One of the greatest decisions we ever made as parents was to have a “standing” Sunday babysitter. There’s nothing complex about it: we just asked our regular babysitter if she wanted to come every Sunday by default. It’s not that we’d give up one of the two non-school/working days of the week with our kids, it’s that we would have one consistent day per week with a third adult floating around the house. For sure, we often took advantage to get out of the house to have some “holy crap, we’re married” time together. But just as often, it meant getting house chores done.
I often use that window to tackle one of my favorite clean up responsibilities: flat folding boxes. I’ve got a box cutter (and replacement blades…I’m not a serial killer). We’ve got two blue recycling bins. It’s zen. I can knock out podcasts or phone calls. I’ve flat folded so many boxes that I know all of the variants and when the boxes can be collapsed rather than cut up. I’ve spent enough time breaking down boxes that I’ve developed a sort of pattern recognition that I’ve been able to incorporate into my practice of maximizing my recycling bin space (I’m a nerd) :
The Amazon “tape” isn’t really all that sticky and can be ripped, but be careful because it’s got “string rebar”
Certain forms of corrugated cardboard emit a “dust” when cut and have to be artfully folded so as to not take up too much space in the bin
If it has a “pouch” label and it’s blocking my cutting lane, best to remove it first
Costco “carrier” boxes should have the bottom cut-out — requiring multiple passes — and then the remaining “frame” is easily folded
Shiny boxes are almost always thin and easy to fold, which can actually be quicker than cutting
“This came from my mom,” so it will have enough clear postal tape to vacuum seal an astronaut and will require multiple passes with the blade
This is a box worth saving for reuse or reapplication
I have more “go-to’s,” but this isn’t meant to be a flat folding playbook1. It may also seem a bit much to have acquired this level of detail around residential recycling habits, so I can understand that one’s response might be, “hey, why are you spending so much time on this? These are just boxes that need to get thrown out and you need to get back inside and co-parent.” Fair.
Though I’m not really a notice-er of things (I’m dreadfully2 oblivious), I am curious; I like learning how things work, why they were designed/built/evolved in a certain way, how people (mis)use them, etc. Said another way, I want to observe and consider whatever is most impactful/meaningful about the box before using (or dismantling) it.
I’ve already written about the perils of conventional wisdom and don’t see many people arguing in favor of “inside the box” thinking (despite it’s pervasiveness). It’s certainly “simple enough” to just do what everyone else does and cut-and-fold these boxes without much consideration. This is fueled by the mentality that the perceived “costs” of this type of analysis are considered too great and that the rewards relative to those costs deemed too small. This is partially cultural: “innovative” leaders are lauded for being risk-takers while rarely evaluated in context of their track record, team, product, market, or environment3. That makes the “goal” often just to champion an idea that others have yet to identify (or have already dismissed), which is backed up by explicitly and confidently insisting that any analysis or contextualization is merely skepticism and small-minded thinking. Some of this is a problem of incentives: the nominal rewards — even if transient — from successful “outside the box” ideas often dwarf any assessment of their likelihood or associated risk from the outset4. Or, inversely, a belief that you can’t get fired for doing the same thing as everyone else that is reinforced by the rewards (or absence of punishment) provided by the safety of incumbency.
I’m not advocating in favor of over-thinking — just thinking5. I can get things done without having to analyze them to death6, I just see value in trying to learn as much as is reasonable (or necessary) to execute at the highest (possible) level. As I’ve noted:
The goal has always been to have enough information to 1) increase the probability of success, 2) reduce the probability of doing something that unnecessarily reduces the probability of success, and 3) ensure that the risk (or probability) adjusted return was large and skewed to the upside.
Thinking ABOUT the box requires perpetual curiosity, humility, objectivity, and ambition, which don’t live in a natural equilibrium. The analysis can lead to disappointing or “less sexy” conclusions that require a high degree of difficulty to execute. It also yields a clarity that can unlock outsized opportunities and uncommonly straight forward solutions to otherwise intractable problems. In short, it is more costly (and more “work”), but the risk and probability-adjusted returns are also higher.
