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Building Your Remote Work Confidence

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By: Tamara Sanderson

A long time ago, in a land far away, lived a Persian poet and Sufi mystic—Rumi—and while he lived eight centuries ago, his words are just as powerful today.


As they say in journalism, don’t bury the ledge, and Rumi adheres, starting this poem, The Sight of the Soul, with an insight that goes straight to the heart:


“One of the marvels of the world

Is the sight of a soul sitting in prison

With the key in its hand.

Covered with dust,

With a cleansing waterfall an inch away”


The poem then spotlights a young man, tossing and turning in bed. Although comfortable, he wants more, which Rumi surmises:


“If a prisoner had not lived outside,

he would not detest the dungeon.

Desiring knows there is a satisfaction

beyond this. Straying maps the path.”


Tamara Sanderson HEADSHOT photo

Tamara Sanderson

The poems continue, but I’ll stop here, to punctuate his point. We often assume we are restricted by outside forces. You might think, if only you were born in a different country, or had a different government, then life would look different. Or, you might find yourself saying, “I’d love to help, but my hands are tied.”

However, what if when you look closely, you realize that it’s not someone else controlling your destiny, but instead, it’s you? Are you sitting in a prison of your own making with the key in hand?

As Ali Greene and I interviewed remote work experts for our upcoming book, Remote Works (working title), to be released January 2023, we noticed a recurring pattern: it takes time for remote workers to trust themselves.

Just take us—for example. Although we’re literally writing and teaching on how to make remote work actually work, we had to learn to trust ourselves along the way. My co-writer, Ali Greene, joined DuckDuckGo as their Head of People, with a vision of more freedom and travel, but it took her nearly a year of working remotely in Philly before she took her remote work lifestyle on the road. And even then, she decided to try-on “digital nomad” life first, traveling only a few months at a time, before diving fully into the lifestyle. And, thankfully she did, because that’s when I met Ali in Cape Town.

Likewise, I spent my first two months working at an all-remote company, Automattic, from my apartment in San Francisco, before setting off as a digital nomad. And while it was relatively easy for me to manage my workload, given my past experience of working distributed and autonomously at other companies, I felt a different struggle. Previously, I worked in large organizations, needing to please lots of stakeholders, and I used body language and verbal cues to validate my performance. Without that, especially in a company where written communication is king, I personally struggled—reading too much into Slack messages and internal blog posts—which made it hard for me to truly “turn off” after work. Eventually, I had to trust in my ability to perform, without relying as much on external validation.

Darcy Boles, a remote work advocate, told us that she believes it takes at least six months (and sometimes up to two years) to truly trust in your ability to work remotely. It takes a certain amount of vulnerability to step out of the 9-to-5 PM paradigm—whether that’s taking a walk in the middle of the day, or opting to work from a cafe or an airbnb.

If you have not lived outside the structures of traditional work, and your main remote work experience has involved a rushed WFH order due to a pandemic, then, in the words of Rumi, you haven’t really lived outside yet. No wonder you may complain about back-to-back Zoom calls, but you do not detest them yet. You were doing a version of the same thing back in the office.

So, where do you start? We recommend energy tracking. Before you can stretch yourself, you need to understand your rhythms. What brings you energy? What drains your energy? When and where do you enjoy working best? The more you understand about yourself, the better you can design a workflow around your best life.

We know it can sound daunting, so we’ve done the heavy lifting for you! Rather than guess at your rhythms, we recommend you carve out a week to track your energy. Think of it as a diary study where you mark at least two-three activities per day—a mix of personal and professional—and record your shifts in energy.

At the end of the seven days, you’ll want to review your entries and look for patterns. Not an early bird? Save your “deep work” for later in the afternoon. Notice that you have lots of one hour gaps between meetings that are too short to do meaningful work, but too long to waste? Try bulk answering emails, or do a few chores around the office. Laundry and washing dishes can be a great palette cleanser between meetings (and give you time to digest what you just learned).

And that’s just the beginning. As you start noticing tasks that could be eliminated from your day, without consequence, or ways that you could integrate more fun and life into your work, the more you’ll notice that remote not only works, but it fundamentally changes how work is done. Maybe we’ll find you one day, coding from a lounge chair by the pool, or taking a three hour break in the day to stroll around a museum because you found you’re more productive at night, anyways.

As you stray away from the 9-to-5 you’ve always known, you’ll start mapping your own path. That’s where the fun begins.

Want to get started with our Remote Works Energy Tracker? We are currently offering it for free by signing up for our mailing list, simply visit our website here to get started, or try out our integration with Gather.