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.

WordPress: An Operating System for the Open Web

A TechCrunch headline recently caught my eye. The headline is a reference to Matt Mullenweg describing WordPress as an Operating System for the Web.

Screenshot of the article on the TechCrunch website

I wrote about the idea of WordPress as an Operating System earlier this year in a piece on Ecosystem Plugins. I’ve been thinking about it more since then and with my talk on the subject this morning at WordCamp US it seemed like a good time to put my thoughts into writing.

Let’s take the idea of WordPress as an Operating System for the Open Web and look at each part of it.

The Open Web

What is the “Web”? I think of it as a digital network of connections. The Internet connects people with other people, with ideas, with products and services, with organizations, and causes.

I met my spouse through the Internet. I’ve developed close friendships around the world. I discovered WordPress, built a business, contributed to causes, and been presented with countless opportunities to express creativity.

And that’s only a glimpse of my own story. We each have our own story about what we’ve done on the Web.

What, then, is the “Open” Web?

I suggest that the Open Web is an ideal state. It’s not a thing, but rather what we have the opportunity to work towards.

I suggest that there are two key characteristics of an Open Web:

  1. Accessibility – An Open Web is one that anyone, anywhere can access, regardless of location, language, or technical capability. It’s not about being able to access everything on the Web, but rather access to the Web itself, to be able to connect to the network of connections and reach those who want to be connected with.

    This isn’t a work that can be “finished”. The point here is continual progress towards a Web that is becoming more accessible to all, not less.
  2. Creatability – An Open Web is one where anyone can create, where you can build a space for yourself and what you care about and make it what you want it to be.

An Open Web is accessible to all and empowers creativity.

Now, let’s consider the opposite. What does it mean for a web to be “Closed”?

If we consider the opposite characteristics of an Open Web, then a Closed Web would be one with:

  1. Limited accessibility – A Closed Web is one where access to the Web is restricted by hardware capability, Internet speed, and government or corporate policy. A Closed Web ignores consideration of the wide range of users who make use of assistive technologies.
  2. Limited creatibility – A Closed Web is one where source code is inaccessible, where proprietary platforms are the most widely used, where what you can create is limited to someone else’s imagination.

    You’re standing in someone else’s walled garden, building within their sandbox if they let you or just sitting on the sidelines and watching.

As much as I genuinely applaud Facebook for their work in facilitating connection (which is what the Web was created for), I don’t want a future where Facebook is the Web to the majority of folks using it and they become limited by their ability to access it and create on it.

The Web exists and it’s amazing. It’s up to us to decide whether we want it to be Open or Closed.

Operating Systems

What is an Operating System? A system for operating something.

The operating systems we’re most familiar with power our smart phones (iOS and Android), our computers (MacOS, Windows, and Linux), our televisions (Android TV and tvOS), our cars (Android Auto, CarPlay, Linux for Tesla), watches, smart home devices, you get the idea.

I think of an Operating System as being made up of three key components:

  1. Audience – Who the Operating System is designed for.
  2. Capability – What the Operating System is capable of.
  3. Interface – How the Operating System is accessed and interacted with.

An Operating System is designed for an audience and provides an interface to access that Operating System’s capability.

With that definition in mind, let’s take a look at WordPress.


I suggest there are three aspects of WordPress to consider:

  1. The Project – This includes WordPress itself, its mission to “democratize publishing”, its nature as an open source project, its history, etc.
  2. The Community – This is all of us who use WordPress, including the small percentage of volunteers who make WordPress and all those who organize and attend events.
  3. The Ecosystem – This includes all the products and services built on and connected to WordPress.

Let’s start with the Project.

WordPress was created with a focus on bloggers and provided them with the capability of starting a blog and an interface for managing it.

A screenshot of the interface from WordPress 1.5

From the beginning, though, you could look past blogging to see the mission – democratizing the creation of content on the Open Web.

Blogging was simply an initial focus.

WordPress’ nature as an open source project, built on the “four freedoms“, gave early adopters the confidence to adopt it and a sense of personal ownership that lead to their investment in the Project.

I believe that the focus on empowering non-technical creators has been a key to WordPress’ success. From the beginning, WordPress was built for creators.

