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.


Challenges

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.


Achievements

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 GrowInWP.com – 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 PluginCurator.com. 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.

Going Solo

After 4 ½ years in the agency world I’m stepping out to start a company of one.

These years have been amazing.

I’ve had the privilege of working alongside some of my closest friends, people who I admire and respect deeply.

And, in the midst of a number of what I consider “once in a lifetime” experiences I’ve had the opportunity to develop a personal mission. This personal mission is driving me and is why I’m now stepping out on my own.

My Mission

I believe in the importance and power of WordPress as an “operating system” for the Open Web. I want to see a strong, healthy, diverse, and vibrant Open Web for our generation and the next. I see the success and future of WordPress as an important indicator of the health of the Open Web.

In my work in the enterprise, and particularly with technology companies, I’ve had the rare opportunity to connect with numerous individuals and organizations outside the WordPress ecosystem, help them see the value of WordPress, and offer guidance on how to be a part of this ecosystem.

As I take off my agency hat, I’m putting on a hat that I’d best describe as the hat of an Evangelist.

My personal mission is to help technology companies figure out and invest in WordPress, the operating system of the Open Web.

I believe that if I’m successful in doing so, then that’s good for the companies I’ve had the privilege of offering guidance to. And as they serve their customers better through WordPress and attract new customers to WordPress, that’s good for WordPress and good for the Open Web.

So what’s next?

I’m open for work again! I’m looking for three types of engagements:

  • Consulting Engagements – One-time or ongoing engagements where I offer my insights, perspective, and strategic guidance. I’m best at helping organizations figure out their WordPress strategy. (I’ve setup a consulting page with more details)
  • Webmaster engagements – Ongoing, month-to-month engagements where I take on ownership of a web property (or multiple properties) and am responsible for “all the things” (e.g. maintenance, updates, support, and ongoing development).
  • Small WordPress projects – Projects where I can come in and “do all the things” (I code, design, write, test, you name it) to get a job done.

Ideal budgets are in the $5,000 to $2,500 range, either per project or per month.

As I work, I’m pursuing the “big picture” side of my personal mission through a few different projects:

  1. GrowInWP.com – This project is intended to serve as a guide for decision makers in technology companies to help them figure out WordPress. I believe strongly in sharing my best thoughts and ideas freely and openly and I’ll do so through GrowInWP.com.
  2. IntegrationIndex.com – This project is intended to help product managers evaluate how well their product integrates with WordPress.
  3. PluginCurator.com – A tiny project (with a minorly ambitious roadmap) designed to help site owners discover new plugins.

Outside of those projects, I’m also working to support HostCamp, the Tide project and Creating Clients.

Thank you for reading! If I can be of help to you or someone you know, let me know.

500 days of pushups

Today is the 500th day in a row that I’ve completed at least a set (and nearly always 4 sets) of pushups. No exception, rain or shine, sick or healthy, on the ground, or in the air.

When I started out I could barely do a single pushup.

At my peak near the end of 2018 I was averaging over 150 pushups per day.

I’ve tapered off since, now averaging around 40 per day.

It’s been great. I’ve gotten better at pushups and, as was my original intent, started a positive trends towards investing more in my health.

It turns out, though, that pushups were only the beginning. As of today, I track 29 different habits, most of which have passed over 100 days.

It seems impressive, and over the span of a year now for many of my habits, I’m noticing real results.

But what’s actually important about my experience with habits and what I care to write about is how ridiculously easy I designed each of my habits to be.

They’re all tiny habits and, as such, even though I still have days where I don’t want to complete them, I do it anyway.

500 days of pushups is a big accomplishment for me. Yet it’s anti-climatic. I didn’t set out to get this far, I just decided that I’d pick something super easy, that I could do no matter what, and keep doing it.

Momentum is a beautiful, powerful thing. As much as I’m sure I’ll enjoy looking back on day 1000, that’s not what matters right now. I’ll complete today’s habits and do them again tomorrow.

