Backpacker to Digital Nomad

by Jen Sasman

When I was 23, I started a travel blog and let me tell you… it was terrible. I was not a writer by any stretch of the imagination. But I needed a platform to keep friends and family updated on my whereabouts during a 6-month backpacking trip, so I created The Travelling Sasman. (Ya I know, super cringy.) Despite never being an A-student in English, I loved writing about my travels, so I poured myself into my little blog. It didn’t take long before the visions of myself travelling the world for free, writing pieces for the Lonely Planet and National Geographic appeared. And so, began my Digital Nomad pipe dream.

I started that little blog started 7-years ago, and today I have nearly 100K followers! KIDDING. It was a total bust. I was a terrible writer, but I was so in love with story-telling that I kept at it anyways. For the next 7-years I travelled the world, backpacking, working in hostels, volunteering, draining my savings account, trying to figure out how the hell I was going to turn my blog into something more than a passion project.

I wrote blogs that went unread, took ‘artistic’ pictures with my point and shoot, built myself not 1 but 3 different websites, wrote some more, fell off the band wagon and then started all over again. I designed a logo, bought a better camera, bought a domain name, and pitched my first story to the Globe and Mail. And they ACCEPTED IT! After 5 years of throwing darts in the dark, I finally got the break I was waiting for.  

Last September, my 7 years of creating for the love of it culminated in a dream job sliding into my DMs one Tuesday afternoon. Within the hour I was on the phone with the founders and had a job! I was hired to work part time for a couple of badass boss babes helping manage their social accounts and curating content. Once I got that first job, everything snowballed from there and I was hired by my second, third, and fourth client. Within 3 months I had quit my fulltime job as a server in Toronto and was registering myself as a sole proprietor. Another 3 months later, I booked a one-way flight to Costa Rica and officially set off as a digital nomad.

Navigating the transition from hardened backpacker to digital nomad over the past year has been a rollercoaster of lessons, lifestyle changes and a complete change in perspective on how I travel.

Taking the leap isn’t easy. There is no magic formula. The journey will be different for each of us, but after countless conversations with nomads from all over the world, England, America, Russia, Australia, Israel, there are a few pieces of wisdom I have collected. And I have boiled them down to the 3 key things that helped me make this transition.

LESSON #1: DO WHAT YOU LOVE…

And the rest will follow. I get asked by everyone, literally everyone, how the hell I managed to make this dream a reality. And I always say the same thing. I relentlessly pursued the things I loved, I showed up online and in person, and I had absolute faith that the right opportunity would come along. Yes, most people roll their eyes at me.

The bottom line is, if you are passionate about something, tell people. Show up. No one is going to slide into your DMs asking you to share your brilliance with the world if you don’t share it in the first place.

Don’t try to show up the way you think you should. In fact, ditch the word “should” completely. It takes away what makes your offer unique, and what makes you unique is where you will find your dream clients. In a world where a million people are trying to do the same thing, your unique point of view, set of skills and passions will set you apart.

I was able to combine my passions for creating beautiful things, spiritual development, travel and mindfulness, into a roster of clients who align COMPLETELY with what I have to offer. I am extremely niched in the clients I work with, but it also means that my name is passed around those circles so even when clients have scaled back there is always work available.

So ask yourself.

What sets your soul on fire? What excites you? What innate skills do you have? And how can you connect the them? Start showing up in those spaces, start sharing, reach out and make connections. You never know who in your network might what to hire you!

LESSON #2: BOUNDARIES

When I made the transition from backpacker to digital nomad, the biggest change was in how I travelled. No more super cheap 20 bed dorms, no more falling off the grid for days at a time and no more carefree exploration where days all start to blend together.

When you travel as a digital nomad, it becomes less about ticking off destinations and more about living your life in various parts of the world. Depending on the type of work you do, building a checklist of nonnegotiable's will help keep you focused on what you need to show up for your clients. Everyone’s list will look a little different but here is a glimpse at mine to give you an idea:

• Compatible time zones and set working hours. Managing my client’s expectations while still showing up for them is a fine balance. Bu tit is also one of the most important boundaries as a digital nomad.
• Access to cafes/co-working spaces. Having places where you can set up and work without distraction are amazing. I also love the atmosphere of co-working spaces and being able to build relationships with other nomads, you never know where it could lead!
• Reliable WIFI/affordable data plans. After trying to work through 3 days of rolling blackouts in Nicaragua, I now purchase SIM cards where ever I travel. Partially so that I am available to my clients during emergencies, but also so I have the flexibility to set up my “office” anywhere.
• Clear understanding/communication with the person that I am travelling with that I have to show up x hours a day to work, so it will impact travel days, tours etc.
• No large dorms or party hostels. This one is common sense but learned that lesson the hard way in Costa Rica. There are also some amazing hostels these days that are set up for digital nomads or that offer co-working spaces as part of the facilities.

LESSON #3: THE NOT SO INSTAWORTHY

Setting myself up as a sole proprietor was something I never thought would happen in my lifetime. And, despite the Bachelor of Commerce degree currently collecting dust in a closet at my parent’s house, there are a lot of behind the scenes pieces I have had to learn how to navigate while setting up as a freelancer.

From registering your business, HST numbers, navigating tax, setting your rates, chasing up clients who forget to pay you, surviving the slow weeks, tracking expenses, more accounting than I would wish on my worst enemy, and the list goes on. There are so many moving pieces but setting up a weekly admin day (or in my case monthly) can help keep you on track with the not so fun stuff.

This is the not so instaworthy part of the lifestyle, but it is the work that has to happen behind the scenes in order to make it a reality.

GO AFTER YOUR DREAM

Making the transition from backpacker to digital nomad is becoming a well-worn path. More and more remote jobs are becoming available and more companies are looking for ways to partner with freelancers/employees (not just influencers) who live and breathe their brand values. The infrastructure to support remote working is popping up all over the map from coworking spaces to digital nomad community houses. And the line between life and work begins to give way, as the possibility of creating a life on the road creeps into reach.

If you are feeling the nudge to make this leap, there has never been a better time to start building an unconventional career. Take what you are passionate about, combine it with the skills you have and start putting yourself out there! Don’t be afraid to push the boundaries of your comfort zone, because when you are living the life you have been dreaming about, that leap won’t seem so scary, just oh so worth it!

Looking to get started working remotely? As you start to build up your client base/business organically, there are some great websites and resources for remote workers.

For teaching English online check out:

VIPKids, QKids and Cambly. There are a variety of requirements from location to education level, but all let you set your hours and some offer very competitive pay.

For Freelancing or VA jobs check out:

Fiverr and Upwork. While they can be oversaturated and competitively priced, it is a great space to start getting ideas of the type of work you want to do or what skills you offer.

Make connections and networking!!

Talking to people about what skills you have and what you are interested in doing can open so many doors. I was able to get work for a fellow nomad while in Nicaragua as my client was looking to hire an ads manager, and I was able to put her in touch with another girl in my co-work. Nearly everyone who I talk to about what I do says “Oh, you should talk to <insert name here>! They totally need someone like you.” So, put yourself out there!