The Care and Feeding of the Remote Worker

Working Remotely Is Hard

Phil Crumm
May 29, 2018 · 7 min read

Remote work is rapidly gaining popularity, with more than half of transportation, finance, and technology workers logging in from outside of a traditional workspace — and several other fields rapidly catching up. While the benefits of remote work are well-documented for employees and employers, many people I’ve spoken to over the years who work in traditional office environments view the switch as entirely upside. More flexible working hours, the absence of a traditional commute, and a lack of workplace distractions seem to be the revolutionary improvements awaiting you on the other side of the transition.

Despite these benefits, there can be a downside to working remotely. For many adults, in-office socialization accounts for a large portion of their day-to-day interactions. For those working from a home office, workplace distractions are replaced with in-home ones — whether it be the needs of an at-home child, the constant mental nagging of uncompleted household chores, or the newly-introduced lack of structure enabled by working independently. In many cases, working remotely can lead to significantly longer working hours — you no longer need to take work “home with you” when work is already at home. After awhile, this promised land can turn into a nightmare of loneliness, overwork, and lack of productivity; particularly for those who don’t make an effort to develop a remote working structure that enables them to remain cognizant of these risks.

Working remotely and balancing your well-being — your mental wellness, your work/life balance, and your interpersonal relationships — requires a dedicated effort. Whether you’re a life long remote nomad, or recently accepted your first distributed role, it’s essential to take the time to critically examine your routines, your habits, and your goals, and ensure you’re taking care of yourself.

I began my career working remotely, and have done so for over a decade. At one point, after roughly six years, I left my remote role to join a traditional office environment at a start-up — the grass is always greener on the other side. Since then, I’ve resumed working remotely, and have made a conscious effort to address the issues that led to my burn-out the first time around.


Develop a Routine

Just because you can roll straight out of your bed and hop on your laptop in your pajamas doesn’t mean you should roll straight out of your bed and hop on your laptop in your pajamas. A daily working routine is essential for helping you get into the headspace of working during the day, and can help you wind down and disconnect from work later on. A popular anecdote at Automattic, one of the earliest fully-distributed workplace, tells of a gentleman who would deliberately wake up, shower, get dressed, and go for a drive around the block before settling in in his home office to get himself into a working state of mind.

While that example is an extreme of what a “routine” might mean, it’s important to have structure in your day. For me, this means waking up at a regular time, showering, and dressing like I am working (usually a button-up shirt and a nice pair of pants). This helps let my brain know that it’s time to be productive, and, at the end of the routine, I feel ready to go.

It’s best to start with simple habits to start and end your day, and fill in additional details based on the requirements of you, your family, and your ability to focus. I often take a 90 minute exercise break in the mid-afternoon, around 3:30pm, and plan to spend no more than an hour, around 7:00pm, catching up on email and ensuring I am prepared for meetings and action items the following day.

I’ve worked with colleagues who will schedule certain days as “work from the coffee shop” or “get out of the house” days to ensure that they’re doing something that’s important for their mental well-being. While this isn’t something I personally need to avoid feeling isolated, I encourage you to routinely evaluate your habits and your satisfaction and consider scheduling anything — whether it be remembering to take time for lunch to a 20 minute Netflix break to recharge — that will help you work and feel your best.


Stay Active

The mental health benefits of routine exercise are well-documented. When I transitioned from a traditional office environment back to remote work, I was surprised by my drop in physical activity (thanks, Fitbit!). The daily walks to the nearby coffee shop or to buy lunch that were part of my office culture were now absent, and this resulted in some days where I barely took 200 steps — or didn’t leave the house.

The Department of Health and Human Services recommends regular physical activity for healthy adults — 150 minutes of moderative physical activity per week, and strength training at like two times a week. Taking a walk is also well-known to improve your productivity, help re-engage your cognitive abilities, and increase happiness. While I’m something of an over-doer — I deliberately schedule roughly 45 minutes a day of cardiovascular stimulation and 90 minutes of strength training — the benefits of even a modest increase in physical activity can’t be denied, particularly for those who work in an office mere steps from their bedroom and kitchen.

