Distributed Work

I resisted the idea of working outside of an office for a long time. Sure, I didn’t mind working from home now and then, but an office was where real work happened.

Around 9 years ago, my wife and I moved across country and suddenly working from home was the only choice there was.

The lack of choice, combined with the thought leadership of folks like Jason Fried and DHH helped me come to terms and then eventually embrace working outside of an office.

Now? It’s hard for me to imagine a situation where I’d give up distributed work.

Today I work at Automattic where more than 1,200 of us work wherever we want to, all around the world.

So how do we make it work? It’s one thing to send everyone home (COVID-19 forced many organizations to give distributed work a try), but how do you do it well?

Key Principles

In my experience, there are three key principles to making distributed work work.

  1. Trust – This is where it all starts. Trusting your team. Not to be perfect, because we’re dealing with humans. To be responsible, though, to do what they say they’re going to do, and to own up when they make mistakes.
  2. Autonomy – Give your team the resources they need and empower them to make the decisions necessary to get the job done. It won’t be perfect. In an environment built on trust, though, where feedback can be given and received, autonomy helps bring out the best in your team.
  3. Communication – At Automattic, we think of communication as oxygen. It’s the life force of your organization. It’s hard work and communicating well means striving for effective proactive and reactive communication, at all levels of your organization.

None of it works without that first ingredient – trust.

How do you build trust?

As a leader, your responsibility is to create an environment where trust can grow. Start with a clear mission and purpose for the work you’re doing. Provide your team with clear expectations that you then trust them to meet. Embrace mistakes and teach your team to give and receive feedback.

Work Practices

There are a few areas of practice that I’ve found essential to distributed work, particularly in teams:

  1. Asynchronous Communication – For most lines of distributed work, including ours at Automattic, communicating without the need for immediate response is a key practice. Documenting thought processes and decisions, debating strategies, offering guidance, teaching, sharing experiences – it can all happen asynchronously, and usually in written form.
  2. Synchronous Communication – It’s important to have tools for live conversations in written form (e.g. chat), voice, and video (or even virtual reality). While these shouldn’t be the primary method of communication, they’re important for collaboration.
  3. Personal Connections – When we’re not fighting a pandemic, regular travel and spending time together in-person is a critical part of building relationships. Personal connections provide context and shared understanding that greatly enrich collaboration.

Favorite Resources

There are a lot of tools and resources available to help facilitate distributed work. Here are a few of my favorites:

  • Remote: Office Not Required – This book helped kick off my journey to distributed work. If you haven’t read it yet, I highly recommend it. Short, to-the-point, and it has great illustrations.
  • P2 – P2 is an asynchronous communication tool, built on WordPress. We use it for everything at Automattic and we’ve made it available to the public. I highly recommend it.
  • Distributed.Blog – A podcast produced by Matt Mullenweg, the CEO of Automattic and the co-founder of WordPress. Great interviews and resources.

Distributed work is the future and the future is here.

Coping with COVID-19

It started with curiosity. Near the end of 2019, I first began hearing reports of “Corona Virus” wrecking havoc in the Wuhan province of China. It warranted a second look or two, and that was it.

Curiosity turned into surprise when I realized that WordCamp Asia, an event I was looking forward to and planning to attend in February, was at risk of canceling. Then, on February 12, WordCamp Asia was cancelled.

Surprise became disbelief as cases of COVID-19 started popping up in my home state of Washington, here in the United States. I started paying more attention to the news. I rationalized the growing level of global concern as overblown.

On Wednesday last week, I was in downtown Coeur d’Alene, Idaho (I live near the Washington / Idaho border) hosting the first of what I planned to be many events focused on serving the local WooCommerce community. Disbelief became alarm as I watched the folks at WordPress.org give their guidance to postpone all WordPress events and meetups until further notice.

I went to Costco that day and disbelief became high stress as I witnessed the local impact first-hand. Costco was busier than I’d ever seen it, toilet paper was gone, and I could see the stress and uncertainty on the faces of fellow shoppers. Fear started to kick in. Was I missing out? Was I not worried enough?

