Can You Actually Be a Digital Nomad at an All-Inclusive? (Yes, But Not How You Think)

We have all seen the Instagram photos. A tanned digital nomad is sitting on a pool lounger, a MacBook open, a fruity cocktail with an umbrella in hand, hashtagging #OfficeForTheDay.

I am here to tell you that those photos are lies.

If you actually try to do that, your laptop will overheat in eight minutes, the screen glare will be blinding, and you will spill a Mojito on your keyboard. Assuming you drink Mojitos. I would spill a Coke Zero on mine. Or a London Fog.

And yet, I love working from All-Inclusive resorts. In fact, I have some of my most productive days there.

How? By ignoring the "Instagram" way of working and leaning into the "Matti" way of working. It turns out, an All-Inclusive is a fantastic co-working space, provided you follow a few specific protocols.

1. The Pre-Dawn Patrol

My secret weapon for productivity isn't an app or a gadget. It’s my built in alarm clock.

I am a ridiculously early riser. Like, I consider waking up at 5:30am to be sleeping in. This isn’t a brag - I wish I could sleep later. Working for myself, there is little reason to be up at 4:30am, and being up that early means I need to be asleep by 9:30pm just to get 7 hours. However, in some circumstances this works out quite well. At a resort, this gives me a superpower. While the rest of the guests are sleeping off the tequila from the night before, the resort is quiet, cool, and empty.

I head to the 24-hour café or the Premium Lounge before the sun is up. The Wi-Fi is blazing fast because nobody is streaming Netflix. The silence is absolute. I get the occasional strange look from the staff as they clean around me, but it is peaceful.

There is a deep satisfaction in banging out a few hours of solid, deep work before 8:00 AM. By the time the "normal" vacationers are stumbling down for the breakfast buffet, I have already finished my workday. My clients get responses to their e-mails, maybe even draft reports or the tax estimates they asked for. A frequent email is “aren’t you supposed to be on vacation?” But this way I don’t finish my vacation with a mountain of work to catch up on. The work is done, the clients are happy, and I can enjoy my oatmeal free from work worries. (Some resorts have the best oatmeal - cooked in milk with cinnamon sticks)

I know there are people who can just turn their brain off and chill - I am not one of those people. Never have been. If you need a steady flow of mental stimulation, and especially if you are self employed and have a flexible work-life balance anyway, this works.

2. The Hardware Check: Beating the Glare

Once the sun comes up, the laptop goes away. You cannot fight the Caribbean sun with a backlit LED screen. The sun will win.

This is where my specific workflow saves me. I do a lot of reading and annotating of PDFs for my consulting work. For this, I don't use a laptop; I use my Boox Tab XC. It’s funny - I used to be addicted to paper notebooks. In a previous post I even suggested that e-ink tablets weren’t a suitable substitute, but the Boox device has changed my view.

If you haven't used a modern e-ink tablet, you are missing out. It reads like paper, which means the brighter the sun, the better the screen looks. I can sit by the pool in direct sunlight, annotating documents with a stylus, looking like I'm just reading an eBook. And the addition of color makes it practical for such annotations - I can have regular notes in blue, important points in red, highlight text in yellow… you get the point. Some e-ink purists will tell you that the color isn’t as sharp as the black and white, and that is true, but it is more than good enough. And the black text is still 300 dpi - which is very easy on the eyes.

This isn’t saying - “work all day and get no rest”. Rather - read some work stuff, make some notes. Switch apps, read a bit of a novel, switch apps again, read a magazine. Fall asleep with the device resting on my chest. Repeat.

This is the only way to truly "work by the pool." Leave the laptop in the room; take the e-ink tablet to the lounger.

3. The Psychology of "Earned Lazy"

I have a confession: I am genetically incapable of just laying in the sun.

If I try to just "relax" for seven days, my brain starts to itch. I need to be doing something. For me, doing a little bit of work isn't a burden—it’s the permission slip I need to enjoy the rest of the day.

If I know I’ve crushed my inbox by 8:00 AM and reviewed a contract by the pool at noon, I can turn off my brain without guilt. Well, sort of. At any given time I have probably 3 or 4 different side projects on the go. When at a resort I am able to bounce around between these at will. Occasionally landing on work from my primary business makes it feel that much more satisfying.

To those in the know, the milkshake beside the laptop is the second biggest risk in this picture

The Matti Relaxation Protocol

Once the work is done, I don't just relax. I "multitask relax."

You might see me sitting in the shade with a milkshake, headphones on, staring intently at my phone. To the outside observer, maybe I'm working?

Nope. I am listening to a history podcast, drinking a chocolate milkshake, and playing a strategy game on my Samsung all at the same time.

It is a chaotic level of stimulation that would drive some people crazy, but for my ADHD brain? It is pure bliss. And if I flip apps and do a little productivity here and there, so be it.

The Verdict

Can you be a digital nomad at an All-Inclusive? Absolutely.

But don't try to be the person in the brochure. Wake up early, use the lounge, get the right tech for the sun, and "earn" your afternoon by the pool.

Just keep the milkshake away from the laptop. .