Questions I get asked about Skaoot.

Because I’m a digital nomad myself.

Over the years, I realized I was limiting where and how often I’d travel, not just because of the cost, but because of the stress that comes with moving across countries, languages, and cultural expectations. Keeping track of everything. Sifting through emails at a border to explain myself, or at midnight to find the address of where I was staying.

Travel trains your adaptation muscle. But there are already enough things to adapt to in a new place. No need to add the redundant ones if we can avoid them.

So I built my own workarounds: email folders, calendar entries, Dropbox for important documents, one app per airline. Each system was noisy. None of them talked to each other.

Then I found Flighty. The elegance, the thoughtful design. Instantly I thought: there should be an app that does this for the whole trip, not just for flights. That’s where Skaoot came from.

I’ve tried them, especially TripIt. Two things stopped me from staying. The design felt dated, and more importantly, the parser felt rigid.

Business travelers, the primary audience for those apps, stay in branded hotels and fly on tickets booked through their company. Plans rarely change. The path doesn’t deviate.

Nomads are a different species. We change our plans constantly. We stay in colivings, in Airbnbs, sometimes in places we negotiated through a Facebook group. We need a tool that accommodates any provider, and that can absorb a change without losing the trip.

I couldn’t find one. Even Flighty, which I love for flights, sometimes struggles to interpret emails about booking changes. That’s what I wanted Skaoot to be: a tool that handles whatever you throw at it, makes sense of it all, and shows you only the information you need, when and where you need it.

Simple: I want our incentives aligned with yours.

If end users aren’t the customer, somebody else is: booking platforms, advertisers, or whoever buys the data. None of those felt right.

Commission from booking platforms would push me to recommend some booking choices over others. But every nomad travels and books differently. Some play points and miles. Some book flights directly with the airline. Some stay in hostels, others in Airbnbs, others in places they negotiated through a Facebook group. I don’t want to assume anything about how you book, or be incentivized to push you one way.

That’s why Skaoot doesn’t touch the booking itself. We help you track trips you’ve already booked, however you booked them.

And I didn’t want to sell user data either. There’s enough of that out there. Our travel plans are personal, sacred in my opinion, and they should stay that way.

Like a lot of nomads, I travel for many reasons. But one of them is this: travel is about awareness. About culture. About realizing that the issues we face on this planet won’t be solved until enough people see each other as human beings first, and as citizens, language speakers, or believers second.

One of the most effective ways to grow that kind of awareness is to make traveling easier. There are real obstacles to travel: socio-economic, geopolitical, psychological. Skaoot doesn’t pretend to solve any of those. But it can remove some of the day-to-day friction and anxiety, and that frees up a little more attention to spend on the place you’re in and the people you’re meeting.

If Skaoot helps a few more people travel a little more often, and helps them notice that there’s more that unites us than what divides us, that’s enough.