Disappointingly, most of what I read and hear (and see) is a bias and encouragement for people to move in the opposite direction — everyone wants a shortcut. One way this commonly manifests is through the (over)use of comparables. While comps can be helpful to simplify the description of a concept, they seem instead to have become a way “force” people to “think creatively” by distilling down their idea. Effectively: the value of your idea can only be assessed if it is described relative to other successes rather than in your own words7. The “x but for y” description for start-ups (“ZocDoc, but for pets,” “AirBnB, but for mobile homes,” etc.) and “x meets y” descriptions for Film/TV (“The Matrix meets Leave it to Beaver,” “Groundhog Day meets Aliens,” etc.) necessarily disregard the detailed underlying attributes of the actual opportunities (and challenges standing in the way of executing on them). The truth is that no new business opportunity is simply the marriage of an existing company to an entirely new product/custom and no new movie is the marriage of two other movies.
“Life Hacks” represent the worst manifestation of this type of thinking:
LET ME TELL YOU THE SECRET WAY IN WHICH SUCCESSFUL PEOPLE WIN AT WINNING IN 7 EASY STEPZ! I (who is not you) DID THIS THING (in a situation you are not in) WITH THESE PEOPLE (whom you do not know and are not the people who seem similar to the people whom you do know) AND GOT THESE RESULTS (which themselves were influenced by all of the factors involved in my doing the things/how I did them) IN JUST ONE SHORT PERIOD OF TIME (under conditions and with lead up that don’t apply to you) FOLLOWING THESE 7 EASY STEPZ (which don’t include all of the other smaller and less obvious inputs and influences that actually led to my “success”). I USED TO BE JUST LIKE YOU (but not really and not in the ways that are determinative for the “success” that I have had), BUT NOW I’M A WINNER AND IF YOU FOLLOW MY STEPZ YOU CAN BE TOO (ignoring that if it were truly this easy then everyone would do it, immediately competing away and/or devaluing the “success”)
Doesn’t exactly scream “I’ve reflected on the factors that determined my prior accomplishments,” while discouraging any desire to understand the specific dynamics underpinning a new endeavor — both of which are highly influential on the likelihood of achieving your goals.
I’ve had more than one experience where Outside the Box thinkers couldn’t internalize the changes created (internally and to the environment) by their own successes. They could not (any longer, if ever) put themselves in context: they were “right” about the “crazy” bet they had made, but ignorant to the sustained impact on themselves, their team, their product, their competitors, their customers, etc. I am not trying to minimize the accomplishments (and ambition) in overcoming the long odds to start something new and/or upend an industry — it’s nearly impossible! If anything, these people have put themselves in a position to potentially compound their advantage(s) and yet seem allergic to the idea that they may have to learn something new (or it may be “just as difficult”) to do it. Up until recently, absent a major disaster8 this may have been perfectly “fine” — I’m not sure how objectively one can assess missed opportunities if you haven’t continuously evaluated the size, shape, and position of your business.
I’ve also mistaken Outside of the Box thinking for About the Box thinking (and conflated the practitioners, of each). There are cultural and financial incentives — benefits which I can often agree with — on the side of the operator to promote the former. I would describe the fundamental behavioral difference as believing in your own innate greatness rather than your ability to do great things. There are countless examples of people triumphantly pivoting to something completely new, as if their achievement in one area will guarantee their success in — or at least enable them to reap the rewards of — another. On the surface, the logic looks like:
“I’m a great film producer, so I will be a great TV producer”
“I’m a producer, so I can run a studio”
“I distributed content, so I can also make content”
“I run Tesla, so I can run Twitter”
It reflects a belief that intrinsic attributes (creativity, entrepreneurship, vision, strategic thinking, etc.) are effectively modular and transferrable — that the specifics are less important than their will to be awesome.
