Almost Paradise: The Remote Worker’s Guide to Lonely Island Survival

The life of a remote worker is often romanticized. But without a doubt it can become lonely, fast. Let's talk about how to survive the loneliness.

by Drew Barton

News & Announcements

Reading Time | 8 min

A lot of people romanticize the life of the remote worker: Wake up at 11, possibly in a foreign country, definitely in pajamas. Of course, there are some very real and practical advantages to working remotely—maintaining a flexible schedule, working with people hand-picked by personality over proximity, not sitting under fluorescent lights from 9 to 5, no fishy microwave smells (unless you’re the person who does that)—just to name a few.

Almost Paradise

So it’s paradise, right? Well, almost. The seasoned remote worker, and her employer, know that for every benefit and advantage there exists a potential pitfall. With great power, and the freedom to work from anywhere, comes great responsibility. Responsibility on the part of the employee to work efficiently and report honestly, and on the part of the employer, to engage, motivate, and connect the team.

Running Aground: A Guide to Ruining Everything

If we know the advantages to working remotely, which are typically obvious and individualized, what are the pitfalls? How can we avoid running the friend-ship aground on the rocks? According to our team, the biggest dangers are a loss of momentum, not seeing each other frequently enough, becoming isolated or lonely—and the resulting fear and self doubt that creeps in.

The World is Hungry for New Things


The Non-Emo but Totally Important Black Magic of Momentum

“There is no reason to be shy. The world is hungry for new things. We don’t come from a background of carefully mapped-out marketing. We just move.

—Carol Lim, Kenzo Creative Director

Lots of factors can contribute to a loss of momentum: a lull in projects, overthinking, overwhelm, writers’ block, personal stuff, illness. The list could go on and on.

Loss of momentum seems to be the biggest danger, the first domino in the train when things fall down. The biggest way to avoid losing momentum is to just keep moving (duh). Making small moves on smaller goals and showing up everyday to push it another inch further. Working alone on a monolithic goal day after day, not knowing where to begin or believing it can be done, is the surest way to lose momentum—fast.

We’re a scrappy, agile team who loves our ability to have an idea, pitch it real quick, build it together, and ship it out quickly. Quickly, not perfectly. Makers are happiest when they’re making, so that’s what we do. Keep it moving.

Fear is a Desolate Boneyard


The Horrible Bullshit That is Fear

“Creative living is a path for the brave. We all know this. We all know that fear is a desolate boneyard where our dreams go to desiccate in the hot sun. This is common knowledge. Sometimes we just don’t know what to do about it.”

Big Magic, Elizabeth Gilbert

The thing about the relationship between momentum and fear is…it’s complicated. Fear can stop momentum in its tracks, loss of momentum can lead to fear. It’s what we in the biz call a vicious cycle (a phrase we just came up with).

The problem with fear is that, in most cases when it comes to productivity and creativity, is it’s a horrible liar. Like the frenemy you never wanted who’s always sabotaging your plans and diminishing your confidence. So, unless you’re working from the edge of a cliff on your laptop, fear should be completely ignored in your work. I mean, behave, but don’t let fear stop you from moving. Just do something, it’s always better than freezing in your tracks. And people don’t care about you as much as you think. I mean, everyone’s usually only judging and thinking about themselves, so just make stuff and keep going.

Meet to Retreat

Last week, we gathered our remote team together in St. George, Utah. It’d been about 18 months since our last one, and some of us (?) had been working with the team for that entire duration without meeting in person. It was overdue, and much anticipated. (You can read about the logistics of pulling a bootstrapped team together here, if you’re looking for some pro-tips and how-tos).

Inspired by recent personal experience and some extracurricular reading, we pulled together a talk about staying connected remotely, navigating the rough waters of working alone, and not running aground on the rocks of isolation, imposter syndrome, and fear.

Before gathering, our team filled out this anonymous survey about their personal experience and general wellness. For context, our team is generally very communicative and engaged on a daily basis, and on a personal level, we’re all great friends. In all honesty, it’s very much a big happy family. Even so, 90% of our team reported feeling disconnected, lonely, or isolated as a result of working remotely. 90% of us have experienced imposter syndrome, feared falling behind in work, or felt anxious about work performance in a non-traditional office setting. If you haven’t checked in with your team, feel free to use our survey as a template for your own. The health of your teammates, or employees, directly influences the health of your business.