The Community came out of the Project and created the Ecosystem that we have today.

(For more on the history of WordPress, I highly recommend Milestones: The Story of WordPress.)

WordPress and the Open Web

If we believe that “Open” is the ideal state of the Web then it should have an affect on the choices we make and the work we do.

I suggest that WordPress, with its focus from the beginning on being accessible and empowering creativity, is well aligned with the characteristics of an Open Web.

Has it arrived? Is it as accessible and empowering as it could be? No. We’re making progress, though, and WordPress is further along than many of the alternatives.

I see WordPress as an indicator of the health of the Open Web. The more accessible WordPress becomes and the more it empowers creativity on the Web, the more hope I believe there is for the Web to become more Open.

That’s where this idea of WordPress as an Operating System comes in.

I see this idea as an important lens through which we can look at the Project, the Community, and the Ecosystem.

That audience of creators (the majority of whom are non-technical), the capability of creating on the Web, and the interface WordPress provides for doing so, are what make it an Operating System.

Alright, so that makes enough sense. Now what? Why does any of this matter?

Let’s take a look now at each of the three aspects of WordPress through this lens and consider some of the implications.

WordPress: The Project

If we think of WordPress the Project through the lens of being an Operating System for the Open Web, what can we see?

Let’s start with the audience.

WordPress’ primary audience is non-technical creators. And, since it’s built for creating on the Open Web it needs to be accessible and empower creativity.

Here are few areas of the Project where being clear on audience might affect what we do:

  • Onboarding – As strange as it may seem to those of who’ve been using WordPress for a long time, there are people every day trying WordPress for the first time. What is that experience like? How can we make it more accessible to them, more empowering? What if we look at WordPress through the eyes of our children? What’s it like for a child growing up on touch screen devices and voice commands to use WordPress?
  • Contribution – If WordPress is for non-technical creators, how do we make it easier for more non-technical folks to contribute to WordPress? How do we empower more diversity of experience, interest, and capability to the mission of the project?
  • Messaging – How do we talk about WordPress? How do we tell its story and explain it? If someone non-technical finds their way to a highly technical aspect of the project, how do we help them navigate it?
  • Advocacy – How do we advocate for those who use WordPress and for an Open Web? Where are decisions being made that affect the future of the Web and what work can we do to represent the mission of WordPress and influence those decisions?

Now, what about capability? If the mission of WordPress is democratizing creativity on the Open Web, are we continuously expanding on its capabilities for doing so?

Let’s consider a few areas where being clear on capability might affect what we do:

  • Technology Adoption – As new technologies for creating are made, what can we do in WordPress to encourage safe experimentation and adoption of those technologies? How can we make it easier for technology creators that don’t know WordPress to make their work available in WordPress?
  • Extensibility – How can we continue to make it easier to add new capabilities to WordPress? And, as we make it easier, how can we help ensure that the capabilities being introduced work well with each other?
  • Integration – How can we make it easier for products and systems to integrate with WordPress? Consider that the folks doing the integration work may not have experience with WordPress. How do we guide them through the process? What examples do we point them to? How do we support them along the way?

Here are a few recent examples of technologies I’m excited about:

  • GraphQL – The WPGraphQL project is working to bring the power of GraphQL to WordPress. In my early experiments with it I re-experienced that sense of empowerment I felt when I first started creating in WordPress. I see a lot of potential for GraphQL to open up new possibilities.
  • AMP – The AMP Project is focused on democratizing great user experiences. There are valuable lessons we can learn and apply to WordPress from the work being done on the AMP Project and I’m excited to see more of AMP in WordPress.
  • GatsbyGatsby is an open source framework for creating web applications, built for speed. I’ve been excited to see their embrace of WordPress and I think there is a lot of potential for new capabilities in the world of plugins and themes for WordPress.
  • TideTide is a new component of the WordPress project, focused on providing automated scans of plugins and themes. I think there is a lot of potential to use Tide to make development best practices more accessible and to improve guidance for end users.

The interface to WordPress, which we commonly refer to as the WordPress Admin, is what enables its audience to access its capability.

