The Hardship of Working Remotely — Being by Yourself

Alessandro Montalto PhD
4 min readNov 25, 2020


An epiphany strikes me while I am preparing a workshop for the Italian company Zupit: remote work is so challenging because it involves being by yourself the whole time.

It might seem a very simple thought and you might think that it would be obvious to me. I can almost hearing you saying “Ale, what kind of remote work coach are you if you didn’t realize what’s so in your face?” and you would be totally right.

I was also caught in the frenzy of addressing the main problems that freshly baked remote workers, who needed to change environment, challenges and behaviours overnight, were experiencing. You know what I am talking about: connection with the team, unplugging, boundaries between work and private life, communication, just to name the main ones.

I allowed myself to get distracted by what seemed to be the most urgent problems. I followed conversations on social media, posts about how difficult it is to work remotely, posts about the fact that the current remote work experiment on a global scale might backfire because of the apparently enormous challenges it presents.

My Mistake

I’ve been working and studying remotely for more than 15 years now and I always enjoyed it. How is it possible, I asked myself, that the benefits of remote work are so overshadowed by the alarming statistics that is constantly produced?

I couldn’t wrap my mind around the difficulties that so many people were experiencing. Too many meetings? Simply reduce the number of the meetings. You feel lonely? You can always count on your social life, covid-19 allowing it. Lack of focus and motivation? Have a walk, take a break, connect to the reason why you are working and go back to what you were doing.

You see, to me the answers to so many burning questions were easy. I didn’t realize that I was making the mistake to think that other people had similar experiences to mine and drew approximately my same conclusions and strategies.

While preparing the workshop for Zupit, I had to address one of their main challenges: how to build meaningful human relationships in a remote environment. Once again, everything seemed so natural and obvious to me, do you feel lonely at work? Nurture and strengthen your social life. And then my point of view about creating an easy and smooth transition from in-house to remote crashed under the weight of a simple association of ideas: people can’t have a healthy social life during covid-19, they can’t have a social life at work feeling lonely and mostly alone the whole time and companies all over the world are trying to reproduce the in-house dynamics in the remote work scenario. All the pieces fell into place.

A Useful Realization

The combination of loneliness and clinging to the in-house dynamics made me stop and truly think about what was going on. The realization of what’s underneath the surface was powerful and simple at the same time: remote work isn’t challenging because you aren’t going to have “water cooler” moments any more. It’s extremely difficult because it calls for a brand new mindset where you learn to be by yourself.

Remote work done properly requires from you to be willing to deal with the true pros and cons of this new scenario. Granted, you can enjoy more freedom and flexible hours, but you also have to deal with the fact that remote work is inherently a solo job in the sense that you are going to have many more online working meetings.

Remote work + covid-19 is a very unpleasant combo, but think ahead. Once the virus will be under control and you can restore your social life, you will be already used to work online and establish meaningful relationships with your colleagues even if you meet them only via Zoom.

Being by yourself is hard, maybe the hardest thing you will ever experience. Constantly dealing with the thoughts your mind yells at you, ranging from “you need to work more otherwise you risk to lose your job” to “damn, another meeting, I can’t do this any more, but I need this job” (and many more), is draining.

What Can You Do About It?

The point is that you can learn how to better deal with your thoughts and to build a healthy relationship with all the scary, unpleasant and useless thoughts your mind shoots at you unexpectedly. Interested? Then start by reading The Happiness Trap by Russ Harris. Do the exercises that he suggests and feel free to share your experience with me if you find any difficulties along the way by simply writing me a message on Telegram, WhatsApp or LinkedIn.

Working remotely minimizing the drawbacks and maximizing the benefits is definitely possible once you learn to be by yourself and decide to give more attention to your thoughts. Bit by bit, you will embrace the possibility to work in a remote scenario without fighting against it. You will be able to put efficient communication strategies in place, set your boundaries based on your real needs and active listening and become a pro in remote work. No need to look outside for a solution. Redirect your attention inwards and be ready to listen with a loving attitude. If you find it difficult, feel free to reach out to me and let’s share our experiences and insights.

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Alessandro Montalto PhD

I mentor people to develop the required soft skills to become successful remote workers —