Lifestyle & Culture

Digital nomad Jason Clark: Beautiful beaches, ugly Internet and a realization that life is short

(Editor’s note: Jason Clark, president and CEO, of Via Studio, spent the past month working remotely from Greece and Croatia. Here is Pt. 1 of a two-part series with his observations and tips about this increasingly popular alternative to conventional work. Jason’s daily digital nomad diary was first posted on LinkedIn and has been aggregated into two posts for Dispatches. You can jump to Pt. 2 here.)

I’m working remote this month. VERY remote, from Greece. I just started this week, but wanted to report in if anyone is considering jumping on the “digital nomad” train.

Balos Lagoon (all photos by Jason Clark)

Post One: Temptations in Greece

I’ve been staying in hostels thus far, which are inexpensive, friendly, fun, and engaging. Think of them as a coffee shop with bunk beds. If you value your privacy, a hostel is not the place to stay, but if you like working from coffee shops, you’d probably like hostel travel. My Athens hostel was $20/night and my Crete hostel where I am now, is $22/night. It’s cramped, but I’m outside pretty much whenever I’m not showering or sleeping.

Finding the right time to focus and get work done would be a challenge for the easily distracted. Just in the past day I’ve been invited to a sunset cruise and a day-trip to Balos Lagoon on Crete. I hate missing things, but I’ve got work to do while I’m here, so I may miss some things. My meetings are trying to align with the morning hours. My 4 p.m.-to-7 p.m. window is your 8 a.m.-to-11 a.m. window on Eastern Standard Time. Even worse if you’re Central Standard Time or Pacific Standard Time.

It’s all good though, because my morning was spent reading the latest Michael Pollan book and dipping in the ocean to cool off.

Post Two: Crete

My hostel in Chania, Crete, had less than optimal Internet, and I had three meetings in a row yesterday. Those did not work out very well for me, and left me a bit embarrassed because it was hard to do “my thing” in those meetings.

Stable internet is required for remote work, so I will have to be vigilant for my next video meetings.

Balos Beach on Crete. Quite possibly the most beautiful beach I’ve ever seen. Today I’m in Herkalion catching up on the bad interwebs from yesterday. ☮🎒

Post 3 of VERY remote work. Here’s a photo album of some of my favorite pictures I’ve taken in Croatia and Greece so far.

Post Four: Santorini

I’m in #Santorini until at least Wednesday. I woke up early and hiked 10 kilometers from Fira to Oia (pronounced “eee-ya”). It was absolutely stunning and wore me out enough to get some work done when I got back to the hostel. The wifi here is much better than Crete, so I’m feeling super-productive (the fredo cappuccinos don’t hurt either). Working on about three proposals and writing a few statements of work for new projects. Everyone has been supportive of my experiment thus far, I think as long as I keep up my end of the bargain.

I hear it’s hot back home. I don’t think it hit above 85 on the hike here, so I’m counting myself lucky.


Post 5: Life is short

This one could be considered a bit dark, but I’m not afraid to go there if you’re not.

I lost a really good friend this week. Someone I have known for decades and love dearly. He was only five years older than me. A friend that was even closer confirmed that essentially he passed away from years of stress. Luckily he passed peacefully in his sleep.

My dad died when he was 51 years old. He worked hard and long hours, and when I was a teenager I asked him why he worked so much and took on so much stress. He told me he was saving for an early retirement and was going to enjoy his retirement after having earned it. Well, when you push off that day that you enjoy life to the fullest, you never know what might happen. Life is short, and oftentimes TOO short.

Americans wear their hard work as a point of pride, but WHY do we work so hard? The happiest people I know have family commitments or hobbies that they do not allow work to interfere with. As a business owner with employees I respect the hell out of that. Knowing why you work hard is important. Being proud of pounding the caffeine to work 16-hour days for no good reason makes no sense to me.

Work hard and succeed in your career, but never forget the WHY.