A recent screenshot of my own WordPress Admin.

Here are a few areas where thinking of WordPress as an Operating System for the Open Web might influence work we do on the interface:

  • Accessibility – While acknowledging that accessibility is a work that can’t be “finished”, are we making continual progress in ensuring that as many people as possible can use WordPress?
  • Choices – Our philosophy in WordPress includes the idea of Decisions, not Options. How can we extend that to the many choices WordPress users have to make? How can we make it easier to choose the right plugins, themes, and blocks? What can we do to improve the experience searching for, evaluating, and trying new capabilities in WordPress?

WordPress: The Community

How might this idea of WordPress as an Operating System affect how we think about the Community?

The WordPress Community includes all those who use WordPress and contribute to WordPress.

Let’s consider some of the most common points of interaction with the Community:

  • In-person conversations – Many people hear about WordPress the first time through a friend, a co-worker, or someone they just met.
  • WordPress events – Meetups and WordCamps have become a key way for members of the Community to interact. Many event attendees are completely new to the Community.
  • Web presence – Support forums, Slack, blog comments, and social media all facilitate interaction with the Community.
  • Service providers – Many people interact with the Community through a service provider helping them build on the Web.

As we think about the Community through the lens of WordPress as an Operating System, that can help us stay focused on the audience (primarily non-technical) and capability (creating on the Open Web).

Here are a few ways that focus might affect us as a Community:

  • Improving how we talk about WordPress – We can use language and examples that make WordPress more accessible and more empowering. We can consider the level of experience and interest of our audience and adapt the way we talk about WordPress accordingly.
  • Keeping events primarily non-technical – We can look at our events through the lens of first time attendees and minimize our assumptions about their level of technical experience and capability. While there is always room for technical focuses (highly experienced and technically capable individuals also use WordPress!), I suggest that we keep the primary focus non-technical.
  • Improving Web interaction experiences – Imagine a new WordPress user joining Slack for the first time. How do we help them navigate that experience? When users ask questions in support forums and social media, what can we do to continuously improve the experiences we create?

Here are a few Community efforts I’m excited about:

  • KidsCamp – I love the work being done on welcoming children into the WordPress community. KidsCamp is a great example of this and I’m excited at the possibilities to make WordPress more accessible to the next generations. What if we take this further and bring WordPress to more schools?
  • Empowering volunteers – There is a lot of great work happening in Make WordPress. Potential volunteers get a chance to observe and find areas they can contribute to and are given increasingly clearer guidance for doing so.
  • 5% for the Future – Awhile back, Matt introduced the idea of 5% for the Future. I’m excited about the work being done to expand on those ideas, encourage more participation, and find ways to acknowledge those who do.

WordPress: The Ecosystem

How might this idea of WordPress as an Operating System impact the way we think about the WordPress Ecosystem?

The Ecosystem is made up of all the products and services built on and connected to WordPress.

There is a lot available already and more becoming available every day.

Let’s look at some common examples of participants in the ecosystem:

  • Plugin creators – From plugins that introduce tiny pieces of functionality to Ecosystem Plugins that introduce entirely new categories of capabilities.
  • Theme creators – From basic designs to complex web applications.
  • Freelancers – From assemblers with basic technical capabilities to highly technical specialists.
  • Agencies – From small business focused to enterprise.
  • Marketplaces – From plugins, to themes, to services.
  • Hosting providers – From small providers focused on specialized markets to major players, serving large percentages of the Web.
  • SaaS providers – From small specialized software creators to the largest in the world.

Each one of these Ecosystem participants can look at WordPress through the lens of an Operating System and focus on the audience and capability.

Here are a few ways participants might do so:

  • Integration Strategy – How does a product or service best work with WordPress? From a technical perspective, does it follow integration guidelines and best practices? From a user experience level, does it feel like a “native” experience within the Operating System?
  • Positioning – How does a participant position their offering relative to WordPress? Imagine introducing an offering as an app on a mobile operating system, what would that look like? How might you apply similar thinking to WordPress?
  • Investment – Organizations set aside budgets to invest in the operating systems used by those they serve. What budgets are being set aside to serve customers using on WordPress? What is being invested in the long-term success of the Project and in the Open Web?

