Michael Youngblood is the co-founder of Unsettled, a global remote coworking community that allows participants to live in international retreats designed to take their work, life, and adventures beyond traditional borders. He is also a TED Resident and the co-founder of Innovations Stories, a multimedia storytelling publication out of MIT.

In this exclusive IVY Magazine interview, Michael expanded on the benefits of digital nomadism, finding yourself through travel, and his belief in the importance of being “Unsettled.”

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Tell us about yourself and how Unsettled came to be.

In hindsight, it’s hard to imagine myself doing anything other than being the co-founder of Unsettled. However, it was definitely not a linear path for a boy from South Carolina to wind up starting a global work and travel company.

Like many entrepreneurs, I didn’t exactly take well to authority growing up. I guess I’ve always been a bit of a rebel at heart. In my most formative years, I was probably what you’d call a troublemaker. I think there’s a pattern among many entrepreneurs to oppose authority because one has to be willing to bend and break the rules in order to launch groundbreaking ventures.

This younger version of myself was rebellious and completely disengaged.

When I turned 18, I put off college and spent a semester riding my bike across Europe. It continued to push me to try to find comfort in uncomfortable moments. I had never been out of the country previously. My family didn’t have money to takes those kinds of trips. It was setting out into the unknown on my own like this that motivated me to go out into the world and begin to bend the way things are done in the travel industry. This experience probably did more to create the entrepreneur in me more than anything else.

That trip taught me the importance of self-sufficiency. You can’t ride your bike across a continent without being able to fully trust your instincts and self-reliance.

These lessons in self-sufficiency went a long way in transforming my orientation toward education — from near dropout to thriving college student. I found a beautiful balance between challenging my own intellectual curiosity, and knowing that no one handed me this opportunity. I had to make the grade for myself.

I started my first entrepreneurial venture the day I graduated in late 2017. I co-founded an ecotourism company, which offered backcountry hiking tours in our National Parks. Little did I know that the greatest economic crisis to face our country in generations was unfolding. Most might think they’d enjoy a good challenge like this, until they’re a 20-something-year-old entrepreneur with less than $100 to their name, little safety net to fall back on, and operating in the worst business climate in 75 years. It just about broke me.

A couple of years in, I ended up moving on, but travel and entrepreneurship was my first love. For the next several years, I worked for MIT, leading publishing and research on innovation. I continued to grow as an entrepreneur, through all forms of capital — intellectual, social, and experiential — and I was impatiently practicing patience, always wanting to start a new venture.

Through my work at MIT, my network grew full of thinkers and doers who work on the leading edge of the economy. When I turned 30, I looked back on the last ten years, and knew I wanted to find a way to bring my two worlds together — entrepreneurship and travel.

In 2014-15, we set out to create the first coworking retreat of its kind. It started with an email to a handful of friends and before we knew it, 45 people from all around the world wanted to attend. We set out for our first 30-day coworking retreat, and what I learned was that while everyone was attracted to the idea of working remotely, they came for reasons much bigger and deeper than pure work.

What we realized in that retreat and since, is that our generation is sick of being treated like unidimensional beings that are expected to show up to an office from nine to five, five days a week, 365 days a year. We’re craving deeper connections outside of work. Religion, marriage, family, community, and other parts of our culture are at all time lows, so where do we turn for fulfillment of our whole selves these days? This was keenly on our minds.

It can seem that our culture is obsessed with work. The first question you ask is, “what do you do?” We didn’t go on that first retreat wanting to exclusively grow as professional beings. We wanted to better plug into our spirituality, relationships, sexuality, and well-being while we happened to work from a beautiful destination.

We realized we were building an open and creative community where people could dive into their life in an unstructured way. We wanted to shift people’s outlook towards space and time and their routine. Conceptualizing this philosophy, we launched Unsettled.

What are key examples of breaking up space, time, and structure?

At Unsettled, we do not believe in work/life balance. If you separate out your work and do not think of it as an extension of every part of yourself, then you’re going to face a crisis in lacking fulfillment. There is no work/life balance. There is life and there is life. We use a philosophy that begins with the fun, adventure, and inherent challenge that comes with travel, and apply that to all parts of our program.

There are three essential phases: 1) Intention 2) Challenge 3) Reflection.

We try to organize any experience around a central pillar: being challenged. But there is also a pre- and post-part to our work that’s even more important. First, before the activity begins, we make space and time for participants to set an intention. What’s on their mind? What are they seeking? What questions are they asking?

Next, it’s the pure essence of the experience, the challenge. It can challenge participants physically, intellectually, or creatively, but the key is that it’s not easy and it brings participants out of their comfort zone.

Lastly, we come full circle and create some space and time for participants to reflect, not on the specific challenge per se, but on how it might be connected to other things happening in their lives.


Where does the name “Unsettled” come from?