As you develop your new schedule, consider adding time for a ten minute walk to start and end your day, and ten extra minutes to your lunch to enjoy some fresh air and clear your brain. You’ll get your 150 minutes of recommended activity in, and likely feel significantly more rejuvenated for the rest of your day.


Stay Social

Working remotely can be lonely. By leaving an office environment, you’ve lost out on the watercooler conversations, coffee shop trips, and lunch breaks that dominate the social activities of many working adults. Just as it’s important to schedule your working routine, it becomes critical to remain cognizant of your social interaction and go out of the way to ensure that you’re spending time with the people in your life outside of work.

I make a point of reaching out to friends to schedule lunch once or twice a week, and aim to spend Friday evenings — and, often, much of the weekend — doing things outside of the house. The upside is that you’re now in complete control of your social calendar — spending time with who you want to spend it with, and on the schedule that makes you happy.

It’s equally important to ensure that you’re regularly interacting and developing bonds with your coworkers. At 10up, we hold weekly “water cooler” and “coffee talk” calls for our team that enable those with a bit of free time in their work day to catch up and talk about their lives outside of work. We also maintain a list of nearly two dozen “social” Slack channels that enable individuals who don’t often overlap in their day-to-day working environments to bond over shared hobbies, whether it be fashion, fitness, anime, or Westworld.


Stay Focused

While the typical workplace distractions of excruciating ambient noise or “do you have a minute?” desk conversations no longer exist, there’s still a plethora of distractions in a remote working environment, whether you’re in a home office, at a coffee shop, or at a shared working space. I’m a subscriber to the Pomodoro Technique, coupled with a regularly-maintained todo list, to ensure that I’m staying focused while still allowing myself regular cognitive breaks. This has actually had the benefit of making me significantly more productive than I ever was in an office environment — I can regularly get through my list of things I “need to do” in five or six hours and dedicate my remaining time to things that could benefit from my attention, or getting ahead on future work. I couple this with RescueTime to enable me to understand how I’m utilizing my time and recognize if certain actitivites or certain portions of my day cause me to become less productive, and alter my routine accordingly. I’ve recognized that I tend to get distracted in sending follow up emails early in the day, so it’s one of the things I tend to tackle later on in the day (or in the one hour block I schedule following my gym time).

While the rigidty of the Pomodoro Technique is certainly not for everyone, it’s important to develop a system that enables you to stay on top of your obligations, hold yourself accountable, and make the adjustments you need to maintain productivity day-to-day and week-to-week.


“Done Working” Means “Done Working”

Even though your laptop is lingering in the other room, it’s not okay to hop on for “a few more emails” after you’ve checked out for the day. Many remote workers I’ve spoken to wear their 24/7 responsiveness almost as a badge of pride — in reality, it’s likely the quickest way to succumb to job dissatisfaction and, ultimately, burnout.

As you develop your daily schedule, provide yourself with a regular, dedicated “stop” time — after that point, you’re done working, and won’t work again until you start your work day the following day. Working past this “stop” time needs to be a deliberate decision you make irregularly for justifiable reasons — an early morning sales presentation the following day, or a lengthy proposal due shortly. If you find yourself regularly needing to work past this threshold, take the time to consider whether your productivity throughout the rest of the day is maximized (a tool like RescueTime can help with this), and work with your boss if you feel that it might be symptomatic of a case of over-expectation, over-obligation, or, for some, an inability to say “no” to more work.


If you strive to develop these habits, working remotely can truly become a vehicle for increased happiness, satisfaction, and professional producitivity. As with all things, you need to make a concerted effort to develop a system that works for you and enables you to unlock your own potential and avoid burnout.

The Remote Worker's Handbook

Tips and tricks for remote working success

Phil Crumm

Written by

Open-source advocate, occasional engineer, and sometimes investor. Director of Client Strategy @10up. I fly planes, too.

The Remote Worker's Handbook

Tips and tricks for remote working success