Juha-Matti Santala
Community Builder. Dreamer. Adventurer.

City Bound Nomadic

In the near future (say, within the next 5 years), I want to explore the possibilities of a digital nomad lifestyle. Working independently of location and time is a compelling idea and having followed digital nomads in blogs and Youtube and Instagram for quite a while, I'd definitely love to give it a try. Seeing the world, learning about new cultures and being able to experience the wonders that the world has to offer — sounds good, right?

I realized some time ago that it takes quite a lot to jump from regular 9-to-5 office job and permanent home to remote-only, timezone varying work with no permanent place to call home. So I decided to start learning the required skills and getting used to things before taking a full leap. I also felt that I needed to hone my skills so I could find enough work to keep me going once I decide to start traveling.

"No home" lifestyle

I've been "homeless" since the beginning of April. I've been living on and off from different places as my friends or friends' friends have been travelling. A month here, two months there, 3 weeks somewhere else. I have everything I need in my backpack and I explore different neighbourhoods of the city. It's very freeing when moving to a new apartment takes 30 minutes of packing and however long it takes to take the subway or the bus to a new home.

As I'm writing this on a Monday afternoon, I'm right in the middle of a move. I picked up my stuff in the morning, closing the door to an apartment that served me home for 10 days. I sit in a restaurant next to our office and in the evening, I'll close my eyes in a new apartment that will serve as my home for the next month.

Remote work

I worked for over 2 years without a desk. Currently I'm spending most of my days at client's office as I work as a software consultant but I try to work remotely as much as possible and I'm hoping to find projects that would allow me to go as close to 100% remote as possible.

I love remote. It puts the focus on the outcome of your work instead of the input and you can choose where, when and how much to socialize. Sure, lacking colleagues who work in the same office than you can easily become very lonely, as an introvert I applaud at the opportunity of gaining better control over that.

But remote is not easy and while it's becoming more and more popular, most teams are not ready for it. Remote is so much more than just not coming to the office every now and then. If your processes and ways of working don't support remote workers as first-class citizens, you'll end up being miserable on both sides.

Four steps for better remote work

  1. Asynchronous communication

    One of the biggest challenges in remote work, especially if the team is spread over multiple timezones is communication. You can't just tap on the shoulder of your colleague whenever you need them, so you need to become good at communication that spans over time.

    Investing in proper tools helps a lot. Instant messaging with Slack or Flowdock, project management with Trello or JIRA, code communication with Github or Bitbucket and actually functioning conference calls with Zoom are some of my favorites.

    But tools won't help you if you don't learn to embrace the new way of thinking. I grew up in the world of IRC so text-based asynchronous communication is natural to me, often even more natural than face-to-face communication.

  2. Default to remote

    Many companies that are now taking their first steps into remote work are obviously starting it with baby steps and there's nothing wrong with that. But to be successful in remote work, remote has to become the default.

    If you need to ask permission to work remote or make arrangements for when you work remote beforehand, you end up with a work culture where individual productivity may rise but the collaborative productivity decreases as people just end up waiting for the remote worker to come to the office "tomorrow".

    By defaulting to remote, you need to build your processes and ways of working around being a productive team even, and especially when, you don't hang out in the same space.

  3. Socialize

    Working remotely can become a lonely grind after a while. Without the constant social encounters that you get in the office, you might end up staying home in your pajamas all day long. Socializing with your coworkers (through instant messaging or video calls) to talk about also other things than strictly work helps build culture and team cohesion. Socializing with other people in cafes, co-working spaces or meetups gives you the physical connection to other people.

  4. Trust

    Remote work will never work if there's no trust. If your employer doesn't trust that you do work when they can't see you, there aren't many good ways to make it work. If you don't trust your teammates and assume good intentions, there will be a lot of assumptions that create unnecessary conflicts between you and hurts the performance of the team.

    Personally I believe that the only working way is that trust is given, not earned. You start by trusting the people you work with and only if things go haywire, you give up on that trust. If you don't do that, you end up second-guessing and doubting people. When trust needs to be earned, it's very difficult to decide at what point the trust is earned. Because you know, it could always be the next time when they let you down.


I don't know when I'll take the leap to a full-remote, digital nomad lifestyle. I hope it happens soon but right now, I'm pretty satisfied practicing. Figuring out the optimal collection of things to own, learning to adapt to new apartments and neighbourhoods faster, honing my skills at work and saving money are my focus points right now.

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