One of my favorite (meta) examples of this misunderstandings comes from The Matrix — a franchise with meaningful dissonance between what the filmmakers were trying to say and what they audience wanted to takeaway. Putting aside the “do we live in a simulation” debate for a moment, consider the seminal scene where Keanu Reeve’s Neo is going to visit “The Oracle” for the first time on his journey to actualization:
Boy: Do not try and bend the spoon. That's impossible. Instead only try to realize the truth.
Neo: What truth?
Boy: There is no spoon.
Neo: There is no spoon?
Boy: Then you'll see that it is not the spoon that bends, it is only yourself.
The common read of this scene is that by imagining the unimaginable, Neo is able to gain superpowers and bend The Matrix (or at least his “body” within it) to his will. It’s a call to arms to think Outside the Box (that they are hard-wired into). But that’s not really my correct.
Take a minute and consider the circumstances: they are “living” inside of a simulation in which software was designed to create the feeling that the physical world is real and subject to the laws of physics. The Matrix is stimulating every one of Neo’s senses and sending signals to his brain. Spoon Kid is encouraging Neo to gain presence of mind about his actual reality: namely that what he perceives in his (very real) brain is simply rendered and thus quite malleable. The guidance isn’t “imagine the laws of physics don’t exist inside The Matrix,” it’s that there are no actual rules, only his perception of them. Neo can fly because there is no gravity. He can slow down time to casually fight Agent Smith because time does not actually exist in The Matrix. Neo’s ascension and transformation into The One is represented by his “seeing” of The Matrix’s code — a literal on-screen argument in favor of thinking About the Box, rather than outside of it.
Back in our reality, how do you put this into practice? As I have described it to my teams over the years, good strategic analysis requires sifting through what’s interesting in search of what’s important (and thus most relevant!). This most often starts with asking questions and trying to learn enough of the specific attributes of the opportunity to evaluate how/why it exists in the first place. It’s ok to start with “cool idea,” but only if it’s followed immediately by, “so what?” Focus on understanding what are actually the fundamental drivers (or inhibitors) of success and evaluating those against your own position/assets to assess the probability of success and what actions will increase/decrease it. Remember that someone else’s status and position is the result of their (non)actions and not their professed strategy. What a market participant is doing may be important to understand as much for why we can’t/shouldn’t do it as for why we should — or for how their success/failure may impact our own opportunity set. The time saved NOT chasing things can be immensely valuable, particularly if you have to battle perception that you aren’t moving fast enough.
I’m not saying you won’t face resistance (or received feedback) that implies you are too cautious, too in the weeds, or not creative — you likely will. This type of thinking isn’t inherently small or incremental or slow to action. You might (and should!) imagine wildly different futures, filled with unparalleled prosperity, but the line to that future starts in today’s reality. No matter what you envision, you will never bend the spoon with your mind. But thinking ABOUT the Box will enable you to bend yourself.
There are no playbooks. What if you have a different type of box cutter? What if you have only one recycling bin or a smaller bin? What if you have arthritis? What if you hate the planet and insist that recycling is a deep-state conspiracy?
Interestingly, I’ve learned to harness the power of my obliviousness over the years (but that is a topic for another time)
Only in the aftermath of the market correction(s) of the last 18 months have I started to see meaningful coverage of the 2nd and 3rd order impacts of a decade of loose monetary policy on “successful” companies and strategies. Sadly, though, it’s been accompanied by close to zero self-reflection about the coverage/evaluation of those same businesses and their leaders during the run-up. Without the subsidies an Uber costs the same as a taxi!? I’m shocked! Self-fulfilling prophecies and unforced errors is a rant for another day
FOMO and not wanting to be perceived as a buzzkill are pretty powerful incentives.
I appreciate there is certainly subjectively around exactly what constitutes “enough” or “over” thinking something, but I’m getting to that
Not an actuary
One negative consequence being that it’s almost a required lens through which all opportunities must be pitched/analyzed
The “costs” of these disasters won’t necessarily be born by the individual making the decisions. Or, at least, given accrued wealth and influence may not set them back to zero


