• Jason

How to Work Remotely: Tips for Being Effective and Happy in a Distributed Work Environment

Updated: May 9, 2019

Digital nomad's survival guide for remote work

To be a digital nomad, you first need to cut the chains to a livelihood that demands you be in a certain location - you need to be able to make some money wherever you are. For a lot of nomads these days, that means taking a remote job, especially in a "distributed company". There are other reasons why remote work is of interest to people: people with children want to be at home to see their kids grow up; property is expensive where work is centralized; and the freedom and flexibility are attractive. Remote work has a bit of a dark side and it takes some critical self-analysis and self-care to understand how to work remotely while keeping yourself healthy, happy and productive when given absolute freedom to manage yourself.

Remote work is a double-edged sword and different people handle the upsides and drawbacks differently. For me, I find it both challenging and liberating. The upsides are plentiful: there is no commute (which represent hours a day reclaimed); I'm a night-owl and periodic insomniac so can indulge my late-night-creativity and/or wrestle with sleepless nights without the same stresses that sleep deprivation otherwise has; I like to work out and can find the time to do so (which helps with the sleep); and now I don't need dog walkers to take care of my dogs during the day.

But I've discovered there are some darker threads under the initial shiny veneer of absolute freedom, and they are very much worth talking about.

Digital nomad working remotely at a campground in Iceland
Working remotely at a campground in West Iceland

How to Work Remotely: Lifestyle Risks

I'm going to discuss a few items here that I have run into and thought about in distributed roles. You want work to be work, and life to be life, so the largest negative impacts, in my opinion, come from the blurred lines that the flexibility and responsibility can bring into your life, as compared to having an office that you go to.

Risk of Overwork

This is likely the single biggest risk. Certainly, you may find yourself distracted periodically, or cutting a day short, but if you're in a role where you are engaged (which is going to be the default state for most people when first staring in a role) then overworking yourself is going to be the biggest risk. You'll find that an "always-on world" is at your fingertips, and the demand for your skills and knowledge never goes away. It can get difficult to turn it off, and it's completely up to you to set expectations and to set your hours. The world is always on but you can't be if you want to make it in the long run.

Risk of Distractions

It's probably obvious, but the flip side is that you can easily build habits and pattens of distraction and ineffectiveness into your routine. At an office, you're observable, which skews your behaviour toward at worst "looking busy", and at best, you'll use it to motivate effective behaviour. In a remote capacity, your output is all there is. Tasks vary in the complexity and time that it takes to accomplish them so much that you are truly the only one that can gauge your effectiveness. I'd describe myself as a productivity hobbyist but even still, sitting at home I have found I have to spend some time analyzing my behaviours to ensure the time that I log is effective.

Ironically, I find self-imposed distraction (e.g. checking Facebook, Hackernews) to be a greater vector to stress and burnout than actually over-working. There are times when you note that you spent 4 hours on your laptop, but, out of those 4 hours you spent an hour browsing the web, and you'll try to "make up" that time by extending your work day or opening your laptop during what should be "leisure time." But that time can end up being fairly poor quality anyway as you're on your 10th hour of being "on."

Risk of Context Switching

For any complex task such as writing a blog or code, "flow" can become a harder state to build and maintain when you're working at home or abroad. Because you have the flexibility to take a break, and your significant other or kids can come and grab you while you're at work, or your dog begs to be taken out in the middle of a complex task, or you have to check out of your AirBnb in 10 minutes, it can become more common to spend time building and rebuilding context in complex tasks which reduces your output and can consequently cause stress.

Risk of Indecision Due to Social Isolation

Somewhere in the middle of overwork and distraction is indecision. You might be actively working on a problem, logging many hours on it, but not making any progress due to lack of clear direction forward. If you're managing yourself well but you're not analyzing your behaviour as you move forward, it's easy to end up with these patterns. Especially as a developer, I found earlier in my career that I could spend a day or two easily waffling back and forth between making a decision about something, or be unable to think laterally about a problem as I lacked the right level of context to see a solution that might be better. In an office environment, I'd pull someone over, but in a remote context, it's common to feel a bit shy about interrupting someone to get the perspective needed to unblock you. Because there isn't anybody there to watch you waffle, and reach out to unstick you, the onus is on you to take the action to recognize that you're stuck, and to get the external insight you need to find a direction forward. Set a limit for time you'll spend on a task before looping someone in. I've observed that this seems to be a larger problem in the distributed environment, but an awareness of this tendency has helped me make better decisions around when to ask people for advice.

Disruptions in Mental Health

It's reasonable to assume that absolute flexibility immediately means improved mental health but that's not necessarily the case. The reality of remote work is that you have to manage yourself well. It's easy to fall off the rails. The risks of social isolation and physical inertia are real when you have the option of sitting at home without pants on day in and day out. You need to organize yourself to exercise and interact with people, to watch your behaviour, habits and patterns, and to "tweak" things to keep you on a productive and healthy track. Some people are pre-disposed to depression and anxiety and the realities of not being forced to be in an office and interacting with people will certainly strike this group the hardest.

