Having spent the better part of the last eight years on the road and met hundreds of other riders in the same boat, I’ve noticed a few patterns that emerge whenever people ask questions about long-term, long-distance adventuring. Some of those questions are hilarious – from “how do you put your helmet on” to “what’s the weirdest food you’ve eaten while traveling?” – but some are…misdirected. It’s not that there’s such a thing as a wrong question, but when people ask about living on the road, often, they inevitably try to confirm their own assumptions rather than find out some good information.

So what are the right questions to ask of a motorcycle traveler that has spent years on the road?

Have You Won the Lottery?

Money always comes up when people want to know how it’s possible to ride around the world indefinitely. That’s natural – but most of the time, they ask whether you’re independently wealthy/have rich parents/have won the lottery/bought Bitcoin in time; and often, it feels like the question is formed that way just to confirm that the reason someone is traveling indefinitely is exceptional and therefore, unattainable for most (luck, trust funds, overly generous family, and the like).

The reality, however, is that most world travelers make their own luck. Some riders have worked for years, invested in property, and can now live from the rent they collect. Some riders have remote jobs that keep them on the road. Others, like me, have found ways to be digital nomads working online, whether it’s copywriting, IT, website design, consulting services, or e-commerce. Others still might be earning an income from a successful YouTube channel, utilizing platforms like Workaway, house-sitting along the way…The list goes on and on – but the bottom line is, during the eight years of traveling, I have met only one trust fund rider who was able to do as he pleased because of extraordinary luck to be born in a family of means. One in eight years – that should confirm it’s an exception rather than a rule, and most riders on indefinite RTW journeys have found different ways to sustain themselves on the road.

The Right Questions for World Riders // ADV Rider

So if you’re curious about ways to have a stable income source while traveling, the question isn’t “have you on the lottery?”. The question is, “how do you make it work?”. And most riders are usually happy to share all the creative ways and all the trial-and-error scenarios they’ve been through to get to where they are right now – free to travel for as long as they like.

Isn’t The Market Oversaturated?

Riders who run successful blogs, YouTube channels, or social media accounts often get asked whether it’s worth it to start something like that now, because the market is so saturated. Everyone’s been everywhere at this point, everything has been said and done in the adventure motorcycle media and social media segment, and it’s extremely hard – nay, impossible – to make it as an ADV moto content creator.

That’s the assumption.

The reality is, people assumed this two, three, five years ago, too, and in the meantime, there have been several new ADV YouTubers and bloggers breaking into the niche and making it – very successfully (think Itchy Boots). The market is far from oversaturated; it may be somewhat overwhelmed by mediocre content that leads nowhere, but for content creators who have something new to say, who stand out in a new, unique way, who work hard, and who offer their audiences something of value, the market is more than welcoming.

The Right Questions for World Riders // ADV Rider

The question shouldn’t be whether “the market is oversatured”. The question should be, what works? How can I create content that is valuable, draws people in, and stands out? If you ask riders who are successful content creators this question, you might get some very interesting insights and advice on how to get started – and make it.

Do You Get Free Stuff?

Sponsored riders have heard this one time and again. “Do you get free gear?” is one of the most frequently asked questions, but, much like the two previous ones, it’s somewhat fruitless, because the answer is no, nobody gets free stuff. Riders get sponsored with gear, motorcycle parts, luggage, or motorcycles because they provide something in return – exposure, content, images, videos, and the like; nothing is ever free.

If you’re aiming for some sponsorships, the better question is, “how do you get sponsored?”. Plenty of riders with brand sponsorships are happy to share their tips if that’s the road you want to go down. But perhaps an even better question is, “is it worth it?”, because the amount of time, energy, and sometimes, resources you spend in return aren’t always proportionate to the “free stuff” you get.


What questions do you think world riders should be answering, but aren’t asked? Share in the comments below!

Images: Pixabay

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