Go With The Flow

I started reading books on time management as a late teenager. One of my first blog posts was about time management! (That, frankly, was embarrassing to re-read – and that means I’ve grown!)

I remember how inspired I felt. I started implementing time management systems and felt like I was figuring it all out.

One book told me to start my day by “eating frogs”.

Another told me to put the big rocks in the jar first, then pebbles, then sand, then water.

Another told me to setup inboxes and work my way to inbox zero.

I tried it all. I was on top of the world. No more procrastinating. I was getting things done, filling my glass jars, and eating those frogs.

The Problem

My time management win streaks wouldn’t last more than a few months. I’d hit a wall, something would fall apart, and before long the system would collapse.

My conclusion at the time, and for years after, was that I just needed to try harder. I needed to exercise more grit, more determination.

There’s something to all that, for sure. It didn’t work for me, though.

As a new husband, I was a few years into my experiments with time management and had just started practicing the pomodoro technique.

My wife called me during a time block to tell me that she was pregnant. I told her that I’d call her back as soon as the time block was done.

I forgot to call her back.

That was terrible. She still agrees.

Time Management Today

I don’t practice inbox zero anymore. My jars are unopened on the shelf and the frogs and I are at peace.

I get a lot done, though. What’s different now?

I think differently about time and about life. My personal time management philosophy today is simply:

Go with the flow.

Two Key Lessons

The application of my philosophy is summed up in two key lessons.

  1. Play to my strengths – What the books didn’t take into account is that we’re all different. That stuff works, it just didn’t work for me.

    I like flexibility. I like variety. I don’t like getting pinned down. Time blocking, rigid scheduling, all of that can work great for a lot of folks – it just didn’t work great for me.

    I had to get to know myself better and figure out how to play to my strengths.
  2. Design an Operating System – We use operating systems to interact with our computers, our phones, our cars, and, whether conscious or not, we use operating systems to run our lives.

    Over the past few years, I’ve invested time figuring out the habits and tools that I need to get things done.

    My operating system includes “tiny habits,” a scattered system of electronic and paper notes, and a few pieces of software to keep light track of “projects” that span longer periods of time.

    The key for me was doing the work of designing. I learned to get to know my strengths and figure out what works best for me.


I have two recommendations to share based on my experience.

  1. Use tools to get to know yourself better – The StrengthsFinder tool is a great resource. My personal favorite is the Kolbe A, which contributed to several significant breakthroughs for me in both my overall thinking and approach to time management. Make use of the tools available.
  2. Design tiny habits to build momentum – Ridiculously small but consistent amounts of progress in the right direction over time is where magic happens. Rather than trying to “fit it all in”, design habits around what’s important to you and build on those. (If you’re curious for some practical examples, check out my (free) book on Tiny Habits)

Managing Time

The great news about time is that we all have the same amount to work with. I’ve noticed that we humans, in general, tend to beat ourselves up about how we use time. It seems to be a fairly universal struggle.

Get to know yourself better.

If you’re in to inbox zero, filling glass jars, or eating frogs – awesome. If not, keep experimenting and design an operating system that works for you.

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.