Leadership lessons from living nomadically

“Oh – are you actually going to work today?”. I just moved to San Diego and the barista at a coffee shop 2 blocks from my house looks surprised as I sauntered in to order coffee doned in my favorite casual attire aka PJs. I chuckled and started to explain my job.

I realized today that I am one of a handful (or the only) nomadic team lead at Automattic. It never occurred to me until this week as a number of stressful situations were thrown my way. I’ve learned A LOT from being a lead of a remote team but I’ve learned just as much from being nomadic while I’ve done so.

Important note: I’m single, childless, petless, and not taking care of elders so keep this in mind. 


I can adapt much better now than I think I ever have in my life. New team member starting next week? Cool – bring it. In the same way you never really know what’s around the corner when you’re nomading, the same is true of leading a team. If you get stuck on one part of your identity as a team or, when you’re nomading, to a place, it becomes harder to adapt to the next location, challenge, etc.

Covering the basics

I travel with my backpack and a tote bag for my shoes + books. That’s it. When nomading, I quickly learned covering the basics should always be step one. For me that looks like this in a day: shower, workout, get food, get caffeine, talk to another human. When leading a team, the same is true but with different basics 😉 Sometimes it’s easy to get caught up in the “new shiny thing” in the same way you might idealize a new jacket you just saw. I’ve found though that I quickly need to remember what the basics means for me as a lead so that my main tasks don’t slip through the cracks.

What do I need to get through today successfully? What do I need to plan for tomorrow? 

I constantly jump between “today” thinking and 1 month, 3 month, 6 month thinking both in life and in leading a team. Nomading requires the same process depending on how you do it. I tend to block off 5 months of my life at a time and loosely plan things out. Somehow I’ve started doing a similar exercise in 3 month blocks with my team. Not only does this help guide what to do today but balancing this “today” thinking with planning for tomorrow helps you see how the two connect. Communicating that to yourself eases anxiety and creates a vision – the same goes for communicating this vision to your team. It’s just as important to know what’s in front of me today as much as it is to know what tomorrow looks like.

How my work and interactions change across timezones

This has been crucial for understanding what it’s like to be in different parts of Automattic and  how folks in different timezones tend to work. Just over half of Automattic is US based currently which results in a wide variety of experiences depending on where you are in the US and, mainly, the rest of the world. Waking up in a PST timezone, for example, inevitably leaves me with a large backscroll to read. Waking up in EST timezone means I’m the one creating that backscroll for others 🙂 When I have traveled through Europe, this means waiting until certain folks are online so we can chat. It also means I interact with completely different people on a day to day basis. It’s fascinating and has helped give me insight as a lead in terms of how our queues look and in how others work. It’s also helped me build rapport with folks outside of just a normal timezone.

Action and solution oriented thinking

I landed at an airport once only to find that I had booked the airbnb I was supposed to stay at for the wrong month. I could sit and talk about all the things I did wrong and that led to this moment or I could find a place for me to sleep that night. Within an hour, I had a new place to stay. This kind of action and solution oriented thinking has spread deeply into my work as a lead. If someone comes to me with a problem, I jump for solutions almost to a fault.

Firm lines for when I’m done with work

The whole point of nomading is to explore a new place! This works great with work as you have very strong motivation to get off the computer and go outside. I have had better work life balance while nomading than I did working consistently in one place. You become more cognizant of how you are spending your time when you want to experience a place to the fullest.

Willingness to ask for help

Oh dear – there are a number of people who helped make my nomading adventures successful. I had to learn to ask for help though and to admit I was lost, didn’t speak the language, didn’t know how to pay for a bus pass, etc. This directly translates to work in very obvious ways. I have zero problem asking for help, admitting I don’t know something, and actively working to do the learning. Ultimately, asking for help is just a sign you are engaged with what’s happening and want to do the best you can.

I’m sure there are other lessons but these stood out to me as things I want to carry forward with me as a lead at Automattic.

P.S. We’re hiring and we want to see you join us.


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