then went back to school for a semester to get a certificate in Teaching English as a Second Language. Then the adventure really started.

Saviour on the Spilled Blood, St. Petersburg

I got a  job leading student groups around Europe for the summer and I did a bit of my own travelling. I came back to Canada and started teaching, both ESL and Italian. I did that for 8 grueling months (it’s not that the work was grueling, but the commuting was) and continued to write. In May, I went back for round two of students in Europe, scored a couple more writing gigs and did some more travelling. Now I’m back in Canada, teaching English for four months and preparing for my next trip.

Two Canucks and the Kiwi hot air ballooning in Turkey.

Oh yeah, didn’t I mention it? In December I’m heading across the world to New Zealand to be the maid of honour in my best friend’s wedding. She’s a bit of a Canadian adventurer too. So’s her Kiwi fiancé. (One day I’ll write their story on here and really wow you all).

I’ve currently got a one-way ticket to New Zealand, but it’s not going to stay that way. I wanted to make sure I’d get there in plenty of time for the wedding, so I booked my ticket back in the summer. Now I’m sorting out my travel details. I think I’ll hit up Australia and Hong Kong while I’m away, because, what the heck? Right? Right.

I’ll probably be gone for about 6 weeks, but it could be longer. How do I get this time off? I have a job that fortunately/unfortunately (but more fortunately, at the moment) is done by contract. Yep. 7-week teaching contracts. I’m here for two contracts, then I don’t give my availability for the next one. If I’m back before the start date of the March term, I’ll probably be able to grab some teaching hours then.

But that’ll all go up in smoke if my Italian work Visa comes through. Fingers crossed, and if the gods of bureaucracy smile upon me, I’ll be heading over to Italy in the spring for some undetermined amount of time. Until I get itchy feet again, and feel the need to go somewhere else.

People ask me all the time where I’m off to next and how I can make it all work for me. I’m still muddling through, making mistakes, but, at the moment I’m happy with this “nomadic” life I’ve created. It means I get to do interesting things, in interesting places, with interesting people.

Having a mud bath in Turkey. Photo credit: Lance Jackson

This post is the intro to a short series I’m planning to publish here, entitled How To Become A Nomad (And Not Give Up Everything). I’m aiming to let you in on a few of the tips and tricks I use to juggle my life, pack in all this extended travel and not have to pawn all my possessions. Look for the first installments in coming weeks.

100 Days of Travel Happiness

Buongiorno readers!

It’s been awhile since you’ve heard from me (unless you follow me on Facebook, which I update a little more regularly). Why the wait? I’ve just returned to my home and native land after 100 days of travel. That’s over three months of backpacks, suitcases, foreign languages, foreign currencies, new sights, sounds smells and experiences. It was phenomenal. I visited 7 countries (knocked a few off the Travel Bucket List), took 13 flights, explored a part of Italy I hadn’t been to before, ate many new foods, met many great people and re-connected a bit with the life I love in Siena. A very productive 100 days, don’t you think?

Sunset over Istanbul

Here are some of the highlights in no particular order:

– Hot air ballooning in Cappadocia, Turkey

– White Nights cruise in St. Petersburg, Russia

– Visiting the sobering site of Auschwitz-Birkenau in Poland

– Seeing the Palio for the 4th time in Siena, Italy

– Visiting the Checkpoint Charlie museum in Berlin, Germany

– Having a traditional Turkish Hamam treatment in Cappadocia, Turkey

– Being a dinner guest at the exquisite Castello di Spaltenna in Gaiole, Tuscany, Italy

There will be more about these great experiences to come. I promise.

Awaiting the start of the Palio. (It’s not quite the same as my logo, but almost!) Photo credit: Marco Zamperini

100 days away from the hustle and bustle of my life in Canada also gave me a bit of time to reflect on the direction I want my life to take in the near future, and the types of things I’d like to dedicate my time to.

Some of you may have noticed a new addition to the menu bar of this blog: the Hire Me menu. Yes, that’s right. I’ve hung up my shingle and am looking to dedicate more of my time to freelance writing and translating. Over the summer I’ve been lucky enough to secure a few new content creation and translation projects, but if you or someone you know needs to hire a writer, think of me.

In June I also started the wonderfully confusing process of trying to obtain a work visa to head back over to Italy for another extended period. (In my books, 3 months no longer counts as an extended period!) The process has been slow, bureaucratically baffling, frustrating and typically Italian. Right now things are at a standstill and I really don’t have any indication as to whether this visa will be a part of my near future or not, but when I do, I’ll keep you updated.