Justin Taylor Raise your hand if you’ve ever set yourself an ambitious goal, and then watched it just…die on the vine as life seemed to get in the way. While browsing my bookmark archives, I stumbled across Scott H. Young’s “Do the real thing”. It’s a good read, and the advice is solid - to get things done we need to do work that actually matters in making progress.
However, it struck me that the practical parts of the article (the rules for doing the real thing) are a little light. A deeper examination of the reasons why we fail to achieve our goals was in order.
For a long time my mental model for success/failure has been one that resembles losing to Pressfield’s Resistance. However, failure doesn’t typically resemble a singular event much less a war to be fought daily. We don’t fail because we didn’t defeat the wolves of resistance on some specific and pinpointable day. Such thinking results in the root causes going unexamined, and thus the resistance persists.
In all energy exchanges, if no energy enters or leaves an isolated system, the entropy of that system increases.
Energy continuously flows from being concentrated to becoming dispersed, spread out, wasted and useless.
– Muse, 2nd Law: Unsustainable
A more useful conceptualization is to think of our goals as a system, or a machine. Like any system, these goal systems are subject to the 2nd law of thermodynamics. Without the constant addition of energy, entropy will increase until the system is at a standstill. (In case you skipped physics, entropy is your coffee going cold as the drink reaches an equilibrium with its environment, or your room getting progressively messier).
Entropy in our goals and projects comes from a variety of sources (much like it does in the real world). It shows up as underestimation in planning, beliefs that hold us back, becoming sidetracked by trivialities, or just life shoveling too many things onto our plate.
This change in concept removes failure as a binary personal flaw (win or lose against “resistance”). Instead, it frames progressing towards our goals as something that is allowed to wax and wane with life’s challenges. The sources of entropy in our system concept stem from things that we all struggle with at times. Framing it in this way enables us to examine these struggles with compassion while making progress (however slow) on our goals and dreams.
The only real failure is letting the system come to a halt and then abandoning it when we still wish for the success we started out to achieve. As long as we are pushing energy into the system, as long as we still dream of achieving what we set out to, and are still trying to get there, we have not failed.
Sources of goal related entropy
There are three common sources of entropy sapping energy from our personal endeavours. False obstacles overcomplicate our plans, while our inherent optimism bias often results in over-estimating how much we can achieve in a given time. Finally, we all fall prey to the trap of trivial distractions, aka bike-shedding.
False obstacles
Our core beliefs are a powerful thing - they are the machinery that our decision-making runs on. They subtly influence our thinking, and can end a desired goal or dream before we even get started. One of the more common effects of these can be false obstacles. They take the form of a laundry list of seemingly intractable prerequisite tasks that we think we must do to achieve the goal.
If we examine these prerequisites closely, we often find that they are ultimately not realistic, or that there is another way around them. In short, they are excuses in sheep’s clothing. The phrase “I can’t do ____ until/unless/because ____” is a good sign that we need to look closer. These false obstacles sap energy and drain our momentum by making the goal seem further and further away.
While they often appear to be the only way to achieve the goal, in reality there’s always another path that can be taken. Consider overseas travel. Most people would get stuck on what to pack, or a need to plan the trip out in minute detail. These are all false obstacles. The only hard requirement for overseas travel is a valid passport, everything else is up for debate.
My brother once travelled France and the UK with a hydration pack (minus the bladder) as his only piece of luggage. The travel writer Rolf Potts travelled for 6 weeks without any baggage as part of his “No Baggage Challenge”.
He also wrote “Vagabonding”, a solid guide to travelling in the absence of trust fund levels of wealth. Communities like Couch Surfing make it even easier now. Personally, during my last trip, I stopped planning in any great detail beyond making sure I had a bed when I landed.
The planning fallacy
The psychologists Daniel Kahneman and Amos Tversky first described the planning fallacy in 1979. It’s one of the most pervasive effects in human history - generalising equally well across cultures, and task sizes whether it’s doing our chores or planning a multi-million dollar infrastructure project. For our personal projects and goals, it explains why we cannot seem to hit a target deadline to save our lives.
The fallacy is the result of an optimism bias - we are realistic about the time it’s taken for us to complete a task in the past, but we are optimistic about the time required to complete a similar task in the future.
In not learning from our own past experiences, we don’t account for the inevitable delays, interdependent tasks, unforeseen obstacles, and accidental stupidity that occur when trying to do anything.
Parkinson’s law of triviality
It’d be great if, once you avoided the false obstacles and chronic underestimation, you were on the easy path to goal nirvana. However, this is when the third horseman raises its ugly head - the law of triviality.
The time spent on any item of the agenda will be in inverse proportion to the sum [of money] involved.
– C. Northcote Parkinson
It’s the tendency we all have to take the path of least resistance when presented with multiple options. This happens even if the easy path isn’t overly consequential to the big hard thing we’re trying to achieve.
For software engineers, it’s known as yak shaving - a stupid, fiddly little task that bears no obvious relationship to your goal, but that is connected by a pointlessly long chain of causal steps.
For a software engineer, it looks like this:
- They want to write more and decide to create a blog
- So they research the best options for static site generators
- Then they build a custom theme
- Then they shave the rest of the yak by wasting more time deciding on hosting
- Finally, they launch a blog with a single post (“how I built this site”), and never write again.
