Rethinking Planning

Plans are important. To author our lives instead of being a pinball, we need to project into the future. Problem is, it’s often overdone.

Much human behaviour is an attempt to tame the mind. Wether it’s meditating, cleaning incessantly or working 50 hour weeks. Planning has therapeutic too – a sense of direction creates mental order.

A common assumption is that success is simply the execution of a superior plan. The domino’s are carefully placed and the lead is simply flicked. A man with a plan flicks a persuasive switch too.

But design is often an illusion.

Superior planning matters, but to become better decision-makers we need to overcome to-do list addiction. We need to overcome the domino myth.

Baysian Planning

A plan is only as good as our vantage point when planning. Only as good as the available information.

Available information at the time of planning becomes privileged. If planning is too therapeutic then all subsequent information becomes highly inconvenient. We charge through it.

All that can be done is the next step. In certain contexts planning step 2 and beyond can be helpful, but what matters more is taking step 1 as best we can. Step 2 planning is best done from a new vantage point, using the lessons learnt from step 1.

Unforeseen doors may appear.

Daydreaming about steps 8-9 is effortless and can lead to creative insight. But brow-furrowing over 8-9 is an inefficient use of mental resources, because steps 8-9 often never happen. At least not in the way we predicted.

There’s more doors we can’t see than ones we can. By sticking to script we miss out on serendipity. Any good plan should have inflection points to reassess and decide if the ships course needs readjusting. As the facts change, so should decision making.

Looking back on anything we’ve put significant effort into, how much was really known about it before starting?

Let’s make it more concrete:

On Vacation

Planning a holiday is important. We want to maximise our time, enjoy the best the place has to offer and to ensure nothing major goes wrong.

There’s more good travel information on the internet than ever before. You know what else has lots of good information? The location itself. The locals, travellers who’ve spent time there, a cool looking street you walk past that google didn’t tell you about.

We want to make the best possible decisions. This means overcoming a bias towards older information and ignoring newer information. Using information based on merit, not order.

At an all-you-can-eat restaurant you want to eat the tastiest food, not the food you see first.

In Business

Businesses make guesses about how customers will behave. A good business will learn from what customers do. A bad business will assume their guess is right.


Trying to craft the perfect plan is to forget that available information is limited. Execution is almost always more revealing than research. Procrastination can masquerade as planning.

First, the downside needs to be defined. If the cost of failure is high then lots of research is important. If not, it’s typically better to pull the trigger sooner rather than later. Looking back, regret is more likely from delay than action.

If This, Then x

How to plan depends on context.

A basketball coach shouldn’t just focus on step 1. Each possession of the game matters. While a coach can’t predict how many turnovers they’ll commit or how many threes will be made, they can make some educated guesses about other things. Basketball is a game made by humans. In this game there are finite options. There’s only so many players allowed on the court, so any good coach will prepare for the different lineup configurations they’ll come against.

A contingency plan for each configuration makes life easier come game time. When it happens, the coach simply opens this prepackaged decision.

‘If coach plays y in this situation, then I will do x.’

Without this preparation, they’d have to spend mental resources on this decision. Leaving less to spend on other important thinking. In the heat of competition we’d prefer to make measured decisions, if pre-prepared they’ll be more levelheaded.

If this, then x planning works best when decisions need to be made quickly, when they’re likely to be emotive and when the downside is high.

Wu Wei

The plan is to write about a specific topic for a few hours. A white page is staring back and you can’t stop thinking about something else. Pretty inconvenient thoughts. If only the plan had been to brainstorm what you can’t stop thinking about.

Like the movie Inside Out, there’s different ‘you’s’. The creative you, the curious you, the social you. If you can’t stop thinking about something that’s curious you. By shifting mood to the forefront you can let curious you take the wheel. That way it’d be effortless, more productive and fun.

Mood can’t be planned.




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