The Strength of the Wolf is the Pack


Operation: Ripcord

As the creeper that girdles the tree trunk, the law runneth forward and back; For the strength of the pack is the wolf, and the strength of the wolf is the pack.

The Law of the Jungle, Rudyard Kipling

So, what can be done? For us, it looks like working together to implement a buddy check system, and develop something we’re tentatively calling Operation: Ripcord—a no-questions-asked, no-judgment-passed protocol for an employee who’s feeling burnt out or in need of assistance. What that looks like may differ from organization to organization, and even individually across a team, but the basic principle is this: we take care of each other. We commit to the longterm success of the individual and the team as a whole. If it weren’t such a trite truism, we’d simply say, It’s a marathon, not a sprint. But for where this team wants to go, the things we want to create, that’s absolutely true.

What if you treated leveling up on wellness and mental health as critically as you do leveling up on work skills and knowledge? What if time off were as important as time on? What would your team look like then?

I’d Like to Talk to HR

One obvious complication to working remotely for a small, bootstrapped team is the total absence of formal structures like an HR department. In that sense, it really is like a family. If there’s an issue, an employee needs to request leave, report a complaint, or ask for assistance, there’s no organizational veil of anonymity. Instead, we to come together like a tribe before the council and face problems together. It can be a lot to take on. So, is it worth it?

At the end of the day, I’m just saying, it is what it is, and, look, here’s the deal: feeling like family is why most of us are here. A lot of us were friends before we were coworkers, helped each other out in the community first, and came together at the end like a friendship potluck. We work well together and we trust each other, which makes coming to work, even if we don’t share a roof, super meaningful for us. Really.

So How Does it (Remote) Work?

If you’ve ever eaten at a folksy cafe or hung around a mom and pop shop, you’ve seen that charming, hand-painted sign hung above the cash register that says, “If you like us, tell others. If you don’t, tell us.” The same rule should apply at the workplace, right? In addition to public praise being a huge motivator, it also builds a foundation of trust.

Culture begins in our leadership by example. That means we never conversationally discuss or disparage a coworker’s performance or behavior that might stem from a personal issue, or burnout. We’ve all come from places where we’ve seen that tear people apart. We’re different, and it’s not a coincidence. Simply put, you can’t implement a no-judgement ripcord and simultaneously allow or engage in insidious, if casual, gossip. You have to insist, as a team, in addressing any issues in performance promptly, productively, professionally—not just passively or to vent. At Site Care, we insist on a culture where, based on example, each person can trust with certainty that they are not being talked about, only talked to.

A Culture of Support and Trust

When we defined our original core values, they were all about people and taking care of each other in different ways. That’s what we believe in most—taking care of each other (our employees, our customers, our community). Like, we’re a support company and we’re a support company.

A policy is just a document, just a protocol to be implemented or referred to when a situation warrants it. And we need that, as all companies do, definitely. But more importantly, we want to continue cultivating a culture of support and trust, from which the policy can be a natural, organic extension. Not just a lip-service-only law sitting in harsh contrast against our day-to-day, never actually to be used or believed.

At Site Care, we insist on a culture where someone feels safe to pull the ripcord, instead of crashing to the earth to save face. We believe in taking care of each other, because it’s what we know and who we are.

It’s why we’re here, and why we’ll be around for a long, long time.

Drew Barton | President and Founder

Drew Barton is the President and Founder of SiteCare, LLC. For over two decades, Drew has helped thousands of businesses grow online. He is the author of the book, Buyer’s Guide to Websites, an Eagle Scout, and he is active in the Entrepreneurs' Organization.


  • Megan Gray 6 years ago

    This is weird what is this

  • Alyssa Johnson 6 years ago

    I’m working remotely and I can agree with almost everything written here! When my work for only started, I thought that I would need to search for something additional, but it happened to be better than I thought and that’s the best experience I’ve ever had!

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