How Pushing to the Edge of Your Understanding is Key to Getting What You Want in Your Career

Hey, social change agents!

In Level 1: Consistency, I walked you through how I whip my brain into shape and keep it sharp for the challenges ahead. Today, I'm explaining my second level of depth in my work which identifies how I choose career capital to pursue, how I judge its value and rarity, and specific activities I undertake to help me identify and push past the limits of my understanding. Let's get experimental!

Level 2: Experimentation

I designed this step to push myself outside of what is familiar and into what is closer and closer to the cutting edge of my field. Without the first step of Consistency, I would not be able have the discipline to keep pushing despite the difficulty of a new subject.

Action / Inputs

Experimentation is where I tackle a tough subject within my field that I struggle to either understand or implement; these are the items that have already been proven to be valuable but have yet to be learned. It is how I decide where I will concentrate my career capital acquisition efforts. I use the heuristic of my inability to understand or implement to help me categorize subjects that I can't immediate access and use to produce additional value in my work. As one who prides myself on the knowledge I have, this step is particularly difficult to be honest about what I truly do and do not know. To help me accurately identify where I know enough to convince another versus enough to convince myself, I ask myself the following questions:

  • Can I produce an easily understandable description of the concept in 1 sentence?
  • Can I cite at least 3 counter-arguments against a concept and provide internally-consistent answers to those arguments?
  • Can I produce a drawing that accurately addresses key tenants of the concept?
  • Can I accurately diagnose systems that are incorrectly using this concept or introduce this concept to systems through a custom implementation plan?

The first two questions are used to judge whether I understand a concept while the last two questions judge whether I can implement that same concept. I give equal weight to understanding and implementation because it is my belief that understanding without implementation is ungrounded theory, and implementation without understanding is living an unexamined life (which is totally not worth living according to both Socrates and myself!). [caption id="attachment_654" align="aligncenter" width="1024"]

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I identified five ways I personally enjoy experiencing new ideas: audiobooks, lectures, exploratory meetings, documentaries, and academic papers. These five things are the tools through which I regularly put my brain through its paces, but they may not be the same for others depending upon their preferences and deep work crafts. As one who enjoys engaging deeply with individuals one on one rather than less deeply with a lot of people, these outputs allow me to have some sense of control in the environment in which I experience new ideas.


Because Experimentation and the next step, Comprehension are done nearly at the same time, the metrics for each are somewhat informed by the other. I judge comprehension based upon the fidelity with which I can reproduce the idea in all of its facets in the form of a conceptual minimum viable product. An example of this would be the ability to use concepts in Algebra to derive the Quadratic Formula (which, by the way, is the opposite of b, plus or minus the square root of b squared, minus 4 times a, times c, all over 2 times a) from a quadratic equation (ax2 + bx + c = 0). [caption id="attachment_655" align="aligncenter" width="960"]

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Image credit:[/caption] I judge Experimentation, by contrast, by idea flow or what new ideas are created through exposure to this new subject or set of ideas. That's why I use the following metrics:

  • Number of implication ideas generated per learning session: I use this metric to measure the merging of my existing knowledge and the new knowledge. In addition to the 4 questions I asked myself previously, I can verify that this new knowledge is 1) related to my original expertise, and 2) that I am unfamiliar enough with it that I can generate questions and potential subjects of additional deep work focus. By writing down and tracking the number of new ideas, I can keep myself focused on fully exploring a challenge concept without being tempted to jump ahead in my process in my enthusiasm.
  • Implementation difficulty rating 1-5: This also goes back to the questions I asked myself and assigns a number value from 1-5, 1 being easiest and 5 being hardest, on how difficult I think it will be to implement via drawing a picture and using the concept to diagnose systems. This matters because the point of the Experimentation level is to make my brain work at something it's not an expert at, so a rating below 3 likely indicates that I'm not tackling a sufficiently difficult subject.
  • Conceptual stretch difficulty rating 1-5: Like the implementation difficulty rating, this rating helps me stay honest with myself on what I actually know and what I don't. It quantifies the first of the 4 questions I ask myself to judge how well I can communicate the concept and answer a hypothetical FAQ. Again, a rating below 3 indicates that I'm swimming in my mental safe zone rather than exploring deeper and more challenging waters. Both rating systems depend upon your ability to be honest with yourself. No one is cheated but yourself.
Blog Ending

As humans, we naturally try to avoid things that make our brain work hard. We use mental shortcuts to help us remember the 9 time tables; we develop habits to help us get through our days without having to think about every single things; and we even develop unconscious bias to 'help' us categorize people and how to interact with them. But, when we take the time to truly challenge our brains in the subjects that matter to us, we are able to unlock a level of curiosity and and knowledge of which we've only seen the barest hint. When you spend time existing in mental discomfort as an exercise in learning, you push the edge of possible and orchestrate breakthroughs that can propel your career much further and much faster than ever before. You've only to develop the courage to know yourself.

Make sure you don’t miss levels 3-5 by signing up for mailing list to receive weekly roundups. I’ll also be modifying the chart as I test with others to make it more universally adaptable (which you’ll get first … if you’re on my mailing list that is!)