This morning, I opened a new tab on my computer to see the following quote prominently displayed:

“All courses of action are risky, so prudence is not in avoiding danger (it’s impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer.”

— Niccolo Machiavelli

I realize that Machiavelli isn’t exactly great to take inspiration from for a variety of reasons, but this particular quote at this specific time seemed alarmingly apt. I would normally take a few minutes to roll the quote and message in my head and then get on with my day, but this seemed like a good opportunity to capture my mentality, my current challenges, and to look back for insights into what I could have done better.

Table of Contents

Discussion Framing

“Risk mitigation” is the term I use when it comes to planning and accounting for risk in my actions. All actions carry risk and have an inherent cost, which can effectively increase the true cost of the action. The cost is paid in terms of resources. This may seem abstract, but I will define some resources to frame the discussion.

Let’s assert that time is the most valuable resource available to any person, as it is the singular means in which we are able to execute actions to influence the world. Let’s also assert for the purposes of this discussion that time is a finite resource. I realize this assertion in itself is complicated; economic and social privilege greatly influence the maximum potential time available for you to utilize.

Let us then assert that the second most valuable resource is health, as physical health gives us the energy and utility to conduct actions with our time. Our ability and efficiency in conducting actions proportionally diminishes with quality of health.

I realize the axiom of the Great Beast, capitalism, is that money is the most valuable resource; I will claim it takes the third spot, as we are speaking in more absolute terms. Money is the multiplicative wild card that influences all other resources. Without wealth, minimal resources and increased health risks can be a fact of life. Those with access to wealth are, conversely, capable of making larger influences more quickly and live longer, healthier lives due to being able to afford any and all necessary healthcare.

I believe information - the factual kind - sits quietly and immediately behind money. This is because especially for our youth, high quality information is sometimes behind multiple barriers (such as a lack of access to good education or even the internet) which could be removed with money. Information begets information, and it allows the utilization and growth of resources and risk awareness. Free and open access to information is certainly at its highest rate in human existence so far, but this can be useless without understanding how to collect and properly use the available information.

There are more major resources, such as social connections (peer learning is a fantastic process), and I only briefly touched on socioeconomic imbalances (which heavily skew everything), but I want to stop here to focus on the immediate internal decision-making and planning process.

To summarize, our Four Key Resources are:

  1. Time
  2. Health
  3. Money
  4. Information

So, we’ve established our resources, but what is our objective, and what is the course of action to get there?

Objectives and Actions

Given limited resources, we want to:

  • Maximize the returned value of actions
  • Minimize the impact of risk associated with those actions

(See? “calculating risk and acting decisively”)

From personal experience, it’s easy to slowly and poorly commit to a course of action, only to eventually realize that you have effectively nothing to show for it. Similarly, following a course of action without considering the risks can introduce a multitude of failure points, such as running out of resources, a forced shift of priorities, or ultimately wasted effort.

To shift from theory to the specifics of Learning Log, my action is to log and prioritize my development learning and notes for the objective of self-empowerment to create and build tools and resources to help people, as well as to grow my career.

(For the record, web learning has also been for personal enjoyment, but that’s a difficult target to measure and therefore more of a bonus in the context of this discussion.)

Risks in Planning Learning

As time is my most valuable resource, the biggest risk to successfully achieving my objective is that I utilize my time sub-optimally. Sub-optimal time utilization in this case means not fully processing new information, not reinforcing and using new information, and not prioritizing learning the “correct” information.

But wait a minute…

There are other external risks that I have been evaluating, but since external factors can usually only be minimized at best, I will be focusing specifically on factors within my immediate influence.

To further break down risks in the form of poor use of time, I’ve split this into two major categories:

  • Incorrect learning prioritization
  • Low information comprehension and retention

Each category has its own costs, contributing factors, and mitigation approach.

Incorrect Learning Prioritization

Incorrect prioritization when learning a new subject is, arguably, one of the highest likelihood risks to overcome. You don’t know what you don’t know, and you’re relying on seeking out high-quality resources to help steer the course of your entire learning experience. You may not know that you’ve been heading in the wrong direction until you’ve sunk considerable resources!