Remote work report: Yesterday I had a great call with a client of ours in the United Kingdom. My contact was proud of me for working remotely, and it also made the call much easier to schedule. 😂 Today I head to Ios island. Leaving the beautiful Santorini in a ferry about an hour from now. I’m missing my family something fierce, but I also hear it’s sweltering in Louisville this week. I think I’ll wait out that weather. 😉


Post 6: Ios

I’m on the island of Ios until Sunday. My phone desperately wants to autocorrect my text from here as “iOS” 😂. I’m less than a week away from heading home, and TBH, ready to sleep in my own bed, snuggle my dog, embarrass my kid, and kiss my wife.

I picked a few days on Ios because it’s a small island and I wanted a break from the crowds of Santorini. Everyone here is friendly, the food is inexpensive, and it’s just beautiful. I had three Zoom calls yesterday from here and the internet is good enough to have those calls with little lag. It still amazes me we can have video chats in real time from around the globe.

Yesterday I traveled to the northernmost point of the island to see what is allegedly Homer’s tomb. The tomb sits on a hill, and as you can see in the picture, is perfectly situated looking out over two smaller islands across the sea. Homer was a poet and a storyteller, known for the classics “The Iliad” and “The Odyssey”, the two epic poems that are the foundational works of ancient Greek literature. I couldn’t help but think how stories can transcend time and space, and help us feel our fundamental humanity.

I’m not sure where I’ll go on Sunday after I leave here. I guess I need to figure that out soon. I was thinking of heading to Athens, but there’s a monster heat wave on the mainland, and I’m a big baby when it’s too hot. I’ll report back soon.

I’ve added a few shots to the photo album here:

Post 8: 109 degrees F

Not much to say except I’ll be enjoying the inside of an air conditioned room today. Good grief!

Post 9: My last post of this VERY remote work thread

I’m going home. I’m happy. My batteries are recharged.

Being gone almost five weeks was fun, challenging, exhausting, and thrilling. In some ways is was easier to work remotely than I thought, but I did drop a few balls while doing it.

For administrative work, conversations and “same page” huddles, writing proposals, etc were straightforward and simple, and everything moved along as intended. More “deep work” or creative type work that I needed to do (other than taking and editing photos) got lost. It seems I need my office cocoon, undisturbed, and focused, to do my best creative work. That’s much less a focus of my role at VIA Studio these days, but I do still love it above most else. If I were trying to do the “digital nomad” thing again, I would try to find more secluded places to hide away for a few days to focus on that type of work.

The next two months will be busy for me, so I’m glad I was blessed to have this last month to look inward, see some amazing sights, meet some fellow wanderers, and gather a few stories along the way. The office is changing, we’re transitioning to a “mostly remote” agency moving forward. My wife and I have started another property management company, and we’re also working on a Halloween dance party for October 30. I’m ready to dig in. \m/ 0_o \m/

Folks have already asked me about some favorites from the trip, so here’s a short list:

Favorite Sunset: Santorini, Greece
Runner Up Sunset: Ios, Greece
Favorite Food: Rovinj, Croatia
Favorite New Food: Feta cheese wrapped in philo dough, fried, drizzled with honey and sesame seeds 😮
Favorite People: Crete, Greece
Favorite Swimming: Rovinj, Croatia
Favorite Quiet Spot: Ios, Greece
Favorite Public Art: Zadar, Croatia (Sea Organ & The Greeting to the Sun)
Overhyped: Plitvize Lakes, Croatia (It’s pretty, but crowded, and you can’t swim in the lakes)
Favorite Beach: Balos Lagoon, Crete
Favorite Tourist Landmark: The Acropolis, Athens
Runner Up Tourist Landmarks: Homer’s Tomb, Ios / Skarkos, Ios / The Acropolis Museum.

Happy to answer questions about remote work or digital nomad tactics. AMA!

About the author:

Jason Clark is President and CEO of VIA Studio, an agency in Louisville, Kentucky providing branding & marketing strategy, design, web development, and other services for an international roster of clients. Jason has been awarded an AIGA “Visionary” Award, and has been named “One of 20 People to Know in Advertising” by Business First of Louisville. Jason’s hobbies include electronic music production, travel, and cooking.

See more here about digital nomad visas in the Dispatches archives.

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