How I Address Remote Isolation

A couple weeks ago, before the flu made its way through the house, I started a post about my remote work week for Wiggle Work. As I was typing away it quickly and organically started to focus on tips for combating loneliness and I decided this topic was a priority and worthy of its own separate, personal post.

One of the greatest, continual challenges concerning working remotely for me has been managing isolation. Whether within distributed teams, as a freelancer, and now as a partner of a company the issue is always there and something I must proactively address each day to prevent it from spiralling out of control.

The Problems

There are a couple issues at play when discussing isolation and loneliness in the context of remote working life. There’s the struggle to genuinely connect with coworkers through a screen and also being physically secluded from society.

There’s no “watercooler” to gather around and ask about how weekends went or how someone’s kid’s softball game went. These conversations are critical to building teams that can work together and enjoy doing so. Being restricted to Slack and calls makes this a bit tricker but not impossible.

Also, something I only realized once I was about 80% through writing this post is that I think it is impossible to not also talk about inclinations towards depression and anxiety when openly discussing the slippery slope into loneliness. While I know many people that struggle with these issues I also know people that simply don’t; they don’t have a need for any of these tips because they are OK and even thrive in isolation. Essentially the two are so closely intertwined that I feel they cannot be regarded as separate afflictions, so I also use these tips to help manage depression and anxiety.

Possible Solutions

I’ve learned and continue to learn a lot of lessons the hard way regarding how best to overcome these isolation challenges both as a manager and an employee. This post is tackled from my perspective as an individual remote worker, though I do feel there is a lot managers can do for employees which would warrant a separate post.


I try to opt for video calls over regular calls or weird convoluted email threads whenever possible; it’s difficult to connect with someone otherwise. These visual cues and verbal feedback can be an important part of navigating conversations and getting to know who someone is.

I’ve started many remote coffee Hangouts focused on talking about nearly anything but work. These were always so fun and I got to know neat things about coworkers I would have never naturally uncovered throughout our typical day in Slack. I always went in to these with a list of things to talk about if things got quiet and bought an obscene amount of animal mugs, which inspired others to share their silly mugs (you can learn a lot about a person based on their mug selection). These 30 minute weekly meetings always became a source of enjoyment and I genuinely looked forward to them.

Photo of a large animal mug collection

A huge bonus: if you ever meet these folks in person on a team retreat it won’t be weird at all after these.

Finding My People

Finding the right community, that is at least partially remote, has been one of the greatest contributors to keeping me energized and out of isolation. For me this community was and is Ela Conf, a conference and remote community I co-founded in 2015. Last year we held special remote events, had Slack office hours, and hosted AMAs and monthly freelancer chats.

While I’ve decided not to be an organizer within the community this year I’ve made lasting friendships and professional connections that are truly invaluable.

Screenshot of Ela Conf organizer video call

Do some research and ask around, making sure you find one that fits and is recommended. Investing time in a rotten community can truly spoil one’s will to make such a big leap again.

Existing Amongst Humans

I have toured every coworking space accessible to me and find that they simply do not suit my needs. While they market the promise of community they seem to be largely deserted and disingenuous, though I realize this is just my experience and am envious if you have found a place you love.

I spent years primarily working from my home office. I should be able to make this happily work, right? After all, people are always telling me how lucky I am for this very reason. Something was always missing, however, and I only recently realized that it was people. I am an anxious introvert that at the very least needs to be physically around other humans on a regular basis. Spending a couple hours at a coffee shop 2-3 days a week and occasionally at libraries to simply exist amongst strangers while I work has had a tremendously positive impact on my moods.

When I’m feeling especially brave I introduce myself to other regulars I see at my favorite spot. These are people I see more frequently than my mom. Introducing myself once is the first step to more meaningful exchanges down the road. We are both adults hanging out in a coffee shop in the middle of a work day so there are definitely common interests to be uncovered.

Taking Breaks

This sounds obvious, but it only seems to be when in a traditional office setup. I lost count of how many times I get sucked into a project and forget to eat several meals in a row. This is isolating and also just not healthy physically; these are exactly the types of actions that lead to more and more negative habits.

I try to force myself to take walks. Parks are great because there are other people there as well and I try to say good morning/afternoon/evening to strangers when feeling up for it. Sometimes these are the only irl people I see and talk to outside of my family for the entire day. Another bonus here is that allowing my mind to rest usually inspires a new solution to a problem I was previously hung up on.

Photo of Delaware mug and a cornfield as the background

Be careful not to let breaks become focused on house chores as much as possible because it is an endless, unwinnable trap. Get out and get some sun and fresh air if you can. I realize leaving the house is no easy task for some so start small with anything that may be somewhat comfortable—even spending some time on the porch or patio can be a welcomed change of scenery.

Hobbies and Pets

Hobbies and pets can easily fill breaks. Many pets force you to go outside regularly and can be great companions that simply like to hang out near you while you work. I recently started growing herbs from seeds and use breaks to check on them and make sure they are getting enough light. I also have a seemingly infinite number of houseplants so watering and trimming is a regular need.

Photo of Gunther the black mini schnauzer

Maintaining Thoughtful Gestures

When I worked 8-5 in an office I made friends with coworkers. Other than being wildly convenient these are people that I spent an incredible amount of time with and the only ones that truly understood what my day-to-day was like. I invited them to dinner, out for cocktails, I sent them all kinds of cards from family photo holiday cards to general thank you cards to congrats on expecting cards. Again, coworkers are people that you spend just as much time with as your own family.

Photo of large card selection on table

I make it a point to send cards still as often as possible and while I can’t invite people to a remote dinner (though what an interesting idea!) I can and have been known to start Slack channels based around all things food. While these gestures may look a bit different now and take on different forms the sentiment and openness to connect and let others in is still there.


This one is quick and easy. I am not sure where I would be without music, but I do know it would be a sad place. Having a daily playlist keeps my mind from wandering too much and focused on the task at hand. It’s also handy when working in distracting environments like coffee shops.

Hire A Local Intern

I realize this is not a super practical suggestion for everyone but if you work for yourself and can afford it this can be a great investment for a number of reasons. At YupGup we hired a design intern at the beginning of the year and it has been great in terms of help with certain tasks but I also I feel like I have gained a friend.

I have the most weekly hours within our small team and it’s very valuable having someone around, in-person, with dedicated hours to talk through problems with and run ideas by. You get to share your knowledge, get some assistance with your workload, and ask “Is this weird?” out loud and have someone answer.

Photo of Joni Trythall and intern Bren Lawler

Bye For Now

For me, working from home has not necessarily gotten easier over the past six years or so. The good news is that over time I’ve begun to recognize triggering patterns and negative habits and am better equipped to correct them sooner before things get too unbearable. I’ve learned to be proactive each day and can snap out of a funk when they do happen must faster. So while it’s a lot of effort it’s worth it because the flexibility is essential.

I suppose I will conclude this by saying that if you are in the Wilmington, Delaware area now or plan to be at some point feel free to reach out and we can sit next to each other in a coffee shop while we work 😉