If you can write your goals in SMART form, you probably aren’t working on anything hard.
The standard way to take on a hard problem is to plan it: break it into milestones, make each goal specific, measurable, achievable, relevant and time-bound, then execute. For a lot of work that is exactly right. But you cannot lean the complexity out of a fundamentally fat problem like getting to Mars or tackling climate change, and on problems like those the plan starts failing on contact. Venkatesh Rao puts it bluntly: if you can literally set goals that satisfy SMART criteria, you are probably not solving problems of any significance.
Take a smaller version. A team starts a company in a market nobody has served. They write a careful plan: the customer, the use case, the revenue by the third quarter. Three months in, the first real customers are using the product for something the plan never imagined. What should the team do with the plan?
Planning versus solving
The planning was not wasted. The process of planning is valuable for forcing you to think hard, but the actual plan is probably useless. Planning draws a map of known territory. Solving navigates territory that has not been mapped, and it is a different activity: creative and exploratory, involving play, skill, insight and orienteering through uncertainty. The team’s plan was a map of a market they had imagined. The customers have just shown them the terrain.
That is why complexity does not reward better maps — it rewards better navigation. For complex problems the map is always wrong, and the skill is in how fast you update when the terrain surprises you.
Rao frames the difference as two kinds of preparation. The essence of liberal education, whether you get it at school, at a startup, or as a blue-collar philosopher fixing motorcycles, is preparedness for surprise. The essence of vocationalism, whether you got it in a PhD program, a finishing school, a meditation retreat, or a welding course, is preparedness against surprise. A team prepared against surprise reads the strange customers as deviation from plan. A team prepared for surprise reads them as the most valuable information it has received.
Derping
The main failure mode has a name. Derping is reiterating your priors in the face of novelty. The founder who meets the unexpected customers by pitching the original use case harder is derping. We derp because humans evolved in cultures of tribal honor and authority, where changing one’s mind was a sign of weakness, insincerity, or untrustworthiness.
Derping sustained long enough becomes a context vortex: a headspace of stale, repetitive thoughts that lacks a central mystery to solve. New information can enter a context vortex but cannot be processed in ways that disrupt it, and the gravity well is escapable only through the external pull of untrapped minds. From inside, the vortex feels productive, because thoughts are moving. The defense is to hold beliefs lightly: the swiftest mind is the one unencumbered by excessive belief, testing its priors often and discarding them when contradicted.
The foxhog
Openness alone fails too, though. The fox knows many things; the hedgehog knows one big thing. A pure fox nature creates next-shiny-thing distractibility, where every odd customer is a reason to pivot. A pure hedgehog nature creates tunnel vision. The foxhog pays attention to everything and says NO to almost all of it. The operative term is almost. For the team, that means noticing every strange use of the product and chasing only the one worth chasing.
What decides which one? Without a sense of values to guide action, more options become a source of paralysis, which is why caring works as a compass: it determines what the analysis is for. The burden is not choosing but knowing what matters enough to choose. The team that knows what it cares about can treat the surprise as surface area for the right thing to find them. The team that doesn’t has only the plan.
References:
- Venkatesh Rao, Breaking Smart, Season 1
- Venkatesh Rao, various Ribbonfarm essays on complexity and decision-making