That high stress built further over the weekend as I watched more news and witnessed more of the local impact. Our local schools announced their closings or switches to distance learning. Lines at local stores grew worse and worse.

On Monday, high stress became my own version of shock. I stayed in bed far longer than usual, reading the news. I picked up our kid’s materials from school, got a few things done, and then crashed. I lay in bed and cried.


A round or two of tears later, a few things started to become clear. I recognized that this whole thing is beyond me. I’ve done what I can so far and that’s all I can do. I can’t control it.

What I can control is my reaction. I can choose to acknowledge myself, accept myself for the broken human that I am, and choose how I respond.

My Path Forward

I don’t know when this is getting better. Folks are saying it could be months, or longer. As far as I can help it, I want as few of those kinds of Mondays as possible.

To move forward, I’m focusing my energy on five areas:

  1. Faith – I choose to acknowledge and put my confidence in a loving Power beyond myself. That gives me comfort – I’m not in this alone.
  2. Community – I choose to focus on more time with my family and the communities that I’m a part of. Even if we can’t connect in person, we can stay connected.
  3. Personal Health – I choose to invest in my health, exercising a bit more, drinking more water, and keeping up with my tiny habits.
  4. Helping Others – I choose to find ways to be of help to those around me.
  5. Positive Focus – I choose to focus on the wins, taking note each day of what has gone well.

That’s working for me for now.

Democratizing Commerce

My father passed away when I was 6 years old. My two younger brothers and I were raised by a single mother, with an income below the poverty level. We didn’t realize it, though! From a young age, Mom introduced us to commerce and the ability to create and provide value to others. We baked banana breads and sold them door-to-door. We harvested and sold pecans at road-side stands. Commerce and the support of our community of friends and family was the key to enabling her to provide for us.

As a teenager, I discovered the Open Web. I was able to connect with others like me (and very different from me) around the world. WordPress and the Open Web gave me the privilege of creating value for a wider audience. I built my career on it, provided for my own family, and have watched many others do the same.

Whether physical goods, virtual goods, services, or information, commerce is a great way to create and share value with others.

Commerce on the Open Web offers opportunity that wasn’t possible before. Where the value an individual creates and offers may have limited interest in their local community, they can often find interest in a global community made accessible through the Open Web.


WooCommerce is an Ecosystem Plugin for WordPress, an Operating System for the Open Web.

Our mission at WooCommerce is to “Democratize Commerce.”

Democratizing commerce means making it accessible to all, regardless of income, technical capability, language, geography, gender, or age.

It starts with Community

WooCommerce is imperfect. As amazing as it is, there’s still work to be done, especially compared to the heavily funded, profit-driven alternatives available today. WooCommerce is built on WordPress, though, and is aligned with the values of the Open Web.

And WooCommerce has something the profit-focused alternatives don’t have, a Community that believes in democratization.

When I first started in the WordPress ecosystem, it was the Community that embraced me, that inspired me, that answered my questions, and empowered me to create.

And in WooCommerce meetups and communities the world over, it’s the same. People are investing their time and energy as volunteers to inspire fellow entrepreneurs and to empower them to share their value on the Open Web.

Community Values

I’m now a part of the WooCommerce team (we’re hiring!) and my work is to support and grow the WooCommerce Community.

Over the past few months I’ve been meeting with Community organizers around the world and learning more about the unique needs and opportunities of each local community.

An important thread in the conversations has been becoming clear on our values as a Community. Values enable us to find where we’re aligned as individuals (and where we’re not) and determine what we do and don’t do as a Community.

As I see it today, there are three ideas that stand out most clearly to me as Community values on the path to democratizing commerce:

  • Inspire – As Community organizers and participants, we have the opportunity to inspire each other with what’s possible. Through stories, through ideas, and through examples we can offer hope and inspiration to entrepreneurs.
  • Empower – As people are inspired, we can educate them, equip them with tools, and connect them with the resources to move from inspiration to action.
  • Include – We can work continuously to build a diverse base of organizers that enables us to connect with all the world, in their language, in their region, at their level of capability.

Join Me

Democratization is, by its very nature, not a work for any small group. Yes, it starts small and we’re still small today, but not for long.

