My True Story: How I Became A Digital Nomad

08/08/2017 04:07 pm ET Updated Aug 08, 2017
Koh Phangan, Thailand.
Kate Smith, WiFly Nomads
Koh Phangan, Thailand.

As I write this, it has been just over two years since my life changed forever. I boarded a one-way plane to Prague and started my journey as a digital nomad. And for those of you that don’t already know, a digital nomad is someone who works remotely while traveling.

I had joined a program called Remote Year as part of their inaugural program. Of the 25,000 people applied and I was one of the final 75 selected to join the program. To be honest, I didn’t even know if I was applying for a job or a program - all I knew is that it meant I could travel while making money at the same time. The money part was key as I still needed to cover my bills and student loans.

Being the first of the program, there was a lot of question as to if this program even existed, or if it was real. You had people screaming “scam” but I decided it was worth the risk and spent $50 on the application fee. And then, once I was accepted I threw down the only savings I had - a $3,000 deposit just to ‘secure’ my spot.

From there it was $2,000 a month for a year. Yes, that’s $27,000.

Now, most people would have thought I was irrational, illogical - maybe even a little crazy.

I didn’t have a full-time remote job

I had no “plan”

I had a $2,000 payment coming out in 4 weeks and I didn’t have the money in my bank

Many would have said:

“Wait until you save up more money”

“Perhaps the time isn’t right for you, you don’t even have a remote job”

And many did say,

“$27,000 - that’s insane! “

“What a rip off”

If there was any sign that this was a bad idea, I had it.

It seemed like a bold move. But perhaps it was the two years leading up to it where I thought:

“I need to make a change. I don’t know what that is or what it looks like but I needed to travel more and I needed money.”

(Yes, those damn student loans). I spent two years getting to this point.

Leading up to my Digital Nomad “Jump”

I wrote out my ideal job and the qualities it would have. By the way, this job description seemed so far fetched because no one pays you to travel the world, right? But I stuck with it anyway.

I started exploring what types of careers interested me and what my hobbies and interests were. After working in a cubicle for so long and working so much overtime, I really had to rediscover what it was that I actually liked to do for fun. I started working with a life coach, reading a million self-help books etc.

I spent about one year “thinking about it all” and one year “exploring” where I actually started taking action. I signed up for jiu-jitsu classes, painting classes, Spanish and sign language classes, and I started crafting. A ton of random things. No, I didn’t think I would become a painter or get paid to speak Spanish, but I knew it would guide me in the right direction and put me on a path to get from A to B. I never once planned that A to B path, but I just kept walking towards B and I did that by following these passions.

It was among exploring these paths that led me to three career options that I started to become more serious with:

  1. Go into health and fitness (dietician etc)
  2. Teach English overseas
  3. And then there was option number three, which became my biggest goal - join Remote Year. I came across an article on Facebook about this program that would take you around the world while working remotely. I didn’t have a remote job at the time, but if that’s what I needed to join, I knew I’d find a way.

Following your Heart Instead of Logic

Long story short I got accepted to Remote Year, as you know. Again, being the first program, there were questions if this program really existed or if it was just a scam. I was hopeful it wasn’t but the thought that this could just be an expensive trip to Prague ($3,000 down payment for the program + $1,000 flight) did creep into my mind. I knew it was a risk, a risk too big for the ‘average’ person. But I think the difference between me and the average person is that I don’t want to be like the average person. I’ve always felt like a black sheep among my friends and family. That being said, for me, I barely thought the idea over before accepting. The decision I was about to make felt so true in my heart that I had to take a leap of faith that it would all work out.

Overcoming Fear of Failure

Really, as long as you have food, shelter, and water - everything else is a bonus. I recognized that after a trip I took to a rural impoverished area in Kenya, so really, it wasn’t that risky at all in my mind. It really comes down to what you’re comparing the risky situation against.

I guess my confidence in the decision also comes from my past.

