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September 🤔: Are we working differently enough? Does it matter?

From our Remote Works Monthly Newsletter. Sign-up today here.


Earlier this month, Ali stayed at a coliving for digital nomads—a mecca for remote workers, with 20 location independent full-time employees, freelancers, entrepreneurs and creatives under one roof. They shared living space, activities (including many rounds of Cartographers and juggling lessons), and meals while working together throughout the day. In the bell curve of remote workers, this community would be clearly labeled ‘early adopters” well before the whisperings of Covid-19 entered our vocabulary. (Ali and Tam met in a similar environment back in Cape Town in 2017.)


Naturally, Ali was ecstatic to be around “her people” again—those who questioned assumptions dared to live differently and shared perspectives about flipping the script around work.


As she settled in, though, she quickly realized her mistake: just because people can work from anywhere, it doesn’t mean they are working differently. At least, yet… She wondered if these digital nomads had merely traded in a cubicle for a cool coworking space. After all, mountain views are better than views of a parking lot, right?


Ali observed her peers working mainly Monday-Friday, from nine to five, packing the weekends full with hikes, climbing trips, brunches, and more. Yes, there were family lunches where people might stop to play a quick board game before jumping back online. Still, the idea to switch off completely for a lazy morning in the park was met with an automated, robot-like response, “I work best in the mornings,” and convincing a group to plan a Thursday day trip in favor of a Saturday work-day was met with debates on whether it was worth taking a Thursday off work to skip the crowds. Ali wasn’t asking people not to work (she also had a lengthy to-list to knock out, a workshop to facilitate, and was in the middle of a project planning sprint with Tam), but rather, she wanted to switch how and when they work. Even in this early adopter crowd, she felt that work was still king.


But what she didn’t fully understand was why this bothered her. After some conversations and much self-reflection, she realized everyone had different comfort zones and routines regarding how to approach work and life. For some, working wherever was enough (and whenever mattered less), already this life gave many benefits from the major change that is office life.


In the evolution of full flexibility, freedom, and focus, most remote workers are only starting to question assumptions and learn how they best work. Ali only wondered what would be next.


Reflection Questions:

  1. What benefits of remote work do you value the most? (e.g., location freedom, time freedom, ability to focus, etc.)

  2. How can you maximize those benefits in your life? What boundaries and priorities do you need to set?

  3. What have you done to unlearn your automatic response to work? What experiments can you try to restructure how you work?

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