Your reading list needs more cowbell.

I wrote this based on a conversation I had with a colleague about reading lists and based on more than two decades of working in and around tech. If you're curious how I think about approaches to reading lists and learning, then read on. This is all opinion, and offered freely, so the usual caveat emptor applies.

General Breadth, Disciplinary Depth, and Industry Context

Leaders are readers, so the saying goes. I agree for the most part, although I'd probably suggest that leaders are learners. There are a lot of different ways that we learn, and as individuals the style that works best can vary a lot. Not only can preferences and best methods change, they can vary depending on the context and content of the information.

Reading lists and book clubs can be useful tools for learning, just not for everyone and not in every circumstance. Reading books isn't an exclusive or even a leading indicator of being able to learn, or lead. Some of the best leaders I know barely touch books; instead they spend enormous amounts of time interacting with others and exploring ideas through conversation.

I approach the "read list" a bit differently. Instead, I think of it as a framework to approach knowledge. How do I find new information, understand that information, and make that information actionable in the framework of breadth of general understanding, depth of disciplinary understanding, and context of industry. That approach can take you into a lot of different places and it turns you into a bit of a hummingbird. A chapter of a book, a college text, a research paper, a YouTube video, a twitch stream, a hands-on lab, a conversation. These can all be sources of highly valuable insights and understanding.

Don't get me wrong. I read a lot, it just isn't usually a book. There's no prescriptive list. Using any framework to guide your learning allows you a lot of freedom to choose what content you spend time on. It puts you in control with a specific perspective on how it applies and what value you can generate from it.

General Breadth

Oh, surely you've heard about books like The Death of Expertise, or Range. Generalist-ism is the new specialty. And there's a reason for that. A general base of knowledge creates opportunities for knowledge transfer into other domains, or bootstrapping into new contexts quickly. Given how fast problems evolve in today's world, the importance of working potential solutions at a speed that keeps pace with the problem is one of the most difficult challenges any modern professional faces.

Just because someone writes a book on how important generalists are doesn't make it definitive or singular. Build competency generally though taking an interest in the world and the things that occur in it. The key is to build consistent breadth, which should be informed by depth in a handful of disciplines and context by industry.

One of the best and easiest ways to do this is to follow the white rabbit (that's an old nod that goes back to Through the Looking Glass). Remember that everything can typically be boiled down to people, process, or technology. Orient yourself accordingly. Find topical areas that bring you joy and use them as levers to be curious about other things.

For example, those who know me know I have a love for Table Top Role-playing Games (TTRPGs). And, although the systems are fascinating, I love the way they could be used as a springboard into entire fantasy worlds. When I was younger, I spent a lot more time reading sourcebooks and thinking about the ways in which people used these tools and processes to create entertainment than I ever did playing them.

By learning about the world around me through the games I played, I got curious and read other things. By jumping from one to another, I broadened my understanding of both the source material as well as the related information. Often times it quickly jumped from the world of fantasy to reality; this was especially true for near sci-fi games or even far futuristic games.

Today I don't have the sort of free time I used to and so I use technology to play that role. I know myself and my interests well enough to define broad topics and interests on Reddit, Quora, and Medium across a multitude of topics. I subscribe to various YouTube and Twitch channels. I follow interesting (and sometimes completely random) people on Twitter and LinkedIn. I use those initial starting points to read things that catch my interest, use them as starting points for other learning, or it may spur a web search for more information. Technology has enabled such powerful information exchange that while you can't Keanu your way into Kung-fu just yet, a quick google search on your phone when a term comes up during a meeting that you've never heard of before can help fill in the gaps and give insights.

Disciplinary Depth

Over the past decade or so there's been a lot of conversations about deep "T" employees. The idea is that in today's knowledge and information economy employees who have breadth (see above) and depth, focus, and expertise in at least one area can create the most value for the organizations and teams they work with. Modern team design has evolved some of the thinking on this, although it isn't discussed often.

The challenge with "T" employees is that it glosses over a lot and disadvantages both the individual, the team, and the organization. Contributors should never been seen in such singular expertise because it assumes that the need for the single discipline is enough to fully saturate the capacity. People aren't machines, however, and trying to design teams and organizations for those types of optimizations can result in negative impacts to productivity and team performance.

Bringing the usual thinking into the modern era consists of converting the "T" into more of a trident with between three and five disciplinary areas of various depth. And the reality is that most people already fit this model. It puts the onus on the organization to recognize the inherent value in team members who have a variety of interests and levels of expertise. For an organization, trident employees can perform better in modern environments where context and problems can change and evolve rapidly.

Trident employees also operate more effectively in emerging, self-organizing teams and organizations as described in Reinventing Organizations. They bring enough expertise and knowledge to be value creators in modern work places while maintaining flexibility and the ability to pivot quickly into new spaces. Sometimes those tines of the trident are closely related, and sometimes they're in completely unobvious areas. The key is understanding, exposing, and encouraging the development of those multiple disciplines.

Industry Context

There's a common phrase that DevOps leaders like to talk about. "Fall in love with the Business Problem." It's the idea that there is a functional process in the busines, something that takes inputs from people, does something with those inputs, and creates an output that ideally creates value for someone on the other side of the process. The science of creating value through applying labor has been a scientifically studied endeavor for nearly as long as the term "science" has existed. And today, there are dozens of ways to learn about how to observe, measure, document, and improve the application of labor to create societal value.

Less common, however, is how the application of that disciplinary area (see above) within the context of a specific set of processes. And the collection of those processes into practice. This practice-based approach is how we define industries. This is the nuance of the pareto principle - the 20% that's different between every organization and vertical. It's why writing a formal document is mostly the same at every organization, and yet the difference is just subtle enough that it isn't entirely portable between organizations and industries.

Because industries tend to be heavily value-oriented, individual organizational success depends on generating enough value on an ongoing basis that they can participate in the market. There is less process information of the industry compared to the disciplines that they are dependent on. For example, medicine as a discipline and medicine as a value-generating activity (e.g. running a practice or a hospital) can be very different things. Learning these contexts is based on exploration, exposition, and iteration of practice.

In plain language, the old cliché of "you had to have been there" applies. And, while there might be books that tell stories and observations of the industry in practice, the reality is that it is very difficult to capture the act of value creation. It really is something that has to be experienced. There are well documented ways to enable these sorts of context exchanges more quickly and bring people up to speed more efficiently, and they should be seen as supplemental to the core activity: participation.

The Cowbell

Here's the part where I get to say that this is an example how one individual manages to understand and grow with the world around him. Everyone is different and if you've read this far, then I'll leave you with a couple of thoughts on how best to apply this approach.

• Make sure you've got a clear understanding of the tines of your trident. They are the aspects that set you apart from anyone else operating in your role.
• Those disciplinary tines are also likely related to things that bring you joy. Use that connection to find learning paths that evoke the same enthusiasm and happiness.
• Industry context matters - invest in learning and participating in the business in the same way you learn your discipline. This focuses your ability to create value by solving problems or advancing opportunities.
• Invest your time consuming a variety of content. Diversity in content gives you more value.
• Be curious. Make time to follow rabbit holes into unexpected places. This is one of the best ways to build breadth.

It took me a long time to get this all down, and I'm sure there are more edits to make. Are you going to try it? Do you have a similar approach? Or something completely different. Feel free to comment below!