I grew up middle-class family, small town, shy and reserved. I can’t quite remember when it was, but I knew I wanted to be something bigger than I was. I felt it inside me already but it just hadn’t manifested into reality. I knew I had to start taking bold actions. These “bold” actions started out small. Until every time I tried something “random” and they always worked out. Like always on some insane, miraculous level.

I wanted to volunteer in Kenya with a program called MetoWe and I had only a few months to fundraise $5,000 so I could join the program. The girl that worked there even said to me, “you know, most people give themselves a full year to fundraise. Are you sure this is enough time for you?”. I replied, “Yes. I’ll figure it out. This is going to happen”. Long story short, I raise the amount needed and “$2,000 of that money came from me selling hot chocolate for $2 out of a wagon during the Santa Clause parades.” Talk about small things adding up! And guess what? Off to Kenya, I went.

Selling hot chocolate at Santa Calus parade, to raise money for my volunteer trip
Kate Smith of WiFly Nomads
Selling hot chocolate at Santa Calus parade, to raise money for my volunteer trip

Then, I randomly won Justin Bieber tickets on the radio. The typical, “Caller number 10 wins the tickets”. I thought, “why not just try”. I called once and I wasn’t caller number 10 (or whatever number it was). “Damn.” So I tried again. And guess who was caller number 10? This girl!! I eventually ended up selling the tickets through to fund my volunteer trip in Kenya. Nonetheless, I tried twice for them and won!

Then I randomly got in a music video - and no, no, don’t get the wrong idea. Nothing sexual. In fact, I was fully covered in a teddy bear costume. This time though, a colleague from work was helping to produce this music video and needed some extras to dress in costumes. It was random but I thought it would be a fun life experience so I signed up.

Dressing up as a teddy bear for a music video.
Kate Smith, WiFly Nomads
Dressing up as a teddy bear for a music video.

Then, I got on a reality TV show. I had just entered the workforce with a “real job” as a project manager at an advertising agency. Unfortunately they don’t pay six figures out of University, and instead, I had $50,000 in student loans. I was trying to get creative in how I could earn extra money. This was before Airbnb and Uber days when a “side hustle” wasn’t such a big thing. I had watched a reality TV show where you could win $5,000 - all you had to do was complete a series of challenges. Long story short, we filmed for about 6-weeks and I landed $6,000 - the most they had ever given out.

Filming TV show.
Kate Smith, WiFly Nomads
Filming TV show.

Heck, even the producers from ‘Ricki Lake’ called me from LA after that. That didn’t pan through but all good.

On that note, there was also a time I tried to get Oprah tickets. She was getting older and I knew there was only going to be a few seasons left. So I signed up to try and get studio audience tickets. If anyone has tried before, you know that you get tickets it’s lottery style. So. you could try 100 times with no luck, or try once and get on. Guess what? Yup, I drove to Chicago for a filming of Oprah to be in the studio audience. No, unfortunately, I didn’t get a free car, haha but it was a dream come true to see Oprah live as I sat in the audience in front of one of my biggest idols. P.S. They are more strict than an airport when it comes to security at these studios and they were adamant that no cameras got inside the studio so unfortunately, I got no snaps of Oprah :(

Attending the Oprah Winfrey show in Chicago.
Kate Smith, WiFly Nomads
Attending the Oprah Winfrey show in Chicago.

Then, I met Ethan Hawke. He came to my small hometown to film so having someone like him in town was a BIG deal. Everyone was crowded around staring at him as he sat in the car between filming. I thought it was weird that everyone was just staring. We all wanted a picture and autograph so why not just ask. I shouted, “Hey Ethan, can we have a picture please?!” So he gets out of his car, makes his way through the crowd, and headed directly my way, snaps a picture and then proceeds to walk directly back into his car. No one else got a picture! For the week after we were known as the girls that got the picture with Ethan Hawke. And again, being a big deal in my small hometown we made it on the front page of our local newspaper for being the only people that actually met him while he was in town.

Ethan Hawke and Kate Smith.
Kate Smith, WiFly Nomads
Ethan Hawke and Kate Smith.