If democratizing commerce is important to you, if inspiring others to share their value on the Open Web is meaningful to you, if empowering others to take action, if including all people matters to you, join me.

Connect with me on the WooCommerce Community Slack or just contact me directly. I’d love to meet you and support you however I can in democratizing commerce in your community.

The Danger of Congruence

Congruence is a word that means agreement or harmony; compatibility. An organization with congruence “gets along” and is all “rowing the same direction”.

What could be dangerous about that?

On Ryan Holiday’s recommendation, I’ve been reading a book called Range: Why Generalists Triumph in a Specialized World by David Epstein.

(As an aside, I’m making a practice of linking to an author’s own site instead of just pointing to Amazon. Strong author presences are good for an Open Web)

Near the end of the book (Chapter 11: Learning to Drop Your Familiar Tools), David walks through stories of the Challenger explosion, wilderness fire fighters, and military parachute jumpers.

He describes situations where the way they had done things, what they were good at, got in the way of solving new problems. With the Challenger explosion, there were engineers who felt there was a problem. NASA, though, was such a data driven culture that the idea of making a decision based on qualitative versus quantitive information just wouldn’t fly.

Fire fighters are trained in specialized tools. They often identify with the tool that they use. In wilderness fire fighting situations where the only safe option is to run, numerous firefighters in the past held on to their heavy, cumbersome tools and died where they could have escaped. In a few cases they were even ordered to drop the tools, but just wouldn’t.

As humans, many of us are drawn naturally to what we know. There’s a comfort and confidence in sameness. It’s part of what’s so alluring about what David describes as “kind learning environments”, including games like Golf and Chess. Mastery is hard, but you know what to expect. You learn through repetition, through safe trial and error, and eventually you can get really good at it.

The real world, though, is what David describes as a “wicked learning environment.” Circumstances are always changing. Nothing truly repeats. What worked well for you one time isn’t guaranteed to work well the next.

A congruent organization is one that has a clear, well established way of thinking about and doing things. Odds are that way of doing things works well! It got them to where they are. Why wouldn’t it keep working?

It feels great to be aligned, to share values, to be “on the same page”. And, often, it’s an efficient and effective way to get things done.

What about when it isn’t, though? What if you can’t see the threat right in front of you? What if you can see it and just have no idea what to do about it? As uneasy as at least a few engineers at NASA felt, they didn’t see another way and just went forward.

Congruence can be dangerous.

Given our draw as humans towards congruence, how do you combat it? How do you prevent getting stuck in a way of doing things?

David suggests the idea of sending “mixed messages” through your organization. Promote a healthy degree of ambiguity. Encourage diversity of thought and action. (Another huge plus for hiring diversely)

At Automattic (where I work), we say “I know there’s no such thing as a status quo” and that we shouldn’t do something just because it’s the way it’s been done before.

That’s incredibly hard to do in practice. It’s worth working towards, though.

As I work through ideas and problems I’ve found it helpful to find tension, to gather and hold opposing views.

Now, with Range fresh on my mind, I want to take that further into my work with others, to send a few more mixed messages, and promote healthy ambiguity.

Thoughts? Send me a note or post a comment. For a few years now, I’ve hated comments. I’ve become a bit too congruent with that idea, though. Time to mix it up again, comments are enabled.

Learning Spanish in 5 Minutes a Day

I’ve been reading Range: Why Generalists Triumph in a Specialist World over Christmas break. I’ve also been thinking about my experiments with Tiny Habits over the past 2 years.

The opening chapters of Range talk about music, which I found especially interesting given my limited background as a musician and my recent foray into learning guitar. I’m now 129 days in (with a few missed here and there) of practicing music for at least 5 minutes a day. Most of that time I’ve spent on the guitar.

We spent Christmas down in Cabo last week and, accordingly, I’ve been thinking about what designing a new habit for learning Spanish might look.

I spend most of my time in my experiments with habits on habit design. It took me months of thinking to come up with my first experiment regarding food.

With Spanish, I had a loose idea. I could spend 5 minutes a day using Duolingo or a similar app. I wasn’t feeling it, though. I wanted to do something, firing up Duolingo again just didn’t seem like the best thing I could do.

