Roadmapping for Flatlanders

People who are bad at dealing with uncertainty, but lucky enough to be well-shielded from it, tend to be aggressively low-margin in their decision-making. They make plans with no slack in them. On the other hand, people who are bad at dealing with uncertainty, but unlucky enough to have (or have had) a lot of it in their lives, tend to be aggressively high-margin in their decision-making. They always make plans with worst-case amounts of slack in them. Let’s call them lean planners and fat planners. Both are varieties of what I call flatland planners, because they plan in two dimensions: time and a second variable, usually money. While fat planning is somewhat better than lean planning, the best solution is not to be a flatlander at all. This involves making uncertainty an active variable in your decision-making and going three-dimensional. The key to this is not plans, but roadmaps. Over the years, I've found the topic of roadmaps coming up repeatedly in consulting projects: whether they are a good idea, how to make them, how to use them, and perhaps most importantly, how to defend them. Because roadmaps create certainty to benefit some parties over others in an uncertain world, often by moving uncertainties elsewhere in a zero-sum way. Which means if they exist, they will come under attack. Have roadmap, must defend.

Roadmaps are near-2d fictions in a 3d decision-making world

1/ People who don’t factor uncertainty and slack into their planning are flatlanders: they make decisions in terms of time and one other variable, usually money.

2/ Other common ones are “happiness”, “family”, “meaning” etc. Whatever your second variable, the point is, its state is seen in a deterministic relationship with time.

3/ If they have no way of estimating traffic, flatland planners factor in no traffic or worst-case traffic when deciding when to leave for the airport.

4/ Lean flatlanders think of unspent slack as wasted time, representing a suboptimal state, and get restless and frustrated if they have to wait around at the airport.

5/ Fat flatlanders view airport waiting time as precious relaxed-mind time. You’re through security! You're at the gate! You have temporarily outrun existential life uncertainty!

6/  If you have to be one or the other, I’d recommend being a fat planner. The payoff is that unused slack tends to a high-creativity resource, where your mind is free to imagine possibilities.

7/ To three-dimensional decision-makers who also factor in uncertainty, flatlanders appear as risk extremists: they are either extreme risk takers, or ridiculously risk-averse.

8/ One reason flatlanders live in flatland is that they see themselves as having no risk management agency at all, or no need for it. This can be a rational attitude.

9/ If you have no financial slack to cover rebooking, and no time slack (perhaps because you’ll miss the wedding if you miss the flight), worst-case planning is rational.

10/ If there are plenty of available flights to rebook on, and rebooking costs are trivial for you, you can get to the airport at the last minute. That’s rational too.

11/ But if you are too early simply because you don’t like anxiety, or too late because you think missed flights due to traffic happens to other people, you might be a true flatlander.

12/ The basic mental shift required to go from being a flat-lander to a three-dimensional planner is to recognize that risk -- the cost of uncertainty -- is a third variable in decision-making.

13/ Whether you’re a (time, money) or a (time, happiness) person, adding risk to the picture is a fundamental act of dimensional leveling up, not merely some extra detail in a basic 2d picture.

14/ Why? Take pure time/money decision-making for instance. Without risk in the picture, we can only think of them in a two-dimensional way: time is money/money is time.

15/ If you don’t have enough money, you can work more (spend time) to get more. If you don’t have enough time you can outsource some work (pay money) to get more.

16/ But if you throw risk into the picture, you can change your time/money situation in a different way. You can win what looks like “free money” (no time spent earning it) or “free time” (no money spent).

17/ A lucky gamble might triple your money with zero time investment (free money). As a kid, snow or rain might lead to school getting canceled (free time).

18/ Learning to think about risk as a third dimension in decision-making has probably been the hardest intellectual challenge of my life. I am naturally a fat-planning flatlander.

19/ The key for me has been learning the skills required to work with manageable known unknowns: things you know you don’t know, but are usefully bounded by things you do know.

20/ The manageable part is critical: acting with foresight must be cheaper than acting with hindsight, otherwise it might as well be an unknown unknown since you can do nothing.

21/ In the last few decades, we’ve gotten so obsessed with unknown unknowns and weirdness risks that age-old disciplines around manageable known unknowns are beginning to slip.

22/ A major conceptual tool for managing known unknowns is the roadmap. A roadmap is a an artistic model of how predictable uncertainty and ambiguity will evolve over time.

23/ Plans are about what you will do. Roadmaps are about what the environment is going to do. Plans are useless most of the time. Roadmaps on the other hand, are incredibly useful.

