1001 Days of Pushups

I did my sets of pushups today, just like any other day and nothing felt particularly special about it.

It’s a big day, though.

I’ve now done multiple sets of pushups every day for 1001 days in a row. No days missed. Rain or shine, on a frozen lake, atop a mountain, on a boat, on a plane, wherever I needed to to get the pushups done.

It’s About Momentum

Practically speaking, what I’m doing today, 1001 days later, isn’t a whole lot different than when I started.

On the pushups front, I started out being able to do 1-2 at a time, four sets a day.

Today, I average about 50 pushups a day and if I want to push myself, I can do about 30 in a row without stopping.

A definite improvement, but there’s more to the story.

I chose pushups because it’s a ridiculously tiny habit. My friends laughed. What difference could a few pushups make? I should join a gym or do some real exercise.

They weren’t wrong in the short-term. A few pushups a day wasn’t going to make a big difference to my health.

Because the habit was ridiculously tiny, though, I kept it up.

Then, something magical happened. I had a habit in place and I wanted to experiment with more.

Pushups became building block habits. And they built momentum.

More Tiny Habits

Today, I track 25 different tiny habits that have helped me build momentum across a wide range of focus areas. They include:

All of these are tiny on their own. Easy to get done and really don’t seem like a big deal.

When I add them up, though, I’ve been able to use tiny habits to create significant amounts of momentum over time.

This experiment with tiny habits has been life-changing for me.

And I’m just getting started.

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.