This Entrepreneur Talks About Forming a Community of Nomadic Creative Thinkers

Several years ago, photographer and journalist Jon Kalan and entrepreneur Michael Youngblood started hosting retreats for entrepreneurs, creatives and others who wanted to work while traveling in order to connect with others in the process. In 2016, they launched Unsettled in response to demand, and many of their monthlong retreats are sold out. However, there’s still space for fall’s upcoming retreats slated for far-flung destinations including Barcelona, Spain; Cape Town, South Africa and Bali, Indonesia.

We caught up with Kalan via Skype to find out why a change of scenery can help spark creativity and how Unsettled builds community one retreat a time. The following questions have been edited for clarity and brevity.

StartupNation: Why did you create Unsettled?

Jon Kalan
(Unsettled co-founder Jon Kalan)

Jon Kalan: Unsettled really came about from two things. One was the incredible rise of more flexibility in the way that people are working: more freelancers, more independent workers, more companies offering flexibility with locations, time, etc. That’s how people more naturally work in their own rhythm.

Number two is that people are looking for more space to have a shared experience and be connected. A two-week vacation, a three-week vacation, the typical experiences that people have been going for is often too short. They don’t give people enough time to really reflect, step back, evaluate and join a community. When you look at the future of work and where it’s headed, the freedom and independence that people are obtaining is wonderful.

At the same time, I think what’s lacking is that sense of, ‘how do I build a community if I’m not rooted in one place or I’m rooted in one company?’

For us, the view is, ‘how can we still have community but also be able to travel and also be able to work independently or remotely?’ So how can we carry on the types of meaningful conversations? How can we meet the same kind of people? How can we really grow?

StartupNation: Who attends your retreats? Were there any surprises about who attends?

Kalan: We’re pleasantly surprised at the diversity of people that we have on these retreats, both in terms of where they come from and also in terms of what they do. We have people from over 35 different countries, from backgrounds as different as somebody whose run multi-million dollar companies down to people who have very small businesses and are just starting out. We’ve had people who worked in corporate for ten to 15 years and people who have just started a career as a freelance designer or a freelance copywriter.

For us, it doesn’t matter what you do, what kind of work you’ve done, your resume. What matters is, are you looking at this as an intentional month to achieve something, to grow, to learn?

The more diverse people we can get in that environment, the more diverse types of thought, types of experience, the more enriching of an experience it ends up being. It’s grandmothers, it’s parents, it’s couples, it’s young entrepreneurs, old entrepreneurs. It’s been incredible and I think it speaks to the idea that there are so many people who want to work and who want to travel.

Related: What is Working (and Living) Life Like for Digital Nomads?

(Creative space, photo courtesy of Unsettled)

StartupNation: Any success stories you’d like to share?

Kalan: We’ve had people who have gone through a really deep process of learning, understanding what’s important to them and have returned to quit their job within a month or three months and take a totally different career track. One woman came and met somebody else who was on the program and two months later moved to Dubai to work full time with her. There are a lot of different stories but I think everybody’s journey is their own. Some people learn exactly what they want to do. Some people learn exactly what they don’t want to do. Some people come away with a better sense of understanding of themselves and what’s important.

StartupNation: Why do you think a change of environment is helpful for entrepreneurs and others?

Kalan: Shaking up your environment, shaking up your routine, it puts you in a heightened sense of awareness. When you’re in a new environment, you are more creative, you’re more aware. It’s times when you put yourself into a situation where you’re slightly uncomfortable that you begin to grow.

You cultivate more of a desire to grow just by bringing yourself into a place like Barcelona or Bali or Beijing, where you’re confronted with different challenges on a daily basis.

The element of exploring the unknown opens people up to what is really possible, whether that’s in your creative life, your professional life or your personal life. You begin to see different opportunities as they emerge.

(Digital nomads in Bali, photo courtesy of Unsettled)

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StartupNation: Do these communities live on in some ways after the retreat?

Kalan: Yes, they have lived on for many years after these retreats. We even had people travel together years after. We have WhatsApp groups that are still exploding months and years later. They exist in a digital form where people are constantly sending each other things, reminders, photos, gifts, tips, help, jobs, whatever it may be.

It’s a physical network, it’s a digital network, it’s a global community we built and it’s continuing to grow.

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