Now, why do I tell you all of this? I tell you this because it was a compilation of all these small events that I realized, “holy shit - this actually worked out and just happened”. So many people are too afraid of failure. So many people are too afraid of failure... In all these situations I thought, “Ok, worst case scenario is a no or a not going to happen”. That’s literally it. I don’t die. Life goes on. So I was thought “why not?”. As you can see that “why not?” mentality has given me some pretty cool ass life experiences and stories.

This is what gave me the confidence to dream bigger.

If all of that could happen, what else is possible.

I’ve also often thought about death. It’s inevitable and it’s just a matter of when. I think getting clear on that, understanding it and respecting it made me realize the lack of time we have on earth. So I decided to be here to LIVE it.

Not only that, I also wanted to be an interesting person and live an interesting life. So when I would do something, I would think, “If I met myself, would I think this I’m interesting” and if it was, I did.

As per above, I’ve done a lot of random shit.

And guess what else? I can die tomorrow knowing I truly have lived my life to the fullest.

Starting my Digital Nomad Journey

So back to becoming a digital nomad. This was the next of my random “let’s try it out and hope for the best” moments.

Unexpectedly as I boarded the plane, tears rolled down my face. It all hit me. So much emotion. Life was about to be so different for me, more than I could have dreamed up.

At the airport in Toronto, Canada, heading to Prague, Czech Republic to start my digital nomad journey.
Kate Smith, WiFly Nomads
At the airport in Toronto, Canada, heading to Prague, Czech Republic to start my digital nomad journey.

It was always in my wildest dreams that I would work remotely while traveling the world. Except at the time, I didn’t even know “digital nomad” was a thing. I thought “teach English” or “dream super hard that I could be a writer and make money as a blogger” (spoiler alert, I actually have a blog that makes me money and second spoiled alert - I don’t consider myself a writer. I just share stories and experiences from my life).

Anyway, after realizing this whole “digital nomad” thing. I started looking online for remote jobs.

I looked online for months trying to land a remote job - all with no luck. As I look back, I realize why this didn’t work but more on that later. I touched down in Prague and had one month to land a remote job or I would be sent packing back home BUT I knew that wouldn’t happen. I was too determined and wasn’t more sure of anything in my life. That doesn’t mean it was easy though. In fact, it was the hardest thing I’ve ever done in my life.

Have you ever put your full 100% effort into something, and still the world seems to work against you? That was my journey.

Two weeks into my stay in Prague I was still looking for a remote job. I had two weeks left or I would be sent packing back to Canada.

Talk about pressure. But then it happened!

At the coworking space I was at one day a bunch of us went out for lunch and a local came along with us. Among conversation, I mentioned that I was actively looking for work in Marketing. All of the sudden, this local brings to my attention that he has a friend looking to hire someone for a similar role. Better yet, this was a fully remote company! All went well and I ended up landing the job and still work with them to this day.

The key takeaway here:

When I was in Canada I was looking for a remote job but I was completely surrounding myself with the wrong people.

Of course, I couldn’t find a remote job in Canada, I was surrounded by people that lived “traditional lives” and worked in offices - unable to fathom the idea of you not working from the office. I was also applying to companies that I had no previous relationship or rapport with. No wonder it was so hard. It’s like screaming “pick me” in a field full of people. And remember, I had been applying for remote jobs for a good three months in Canada all with no luck.

It was only when I was surrounded by the right people (coworking spaces are full of remote workers, and people who think differently) that I was able to land the remote position.

Then... my laptop died.

Then my laptop died. Yup, this story isn’t an easy one. And, I didn’t have the money to buy a new one $2,000. After breaking down and crying in the middle of a grocery store in Prague for a bit, I decided on the credit card it went. The Laptop was purchased, even though it took a week to get an English keyboard shipped in. Either way, I wasn’t giving up.

I didn’t have the money for that laptop but I saw it as an investment. The laptop would help me achieve a new way of LIVING for me. It wasn’t just a trip, I was creating a lifestyle. A lifestyle beyond my wildest dreams.