24/ Launch windows in space missions should be the anchor example in your head of a roadmap feature: Something that you can’t control, but can predict and manage work around.

25/ It doesn’t matter if your rocket-building plans are all agile trial-and-error, or heavily waterfall-planned with Gantt charts up the wazoo. The launch window is a hard roadmap constraint.

26/ Many other phenomena fit this description. Moore’s Law is a roadmap phenomenon. Climate change is a roadmap phenomenon. An aging population is a roadmap phenomenon.

27/ Roadmap phenomena are of two kinds: cyclical and secular. Cyclic phenomena can be thought of as seasonality in roadmaps.

28/ Literal seasons and weather are the obvious example. Crop lifecycles, soil nutrient cycles, and monsoons affect roadmaps in the agricultural sector.

29/ There are also other kinds of “seasons.” Apple’s product unveilings constitute a season pattern in technology roadmaps for mobile app companies.

30/ Microsoft’s second-Tuesday security bulletins are a weather pattern in information security. Intel’s chip architecture updates on its tick-tock cycles are a 2-4 year seasonal cycle in hardware.

31/ Cyclic roadmap phenomena are the easiest to deal with because you can develop good habits and efficient response protocols around them.

32/ Habits don’t quite pop you out of flatland into full 3d, but do get you managing risk in ways that are in-between worst-case over-preparation and full obliviousness.

33/ For example, if you are an app developer, you can build more slack into your schedule for the month after a major Apple announcement, instead of having high slack everywhere.

34/ Such risk-management habits can be thought of as 3d patches in fundamentally 2d decision-making. “Risk models” typically exist within these localized 3d bubbles of (time, X, risk)

35/ Non-cyclic roadmap phenomena require more complex anticipatory decision-making. Y2K and the transition from IPv4 to IPv6 are examples that were handled well.

36/ An interesting one I just learned about is the upcoming Ethereum "ice age" based on a "difficulty time bomb" built into the mining protocol as a hard-coded feature.

37/ The main thing to be wary of in designing cyclic risk management into roadmaps is to guard against over or under reaction.

38/ In the early 90s, universities worried about not having enough faculty to handle the Millennial enrollment surge and over-produced PhDs for example. An over-reaction.

39/ Over-reactions are a case of the solution becoming worse than the original problem. Large structural oscillations in the PhD labor market for example.

40/ Today, we are likely under-reacting to climate change. Under-reactions lead to problems transitioning from manageable risk regimes to unmanageable risk regimes.

41/ This is what climate skeptics and deniers miss: if there is even a small chance that the many climate models are correct, it pays to react.

42/ Why? Because the problem may transition to unmanageable. Beyond the compensation powers of either institutions or markets.

43/ This is a version of Pascal’s wager: you can’t manage your risk/reward at all if you are already in hell/heaven. Your religion’s gods are in charge there.

44/ So if there’s even a small chance that religion is true, it pays to be “good.” Infinite utility times small probability = worth it.

45/ So the climate skeptics are right about that: there is an element of religion here. The negative utility of a borked planet is so high, it’s worth acting on even a tiny roadmap risk.

46/ The mistake they make is in assuming that because one part is like religion, the whole thing is a religion. Arbitrary mythologies perpetuated by willfully lying priesthood.

47/ This is not an accident. There are aesthetic and leap-of-faith components to all roadmaps. One person's roadmap is another person's religious conspiracy.

48/ Roadmaps are as much about who you trust as they are about what you know. The truths in your roadmap are only as good as the people whose word you are taking about them.

49/ Roadmaps model patterns of avoidable risk based on information from less-than-completely-trustworthy counter-parties who share some of those risks. The classic example is the failed harvest.

50/ Commodity futures trading was invented to manage agricultural roadmap risks. Notice something? It's a scheme based on who trusts whom to lie/tell the truth about what.

51/ Should you have a roadmap? If there are manageable known unknowns that might drastically affect outcomes in your future, yes you should.

52/ How should you make one? Two things to NOT do are to treat roadmapping as a subset or combination of trend forecasting or planning.

53/ Trends are objective phenomena described on their own terms. Roadmaps capture the significance of those phenomena -- and the people telling you about them -- for YOUR situation.

54/ Moore's Law as a trend is transistor density doubling every 18 months. But on your roadmap it might mean a threshold beyond which a certain business model becomes practical -- according to somebody you may or may not trust..

55/ So to make a roadmap, simply capture a "hard calendar" landscape of cyclic and secular phenomena in terms of their significance to YOU, along with trust assessments of the information.

56/ How do you use a roadmap? Think of it a canvas on as which your decision-making plays out. If you've defined your roadmap well, your planning can be highly agile/improvisational.

