Home Remote Work Lessons from my first 3 months as a ‘digital nomad’

Lessons from my first 3 months as a ‘digital nomad’

by Simon

God I hate that word. Calling yourself a digital nomad makes you sound like an intrepid explorer, a digital first counter-culture entrepreneur. The reality is that you just work remotely. Giving yourself the digital nomad stamp feels a bit self congratulatory to me. Everyone loves to travel, you’re not special.

Whichever nomenclature is chosen, in December 2020 I decided to leave London to work remotely for the foreseeable future. My first stop was the Dominican Republic – a destination that had not previously been on my radar but due to the current restrictions it seemed like an adequate choice.

I got to surf in the morning. It was a Caribbean island. I was staying in Playa Encuentro which is a very small surf town (*town is being used in the loosest of terms) so distractions should be at a minimum.

It was time to start this chapter of my career.

This is what I learnt from my first three months of being a digital nomad, remote worker, location independent, [insert any other name you can think of].

Give yourself a few weeks

I started working remotely from the Dominican Republic with a 2 day a week contract. I figured that would pay the bills and would leave me with 5 days a week to explore the area.

Similar to millions, if not billions of people worldwide, I had been working remotely since March 2020 so the only change was the time difference and location. That turned out to be a little naive.

The problem was that settling down to a full days’ work was difficult. My distractions were fairly limited – was the surf good? Where would I eat lunch? Should I go for a run? Fairly normal stuff (except the surf). It was just the novelty of the location that was distracting. I wanted to get settled and meet people, which takes time.

The result was that I ended up working half days but I still had to fulfil my time obligation of 2 days a week. As such, in the first month I ended up working 4 days a week at a relatively slow pace. Not the end of the world, but I’m a big believer of not doing face time. When you’re working or at your desk you should make the most of that time. That was certainly not the case here.

What’s the remedy? Well, if you’re just starting out like I was (and still am), I would highly recommend that you take a few weeks off work the moment you land. It allows you to get used to the novelty of living near a beach or in a topical environment. To use a phrase, you can “get it out of your system”. In fact, I’d allow a portion of time wherever you are travelling to. I allowed myself a week after the Dominican Republic when I travelled to Costa Rica, just to get used to the new surroundings. After which, it’s time to start working.

Get Over Yourself

In much the same fashion as giving yourself a few weeks, you also need to get over yourself and your surroundings.

My intention when I left London was to carry on living a fairly normal life. I wanted to work. I wanted to have a fairly similar working week, it was just that on the weekend I would immediately be in a holiday destination. That was harder than I thought it would be.

Perhaps it was due to the fact that I was surrounded by people that were there on holiday. Maybe it was a bit of smugness that I was where I was, when London experienced its 3rd lockdown.

Whatever the reasons, I started to resent work a little. Scheduled calls were cutting surf sessions early. Why was I working when everyone I was surrounded by were on extended holidays? What’s the point, I’ve saved a decent amount working in London for 10 years, I don’t need the cash in the short term.

It is my view that such thoughts can be dangerous.

It’s all too easy to fall into a lethargic state. All too simple to burn through savings and let your industry knowledge stagnate.

Remote workers are typically going to find it harder to land jobs than those that can be in the office permanently. As such, your profile and knowledge needs to be that much better. I didn’t want a short few weeks break to turn into a short few months break, which quickly turns into a few years break. Suddenly I’d be out of touch with my industry, my connections would have decayed for referral projects. I might be better at surfing but that’s not going to contribute to a pension.

An overriding thought during my first 3 months was that I needed to get over myself and settle down to a more normal working life. You’ve worked hard to facilitate this type of lifestyle, well done. Now don’t fuck it up by being lazy.

Routine & focus are everything

Working remotely from a tropical location is not the same as working remotely from your kitchen table in London. It’s the same in principal but it’s not the same in reality.

There’s stuff going on during working hours. There are the aforementioned distractions. If you’re working outside, midday is too hot to concentrate.

It’s just different.

This is highly linked to getting over yourself. You don’t want a routine, you’re on a Caribbean island. You want to live free with salty hair and a tan. You want to work when you feel like it. You don’t want to be beholden to the capitalist nine to five office hours.

Fucking get over yourself. Have a listen to what you’re saying. Of course you don’t want that, very few people want to work 8 hours a day. That’s why they call it work and why someone has to pay you to do it.

I briefly mentioned before that I’m not a fan of face time. I ended up doing my own style of face time, for my own gratification. I’d open my laptop and work incredibly inefficiently for 8 hours. I guess my validation was that I had been in front of my laptop for 8 hours, good work Simon. That’s a healthy mindset.

The quicker you get into the routine of waking up and actually working normal hours, the better it will be (at least in my experience). Don’t think that you can get stuff done in the evenings. Guess what? Shit happens in the evenings, you’re tired, you need to eat, people come back from the beach and want to talk.

A routine isn’t enough.