Contributing Factors
  • Unsure where to begin
  • Unsure of what is high-quality or high-value content
  • Unsure of an effective learning sequence
  • Unsure when to use what tools
  • Unsure of which skills are important to learn in the first place
Resources Consumed
  • Time
  • Money (depending on learning approach)
Risk Mitigation Plan

Referring back to “information begets information,” there will be some nearly unavoidable discovery period when learning a new skill. If there is a central source of verified information (main site, high-quality wiki, etc), that’s an excellent place to start. In lieu of that, or perhaps in addition to it, I find that trying to read just about anything you can come across relating to the specific topic is helpful to at least expose yourself to the terminology, and maybe some general concepts. From there, you can use the terminology and concepts to seek out more detailed explanations.

Additionally, try to make connections with people in the skill that you are trying to learn. If they can use their experience to recommend resources that helped them when they were starting, or help steer you or answer questions, then that is an excellent boost!

I am very fortunate in that many of my friends are already developers, so I have access to many great connections to ask questions and for help. Discussions with my friends have helped to guide me towards skills that are currently in demand, where to get started, and what tools to use.

Determining high-quality learning content, however, has been in itself a learning experience. I have discovered and had some great resources referred to me, but I have also organically encountered information that was either low quality, or too complex (out of sequence) to impart helpful information. Determining sequence is currently my next challenge with this site, as I have amassed a collection of resources that seem to be regarded as high-quality learning materials among other learners, and I need to sort and order them in a sequence that will allow for efficient skill progression. A properly sequenced learning item list will also make my Skills table progression value a more direct representation of my approximate familiarity with core skills.

Low Information Comprehension and Retention

Information comprehension and retention is an ongoing resource management struggle. You’re not just devoting time to expose yourself to the material, but you also need to allow for mental time to recharge, ample sleep, repetition, exercise, proper nutrition, and focused practice.

Contributing Factors
  • Physical resource deprivation
    • Poor sleep
    • Not enough exercise
    • Poor nutrition
  • Mental burnout
    • Not taking breaks regularly
    • Poor content pacing, overloading/cramming
    • Not allowing for recreation
  • Lack of focus
    • Not properly blocking distractions
    • Non-value-add tasks taking up the majority of time spent
    • External stressors (COVID-19, state violence, etc.)
Resources Consumed
  • Time
  • Health
Risk Mitigation Plan

Learning is so much more than just a mental activity. Your brain needs time to process new information in a diffused mode, resources to work at full capacity, repetition to strengthen memories of new content, and patience. It seems counter-intuitive that taking a break and going to bed on time can help you learn something you’re focusing on.

I struggled with this for the first few months (and, to be honest, slipped back into the pattern a few time since). I was taking on more than I could handle, and spending every free minute trying to absorb and expose myself to as much information as possible. I knew better, but with a looming and ambiguous deadline, I wanted to immerse myself as much as possible - let’s call this a “mistake of ambition.” I wore myself out twice trying to find a good and sustainable cadence, and you can see this reflected in my GitLab activity chart:

My nice new tabs

Dr. Barbara Oakley’s Learning How To Learn course is a fantastic resource, and one that I wish I had experienced years ago. Try as I could to overcome physical limitations, the lessons from the course hold strong, and I am trying to practice the teachings better. I now use an AHK macro called FlowTime to help me manage breaks in a slightly more flexible format than Pomodoro, and I try to make an effort to make time for true recreation (something I have always struggled with 😬).

This Learning Log site has also helped me to focus in more tasks. I’ve mentioned in previous logs that I was trying to migrate board tasks out of my Todoist account, and I have similarly made an effort to create issues in GitLab for other projects instead of tasks. This helps to keep me more focused in the mode of work I’m operating within, rather than changing levels of focus and not being as productive as possible. I have also given up multiple monitors for a single large monitor, which allows me to fill my workspace with only what I’m working on and nothing extra, helping me to focus in without notifications popping up on a second screen.

Cultivating an effective ritual for learning and reinforcement which is sustainable for the long-term is, essentially, an exercise in general self-care and personal health.


I’m sure there’s a tidy, Bayesian way to model the expected value of courses of actions given my current information, which may be an exploration for a future post. I hope that I have been able to demonstrate my thought process and how I seek to tackle complicated tasks with limited resources. The balance of time, health, money, and gathering information is delicate and fluctuating, but by learning what you can, and identifying risks, ambitious actions can enable you to chase the dreams you have always wanted to follow.