Here are a few examples of newer participants I’m excited about:

  • Google – Google’s efforts on the AMP for WordPress Project and Site Kit are great examples of bringing the power of technology to WordPress. They’ve also been actively involved in contributing to WordPress and advocating for it within their spheres of influence.
  • BigCommerce – BigCommerce is working on bringing their experience and capabilities as an ecommerce platform to WordPress. The BigCommerce for WordPress plugin is a great step in that direction.
  • HubSpot – HubSpot is working on bringing their experience and capabilities as a marketing platform to WordPress. Their HubSpot All-in-One Marketing plugin and partnerships with other Ecosystem participants are great examples.
  • Block Lab – The team at Block Lab is working hard on empowering non-technical users to create blocks in the new WordPress Editor. Block Lab is a great, free plugin with a growing ecosystem of its own and I hope to see more plugins like it.

I suggest that success in the WordPress Ecosystem is dependent on the ability of a participant to acknowledge the audience of primarily non-technical users, to empower creativity on the Open Web, and to work well with the interface.

(Earlier this year I created OpenRank as the start of a tool to make it easier for SaaS providers to create good integrations with WordPress. I’d love to see an expansion of that effort and more efforts like it.)

Those are my thoughts so far. My hope is that this lens of WordPress as an Operating System provides a helpful way of thinking about WordPress today and its future. It has for me and I look forward to continuing to discuss and explore the topic. Have comments or questions? Contact me.

523 Days of Cold Showers

A minute passes. I’m still standing in place, my mind wandering. I feel the cold water on my toes – I’ve gotten used to that by now. I’m not just not quite ready to step in.

I know I will. I also know I can turn the water off (or to warm) and stop this cold water craziness.

I don’t want to, though – I’m hooked.

Today is the 523rd day in a row that I’ve taken a cold shower. It’s still tough. I still entertain the possibility of not doing it.

While I have grown to look forward to it, I can’t say I enjoy it – especially that first moment, stepping in to the water.

Why do it, then?

There are good reasons to take cold showers. There are numerous health benefits and perhaps even some financial ones (money saved on hot water?).

Those aren’t what do it for me, though. There are plenty of things that I know are good to do but still don’t.

A cold shower is a choice I am making, every day, to do a hard thing.

Many of the things in life that are worth doing are hard. Taking a cold shower reminds me that I can do the hard things, whether I feel like it or enjoy it in the moment or not.

I’ve had difficult days. There are days when that reminder has been exactly what I’ve needed. “Jonathan, you take cold showers, you do hard things, you’re going to be just fine.”

And then, it’s done.

I feel great afterwards. I always do. I feel great physically, mentally, and emotionally. And I’m encouraged and reminded that hard things are worth doing.

That’s why I keep taking cold showers.

The First Month

It’s been a month since going solo. A lot has happened! I’ve learned lessons, worked through challenges, and celebrated wins. Time for a recap!

Lessons Learned

Several lessons stand out in this month’s experience:

  1. “Flow” is a state that can be consistently achieved
  2. My sweet spot is the contrast of a clear long-term mission against a focus on doing my best, one day at a time
  3. More than ever, Tiny Habits continue to keep me “on the rails” and building momentum

Achieving Flow

A state of flow, for me, is a period of time where everything just clicks. I move from moment to moment, doing my best work, and experiencing an ongoing sense of peace, accentuated by mini bursts of joy when I achieve breakthroughs.

It’s the best kind of addictive, it’s highly productive, and this first month has had a lot of flow in it. I want to keep that state of flow going.

