"How 30 Strangers in Bali Helped Me Become An Entrepreneur"

By: Carly Helfand, Unsettled Bali alum

“Wish and Gift.”

This was the unofficial name of the very first Unsettled workshop. Ever.

It was late 2016, and I was sitting in the breezy conference room of a Balinese coworking space that would be my new “office” for the next four weeks as one of the first-ever participants of Unsettled. These were the early days.

While we were still unsure of the workshop format, we knew what we wanted from it. My fellow Bali participants and I were taking turns listing off things we could help people learn over the course of the retreat (the gift), along with the things we’d like to learn ourselves (the wish).

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It was a list that would help facilitate the skill-sharing and co-creation and become a big part of our month-long experience in Ubud. Also, at the time I didn't know this would be responsible for the next phase of my career.

I went first.

With my journalism background, I offered to help people with writing and editing as my ‘gift’. However, my ‘wish’ wasn’t as easy an answer.

I’d come to Unsettled dreaming of becoming an entrepreneur, and I wanted to use this month to soak up all entrepreneurial skills. While I loved my day job, it had become routine, and I was looking for a new challenge.

There was just one problem: I still hadn’t fully decided what I wanted that challenge to be, and beyond that, I had no idea how to start a business.

After discovering Unsettled online, I decided to sign up within minutes, imagining it’d be the perfect breeding ground for new ideas and opportunities.

Fast forward to this room full of complete strangers, who I was too scared to share all my entrepreneurial dreams with just yet. Instead, for my ‘wish’, I asked them for help with photography. 

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For the next 30 minutes or so, I listened in awe as my fellow participants talked about their businesses and listed their skills and accomplishments. 

These were all new conversations for me; my friends back in the States in Washington D.C. largely worked in politics, policy, media or law. I’d never met an entrepreneur, let alone be in a room full of them.

As I thought about all the things I wanted to learn from this group, I found myself wishing there was something else I could contribute that people would be more interested in. 

And it didn't take long before I had a lightbulb moment. I jumped in, out of turn, to add to my list of offerings: “I can help someone use points and miles to travel for free, as I’ve been doing this successfully for years”.

I saw eyebrows go up around the room, and instantly, I relaxed. I’d caught people’s attention. This was how I’d repay my cohort for the valuable lessons they’d teach me over the next 28 days...

Over the next couple of weeks, conversations about rewards points and frequent flier miles with Unsettled friends turned into conversations about how to monetize my knowledge. As more people showed interest in flying for free, I grew convinced I had a solid business idea on my hands.

Within week three of my Unsettled adventure, the seed was planted: I would develop an online course about using points and miles to travel for free.

I couldn't have imagined a better space to lay the groundwork for a new venture or passion project than on an Unsettled retreat. For everything I needed help with and every question I had, there was someone with experience in that field willing to assist. The once-strangers became my new family members and career advisors.

Piper introduced me to the world of consulting. Pramit gave me a rundown on the basics of audience research. Colin counseled me on the value of good website design. Erina taught a great photography workshop, and Unsettled co-founder Jonathan gave me a tutorial on photo editing with Adobe Lightroom. Anita and Rebeca eased all of my startup fears and became my much-needed cheerleaders.

I continued to draw on my new Bali friends for support well after I returned home, too. Asya and Michele were among my first guinea pig clients, and they later wrote me testimonials that helped me secure my first paying customers. David connected me with resources that would help bring the vision for my online course come to life.

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Best of all, not long after I got home, an Unsettled alumni network was born. As retreats wrapped up every month, the alumni network grew with inspiring individuals who were just as willing to lend a hand; it didn't matter that they didn't know me personally, or that Unsettled was our only common thread. Today, there are 700-something entrepreneurs and creatives in that network, and I can say firsthand that they make for a pretty solid support group.

Only a few months after returning from Bali, I drew on the alumni community for audience insight and enrolled them in my course’s BETA launch. I walked away from the experience feeling like I’d made new friends and professional contacts despite never having met a lot of them in real life. If this isn’t the power of a community, what is?

Today, I’ve got my first official cohort of students working their way through Module 1 of my air miles course, and I’m preparing to scale the business with a larger follow-up launch.

To say I wouldn’t be in this position without my Unsettled family would be a huge understatement. Not only would I not have had the know-how, tools and support to start the business if I hadn’t gone on my Unsettled trip to Ubud, but on my own I wouldn’t have had the confidence to take that entrepreneurial leap.

If you want to learn more about how to travel the world using your air miles, sign up for Carly’s starter resources here.