After I quit my job in 2017 I spent 5 weeks in Europe. It was the longest break from the “real world” I had ever taken and in the second week, I started to feel extremely guilty. I became hyper-aware of the script in my head that said I should be working or that at minimum, I should be trying to make money. By the fourth week, I started to relax in a way that enabled me to look at my life in a way that I hadn’t in nearly ten years. What was happening? …

The alumni of top consulting firms are part of all types of organizations around the world. Consulting firms like McKinsey, Bain, and BCG can claim world leaders, public company CEOs, heads of non-profits, entrepreneurs and even musicians.

These firms produce many impressive alumni because they tend to recruit and attract some of the most driven young people around the world, the work is oriented towards helping senior leaders of top companies, and the fact that there is an expectation that most people who work at these firms will not spend their entire careers at them. …

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…

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.

I thought I was alone in pondering this question until I stumbled upon a small reference to Agnes Callard’s work in a New Yorker article about decision making. Here is that passage:

Agnes Callard, a philosopher at the University…

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…

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…

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. …