It was a long time coming, but boy has it ever been worth it.

How Life Has Changed Since Being a Digital Nomad

The last two years have been HUGE for me. The biggest, most impactful, powerful, challenging and rewarding years of my life. The amount of growth and development I’ve experienced, both professionally and personally and inexplicable - I honestly feel like I’ve had five years of growth in two years. I’ve never felt more empowered, free and most of all I’ve never felt so much passion in my life. My soul feels fulfilled.

I made the bold decision to book a one-way ticket to Prague to start my digital nomad journey. The thing is, I took the leap without a full-time remote job. It took me nearly two years to finally get to this point, so perhaps that’s why it didn’t feel like such a bold move.

Koh Phangan, Thailand.
Kate Smith, WiFly Nomads
Koh Phangan, Thailand.

So what exactly has happened these last two years?

I have:

Lived in 11 different countries around Europe, Asia and South America (Prague, Croatia, Slovenia, Turkey, Bali, Japan, Thailand, Vietnam, Buenos Aires, Peru, and Chile).

Machu Picchu, Peru.
Kate Smith, WiFly Nomads
Machu Picchu, Peru.

Been seen in BBC, CNN (x2), Fast Company (x2), Etihad Airways in-flight magazine, The Hindu, Mashable, BuzzFeed, countless podcasts, publications and newspapers across the world (Slovenia national news TV and the Dubrovnik Times newspaper) and soon Huffington Post.

Podcast Interview.
Kate Smith, WiFly Nomads
Podcast Interview.
Slovenia National News.
Kate Smith, WiFly Nomads
Slovenia National News.
Kate Smith, WiFly Nomads

Started a blog - got my first paid press trip (yup, I got paid to travel and post about it on social media, pretty sweet eh?) and I started earning revenue from my blog.

First press trip in Slovenia.
Kate Smith
First press trip in Slovenia.

Extended my personal and professional network across the globe. It’s hard to go to a country and not know someone who is also in that country.

Started a startup and even brought on our first staff member.

Got approached by the same investors who invested in Pinterest, LinkedIn, Blue Apron, Shopify etc.

I don’t bitch and moan about the commute.

I don’t sit in a cubicle.

I don’t come home exhausted, waiting for retirement.

I wake up, wherever I want to be in the world, and I have the complete and utter freedom to live life on MY terms. It’s pure freedom and pure joy.

Bali, Indonesia.
Kate, WiFly Nomads
Bali, Indonesia.

Sounds like a dream, right? I don’t blame you. I’ve met people traveling that literally didn’t believe that I just worked remotely while traveling the world.

“That was a key moment for me. It’s like damn. This is it. This is real.”

My life is so awesome that people think I’m lying. As much as that sucks that someone thinks you’re lying, it’s so incredible at the same time. It validates your accomplishment. This is real life. This is my life and it’s awesome.

Starting Your Own Digital Nomad Journey

When I started my blog, I wrote about my experience working remotely while traveling the world. I couldn’t believe that people were actually interested in what I was writing. Within months I had my first press trip and I always had people reaching out to me asking me two main questions:

How do I get a remote job too?

How do I get started?

I always wanted to give thoughtful responses but quite frankly, what they needed to know wouldn’t fit within an email. It was so hard to convey all my information and knowledge into a short email. I needed a better way to do this.

Among The Remote Year program, I was on, I also noticed that a lot of people wanted to join but they didn’t have a remote job. Helping professionals land a remote job was a huge opportunity and gap in the market that I noticed. Why weren’t other companies offering this? I mean it’s quite obvious. It’s hard work. It’s more fun to globe-trot people around the world than really sit down and do the hard and dirty work with them.

With those thoughts in mind, I knew I needed to create a solution that could help people start living this lifestyle. It has such a profound impact on my life that I needed to share it with others and help as many people as possible.

