Essentialism in Nomadic Working

I’ve culled my wardrobe and office. I’ been thinking about how I make new purchases, and now I want to focus on the thing that got me on this kick in the first place: the book Essentialism by Greg McKeown.

Talking points

As I mentioned previously, the easy place to start with becoming an essentialist is to start going through all the shit in your life, like I did: physical objects I own, side-projects to which I had committed, and everything else under the sun that is a part of my life. Now that I’m down this path a bit, I want to talk about that experience.

Real life application

As a nomadic worker, I have known for years that active curation is an important part of the routine. I’ve been curating my time, routes, transportation and pack since 2005. No biggie. But as I learned when I first started doing all this was that the boundary between work and life is NOT something I wanted to focus on — quite the opposite. I found that it was far easier and more rewarding have to blur that boundary, rather than reinforce it. I’ve been doing that now for 11 years, and it’s probably the best decision I ever made when it concerns how I work. It’s become a fundamental part of nomadic working.

It doesn’t mean I work all hours of the night, or don’t have ‘set’ work hours. I have a wife and two young kids, and that obviously requires that I spend time with them. Work is not my life, and life is not my work. that’s always clear. When I talk about blurring the boundaries between work and life — yes, the “work/life balance” — I’m not talking about making a life of work, or even making a work of life. Rather, it’s that having a hard line between the two is more harmful than helpful. It’s a mindset. A paradigm shift. This probably only applies to remote workers who don’t need to follow a strict, time-zoned nine-to-five. (It’s not everyone)


Greg’s book is so impactful. There are so many principals that directly relate to nomadic working. Let’s dive into some of those now.

  1. Less, but better Is a core tenet. Where it intersects with nomadic working is when it comes to strategic optimization. While this, of course, is not a new concept, it remains something that is strangely absent from common modern lives. As the thinking goes, to do something well, you just be able to to focus on it. To achieve a state of focus, distractions must be removed or avoided — that’s one end of the spectrum. The other end is about training yourself to go deep, and even creating or seeking environments and circumstances that further enable it.
  2. Curation Is a core tenet, and the logical next step. To create an environment in which you are able to focus on essential things, you must drop the non-essentials. Being able to make the hard decisions — the yes or no answers — requires brutal curation and a laser-focus on a goal.

I wish these two simple concepts were easy to implement. They’re not. They’re quite difficult once you start attempting to apply them. For me, this manifested in a few different ways so far: 1) Leaving my board position at the Fort Collins Archery Association, 2) Permanently discontinuing the international fixed-gear cycling directory I started in 2006, and 3) brutally culling my wardrobe and office. I’m not done making cuts, but I’ve made some progress.

The hard parts

I consciously chose to start with physical belongings because I knew they would be an easy win. I have complete control over them; no one is going to be disappointed if I send a t-shirt to the charity shop. And it was easy — it gave me the quick win and momentum I needed to keep going. Then I started on harder parts — some of the projects I was involved in.

Leaving the board at the archery association was difficult because I had grown to have a sense of ownership over the quality of the things I was doing; their branding, the experience of becoming a member and managing the website. I joined the association in the first place because I needed a way to meet people in my new hometown. I realized that that had been accomplished, and that — even though the association would be put into as difficult position by my absence — it wasn’t driving toward any of my core goals, and I had already met the people I wanted to meet.

The international fixed gear cycling directory was another very difficult choice. I knew that I had a lot of people relying on it. I had historically made effort to pass it on to others in the industry, which proved unsuccessful. Even with the insane amount of unique traffic each directory was receiving every day, I knew I didn’t have the bandwidth or time to monetize it in the way it needed to happen, and I couldn’t even give it away for free (without it already being monetized), and so it went. I messaged my beloved 85,000 subscribers and asked them for their help. I fielded replies for two months. I talked with Crumpler, Specialized, Cannondale, Giro and countless small cycling organizations about taking it over during that time. No one, in the end, had the bandwidth for it. It was a sad day indeed to close the doors of that community I had fostered for the last 10 years. But it wasn’t essential. I overcame the sunk cost bias.

What IS essential?

For me, there are only a handful of things left to work on. My home — which is still a usability nightmare. Every other room in the house needs the same level of treatment. The garage is a cluttered workshop. Aside from the home, there are still a few smaller things I’ve been simplifying; the legacy of web-related work from years passed, the remaining websites I manage, the Fort Collins IXDA group, and of course work and family life.

I recently had to defer a few projects — one from a close friend who is making a high-budget feature film — and which I had been wanting to work on for years. I’ve been very cautious about what new things I take on. When people from past projects ask for help (which is a regular occurrence), I have pointed them elsewhere or explained that I don’t have the time. Every time it’s been hard, because I care about the quality of these projects.

There are no easy answers. Each item is something that requires deep meditation. Choices are difficult, and only come with time. But even those things are just scratching the surface.

Learning how to BE an Essentialist

Stuff and projects — believe it or not — are the easy part. The hard part is un-learning all the bad habits, and then re-training yourself with good habits. This is where things really get tricky.

Sure — make the easy cuts first. That’s what I did. It was a great way to gain some easy-wins early on and gain momentum. Cull the wardrobe. Cut some projects. Curate the notifications coming from your phone. Pick all that low-hanging-fruit you can find. But when you’re done, savor that momentum because you’re going to need it.

As a people-pleaser, it comes naturally to me to say ‘yes’ to just about everything people ask of me. I have to un-learn that. It’s hard. I’ve had to disappoint some people who are very dear to me. It didn’t feel good, but I knew it was the right choice. I’ve always enjoyed having several high-value projects on at the same time, but after going through a self-imposed exercise involving a list of my current projects and their value, I cut or deferred just about everything in favor of investing further into my work at Calorie Cloud, because the results are so valuable. The only ‘other’ thing I’m still doing (professionally) is publishing books with Upptäcka Press.

On the side of building good habits, I’ve been constantly and actively conscious of working more deeply. I’ve killed almost all the notifications from my phone. I no longer keep my email or Slack open all the time. I allow myself use of Facebook and Instagram only outside of work hours. Those are basics.

Beyond that, I’m spending any spare moments actively engaging in things that give my mind the space to subconsciously process the difficult problem-solving items that come from working at my job. I’ve started sketching again with pen & paper. I’m consciously being more ‘still’ when I have a spare moment — trying to be ‘okay’ with filling my time with nothing.

In closing

I can already tell it’s going to be a long journey. We’re talking years — not months. I love what I’m learning so far. It feels great. I can’t wait to report more as I go through 2016.