Designing effective habits is about identifying tiny actions that create momentum over time. Momentum that you can take periodically and burst into breakthroughs.

I wrote my first book in 5 minutes a day, followed by an evening of focused effort when I decided I had reached the finished line.

So Spanish. What could I do in 5 minutes a day that would help me learn?

Here’s where Range came in. What’s resonating with me especially today are the early chapters on how we learn.

Concepts that stood out to me so far include:

  • Embracing mistakes – Being OK with and even encouraging mistakes is key to effective, long-term learning.
  • Spacing – Time between practice is important. Make use of deliberate non-practice.
  • Making connections – Look for ways to connect seemingly unconnected things. This creates stronger neural links and deepens learning. Analogies are our friend in learning.
  • Resisting easy – Students that received hints from teachers did better short-term and poorly long-term over those who took a harder path and struggled. Struggling is useful and learning is often more productive when it’s hard.
  • Slow – Effective learning is the work of a lifetime. It’s not a thing to rush into or force. Doing so may make it seem that you’ve learned, but you’ll just as quickly forget. Build momentum over time.

I was laying in bed thinking about all this while listening to music. After a bit of listening, I wanted to hear a Spanish song. I searched and came across a song I was familiar with and liked.

I listened and enjoy it. And then an idea surfaced.

“What if I tried to translate this song?”

Applying what I had been learning from Range I asked, “What if I tried to translate this song, without looking up the words?”

At first, that struck me as preposterous. My guess is that I knew about 10% of the words in the song and my comprehension of the song was close to 0%. I just really liked how it sounded, how it felt.

How could I translate a song like that without looking up the words?

As I started to think through the concepts I was learning, light bulbs started turning on. Translating without looking it up would be hard. I’d make a lot of mistakes. I’d also be forced to make connections and stretch the limits of my current understanding.

I got excited about it.

What if I spent my 5 minutes a day doing that? What would happen over time?

My guitar playing over the past few months has been pretty rough. 5 minutes a day doesn’t take you very far and there were many days were all I’d really do was practice finger movement and play a cord here or there.

Today, though, I had a breakthrough moment. I played for fun, taking everything I knew and things I didn’t, and just played. I had so much fun playing that I broke my guitar pick! It took months of what seemed to be fairly non-consequential practice with with a lot of “mistakes” and failing before a breakthrough occurred.

Through my experiments with habits I’ve learned to not only be OK with the slow process but to embrace it. I still don’t like taking cold showers every day – but man, I’m hooked. It’s a struggle each time and, each time, I make it through and I feel better on the other side.

I grabbed some pieces of paper and got to work.

On one sheet of paper I wrote out the words for the opening stanza in Spanish. On the other, I attempted a translation.

Now, importantly, because this was in the context of a song I was not only trying to translate but apply meaning. This is music. I didn’t want a rote, literal translation even if I was capable of producing such a thing (which I’m not). So, I wrestled with the words and tried to supply meaning.

While I don’t know how well I did, I’m certain it was a fantastic failure. And now I’ve got a whole set of new Spanish words bouncing around in my head. I’m curious about them. I want to know what they mean.

If I’d have looked it up, I could have had the answers in seconds.. and that’d be the end of it.

So, back to Spanish.

I went for a walk and gave it more thought (I do much of my best thinking while walking) and settled on the start of an experiment.

I’m going to dedicate 5 minutes a day to learning Spanish. I’ll spend my time on any one of the following list of likely to be expanded activities:

  • Translating a song from Spanish to English (or vice versa) – I’ll work on a few lyrics at a time.
  • Listening to music in Spanish (that’s an “easy” one for tough days)
  • Watching Spanish “concept” videos on YouTube – I’ll work on building a playlist. The idea here is to find good teachers that can expand my understanding of how to think in Spanish.

Then, periodically, I’ll seek opportunities to apply the momentum in a “burst”. Having a conversation with someone in Spanish, attending a Spanish-speaking event, etc.

I’ll edit and iterate on the habit as I go. I’m really happy with the start of it, though, and am looking forward to seeing where the momentum takes me over time.