That’s when I came up with the idea for WiFly Nomads. It’s program I launched to help professionals transition into this digital nomad lifestyle. It’s my way of sharing all of the things I had learned from my experience of:

  • How to land a remote job if you’ve never worked remotely
  • How to get started with freelancing or running your own online business
  • How to live the lifestyle. Everything from mindset, visa, taxes, budgeting, cultural integration, staying productive, where to work, how to get around etc. And yes, the internet is NOT created equal around the world and there will be the most random things you encounter that you never know you needed to know.
  • The challenges that you will face and how to overcome them - you know, loneliness, the challenge of being black sheep and thinking different, the challenge of being homesick, the challenge of always saying “byes”, burn out and more

The inaugural group will join me and other experts such as Daniel DiPiazza, Founder of Rich20Something, in the digital nomad hotspot of Bali this September to start their digital nomad journey.

What It All Really Comes Down To

Here’s the thing.

I took a risk with WiFly, as I did with everything else that got me where I am today. If it wasn’t for those bold moves, those risks, and relying on faith probably more than I should, I wouldn’t be where I am today. I’ve done things before ‘I’m ready’ before it’s the ‘right time’.

There are countless sacrifices I’ve made financially, socially, personally, etc. to make this happened. But yet again, it felt right. It felt true to me.

I’ve come to realize so many people stop at fear. And that’s about the saddest thing that can happen to a person. Too many people live their lives on autopilot. And I think it’s important to note, I’m NOT from a wealthy family and I don’t have a trust fund. Yes, I once had someone ask me if I actually work or if I just have a trust fund. I’m where I am today as a result of a lot of hard work and yes, full-time work. I’m a small town girl. My parents don’t have “connections” and I graduated $50,000 in debt. I’ve worked so incredibly hard to get where I am. It’s the furthest from luck. I have been intentional to make this happen.

At the same time, I want to be sure here to not diminish the support that my parents have provided me with. I simply wouldn’t be where I am without their support. They’ve always put my brother and I first so that we could go on and create the best lives possible for ourselves. If you look at the most successful people they’ve always had a team of people or support system behind them. And my parents are part of that support system. Something I’m eternally grateful and quite frankly the best “gift” you could ever give a child. You don’t need your parents on board to make your dreams happen, but it’s important you have people in your life who support you. And if you don’t have that, you need to go out and find them.

For those of you reading, you’re going to find an excuse or you’ll find a way. The decision is yours.

I’ve always been the “I’ll find a way type”. That’s the difference between people living these “dream” lifestyles and those who run their life based on fear.

I never thought in my wildest dreams I would be featured in major publications around the world or have founded a startup. Anyone looking at my life would have thought “this isn’t the life for her”. My path, based on how I grew up, would have been some office job, work 9-5, come home, have some babies, get married, wait for retirement and call it a day. Now, don’t get me wrong. That fulfills some people and that’s ok. I’m not here to judge what fulfills you, but I am an advocate of living a fulfilling lifestyle. You don’t have to work remotely and travel the world to live a fulfilling life, but let me tell you, most everyone I speak to about what I do says, “I wish I could do that.” And I still definitely want marriage and kids but I also know I need to be fulfilling my hopes and dreams in order to be the best version of a wife and mother I can be.

I’ve made very intentional and deliberate choices in my life. Choices that push me out of my comfort zone and decisions that made me take action well before I’ve been “ready”.

Do you know how surreal it is that now I’m networking and know authors, lawyers, successful founders, influencers - people who have accomplished great things in their life?

Kate Smith and Jen Sincero, Author of ‘<a rel="nofollow" href="" target="_blank">Your Are a Badass</a>
Kate Smith, WiFly Nomads
Kate Smith and Jen Sincero, Author of ‘Your Are a Badass

This isn’t something that comes from a small town. This is something that happens when you decide to level up and become something bigger than yourself.

This all comes down to a choice. It’s not luck.

You make the choice, you take the leap, and just like me, you pray to the universe, God, whatever you want to call it, to guide you and have your back as you make a bold me.

If it’s deep enough in your heart it will manifest at some point, in some way. It won’t always be an easy journey but boy oh boy, is it ever worth it.

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