3 Questions for Digital Nomad and Yellowdig CMO, Deb Bolton | Inside Higher Ed

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Deb Bolton is the Contract Chief Marketing Officer (CMO)  at Yellowdig. When I learned that Deb is navigating her edtech career as a digital nomad, I asked if she’d be willing to answer my questions. Deb graciously agreed.

Q1:  Tell us about your work at Yellowdig, and the career path that brought you to your current role?

My work at Yellowdig is one of the most interesting challenges I’ve taken on – how do you navigate the path to success when every consumer, company, and market has changed since the onset of COVID? When I joined the team last fall, I focused primarily on understanding the journey our learners and educators have been on to better define what aspects of our product and services offerings are most valuable. What we’ve learned since then is that the change is constant – an immediate need for solutions in 2020 has transitioned to initiative fatigue and straight burnout in 2021.  Thinking about how we support learners and educators while not also being a burden is what keeps me up at night, especially now given we have yet another virus variant on the way.

When I think of my career path, zig-zags and roller coasters come to mind. It’s been a lot of fun. I was introduced to the higher ed space in 2010 by a good friend who had been nagging me for years to check out the work he was doing with an early OPM company.  It was pretty clear the future was going to be digital, and I was worried the pharmaceutical industry I was currently in may not be an innovator in that space so I took the leap 🙂 

High ed has been a fantastic whirlwind – I was working in online education when we could still be laughed out of a University meeting room for suggesting it, then followed it up with a company creating a new online transnational education at AVENU Learning. (The online transnational concept also got some strange looks until student mobility ground to a halt in 2020!) The best part of my career path though has been the people I’ve had the opportunity to work with over the years – being part of teams where there is a strong balance of smarts, sarcasm and spirit is a winning combination.

Q2:  So you are from Canada, but you are now working in Barbados. Why did you and your family decide to move to an island in the Caribbean to live and work?  What are the upsides and downsides of working remotely from Barbados? 

To be super honest, we decided to go because we’d been in lockdown for 8 months in Toronto and we lost our minds. I’ve worked from home for years, although working remotely wasn’t new to me, what was new was wondering that If I could be anywhere with my laptop, am I where I want to be right now? Within 4 months this year, my partner and I decided to go, coordinated logistics, second-guessed ourselves 1,800 times, and then made the leap. There were so many considerations – older parents, a young child needing childcare, safety, finances. Is this the right choice for us? For our daughter? Will we miss out on important experiences with our friends and family? What about COVID? What we’ve realized is what happens with COVID is everyone’s challenge no matter where we are. If this is going to go on for two more years, we need to figure out balancing taking care of ourselves, our communities and still design our lives.

The upsides, I’m sorry to admit, are everything you would imagine about being in the Caribbean. Vitamin D all day every day, palm trees, everything runs on island time, the million and one sandy beaches, and the amazing, friendly, and welcoming people.

The downsides are also likely what you’d imagine. New places take a while to feel like home and we are far from family, COVID makes travel more uncertain and it’s just not as easy as it used to be to just hop on a flight. Here with our daughter, we had to build and replace the support network we’d had in Toronto. Our daughter had a grand total of 3 days of in-person school on the island before it went online. We almost went home at that point, as navigating online learning for a 4.5-year-old in a new place was pretty overwhelming. Luckily, the school she is at has been nothing short of amazing and we’ve found some great support on the island to help minimize the number of times she runs naked by my zoom screen in a week!

Q3: Based on your experience, do you think the future of edtech work is remote? What advice might you give to others considering working wherever they might want to live in the world?  Where do you think you and your family might go next?

I believe the future of edtech work is definitely remote, or at the very least, hybrid.   I’ve actually only met one person from the Yellowdig team in over a year of working with them, and it’s because she happened to be in Barbados too for a while. (Yes, we did have at least one meeting on a beach because..why not?) The work edtech teams are focused on is about how we improve the learning experiences and outcomes using technology. I think the nature of folks drawn to that type of work is very well suited for hybrid/remote.

The best piece of advice I could offer anyone considering a move, in all seriousness, is not to forget any of your kids’ favorite things. Trust me, that is not a great first-week experience! Also, I think you have to be up for the full adventure. It won’t always be pretty. You might get palm trees and white sandy beaches, but you also won’t know where to get groceries, how to drive on the other side of the road, and how to help your child adjust. If everyone is all for both the fun and the ‘character building’ you will be in good shape.  In the end, you’ll find the grocery store, drive without going into oncoming traffic and your child will be fine, it’s just going to be a bit bumpy to get there.

Go next: Costa Rica is at the top of our list! We actually hadn’t thought about being digital nomads for longer than this trip, but are really enjoying and wondering about what might be next for our family. Our wish list for our next place is great (warm) weather, lots of animals/nature/hiking, beaches, the opportunity for my daughter and me to learn Spanish, strong wifi, and ideally a CST/EST time zone. Suggestions welcome!



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