Buckets

One continuous source of conflict for me is the tension between seeing myself as “a whole person” while also balancing my many different goals, roles, and responsibilities.

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Image Credit: PublicDomainPictures (Pixabay)

I’ve started to realize that in order to sharpen my focus, I need to start intentionally designing some distinct buckets to pour my efforts into. These can’t be activity-based or project-based, but instead need to be visible from the 10,000 foot view of my life.

And so as I think of that, I find three areas that really matter to me, that I think will serve as my buckets throughout 2017 and hopefully beyond: Business operations and analysis, research and development, and family life.

Bucket #1: Business operations and analysis

I’ve gone through life labeling myself as a software developer, but in truth it’s my experience with working on and solving challenging business problems that I’ve built my professional reputation on. This is what I enjoy most in my consulting work, and what I’ve had the most objective success with, and so I intend to triple down on my strengths.

The transition from “software developer with some business skills” to “business analyst with software development skills” happened quite a while ago for me, and I wish I had updated the relevant labels a whole lot sooner because it would have made life easier.

But now I want to take things even farther than that, by truly diving head first into an operations management role. I’ve been doing a bit of that in my fellowship with Madriska this year, but as we head into next year Brad and I intend to take our strategic partnership even further so that I can begin to shape the direction of the business as a whole and try out some of the ideas I’ve been thinking about for a very long time.

This is going to be my first foray into building a brand around something other than my own name and independent projects. Because I’ve been so deeply invested in Madriska (and vice-versa) over the years, it makes perfect sense… but it’s a new thing for me to be flying under a shared banner. That said, this also means that I’ll be working with a whole lot more resources than what I’d be able to muster up on my own, and so I’m very excited.

Bucket #2: Research and development

The part of my professional life that has always taken the most of my time has not been my commercial work, but a broad range of activities I’d categorize loosely as R+D.

This includes work on open source projects (like PrawnPDF), all of my writing work, the tremendous amount of formal and informal teaching I’ve done, the endless amount of 1-1 conversations I have each month to learn about the industry as whole and how people fit into it, time spent on collaborations, conference talks, etc.

I’ve at various points in my life attempted to properly bootstrap my R+D work into a full time gig. Although technically speaking there have been stretches of a year or so at a time where I was “ramen profitable”, it has always been a great struggle with to try to make a living primarily off of R+D in a way that fits what I really want to be working on.

As I get a bit farther along in my career, I’m basically content to take a slower road to being 100% self-sustaining if it means getting there at a bit more of a steady pace with my wits intact. So while I will still continue to look for ways to fund my R+D work, it doesn’t need to bring home the lionshare of my revenue any time soon.

Historically, my research efforts have sort of followed the pattern of “wherever the wind takes me” and that’s something I want to get a little more control over. So what I’m doing now, and what I’ll do more and more of in the months and years to come, is begin to orient my R+D efforts around the main ideas of Mel Conway’s #HumanizeTheCraft movement.

What I love about Mel’s work is that it’s so shockingly ambitious that it will cover everything from pedagogical theory to possibly building programming languages and frameworks from scratch to support the features we’d need to build truly human-centric software development tools. So it’s not like my scope will need to narrow in order to focus on this theme: it just means being intentional about looking for the connections between what I want to learn and a deep underlying purpose.

My dream is to one day run a self-sustaining and independent field research group, with half a dozen or so people working with me to explore stuff along the frontiers of our industry. But that is like… decades away still.

Bucket #3: Family life

In a single blunt sentence: I suck at taking care of myself and my family.

So I need to figure out how to pour a whole lot more of my efforts into that side of things.


This idea of “buckets” is somewhat new to me, and so it’ll be interesting to see how it influences my decisions and my working habits. I have been fairly successful at rising above activity, task, and project-level thinking, but historically have operated mostly by intuition as a result of that. This feels a bit more intentional, and so I’m very curious to see how it all pans out.