Jump Into the Unknown
Executing with Doubt and Uncertainty
Welcome to Polymathic Being, a place to explore counterintuitive insights across multiple domains. These essays take common topics and explore them from different perspectives and disciplines, to uncover unique insights and solutions. .
Today's topic rethinks and recontextualizes a theme within Polymathic Being of slowing down, stepping back, and analyzing more before executing. The challenge is that there is a case for taking action in the face of doubt and uncertainty especially when facing wicked problems. Let’s find out how to balance these two ideas together.
A Look Back
First off, today is a celebration! Two years ago I launched Polymathic Being with a start of 5 Subscribers. This is the 106th Essay and we count over 3900 of you wonderful, Aspiring Polymaths in our dojo where we embrace our White Belts and Learn, Unlearn, and Relearn! As a backstop, here’s the first and foundational essay for those who are new!
As I look back on these past two years, I realize how much I’ve learned and also how much my original mission of providing counterintuitive insights across domains and disciplines has resonated in a world of hot takes, trending platitudes, and outrage writing that tends to permeate the online world. Don’t worry, I plan to keep that mission as my north star long into the future.
Intro
Shifting back to today’s topic, I wanted to recommend some advice from the business and writing worlds to stop overthinking and just start doing. Too many things in business and our personal lives are shackled by analysis paralysis driven by uncertainty and need to be set free.
I faced my own analysis paralysis with the daunting task of writing my first book. I had all the ideas and the outlines back in 2018 and in 2023 my wife finally told me to “just start writing.” She was right, I needed to step into the scary unknown.
It was similar when I started this Substack. I had lots of ideas but I wasn’t exactly sure what the plan was. I finally focused my direction on just two areas and let go:
Polymathic - Intentionally cross-disciplinary so I can continue to learn as well as both permission and a requirement to avoid being pigeonholed.
Counterintuitive - Purposfully shifting perspectives and see if the problems or concepts change so we can learn, unlearn, and relearn.
These guidelines let me sit down and start writing with the freedom to adjust.
A long-term reader might be raising their eyebrows right now because I’ve written extensively on pulling back from the common tropes of ‘Just do it.’
The entire foundation of Systems Thinking is to step back from the problem and look bigger before diving in
I recommend more time in design upfront to avoid proofs of concept failure
I advocate non-action and the concept of Slow is Smooth and Smooth is Fast
I typically abhor the application of Fail Early, Fail Often
Recently, I wrote about the hubris of Confidently Answering the Wrong Question
Hell, I advocate for Lazy Leadership!
Lastly, one of my favorite quotes is attributed to Einstein; “If I had only one hour to save the world, I would spend fifty-five minutes defining the problem, and only five minutes finding the solution”
I do push back on most of the ‘Just do it’ crowd because there are a ton of bad takes, bad advice, and bad execution but today I want to flip the script, balance the scales, and show how to confidently execute with doubt and uncertainty.
The Case for Action
I came across
in a Substack note by . I won’t deny, I was skeptical of the title and specifically the image of his essay “Let it Rip,” but I dug in. (yes… yes I do judge like everyone else) While reading, I quickly had the realization that my biases against that trope of execution were causing me to look for any indication that his essay was wrong! I felt a little bubble of self-righteousness in my chest raising a big red flag that I needed to slow down and consider the points.
The truth is, analysis paralysis is a problem. For every hot-head, Silicon Valley tech bro kicking off a hack AI project and ready to pivot on a whim there is a talented writer who won’t start because they’re too worried about perfection. For every team I want to smack for confidently answering the wrong questions, there’s a team never willing to step up to answer the right questions. For every leader who charges headlong into chaos, there’s a leader who never challenges the status quo.
That’s why I liked the graphs Josh made which challenged that binary. In the first, the Y axis is time thinking and the X axis is time doing. There are three rectangles with one spending more time thinking, one spending more time doing, and one balanced. The point Josh was making is that the balance of thinking and doing resulted in a larger surface area of action. The second shows that balance along a curve. Always thinking and never doing will never get anywhere. Always doing and never thinking gets you nowhere you want to be.
I’m going to add another dimension. With hyper-simple problems, imagine deciding what groceries to buy, we can take option C. Spend more time doing and less time thinking. However, if you want to keep to a budget or want to eat healthy, you’ll need to increase your thinking and shift to B. That’s because we’ve increased the complexity and complexity requires more thought.
Compare that to the quote from Einstein: “If I had only one hour to save the world…” OK, that’s a hyper-complex problem. Something we might even refer to as a wicked problem. As such, we need to ensure we’ve defined the problem properly or any action we take will have limited to no effect.
With a proper definition, we can also start to break the problem into its constituent parts and approach each element with a different mix of strategies. Some might be a “go-do” type task, others might be larger efforts, and some might need to wait for more information where no action is taken at all.
This is where the charts above are useful, especially with a bit more context. It’s not all thinking, or all execution but needs to include accurate problem definition, intentional execution, and agile adaptation as new information emerges. It also helps if we rethink the definition of failure that we all worry about.