Experimenting with early mornings

I’m on Day #9 of a new tiny habit, which I’m tracking as “Prepare tomorrow morning’s routine (set out clothes if needed, water, etc)”.

Prompted by a few friends a few weeks back, I sped-read through a book called Miracle Morning and decided that it was time to give early mornings a try again.

I’ve historically been a big fan but got into the badhabit over the past year of both getting to bed really late and then staying in bed till my wife takes the kids to school (which, not a big surprise, she isn’t a fan of).

Now, for the past 2 weeks I’ve set my alarm for 5 AM on most mornings and so far I’m really happy with the results.

The biggest difference is time to be awake in the quiet and thinking, reading, and working before the day kicks in for everyone else.

It hasn’t been easy.. There were a few nights where I still got to bed late and got up early anyway. Those days were a bit rougher, but I made it.

If you’re interested in experimenting with early mornings, there are two key takeaways from my experience thus far that I’d like to pass on.

  1. The key tiny habit is to prepare the night before – I set out my clothes, fill up a water container, and put a book out by my couch in the living room. When I wake up in the morning I get up, get dressed, and go straight to my couch to begin my breathing exercises. I’ve prepared a routine for myself that I don’t have to think through in the morning. Figure out a routine for you that gets you out of bed without thinking about it.
  2. Your mindset matters – The most helpful thought for me from the Miracle Morning is this idea of telling myself, before I go to bed, that whatever sleep I get that night is going to be enough. It seems counterintuitive at first, but it works. I’ve felt anxious in the past.. “Oh man, I have to get my 8 hours in or the morning will be terrible..” and instead I’m saying “You know what, whatever I get tonight will be just fine. I’ve done my best and I’m grateful.”

Now time to get ready for bed.

Choosing a Habit

I’ve been asking for feedback on ways to make the first edition of Tiny Habits more useful.

One suggestion I received was to write about the thought process behind choosing a habit.

My original motivation for experimenting with habits back in 2017 was improving my health.

I chose my first habit, pushups, because I believed it would get me started in the right direction. And it did!

But as important as exercise is, the big thing I wasn’t addressing with regards to health was my relationship with food.

See, for a long time I just couldn’t figure out how to form a helpful, momentum-building habit around food. I thought of a few different food related habits I could experiment with and they all just felt wrong.

The whole point for me behind experimenting with tiny habits was to choose things so ridiculously easy that I wouldn’t have any trouble keeping them up.

And that’s worked. I’m coming up on 500 days of pushups soon without missing a single day.

Food, though, I just couldn’t crack.

I kept thinking about it, though, and after a few months I settled on an idea.

I started tracking the following habit: “Take a picture of or record at least one meal”

Why a photo? What’s the point of that?

Well, my thinking went something like this..

Trying to limit what I eat or eat more of something is going to be hard to do, especially without breaking a chain. I might be in good shape for a week and then it’s a special event or we’re eating out all day, etc.

I don’t like the unsustainability of forming habits that restrict me.

What I actually want is to make it easier for me to make better choices.

In order to make better choices I need to know what choices exist and that requires awareness and keeping the subject matter in mind.

Speaking of awareness.

Take a random skill, like juggling, card tricks, calligraphy, playing an instrument, learning a new language, etc.

Now, look back over the past 10 years of your life.

For one of those skills where you don’t currently have any ability, if you had thought about that skill at least once each day, would that have made a difference?

I suggest it would have. When you’re aware of something you’re more likely to take action, however small. You’re more likely to ask a question, given a relevant opportunity. You’re more likely to pay attention a moment longer when you notice something related.

So, while I’m my thoughts and ideas on the matter are still in development, I’d sum it up like this.

Take a big, difficult “goal” (I don’t like the word goal, but that’s a topic for another time) you have in mind like improving health. Break it apart into “sub-goals” like eating better or exercising more, then form rediculously tiny habits that you can start that build momentum towards that goal.

And, if you can’t think of anything tiny enough (e.g. the equivalent of pushups), start by just forming a habit around awareness (e.g. taking a photo).