A routine can carve out blocks of time, but if you’re still doing Simon’s stupid version of face time then it’s really not helping you at all. I’ve had to build out ‘remote working rules’ for myself. A major one of which is that when I’m in a working space with my laptop open….I’m working. I’m not messing about. If I can be super focussed for 3 hours and get work done that might take me 8 hours of unfocussed time, it means I have 5 more hours in the day to do the other stuff I want to do.

Routine & focus are everything.

Pay for a work space

Everyone wants to be the exception to the rule.

They want to be able to ignore distractions whilst working in a coffee shop. They want to be able to work from a hammock. They believe they have the self control to not engage in conversations that your friends are having at the hostel whilst you work.

Accept that you’re not the exception to the rule.

I didn’t have much choice in the Dominican Republic. The closest coworking space was a 10 minute drive away. I didn’t have a car and public transport felt like too much hassle. So…..I struggled along for 3 months.

I’m in Santa Teresa, Costa Rica now and have paid to use a coworking space for a week (at Selina North). Coworking spaces are fairly common in London and I’ve spent my fair share of time in them.


I thought I was the exception to the rule. I didn’t want to pay the $60 a week. I could sit in my room or in the communal area and be productive.

Get over yourself.

The great thing about coworking spaces in beach towns is that everyone is in the same position. They’d rather be at the beach but they’ve got shit to do. They’ve got calls scheduled or projects to deliver. They want to get their stuff done quickly so that they can go enjoy themselves. So the general vibe is “shut the fuck up, I’ve got to get my work done quickly”.

I would conservatively say that having a dedicated space where everyone is working makes you at least twice as productive….conservatively. I’m writing this on a Saturday, in the coworking space with the curtains closed and one other guy who is also doing his thing. Lovely.

Pay for the privilege. You won’t regret it.

It’s not just the lack of distractions. The Dominican Republic was hot between noon and 4pm but just about manageable. If you’re outside in Santa Teresa during the early afternoon you can barely think, let alone work. It is critical that you have a space that has adequate environmental control*.

*read ‘fan’ or ‘A/C’.

Work makes everything better

Okay so I’ve spent a decent amount of time in this article shitting on work in general.

The really interesting revelation is that I don’t now what I’d do without it. Seriously.

There’s a caveat to that. I’m working 2 days a week and have a few marketing projects to do. Let’s call it 4 days a week. However, I’m also trying to build out the amount of content on the With the Sparrows Youtube Channel. I’ve got videos to plan, film and edit which on average takes about 8 hours work per 10 minutes of video time. I want to do 4 videos a month so I’m actually quite short on time.

I don’t say that to sound like a Gary Vaynerchuck fanboy, telling you how hard I’m ‘grinding’. I hate that.

I bring it up because in my relatively short 33 years it’s taken me too long to realise that contrast has a dramatic effect on perception. That’s why the Summer in London is so good. All too often London has sub par weather, so when it is hot and sunny we tend to enjoy it that much more.

It’s the same with working as a digital nomad. Beaches are cool. I like surfing. Girls in bikinis are a nice sight. Having a beer watching the sunset is relaxing. The problem is that it all gets normalised way too quickly and the suddenly you don’t have any contrast. It’s all just too much fun.

I’ve put a good shift in this week. I’ve got my coworking space now and I feel like I’ve completed a lot.

I cannot understate how important that feeling is.

I left the coworking space yesterday at 5pm. When I walked out into the tropical humidity with the sun setting, it was genuinely the first time in 3 months when I had that Friday feeling. I forgot how good that feeling is.

If you don’t work hard, everyday is a Friday, just without the feeling. It’s normalised.

Get your routine down. Focus. Accept that work sucks but it’s a necessary evil to provide the contrast. It makes you enjoy the good stuff that much more. Chase that Friday feeling.

I can guarantee that there will be other lessons to learn but those are the highlights from the last few months. Hopefully they are helpful for anyone looking to start working remotely as a digital nomad.

I’m going to go and wash my mouth out now. I’ve said digital nomad too many times.

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Joe 22 March 2021 - 12:19 pm

Good point about Fridays.

Someone once asked me what it’s like, not having that dreaded Sunday feeling about going back to work on a Monday. I said it’s great, but the pay off is you don’t get that amazing Friday feeling when the work day is ending.

Good luck on your travels!

Simon 22 March 2021 - 2:58 pm

I think you can have both though? Sure, you can minimise the Sunday fear but if you put in a good shift during the week you can create that Friday feeling for yourself!

Piya 22 March 2021 - 4:47 pm

Great tips! I’m trying to become more stable myself before trying out the nomadic lifestyle. I was surprised to learn that you pay for workspaces, even when you’re abroad. A hotel room isn’t enough?

I work from home currently, and I enjoy it, but I do have a dedicated work area.

Simon 22 March 2021 - 9:41 pm

It’s more a matter of having a desk in my room. The places I’ve been staying haven’t been conducive to working in and I find that for the $150 a month it more than pays for it in productiveness!


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