Ian Ord on Running Travel Tours Where Sidewalks End

Like me, Ian Ord is based in Mexico. He lives in Oaxaca, which frequently tops “world’s best cities” lists from glossy travel mags. He runs the tour company Where Sidewalks End and was one of the first to transition from writing about travel to leading travel tours.

After we connected in the past year at ATMEX and TBEX conferences, I wanted to get his take on what’s working for a travel writer turned tour operator. 

What did you do before you became a travel writer and photographer and how did you get started with this pursuit?

My first solo trip was in 1997, where I hitchhiked across Canada. I caught the travel bug early, though I had no idea where it would bring me at the time.

In a past life, or at least the beginning of my professional career, I worked in a film lab—back when people developed and printed film photographs. That was a result of having spent a year on the road, doing a “round the world” plane ticket back in 2000, and coming back with too many rolls of film.

During that time, I had a small blog on an old MSN journal and photo album feature they eventually parted with. Time went on, and I studied tourism and worked in the tourism industry in Toronto for a number of years before hitting a glass ceiling and deciding I needed a change. I bought a one-way ticket to Asia back in 2011, and decided to revisit the travel journaling and photography from a decade prior. The rest is history.

I’ve been an expat with nomadic tendencies ever since, though I have worked in both tourism and photography my entire professional life.

You were living in Chiang Mai a few times and crossed paths with a lot of other travel bloggers who were some of the pioneers in this space, the ones doing this before it exploded. When was that and who was in town then?

Chiang Mai still felt pretty sleepy back in late 2011. The bloggers who were calling it home with me back then were Jodi Ettenburg (Legal Nomads), Dustin Main (Skinny Backpacker, at the time) and Dave Dean (What’s Dave Doing? & Too Many Adapters). Matt Kepnes (Nomadic Matt), Anthony Middleton (Man Vs Clock), and Johnny Ward (One Step For Ward) also frequented Chiang Mai back then.

Within two years, Chiang Mai already had co-working spaces being built, and new shopping malls. Digital Nomad had become a term, and remote workers and bloggers were flooding in by the thousands.

Now you live in Oaxaca, Mexico. How did that come about and what are the pros and cons of being based there?

After five years in Thailand, between Chiang Mai and Bangkok, it was time for a change. My father had passed away while I was overseas, and the visa situation was a constant battle in Thailand—doing runs for a border or nearby country every month or two to renew my stay. All things eventually started leaning towards Mexico. To be in a similar time-zone to my family (as well as a closer flight in case of emergency), and the six-month visas were also a blessing.

Oaxaca was called to my attention through an old friend from Chiang Mai, Jodi, who had relocated here only a year or two prior. I landed during Day of the Dead, which coincides with my birthday, and my one-month travel plans here turned into seven years, with no plans on leaving. A dog, a car, and a Mexican residence later, Mexico has become home.

Of course, living anywhere in the world has its own pros and cons. Rent and food are generally inexpensive, while furniture, or foreign commodities like pickles or cheeses can be exponentially more expensive. Culturally there are of course many differences, but I found it much easier to connect with locals than I did while in Asia, language being a key factor. I’ve learned to speak Spanish fluently and Mexicans have a similar sense of humor to my own. I’ll always be seen as a foreigner, regardless of my integration, though this holds true in most countries.

For any con that might come up, I feel they’re more a challenge, than a strike against living somewhere, and there will be 10 pros to counter them as well.

You recently gave a talk at TBEX North America about working with local DMCs (Destination Management Companies) to lead tours for your followers without having to plan every single detail. How has that worked for you in practice? What kinds of tours have you run?

I’ve always been passionate about sustainability in tourism, and making sure that a cultural sensitivity is practiced and a positive impact is made through the tourism that passes through a destination. As a result, any client I’ve worked with, I’ve been able to help steer them in the direction where those values and ethos can be built into the tours, even if not requested or intentional by the clients themselves.

Having had a background in tourism (working for a global tour operator, prior to my own tours and travel blog), gave me an incredible global network. I can confidently run tours in more than 40 countries for clients, while holding on to those sustainability roots.

Tours we’ve run have varied from food-focused through Thailand, to Women Empowerment tours in Morocco, to Self-Empowerment (face your fears) in Mexico, to uber high-end luxury, surrounded by the jungles and volcanoes of Java, Indonesia. And more…

What are your various income streams like these days and which ones are the largest?

Being completely focused on tourism, income has been seriously impacted since the start of the pandemic. The first two years there was a trickle, but almost non-existent. The past year has had ebbs and flows, but is not consistent, and is still not back where 2019 levels were. It’s also been harder to predict the seasons. They haven’t been consistent.

I find I’m just using the downtime to branch out into other countries, which have different seasons than our main engines Thailand and Mexico (which have similar tourist seasons). Luckily, as with much of the world, everything is coming back in its own new way.

Around 90% of my income comes through tours and tourism and 10% through press campaigns or affiliated sales (like travel insurance or travel gear).

If you were advising someone starting out today as a travel blogger, what advice would you give them for standing out and spending their time on the right things?

I had the good luck of rubbing shoulders with some of the OGs while they were still pioneers too. The biggest lessons they taught me, and I’ve always passed down to those starting out too, are the following:

– Treat your blog like a business from the beginning. What are you selling or what service are you providing? Everything you write should have that business behind it and in mind.

– Money doesn’t happen overnight. Make sure you’ve got some supplemental income, or enough savings to get you through the first two years, but don’t give up. Those first couple of years will be hard, but things will come around if you push through and keep your eyes on the goal.

– Remember what part of your businesses you own. If you put all your time into a social media platform, they can go belly-up overnight, be blocked from a certain country, or change their algorithms and you’ll lose everything you worked on. You will always own the content on your website, as well as the names in your email lists. Social media should only ever be a tool to promote the business you are creating on your own platform if you want longevity.

– Work hard, but live with equal ambitions. That doesn’t mean you have to live frivolously—just remember to unglue yourself from your laptop to keep a work-life balance.

– Grow your personal network. Go to conferences and meet similar-minded people. In the end, your network will be your biggest asset, both professionally, but also personally if and when times get hard on the road :)

Ian Ord is the founder and creative director of Where Sidewalks End, also known as WSE Travel. His life mission is to inspire as many people as possible to break free from their comfort zones, and experience some of the many wonders the world has to offer. Travel continues to change his life for the better, and he wishes to share that type of experience with as many people as possible. See their various tour offerings here.