How I Do Walk and Talks With Interesting People

Every month, I visit an urban location, usually one I haven’t been to before, stay for about a week, and go for walks.

Each day I walk in the company of an interesting local.

A walk and talk is an opportunity to hold an interesting conversation with someone I wouldn’t normally meet.

I enjoy these casual conversations.

There’s a conviviality walking side-by-side, exploring new terrain with a new companion.

For me, these walkabouts are a near perfect blend of comfort and adventure.

Having one foot out in the world where I don’t know what’s going on, experiencing the unknown.

It’s enlivening being the foreigner.

The stranger.

Makes me feel alert, active, and engaged.

And a bit off kilter too.

It’s this active engagement with place and person that gives me a sense of being.

Wandering around new locations, or revisiting favourites, in the company of a new or familiar companion, is a way of constantly updating myself.

Information flow is maximised.

New knowledge gained.

New perspectives explored.

New insights discovered.

I’m really into these walkabouts because I feel like I’m in the right place, with the right person, at the right time.

Hopefully I won’t blunder into the wrong subdivision of the underworld along the way, but I guess we will see.

People

I have several attributes in mind that I look for in my co-walkers. 

They must be flexible travellers.

That means they tend not to complain. 

I also look for good conversationalists.

I like to connect with people I don’t know, but probably should.

I do these walks primarily to cultivate new friendships and catalyse unexpected connections with the largest gamut of interesting people.

The goal is simplicity, sensibility, connection.

Duration and Distance

The goal on a walk is to have a deep, one-to-one conversation, extended over hours.

I usually walk about 10 km per day, mainly in walker-friendly storied environments.

Nothing too strenuous.

A 10km per day pace permits easy shoulder-to-shoulder conversation, with plenty of rest stops. 

I can walk longer than this once I get into the groove.

But after about 18km, weariness sets in.

And walking like this for more than seven days straight starts to feel exhausting.

So keeping the walks reasonable keeps me on my feet and widens the aperture of who can join me.

Meals

Food is not the focus on these walks. 

I keep it simple. 

After a long day of walking, there is zero interest in travelling far in search of fancy food.

And the longer the day, the less interest there is in eating much at all.

Lodgings

Simple; hotels mainly. 

Planning

I like to line up my walking companions weeks, if not months, in advance.

Many of the people I want to walk with are busy people.

And giving them more lead time tends to help, although this isn’t always the case.

Communications

I use WhatsApp to communicate with my walking companions to plan and coordinate our walks and often continue conversations long after the walk, sometimes for years.

Documenting

One of the great joys of the walk-and-talk format is forming intimate, trusting connections.

Quickly.

But recording the walks can get in the way of forging that connection.

So I don’t record the walks.

But I do take photos along the way.

And afterwards, make a print-on-demand photo book of curated images, along with a map. 

This small, private book becomes a personal artefact of the walk for each of us.

Gear

Daypack

I carry very little during the day; a small daypack with water, a rain jacket, and sundries.

This liberation is essential.

The smaller and lighter the pack itself, the better.

I use the Tom Bihn Synapse 18.

And I always take a garbage bag with me so I can shove the bag in there in the event of a downpour.

I take small travel umbrella too. 

They are surprisingly useful.

Footwear

My choice of footwear is the Brooks Glycerin GTS 20 in black. 

Lighter is better with footwear, and these are as light as they come. 

I always take some kinesiology tape with me too. 

Good for dealing with joint pain and a blister-stopper.

Clothes

For clothes, the mantra is layers, layers, layers.

And smart/merino wool is fundamental to a good walking wardrobe.

A simple outfit might be: merino wool underwear, socks, and upper base layer.

I pair that with some light hiking pants, a sweater or windbreaker, and a hat.

Ultra-light down jackets are also great – they pack easily into my daypack and offer plenty of warmth when paired with a rain shell and a wool hat if I’m walking in a cooler season. 

I always have a hat for sun protection.

Technology

I wear an Apple Watch Ultra for the big screen and great battery life. 

This device can show me the route for the day (if it’s been pre-planned), always available at a glance, and it alerts me when I deviate from the route.

For the Ultra, the WorkOutDoors app is great for keeping track of walking and route data.

A smartwatch with a good screen like the Ultra is really useful because it means I can keep my phone tucked away – verifying the route is as simple as lifting my wrist.

Phones

I like to set an ‘offline’ tone for a walk.

So I keep my phone in my backpack and don’t reach for it during meals or breaks.

This helps keep a ‘radical presence’ between the walkers and the routes we walk.

Going offline, however artificial it may be, goes a long way to promoting this sense of presence.

Camera

I bring a pocketable point-and-shoot camera with me.

Weather

I try to walk in weather that would be considered temperate – this is, sunny days with afternoon temperatures between 20 and 28 degrees celsius. 

It is possible to walk in warmer or cooler weather of course.

But temperate weather simplifies packing, lodging, and logistics. 

It also makes for easier conversing during the day. 

Hot weather walking is possible.

But I’m not that keen on it.

Hot weather (30 degrees C+) requires significant amounts of energy, water, and shade.

If I absolutely have to walk in hot weather, I get started around sunrise, and finish by noon.

I embrace the afternoon siesta.

And as an introvert, I like to recharge with a little alone time too.

Even though most of my walks are through urban locations, on bitumen and concrete roads, I like to get into rural and off-road areas like footpaths, fire roads, dirt farm roads, and quiet off-road trails too.

If I have a choice in the direction of a route, the most enjoyable method seems to be starting in a remote place and walking into a city, town, or neighbourhood, rather than starting in a city and walking out to a rural area.

The latter seems more logical, but the former maximises differences, and heightens the specialness of the walk.

I get excited to see the lights and comforts of the city, which I often take for granted.

Conclusion

These walkabouts are some of the most rewarding weeks of my life, so I schedule one monthly, organising my responsibilities around them.

Walking the earth like this works for me.