57/ How does this work? Even if you consciously think in 3d, your subconscious is a 2d (time, something) subconscious. You can exploit this.

58/ Your mind turns objective clock time (chronos) into subjective event time (kairos), and objective utility (like dollars or number of friends) into subjective utility (material lifestyle or happiness)

59/ This shift from objective to subjective is how your mind sneaks 3d risk-factored realities into a 2d subconscious. Your 2d (time, X) stream of subjective experience flows in 3d space.

60/ Uncertainty shows up as felt emotions: anxiety at being late, exhilaration at beating odds, felt freedom at being early, anger at being betrayed, gratitude for being unexpectedly aided.

61/ Your roadmap is simply the landscape of upcoming known-unknowns (including, crucially, around people/trust) made legible enough for your instinctive management behaviors to kick in.

62/ For this to happen, they must provide a sense of subjective proportion/importance in ways that cue emotional responses to people, events, and new information.

63/ A roadmap that does not evoke emotion is not a roadmap. Work the aesthetics till your emotional responses are in harmony with your conscious sense of what is true and important.

64/ Our strongest emotions are tied to beliefs/trust about people, especially people who supply beliefs. So a roadmap without names of people/specific organizations isn't a roadmap.

65/ This is why it is best to use aesthetic techniques for roadmapping rather than logical/Platonic ones. I like storytelling and figurative map-drawing. Your techniques may differ.

66/ This is the deeper significance of the idea that you manage what you measure. Measurement is about instrumenting your roadmap for live updates to drive emotions, not thoughts.

67/ How do you use a roadmap? Well for starters, keep it updated. An obsolete roadmap can be worse than no roadmap. If you navigate by a static and wrong roadmap, you're begging to be exploited.

68/ Second, allow yourself to react to it. Emotional responses to roadmap events are a feature, not a bug. Roadmaps are a prosthetic spidey-sense. They are meant to tingle.

69/ Situation awareness is roadmap awareness. Monitor it at two levels: changes that require changes to your anticipatory behaviors, and changes that require redrawing the roadmap.

70/ The former is simple feedback control. If you're behind schedule and the launch window is coming up, trade money for time and accelerate. The launch window is a high-risk phase.

71/ The latter is OODA loop reorientation. If your roadmap starts to get seriously garbled or behave in mysterious ways, or worrying things accumulate in your peripheral vision, act.

72/ Reorientation means reinventorying the phenomena that go into your roadmap, and reprioritizing how large they SHOULD loom in your imagination.

73/ One of the main reasons you might need reorientation is that any FUD you experience with it may be caused by somebody else attacking it. Somebody getting inside your OODA loop rather than natural events.

74/ When this happens, you need to react by plugging information deficits: casting a wide net around the key discovery questions "what the hell is going on?" and "who is doing this?"

75/ But if you stop there, you'll succumb to FUD. The next trick is the crucial one: letting your emotions guide the aesthetics of your new story.

76/ For example, under certain circumstances, a CEO might consciously shift their narrative from peace mode to war mode. That's a true reorientation. The emotional texture changes.

77/ The roadmap will reflect such things. A war-mode dashboard or roadmap presentation looks very different from a peace-mode one. It captures and highlights very different things.

78/ More importantly, it cues different emotions, and different reaction speeds for the things it instruments, measures and cues you on.

79/ And most importantly, it primes you to refactor people equations. Ultimately, the roadmap is only the terrain. As John Boyd once remarked, fight the enemy, not the terrain.

80/ This means when your roadmap shifts, your assessments of who is an ally and who is an adversary will shift.

81/ A clear sign of this: your patterns of permission and forgiveness change. You say yes and no differently to different people. Like Michael Corleone did with Tom Hagen in The Godfather.

82/ People who are used to assuming your consent for their actions and asking for forgiveness rather than permission suddenly find you saying no, and being unforgiving about your mistakes.

83/ People who are used to having you say no all the time, and conditioned to ask for permission, suddenly find you saying yes all the time, getting blank checks, and being forgiven for errors.

84/ This is all natural. The key is to recognize what is going on: you have created and are using a roadmap, and are reorienting periodically to defend it under changing circumstances.

85/ That's how you create certainty in an uncertain world. Eggs may be broken, and feelings hurt in the process. If you lack imagination, roadmaps may lead you to tribal mind-closing.

86/  But if you use them well, roadmaps allow you to exit flatland, get ahead of uncertainty, and live a fully 3-dimensional life as an imaginative and generative decision-maker.

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