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Finding Simon

‘‘ I always thought of myself as confident and outgoing. The more I travelled, the more I discovered an anxious, socially exhausted side of myself. ’’

By Simon StilesSeptember 7, 2017

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Hi Simon, can you briefly describe your channel (Finding Simon) to new viewers?

Finding Simon is a travel vlog. It is all about full-time traveling on a budget. I share the ups and downs, the cool people I meet, great food, amazing sights, and tips for your own adventures.

[Daniel: In 2015, Simon sold his apartment in Ottawa and bought a 1992 Dodge B350 Camper Van. He has been pursuing “full-time travel” as a way of living. Through Finding Simon, he shares his adventures and the everyday realities of life on the road.]

What was your professional background before Youtube?

I was a freelance photographer for 6 years before getting into YouTube. I got into Youtube to become a better filmmaker. After 450 episodes, I’ve certainly learnt a lot.

How did you make the momentous decision to sell your apartment and live life on-the-road?

Living on the road wasn’t a long term plan at first. I was just setting out on a trip. But that trip ended up changing the way I looked at my life goals. I realized I could achieve so much more by just setting out full time on the road.

[Daniel: In another interview, Simon comments that he romanticized the idea of vanlife. He said “We started getting hooked on [the idea of RV life], all of those Instagram pics that we saw of people parked in state and national parks. And everything looks amazing […] That was a huge sales pitch.” But Simon realized that the reality was quite different. He continued “And then we got into maybe like the first week of it and we were parked in the Walmart for like, the third time.”]

Simon, you recently sold off the Dodge Camper RV and replaced it with an (amazing!) sidecar bike. Can you tell us more about the bike?

The bike kind of fell into my lap. At first I was looking for some sort of off-roading adventure bike setup, since sidecar motorbikes are typically way out of my budget. Then this 1999 Yamaha VStar (1100 cc) with a crazy sidecar appeared on the local classifieds and I knew I could make something out of it. The whole package was about $4000. It wasn’t running, and it had been sitting for a long time, but that’s exactly the kind of project I love. Check out the video below.

So I got it and set out across the country. It’s really just an in-between before I buy my sailboat and set upon my next huge build project.

What does your weekly schedule for Finding Simon look like?

Currently I’m uploading every other day. I try to film everyday so I can give myself a buffer in case I need to spend a few days working to rescue the travel budget. I’d say I’m always planning. One part includes research, either by destinations or collaborations, keeping up to date with emails and the business side of the YouTube world. The other part is just getting inspired, and trying to find ways of keeping the content fresh and my skill set growing.

What books (or individuals) have had a strong influence on your life?

The books Finding Momo and Maddie on Things (which both started as pictures on Instagram accounts) really inspired me to first set out in the van. As for travel inspiration I’m a huge fan of Departures, a Canadian TV show following two guys who grew up not far from me, and travelled the world.

How do you support your full-time traveling? Would you recommend it to other creators who want to be digital nomads?

I support myself as best I can through my YouTube, primarily from Patreon and my merchandise shop. You can check some of my gear below.

Finding Simon HatFinding Simon Painting Finding Simon Shirt

That makes up a third of my budget, the rest I make through real estate photography work, the odd corporate video client, a few private clients left over from my photography practice. Mostly I suggest keeping your overhead low and flexible. There’s a lot of ups and downs to this lifestyle and the best thing you can do is save up and diversify.

Most memorable road you have driven.


There are so many, but to date my favourite is the 99/Sea-to-Sky Highway in British Columbia. Honourable mentions go to the Blue Ridge Parkway, Pacific Coast Highway, UT-12, i70 in McInnis Canyon, and AZ-89A.

Life on the road must be filled with surprises. How do you deal with the uncertainty, anxiety and change?

It’s a bit of a cop out to say you just get used to it, but the truth is that you do. To be honest, those uncertainties will drive you crazy at first. They’ll give you so much anxiety you’ll fall apart – but they don’t go away. The only way to truly limit those uncertainties is to return back to the life you knew before, to the 9-5 and apartment. If that’s not an option, then you’ll just learn to live with the reality of that uncertainty eventually.

In the end you’ll realize that everything for everyone is uncertain, and the more we attach ourselves to the temporary luxuries the less we really appreciate them, and the more we’re hurt when they’re gone.

Did you make a conscious decision to travel alone? Would you be open to long-term travel with a friend or significant other?

Actually, I first set out as a couple and I’d be happy to travel alone or as a couple. But make no mistake, they’re very different from one another. If you choose to set out on your own, you’ll discover so much about yourself so fast – it’s life changing. You’ll be so flexible and open to possibilities that you can catch every opportunity as it arises. You’ll be lonely sometimes (it’s true) but you’ll also accomplish so much. Travelling as a couple can limit you in your ability to jump on opportunities as they arise, but on the flip side you’ll grow together so much so fast that if you can go the distance, you’ll be a better and closer team for it.

What are some unexpected things that you have learned about yourself through this journey?

I’ve learnt a lot about myself along this journey, but some of the more unexpected ones were the negative realities of my character.

I always thought of myself as confident and outgoing. But the more I travelled alone, the more I discovered an anxious, socially exhausted side of myself.

I discovered a lot of things about myself that I didn’t like, but it helped me to become more at one with the person that I am, and that led to a lot of positive change in my character. It’s hard to summarize in just a few words, but maybe the best way to describe it is an acceptance that calmed my turbulent nature.

What were your biggest mistakes, or biggest wastes of time/money in growing your channel?

My biggest mistakes have always had to do with communication. I’ve never had trouble clocking in the hours, making video after video, going the distance for quality content. What’s been my consistent weakness is the rest. Communication, emails, shaking hands, meeting people, pushing for collaborations or sponsorships, getting my videos in front of new eyes. I believed for a long time that just honest hard work would always be enough but it isn’t. So much of this is the rest, the behind the scenes, the stuff that no one will notice, and sure won’t help your videos look better, but in the end grows your channel so much.

What do people never ask you guys that you wish they did?

People never seem to ask what I actually make in terms of income. The truth is most people believe it is taboo, but I believe some transparency will do the online social world a great deal of good.

I made a total of $989 off YouTube, Patreon, Affiliate Links, random donations, and my merch shop together last month.

That’s less than any part time job I know of. I spend the equivalent of a full time job if not more at this. People think this is a cakewalk, and that these companies will gladly fork over bags of cash for your internet videos, but the truth is the margins are getting skinnier and skinnier and so long as we don’t talk about it, it’ll only get worse.

What’s next for you?


My next step is the most budget strapped big sailboat build YouTube has ever seen. I’ll be building a massive sailboat to travel around the world in, and documenting the budget, trials and triumphs as I go on my channel. It will be a very different kind of adventure.

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  • barbaracobble

    What a refreshing interview. Love the honesty and transparency of this. Much better than the thousands of wanderlust channels on social media.

  • Bryan3478

    Hey Simon! I checked out your recent video and it seems you have indeed made the transition to a boat! Love the new Sink or Swim series man.