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


Not Just Another "Dolce Vita"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.

knowledgepower3. 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.

decision-tree5. 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.

keep calmWhy? 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.

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2 thoughts on “How to Become a Nomad: It Takes a Lot of Planning to Be Carefree

  1. Hi, I love your blog, I’m planning to go on an exchange to The university of Bocconi in Milan, and your blogs taught me a lot about traveling through Italy
    By the way I hope you enjoy your trip to NZ, I’m from the coromandel and the weather is beautiful in December, just make sure you plan to spend some time at the beach otherwise you’ll miss out.

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