Rethinking Failure
recently wrote Don't Try Too Hard which explores how our inaction is often a cover for our fear of failure. This fear drives our ego to give us an excuse even though that inaction can often lead to a whole litany of different failures. His case for imperfect action lines up well with an essay I wrote almost two years ago titled Embrace the Divergents where I proffered a different mindset around failure:
What if we totally re-conceptualized the concept of failure? Because a paradox emerges where avoidance of failure often begets even worse failure.
System acceptance testing is a great example. We test in order to prove the system will work. We want to pass this test and if the incentive is high enough to avoid failure, we will often design the test in a way that increases the probability it will pass, even if it reduces the probability that the system will work as desired. I’ve seen this as the root cause of many actual systems failures which passed the acceptance test.
But what would happen if we applied the rule of hypothesis testing from statistics? You don’t test to prove it right, you test to prove it wrong and only fail to reject the null hypothesis if you can’t prove it wrong. Likewise, instead of testing to pass, what if the outcome was a decision? Do we go with design A, or switch to design B? If design A ‘fails’, that answers the question. It also helps to reduce the risk of passing something that shouldn’t because we aren’t married to design A passing. We want to ensure the best design makes it. We need to look at aligning our incentives to reward risk and rethink, and stop penalizing, ‘failure’.
Even better, reframing failure as learning opens up a whole new opportunity to build experience. Instead of seeing it as a setback, look at it as a step towards something better. This reduces the perceived risks and allows us to execute with more uncertainty.
Executing in Uncertainty
SpaceX, led by Elon Musk, is a great example of executing with uncertainty. He created a culture that embraces the risk of failure intentionally and intelligently. He accepts uncertainty and uses tests to learn from, not ace.
Similarly, in the Army, we follow the Troop Leading Procedures bound by the acronym RIMSRCIS to execute in the most uncertain conditions; war:
Receive the Mission - Ask questions and fully understand the whole picture.
Issue a warning order - Let your team know what’s happening in general.
Make a tentative plan - Get an idea of the main thrust of the operation.
Start necessary movement - These are things like ensuring resupply, staffing, team assignments, etc.
Reconoiter - Go look at the objective and verify reality.
Compete the plan - Adapt to changes, get final feedback, and lock it down.
Issue the completed plan - Ensure everyone knows what’s happening and why.
Supervise - Keep your head up, have strong lines of feedback, and adapt.
Oh, and everything is METT-TC contingent. This means the Mission, Enemy, Terrain, Troops, Time, and Civilian considerations are subject to change at any time and we need to anticipate and adapt to these changes during planning and execution.
So how does one execute? Simply, we eliminate as much uncertainty as possible, develop structured execution plans with intentional feedback loops, and allow adaptability to contingencies. We ensure cyclical iterations to reduce uncertainty and ensure success. “Let it rip” but with structure, intentionality, and adaptability.
The Balance
More often than not, what the “Just do it” crowd is pushing back on are those who are too paralyzed by the fear of failure to take a step anywhere. This is a lesson I learned when I took my wife’s advice and just started writing my novel. It also helped that I came across a wonderful adage that I’ve made my own and recommend for everyone:
“Good writing should suprise the author.”
This mindset gave me the freedom from failure to kick off Polymathic Being and write the first two books of The Singularity Chronicles. It also allows me to relax and let the topics and characters explore themselves without trying to plan everything out. It lets me adapt to changes and pivot when necessary.
On the other hand, we also can’t just barrel into uncertainty with zero ideas except to wing it. We need to plan first, set up our objectives like the two I chose, define our goals, and then give ourselves permission to explore, experiment, and learn. In the case of our Polymathic mindset, it’s also to Learn, Unlearn, and Relearn.
Those with analysis paralysis can’t execute and those with over-confidence shouldn’t execute. Doubt and uncertainty are valuable to have and embrace which keeps us curious and humble. So “Let it rip” with structure in your goals, discipline in execution, and embracing doubt and uncertainty as motivators against overconfidence.
This is a lesson I learned with you over the past two years. Thanks for being here and thanks for supporting Polymathic Being! We are a reader-supported publication that follows the Wikipedia model of funding. I want these essays to be open for everyone and your financial support helps ensure that continues. Join us for just $24 a year which is only $2 a month or about 50¢ an essay. A little support goes a long way.
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Further Reading from Authors I Appreciate
I highly recommend the following Substacks for their great content and complementary explorations of topics that Polymathic Being shares.
- All-around great daily essays
- Insightful Life Tips and Tricks
- Highly useful insights into using AI for writing
- Integrating AI into education
- Computer Science for Everyone
These kinds of conversations are what make Substack great. Thanks for the riff on this thread!
One point I wanted to double click on is the importance of having a framework set up before “letting it rip.” This is the biggest heuristic for me. If you’ve got the system in place, then just get moving. Your system will help you course correct. But if you haven’t thought through some of the directional questions it’s time to take a step back to hit the slow is smooth and smooth is fast rhythm.
There is a children’s book called Scaredy Squirrel and he learns to jump into the unknown. <3