The Tradeoffs of Working Remotely

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“A communications satellite, it will make possible a world in which we can be in instant contact with each other wherever we may be. Where we can contact our friends anywhere on earth, even if we don’t know their actual physical location. It will be possible in that age, perhaps only 50 years from now, for a man to conduct his business from Haiti or Bali, just as well as he could from London”

Arthur C. Clarke in 1964

For the past two years, I have been working remotely. Often glamorized, working remotely comes with its tradeoffs, as does everything in life.

Hell is always in close proximity to hell. What may be paradise in one moment is just a few steps away from being torture in another.

You’re a million miles away from home, thriving in a climate which is incomparable to the one you were raised in. You’re surrounded by vibrant people, with energy so palpable that it becomes a part of you. You are basking in a new culture, welcoming every fresh experience that comes your way. You are nurturing relationships, and welcoming new ones.

You’re a million miles away from home, in a land of strange tongues. You’re mentally and physically lost. You have met people but you feel a strong disconnect towards them. You know you should be open to new experiences but nature pushes you to close yourself. You are trapped in a dead heat, breathing an air entirely different to the one of your homeland.

Personally, I have found that both of the mental states described can be experienced in the same location. At times, you are thriving but being mentally and physically lost can be close by, especially when you are new to a place.

Working remotely, popularly known as being a digital nomad, is a very special prospect of today’s world. But it is also extremely romanticized and it can be easy to lose touch with the tradeoffs it entails.

Everybody’s experiences are entirely their own and can only be generalized to a very limited extent. On that note, here are what I have found personally to be the biggest upsides and downsides to working remotely.

The Upsides

The world is at your fingertips. If you can earn an income comparable to that of your standard Western corporate slave while being able to work remotely, your optionality skyrockets. You not only gain the liberty to base yourself in anywhere where your living expenses fall below your income but you also regain control of the only scarce resource which exists – your time. The power of this cannot be underestimated, and it may be the single biggest upside for me. Some people choose to spend their time hustling hard seven days a week. Others go for a more relaxed approach where their time gets split between work, leisure, family time, adventures, etc. Many tap into ways to increase their output per time input by processes such as hiring, automation, and scaling their business. There is no right approach but the key value add is that you can spend your time where you feel it matters. The implications are far reaching and can completely change the way you live your life. For instance, an alarm clock, one of the countless surreptitiously harmful symptoms of modernity, can oftentimes be lived without. The power to control your time simply translates to the ability to take back control of your life. For many people, this is never experienced. They spend their younger years in education and the corporate workforce which make unreasonable demands on their time. When retirement approaches, youthful exuberance has long passed.

“The wine which is poured out first is the purest wine in the bottle, the heaviest particles and any cloudiness settling to the bottom. It is just the same with human life. The best comes first. Are we going to let others drain it so as to keep the dregs for ourselves?”

Letter CVIII, Letters from A Stoic, Seneca 

Another angle derived from the time perspective is your energy levels. Imagine you’re a Duracell bunny with a full energy bar. An entity which only exists in the intersubjective reality takes 80% of that energy bar and lets you play around with the remainder. Your key energy is dedicated to them. This can actually be a strong motivator to break from this cycle, driving hard hustling in the personal time which is left over. I vividly remember spending my evenings and weekends studying cryptocurrency blogs while working in corporate finance.

Business is interesting. Sometimes, you just have to sit back in awe at the type of working relationships made possible by remote work. For instance, at one stage, I was in Greece working for an Asian company while getting paid into a business entity established in an entirely different country. Another time, I was on a call with a pseudonymous character called dog. We never progressed past the pseudonym stage of our relationship so I continue to call him dog.

You can take the blue pill, or… Your experiences are a shockingly small sample of what is actually going on in the world. Let’s say your experiences are 0.000000001% of what is going on. Putting it this way, it is kind of crazy to model the world based on your own experiences. Despite this, we all do it to some extent. However, travelling vastly opens this up. You tap into different cultures, meet fellow travellers, experience various relationships. A recipe with one ingredient makes for a bland taste. Travelling mixes and matches ingredients until you find the right combination.

The Downsides

You’re away from family and friends. This is huge. By the time you leave home for college, you have already consumed the lion’s share of your total time with family and childhood friends. You have more time left with some, less with others. But the reality is the same for everyone. If you decide to live a life away from home, you are certainly making a choice to give up the type of lifelong bonds which some people succeed in nurturing. It doesn’t mean that you can’t have a great relationship with them. You can call them regularly. You can visit them several times a year. But it does mean that you will ultimately be away for the majority of moments. 

Almost everything takes time to flourish. Friendships, relationships, businesses. There are very few exceptions. This is true both mathematically and generally. Mathematically, the concept can be expressed through nonlinear power laws or the lindy effect. Generally, if Sally meets David but David and Sally are only staying in the same location for three months, it puts a big blot on the natural evolution of the relationship. 

Black swans may be blacker. Those unforeseeable rare events where life gets turned upside down may be exacerbated by the realities of the country you are living in. Healthcare may not be up to scratch. The local lingo will complicate communications. How much can you trust local authorities? The general safety cushion that many of us have in our home country may be replaced with a rock hard bottom that hits us hard when we fall. 

Isolation. Inevitably, we all feel lonely sometimes. This feeling can certainly be exacerbated when you are living in unfamiliar terrain. There are many places where you will be surrounded by fellow travellers and remote workers. But if you venture off the well-beaten track, you may find yourself in a place where you can’t wait to leave. You may feel an extreme sense of isolation that leaves you counting down the days to your departure. This has only happened to me twice. Both times, I knew what date I was leaving and I also had the funds to book an earlier flight if I needed. I can’t imagine what that feeling is like for someone who doesn’t have the liberty to leave.

In many cases, you give up some stability. When I started freelance work, I could be extremely busy for months. But suddenly, everything could dry up. I would be forced to drop rates and start hustling hard. The first few times this happened, I thought to myself that “the gig is up”. It might be time to start searching for high paying corporate slave jobs again. I progressed past this stage to a point where I had steady clients but it was certainly an interesting experience. I have come to realize that contractors and freelancers are far more in tune with the market. To be a freelancer mostly means giving up all of the safety net associated with being employed by a huge corporate company. Nassim Taleb would argue that this is a better position to be in as you can respond to market needs as they adjust whereas a corporate employee enjoys steady pay until they don’t.

“Artisans, say, taxi drivers, prostitutes (a very, very old profession), carpenters, plumbers, tailors, and dentists, have some volatility in their income but they are rather robust to a minor professional Black Swan, one that would bring their income to a complete halt. Their risks are visible. Not so with employees, who have no volatility, but can be surprised to see their income going to zero after a phone call from the personnel department. Employees’ risks are hidden.”

Antifragile p.84, Nassim Taleb


Do you want to work remotely?

We live in an exciting era. The option for some professionals to work from their laptop anywhere in the world opens endless opportunities. But everything has its tradeoff. Not everyone has the skills to work remotely. As more value continues to transition online, it seems likely that we will see a trend of more professionals doing this kind of work. Not everyone has to take it to the ends of the earth. A father who can freelance from home will benefit from the liberty remote work offers in much the same way as a young professional benefit from the liberty by experiencing new countries and cultures. It’s certainly not for everyone. Some like the structure of a 9-5. Some live for the big city rat race. Some need the corporate safety cushion. For me, I wouldn’t have it any other way.

Bringing it back to the start, everybody’s experiences are entirely their own and can only be generalized to a very limited extent.

If you work remotely, I am interested to hear what the key tradeoffs are for you.
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