It's All in Your Hands: The 5 Most Important Things To Do To Stay Healthy and Happy

Sometimes when you get in a rut, it can be hard to see a way forward. But the good part is that you have the power to change, and to build healthy habits and patterns. There is a bit of a learning curve, and you need to take time to reflect on how you're really doing and make little adjustments and tweaks. Here are my personal takeaway points:

1. Exercise

The easiest way to keep mentally fit is to exercise! It's easy and fun and is a known cure for mild depression. We go kickboxing every day or two - it's incredibly intense, and engaging. I personally find treadmills boring so discovering kickboxing was a real boon. I lost 40 pounds and am in the best shape of my life!

2. Mindfulness

Being aware and creating some space for objective observation of your state of being has many benefits. Science is "catching up" and discovering what Buddhism has been teaching all along: mindfulness and meditation are incredibly good for your brain! On the advice of a good friend, I'm going to take an MBSR (Mindfulness Based Stress Reduction) course, which is an evidence-based meditation course with a blend of theory and practice. Because it's evidence-based, it's possible to get health care coverage with a referral from a doctor.

I use insighttimer to keep track of my meditation practice and to create some accountability. I use Slack to remind me periodically to take 10 minutes to recenter. There isn't any reinforcing "dopamine" hit from meditation, so it can be hard to prioritize and to get going, but with regular practice, transformation does start to occur.

3. Journalling

The self-awareness that comes from mindfulness is an important cornerstone in identifying problematic behaviours and correcting them. Another useful tool is the journal. Giving yourself space to formalize your thinking and observations on your behaviour and emotional response is incredibly valuable. I keep a journal on my phone with Journey, and when I was younger, I was an avid user of LiveJournal. The medium doesn't really matter. There is definitely something to be said for the classic pen-on-paper. Start writing your thoughts to crystallize your perspectives and help to identify ways that you can move forward. Write about your emotional response to different situations and circumstances as well. Many of the "effective" people I've met throughout my life have also advocated journalling. Don't take my word for it: there have been some studies done that support the positive effect of Journalling on your mental health.

4. Maintain and Deepen Your Social Life. And Be Really Honest with People

I feel blessed to have an excellent manager who is always happy to discuss some of the "softer" skills and who I can be really honest with. And I have a few close friends with whom I regularly share little insights and bits of my most personal thoughts, fears, insecurities, etc. Working in a distributed team has had a positive effect on my social life because I feel the need to reach out and connect with people and to sustain my social life now that work doesn't provide much face-to-face social engagement. I've found new levels of depth in some of my friendships as I discovered that other people are also trying to figure out how to really live. I cherish those interactions - having real friendships is an incredible thing. Talking to people about things that are deeper than what's on the surface really propel friendships forward.

5. Be Maximally Effective with Your Work Time - Work in One Place, and Set Boundaries

I try to set hours for work (9-5ish, putting in longer hours if I get a kickboxing session in), and have dedicated a space for working when I'm at home. While on the road, it's all about setting yourself up the same way - give yourself a dedicated block of time, and a dedicated space and enter your "work mode" for the duration.

I find that distractions like social media cause me anxiety. I have a tendency to wander and check into social media too much while working on a very difficult or abstract task. To help with this, I have a tool installed on Chrome called StayFocusd that limits the amount of time I can spend on Facebook and Hackernews to 15 minutes a day. It's installed on all my devices!

Journalling helps me focus and identify what's going well and what isn't, and I regularly talk to my manager and peers about self-management topics, and just try to be "real" about the realities of distributed work and any challenges I'm facing.

I use GTD to help me keep focused on what needs to be done (I'm using emacs + org-mode but post-its work very well as well), and if I'm really struggling, I use the Pomodoro technique to burn through work. Essentially, the goal is to be maximally effective while you're working so I can feel good about my productivity. I do find bad days cause me some stress so I do whatever I can to be the most effective person I can when I'm in "work mode." If I need a real boost to plow through some unit of work, nicotine patches are the secret weapon in my arsenal. There is emerging evidence that suggests that nicotine patches may be as effective as stimulant drugs for improving focus and attention.

As mentioned, I find indecision to be a problematic pattern in a distributed work-space, so I try to time-box analysis and if I can't see an obvious solution by the time that window expires, then I'll get someone on a call to talk through the problem.

When it Gets to be Too Much (Especially When Starting Out!)

It's easy to think that you're alone, odd, and the only one struggling, but you're not. I periodically reach out to new people I see coming in and give them a bit of perspective on the first few months of remote work as I've seen several people comment about their struggles and anxieties at the start. Know that you're not alone, and reach out to someone and tell them what you're experiencing if you feel that it's safe to do so. While for many it is possible to manage, and things will improve, if you're really struggling you should seek professional attention. People have become overwhelmed by depression and anxiety while become climatized to remote work. I personally struggled with anxiety and depression in my first month or two of remote work at the end of the Canadian winter (already a challenging time for many emotionally due to "Seasonal Affective Disorder"). For many, including myself, emotional balance will come along with acclimatization and familiarity with the new patterns in life, but sometimes things spiral. If you're having a hard time, know that there is nothing wrong with seeking therapy or medical attention. It's not at all uncommon - so many more people struggle with their emotional health than you realize.


Hopefully this discourse helps anyone who stumbles upon it. Remote work has the power to be a blessing, but amidst the good, there are some risks. Fortunately you have the ability to analyze and change your habits and behaviour. Good luck on your journey, and please leave a comment with any insights or discoveries you have made!

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