Looking back, I notice several key ingredients to achieving flow:

  1. Being free of distractions – Doing deep, creative work requires focused, uninterrupted time. Since I started tracking earlier in March I’ve averaged 6 creative hours per work day. Since being on my own I have very few recurring meetings on my calendar, giving me the flexibility to set aside large blocks of time in advance for focused work.
  2. Doing work that matters – I have a clear sense of personal mission and I’ve said yes to work that fits that mission and no to work that doesn’t. Regardless of outcome, I have a personal confidence that I’m doing both the best that I can and I’m applying my talents and energy to work I believe in.
  3. Personal acceptance – I read (and recommend) a book this month called The Four Agreements. A key takeaway for me was the importance of being comfortable in my own skin, of accepting who I am and embracing it. This has meant paying more attention to and following my instincts and impressions about what to do and not do in a given moment.
  4. Directional autonomy – I had several themes to my work in March but beyond that, I was flexible and gave myself permission to change directions at anytime. My use of autonomy is influenced by my personality and instinct for action – I’m all about taking good shortcuts and achieving quick wins. The key here is having autonomy and the ability to change directions.
  5. Simple routines – I’m awake at 5 AM most mornings and I do the same simple things most days. Get out of bed and get dressed, deep breathing, read a devotional, go for a walk. On most days, I work for a few hours till my first call or breakfast at 10 AM, whichever comes first. At some point in between, I usually get in my daily cold shower (I haven’t missed one in over a year!).
  6. Regular breaks – I do most of my best work in 20-30 minute increments. I’ll often set a timer on my phone. Once the timer goes off, I’ll get up and step away from my work for a few minutes. The types of breaks I take vary quite a bit. I might take just a minute or two to stand up, stretch, and perhaps refill my water. Other times I’ll break to do some chores around the house while I think through what I’m working on. Several times a day I’ll go for a 10-20 minute walk to think / talk through whatever I’m working on. Many of the breakthroughs in my work have come during breaks. Regular breaks lead to regular breakthroughs.

Living in Contrast

I’ve learned to love contrast in my life.

Take reading as an example. I read to be persuaded by an author’s perspective. Their perspective, though, is shaped by their own biases and personal agendas. While I want to be persuaded, I also want to be aware of bias and agenda. The best way I’ve found to do so is to read books by authors on similar subjects that have different perspectives. Doing so helps me work through contrasting ideas and develop my own perspective.

Contrast presents itself again in my personal missions.

I want to do everything I can to help WordPress get better as an Operating System for the Open Web. There’s only so much that I can personally do, though, and I only have one day at a time to do it.

The achiever in me wants to do all the things and get the results I’m after as quickly as possible. I’ve chosen work, though, that can’t be finished in a day.

And so I’m learning to just live in the contrast.

Over the course of the month I’ve made my best guesses on the types of work that I can do to make progress towards the big picture. That’s influenced what I’ve said yes and no to throughout the month.

Then, I live in the day. I can’t know for sure if I’ll have another day so I focus on doing the best I can for that day and choose to be happy with whatever I get done.

Staying on Track

Today is Day #548 since I began my experiment with Tiny Habits. As of today I’m tracking 30 different daily habits.

As I look back on over a year of doing this and particularly the past month, Tiny Habits have clearly been a key to what I’ve been able to achieve.

It’s been a great month, I’ve experienced a lot of flow, and I’ve gotten a lot done.

I’ve had difficult days, though. I’ve had days where I woke up and really didn’t feel like doing much. Today, I’ve got a head cold.

Habits have kept me on the rails, though, building momentum over time.

And tiny has been the key.

I’ve had a lot of streaks in the past. Then I get bored and lose interest followed by motivation. 2-3 months tends to be the longest I’ll keep doing a given thing.

548 days in a row is a long time for me.

What I finally figured out is that my habits needed to be ridiculously easy. 5 minutes is the cap and most of my habits I can do within a single minute.

I put effort up front in designing habits that will build momentum where I want it and then just execute, day in and day out, and let momentum do its work.


Part of what makes life great is working through challenges. This first month on my own offered me a number of opportunities for greatness!

A few particular challenges stand out:

  1. Adjusting to Independence – There is a comfort that comes from being an official, employed part of a bigger team. After 4 1/2 years in bigger company going back on my own required some adjustment. There were tools and services I no longer had access to and a paycheck that was no longer being regularly deposited.
  2. Mission ? Money – A handful of companies expressed interest in hiring me full-time, which would have solved the regular paycheck issue. With a clear personal mission, though, I felt strongly that full-time at any one company would slow down progress. I began the month with only one development client at 30% of our revenue target and nothing guaranteed for any of the months thereafter. My wife is happy that I have a strong sense of mission, she’s just also counting on me to get her the money to pay the bills.
  3. Contrasting Advice – A number of folks I respect offered me advice and some of their advice both disagreed with each other and with my own sense of direction. Much of the advice I took and I felt grateful for all of it. The challenge was appropriately separating my relationship with the individual from my relationship with their advice while doing my best to affirm how much I valued their sharing.