Unsettled means to lack order or stability; to not yet be resolved, and to be continually moving and changing. It helps to shake things up when there is a lack of order, and this is one of our goals — to shake up your routine.

We also love it because it puts a positive spin on a negative. We wanted to show the positive elements of living in edgy places because we find that when stability is gone, it helps people ask those harder and larger questions about life, which lead to growth.

In your own words, what is a digital nomad?

The expected answer is somebody who makes a lifestyle out of being able to travel and work at the same time — and living and working on the road for multiple months, if not years.

I believe the reality is different. The reality is that people who may self-subscribe to being a “digital nomad” do not fit this definition perfectly. I’d argue this based on two points. First, digital nomads may not travel as frequently as we think. They may live in one location for six months out of the year, settle for a year or more, or live full time between two homes. It’s a lot harder than one thinks to be constantly traveling and moving all the time.

Second, a large percentage of the people who are traveling and fit this digital nomad lifestyle are more likely to be in transition than actually working a remote job. There are data from U.S. Department of Labor that say the average employee today changes careers every four years. That means every four years you need to reinvent yourself and learn new skills that you can apply to a new career.

What that says to me is that as people go through this period of transition, they need to hit “reset.” They do this through travel. Travel can be a great catalyst in helping to help press “reset.”

How is each community built? What do you look for in candidates for the retreats?

We have put a lot of thought into how we build each community. It sounds clichéd, but it is built through fun, playfulness, and joy. We talk about these workshops but none of this comes unless we are playful and making moments of pure, uncanny laughter within the experience. For example, we do a lot of improv comedy. It relaxes people gets everyone laughing. When you are relaxed and having moments of pure joy, that’s when you can dig deep and become more open and aware. It may sound ridiculous, but we ask: “how can we design experiences and environments that are playful and fun?”

In terms of candidates, we don’t look for people with the ability to work remotely. We look for people that are a) excited! b) not assholes, and c) coming to this with a certain amount of thought and intention. They want something out of this.

Anyone can travel. We want people who are looking to learn from each other, connect, and understand their differences. We want people to ask, “how can I learn from these people who have started a business?” We look for people who want discovery and have a keen sense of curiosity about themselves and the world.

What is the average Unsettled age?

Our average age is about 33-34 years old. Typically people of this age hit a wall. They have eight to ten years of work experience and are looking for the next phase in life. But we have a lot of diversity. We’ve had participants from more than 65 countries. We’re about 60% female to male. We’ve had more people from Beirut than New York and more from Cape Town than San Francisco.

What city do you find to be the most productive?

It’s hard to say, but maybe Porto, Portugal is great location if you really need to be productive. It is one of the older cities in Europe and has a slower pace to it. It gives you the space and time to be productive and the ability to breath. It is also a very walkable city with a slower, older charm.

What city do you find the most “Unsettled” or edgy?

It’s hard to just select one. Bali is incredible. You can go to the rice patties after work. Surf over the weekend, and then go on an amazing hike the following weekend.

Buenos Aires has a super rad nightlife. People truly make the most they can out of the nightlife. It’s very easy to integrate with locals and expats and easy to plug into the city. There is definitely a mix of energy. It is quiet and slow during day, and then there are ten times as many people having fun at night. We have a local staff member who is in music industry and knows every band in the city.

We have some upcoming locations in 2018, so you’ll have have to check back on our site.

Any success stories you would like to share?

I send every participant a follow-up email and ask, “how was your trip?” A participant from November wrote back and said: “I’m sorry this email is 45 days late. I realized I had to quit my job as an investment banker in Dubai. I put my stuff in a storage unit. I have been on the road since. I realized not by traveling, but by interacting with people on the trip that I needed to travel and explore more of the world.”

I thought that was pretty cool. We have so many success stories. Of people quitting jobs. Starting new businesses. Going home with new perspectives. Falling in love. Hiring and being hired. This work has more impact than anything I’ve ever done. It comes with a warning, though: you can set intentions and hope for change, but the higher your expectations are for any type of change or breakthrough, the harder it’s going to be to realize them.

What is your greatest piece of advice to other entrepreneurs?

To get comfortable with the uncertainty. As an entrepreneur, you are forced to make decisions without all of the information. When you are running a startup, there is a hell of a lot of discomfort and uncertainty. Get used to that feeling: get used to being “Unsettled” and embracing it.

What message would you like to send out to IVY members?

A lot of people set out to reach a destination in life. They want this house, this car, this certain life — all of this by 35 years old. Very few people meet these expectations.

Stop thinking about the destination. Stop even thinking of it as a journey. Think of it as a process. If you can dig deep and understand the process you are in, you will come back out of that process. Our generation creates extraordinary pressure on ourselves to find a great job, find purpose, make money, have time off, and on and on. Don’t set these expectations if you can at all avoid it. Just get out there and do it instead.

My Ted Talk, “Discovering your true north,” goes further into this.