I rolled out of my twin bed and stumbled into the common room. As I started the coffee maker I started thinking about my day and had a feeling of emptiness.
I had nothing to do.
It was sometime in early September in 2018. I had just moved across the globe to Taipei. I was technically a self-employed freelancer but didn’t have any clients. I was single and had declared to my friends a month earlier that I was going to embrace a life path as a “cool uncle.” …
What follows is a transcript of a video I created reflecting on the last two and a half years of travel at the end of 2020. I’ve been living and working as a digital nomad living in several different countries since 2018.
Three years ago my friend said I was heading out on a walkabout. I didn’t know what to expect but I knew I was going to encounter things I couldn’t predict.
The one thing I didn’t realize is that travel has become something different.
Different from what I experienced as a child. It wasn’t something that I was racking up experiences. It was something that I was putting myself in different environments around different people in different places and not knowing what will happen next. …
To others, I made a bold decision to quit my job and chart a different course in 2017. Yet in my own experience of the event, there was no singular moment or decision made. This disconnect between my own experience and the narrative of bold all-or-nothing leaps has mystified me and driven a lot of my own writing about the process.
Agnes Callard, a philosopher at the University of Chicago, is skeptical about the idea of sudden transformation. She’s also convinced that, no matter how it looks or feels, we choose how we change. In her often moving, quietly profound book “Aspiration: The Agency of Becoming,” she writes that “becoming a parent is neither something that just happens to you nor something you decide to have happen to you.” Instead, Callard maintains, we “aspire” to self-transformation by trying on the values that we hope one day to possess. …
Starting your own business is a secret dream of many and with the emergence of more clear paths to make money online, many knowledge workers are deciding to test the waters of self-employment and entrepreneurship. In making such a leap many people hope to increase the amount of freedom and fulfilment they have with their work. However, because of how little we think about the way we work, many find themselves caught in one of many hustle traps.
A hustle trap is something that we fall into without asking “why?” Many of the traps exist because of outdated work beliefs or behaviors we have carried forward from full-time employment. Many people only realize they have fallen into a trap when they find themselves burned out and noticing that they have created another job for themselves. …
During the initial months of the Covid crisis you were bombarded with tips about how to optimize your day while working online and how to be more effective than ever while multi-tasking zoom meetings, slack chats and conference calls.
For many, working remotely is unsettling. They start questioning their relationship with work, worry about how to continue to “perform” work without the established in-person norms and often find themselves completely unmotivated to get started without the ritual of commuting to an office.
For many people who are self-employed, freelance or who work in companies who know how to work remotely they know the “secret” of remote work — namely that it unlocks an enormous amount of freedom and responsibility in terms of how you manage your time. …
Remote work is poorly understood and for good reason. What most people have experienced is merely being “allowed” to work remotely on occasion, having to stay home with someone sick in the family, logging in while traveling or waiting for the cable guy to install internet.
While I am a fan of remote working I am not sure that most companies realize that experimenting with remote work until the end of the covid-19 crisis is a free strategy option. …
Greetings from Las Palmas and day 41 of lockdown here. Grab your coffee and enjoy these Saturday morning Boundless thoughts.
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Over the past few weeks I had a number of conversations with people who reached out to me or friends who wanted to reconnect. People tend to reach out for a number of reasons:
When I was working in consulting there was an unspoken truth. To say it would undermine 75% of the work that these firms do each day.
That truth is that most companies will not change without a genuine crisis.
Right now, every company finds itself in a crisis. From the supermarkets who are realizing they are the most essential business in their community to the office that has completed a 100% shift to remote work in less than 24 hours.
This short essay is a letter to the leaders of the companies in that second category who’s work is already digital, but the operations and day-to-day reality of the company are still rooted in an office-based existence. …
I’ve been self-employed for three years and after landing remote gigs in my first couple of months and enjoying the freedom and flexibility, I decided to “default to remote” with everything I worked on.
Two years ago I moved to Asia and “default to remote” went from a nice idea to the only option to continue to with my consulting business. In addition, it gave me useful constraints that forced me to think more deeply about how to build a lasting life and work by creating and working digitally.
Over that time, I’ve worked in many different ways with Zoom as the central tool I’ve used. …