This is evidently an insane course of action - our notional software developer should instead have opened a text editor and started typing. But this kind of behaviour is common to us all. How many of us have sat down to Do The Thing, and ended up reading our emails, browsing reddit (“research”), or some other easy and inconsequential activity.
Two very simple rules:
A. You don’t have to write.
B. You can’t do anything else
The rest comes of itself.
– Raymond Chandler
The titan of detective fiction, Raymond Chandler, was onto something with his two rules for writing. By removing the option to shave yaks, we can either do the hard thing, or do nothing. Either outcome is preferable to wasting time on inconsequential activities that make us feel like we’re working on our goals (but are in reality standing still).
Powering the system
To help overcome these three horsemen of goal entropy, we have a few tools. It’d be easy to simply say “do the work”, but that is both obvious and unhelpful. Instead, we need some tools to help define the space and scope of work we need to do.
We’ve often heard the phrase “start small”. This, for me, does not fully answer what I’m supposed to do with all the cool ideas that spring forth when I start out on a project. Instead, I prefer to start with a minimum essential core of a goal. I start a new project with a blank note, and I dump every cool idea and thought I can into it. Once the brain-dump is complete, I can sift through the result to find the minimum lovable core of the idea. We must be ruthless in this stage - each additional element means more time required, and increases the likelihood of entropy overtaking us.
This essential core is what we start with. The remaining good ideas you’ve had? They can still be done, but only after you finish the first and most essential version of the project.
A good example of this is in learning. I learn best by working on a project of some kind. If I were to learn iOS development, I might start by dreaming up a really cool app. Perhaps I decide to build a tool to help myself plan events with friends. I might have a sign up, log in, the ability to publish an event to the web to share, and more in my brainstorming file.
The essential core of the app is more barebones - local first (using SwiftData), composed of 3 basic screens (create event, list events, view event), and built with whatever the default styling is. There’s no authentication, no complex data storage, no networking, no animations. These can be added later. I don’t even launch it in the App Store - it lives in the simulator or in TestFlight at most.
The second thing we can do is spend some time thinking of ways we can make working on our goal simpler, easier, and more fun to do. The more fun the better. We want to want working on it.
A good way to start making your goal simpler and easier is to systematise it - you are looking for small actionable steps that can be done continuously. For my example of learning iOS development, this might look like “After clocking out, spend 30 minutes working on my event planner project”. I work from home in the afternoons, and my day job is software development, so this fits neatly into my existing processes. I’m already sitting in front of my computer, and I’m already in the mindset for programming. It’s simple, easy, time boxed, and something I can do 5 days a week without much change.
Making things fun doesn’t need to be complicated. Grab some graph paper (or make some with a ruler), and create a rewards chart for your goal. Like earning that free 10th coffee from your local cafe, you can check off your progress. When you hit 10 successfully completed items, take yourself out for breakfast, buy a book you’ve been thinking about, or just have a bar of chocolate. Whatever the reward is, it should be something to look forward.
To account for the waxing and waning of life’s unpredictable nature, we can also make a list of the tasks/chores/other goals that we’re going to skip and sacrifice and do halfassed in pursuit of our goal. Making the decision on this load-shedding before life hits us with a bat is vital - you don’t want to be making this choice while in a time crunch and stressed
I experienced a great example of this just last week - my kitchen had gotten out of hand. I could have bludgeoned myself over my inability to keep things clean. Instead, I followed the plan. By emptying the dishwasher and stacking the clean stuff neatly on the island counter, and reloading the dishwasher I was able to tidy up the kitchen sufficiently to feel better. It wasn’t perfect - my cups and bowls were not put away. But having a neat stack of clean dishes in the open is head and shoulders better than having a landslide of dirty dishes and a dishwasher screaming to be unloaded.
Momentum isn’t just physical, though. It’s mental, and for me it’s also emotional. I gain so much energy from staring at a bunch of colored-in checkboxes on the left side of a list, that I’ve been known to add things I’ve already done to a list, just to have more checkboxes that are dark than are empty. That sense of forward progress keeps me enthusiastically plugging away at rudimentary, monotonous tasks as well as huge projects that seem like they might never end – Adam Savage, on his use of lists and checkboxes
Finally, we can build up our motivation by tracking momentum. Adam Savage, in an article for Wired on his use of lists and checkboxes, relates how using a visual checkbox system helps him build mental momentum to keep going on a project. Seeing the completed work stack up on the page is a powerful antidote to the three horsemen of entropy. Using a pen and paper enables this by default, and most to-do apps have an option to keep completed tasks visible.
Concluding thoughts
In changing our view of our goals from a binary win/lose to being a system, we gain a fresh perspective. Failure is no longer a binary personal flaw, but a far distant possibility that only happens if we abandon the goal. As long as we keep adding energy to our goal systems, they stay alive and progress.
One of the most useful elements of this change in perspective is that failure is not final. The system can always be restarted, and there’s still time for you to succeed and achieve the thing you set out towards. The opportunity needs only your effort (in whatever capacity you can give). It’s still waiting for you, no matter what you are pursuing.
There’s never a better time to re-energise whatever your goals are than right now. Figure out what the essential core is, make a load-shedding list, make it fun, track your momentum, and get after them.