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.