Life without challenges would be boring and, in the grand scheme of things, the challenges that I’m working through now are minuscule.

I’m grateful for the challenges and really happy with how I embraced and worked through them in March.


One of the highlights for me last year was starting Strategic Coach. There are a lot of things to love about the program. A particular highlight for me, though, is the practice of looking back and celebrating wins.

As humans, it’s easy to look ahead and focus on all that remains to be done and lose sight of what already has been done.

Each week, I take time to look back on the previous week and identify the wins. It’s proven to be a consistently encouraging and inspiring exercise.

As I look back over the past month, these achievements stand out:

  1. Tiny Habits Momentum – Beyond my own personal progress with tiny habits I’ve had the opportunity to talk about habits more broadly. Wes Via invited me on his podcast and we recorded an episode together. I’ve talked about habits in a number of personal conversations and have been really happy to see folks experimenting with habits of their own. I also finished publishing my book online! You can buy a signed copy (I still have a few left!) or read the whole thing online for free.
  2. Developing Again – After multiple years of being around code but writing little of it myself I jumped into the deep end this month, doing WordPress development on a client project and multiple personal projects. It’s been great. I’ve had to brush up and learn a few new things but overall I was able to accomplish a lot. Going forward, my plan is to stay connected with development and average a day of week of working in WordPress and writing code.
  3. Client Onsite – I flew out and spent a day with my development client at their office and was also able to have dinner with friends in the area. Having time with the client and their team in person was really helpful in building context and prioritizing efforts. It was also great to have the travel time to think and process.
  4. HostCamp Progress – I’m co-organizing an event scheduled later this year to bring together leaders in the WordPress hosting industry to focus on “Advancing WordPress infrastructure”. I’m part of a great small team and we made a lot of progress in March.
  5. Advising / Supporting – I’ve been able to invest time and energy advising and supporting a few WordPress projects (and the people behind them) that I care about. Highlights include WP GraphQL, Block Lab, and Branch.
  6. Research Project – I started and completed the first phase of a research project, looking at 100 different product companies and how they’re using / not using WordPress. It was intense, a lot of work packed into a fairly short period of time, and a lot of fun.
  7. First Report on – Drawing from the results of my research, I wrote and published a report, introducing and explaining the concept of an Ecosystem Plugin and highlighting the opportunities I see to develop these plugins for WordPress. I’m really happy with how it turned out and particularly happy with the progress I was able to make in better defining the idea of WordPress as an Operating System.
  8. Creating OpenRank – I created 1.0 and 1.1 of OpenRank, a set of scoring criteria for evaluating WordPress plugins.
  9. Expanding Integration Index – I added 80 products to the Integration Index in March, drawing heavily from the companies I looked at during my research.
  10. Plugin Curator Progress – I’m creating a plugin to accompany I developed a working prototype (powered by GraphQL!) and am getting closer to making it available for testing.
  11. Added Four Clients – I added two ongoing development clients and two consulting clients in March, taking me to my cap on development (I set a maximum of three) and only two slots left on consulting. I’m expecting to add one more consulting client in April, leaving one slot remaining.
  12. Creating Clients Membership – My good friend and former student Luke Farrugia has been running Creating Clients on his own for a few years now. I started contributing content again in March, sharing a weekly update with community members.
  13. Local Involvement – I serve on the board at our local private school and recently began working as chairman for a Capital Campaign Committee to raise funds for a new facility. I’m part of an amazing team whom I’ve really enjoyed working alongside. We started meeting / planning together in March.

Whew! And that’s a wrap! It’s been a great first month. I’m really happy with my progress, both personally and professionally. I’m looking forward to what’s ahead and also happy to keep taking life one day at a time.

Special thanks to Joshua Wold for the illustration.