What are plans for?

Part of Ultraworking’s work cycles process involves defining a plan at the start of a work session and then making regular pace checks to see whether there’s anything you need to adjust in order to hit your goal. One of the adjustments that often comes up is asking whether it would make sense to “re-scope”. This just means adjusting the scope of your goal for the session.

For example, if you set out at the start of a work session to complete ten exercises from a textbook and halfway through the session you’ve only completed two, there isn’t much point in spending the second half of the session trying to complete the remaining eight. It’s exceedingly unlikely that it would be possible, and during that time the unattainable goal will just be a millstone around your neck, sapping your motivation. Much better to acknowledge that the original goal was unrealistic and set yourself a new goal, probably aiming to do two more exercises in the rest of the session and leaving any notes that you’ve made in a good state to be picked in a future session. This would be an example of re-scoping.

Re-scoping isn’t always about choosing a smaller scope. You might find yourself ahead of pace, and then it can be good to plan some additional work. As Sebastian Marshall is fond of saying, the ability to define work degrades faster than the ability to do work. So planning is something that it’s often better to do while you’re fresh and have a good amount of energy. After that you can just execute, which, if you’ve defined the work well, is usually less cognitively demanding.

One thing that I frequently observe is that people initially tend to have a lot of resistance to re-scoping. They are very reluctant to change plans having made them, even when it’s clear that they are now unrealistic. This raises a question: what is the purpose of a plan?

I see a plan as your best guess at the current time of the sequence of actions that will most likely produce the outcomes that you want. The reason to make a plan is to channel and direct future actions along that path. If a plan is for directing future action, then as soon as it becomes stale you should make a new plan. If you find that you’ve failed to follow the plan for whatever reason then you just need to take those reasons into account in the new plan. This applies whether those reasons were external or internal.

A few days ago I wrote on Twitter:

I frequently see people making plans, failing to follow their plans, and then using the plan as a tool to beat themselves up with. Where does this mindset around planning come from?

The responses raised some interesting possibilities:

If your experience of plans is that they’re made by authority figures who can then punish you for failing to follow their plan then it’s entirely possible that you could internalise that idea: Failing to follow instructions attracts punishment. Plans are instructions to yourself. Therefore if you don’t follow them you should punish yourself. Rather than being a way to direct future actions, the plan then becomes just a yardstick to measure oneself against.

And there are different parts of your personality. The “good” side of you makes a plan and the “bad” or “lazy” side of you fails to follow it. (Failing to take into account the possibility that the bad part of you might have legitimate concerns about the plan, and might be trying to protect you by not following it.)

It seems like people think that if they just create a plan then the work will magically happen. Perhaps imagining a plan creates an expectation that that is how reality is. This might explain the fact that people seem unwilling to revise plans even when the obstacles are external, e.g. the work was harder than they initially thought. They’ve already fooled themselves into thinking that the work can’t be like that.

In 1871 Helmuth von Moltke the Elder wrote in Über Strategie:

The tactical result of an engagement forms the base for new strategic decisions because victory or defeat in a battle changes the situation to such a degree that no human acumen is able to see beyond the first battle. In this sense one should understand Napoleon’s saying: “I have never had a plan of operations.”

Therefore no plan of operations extends with any certainty beyond the first contact with the main hostile force.

It seems to me that Moltke is arguing against the idea that there’s a perfect plan which guarantees victory. Perhaps this should be obvious, but my guess is that Moltke was writing that in a culture which thought that, by choosing the perfect military strategy, they could guarantee victory.

Moltke is pointing to the limitations of our knowledge of the world. It’s only when your plans encounter reality that you realise where your understanding was wrong. Clearly this applies to situations in which one is facing an adversary, because they can act in ways that you can’t anticipate. But it also applies to anything with any degree of complexity or uncertainty. Until you begin the work, you don’t know exactly how easy or difficult it will be. And it also applies to yourself: you are complex and you will act in ways that you can’t always anticipate beforehand. Maybe you’re more tired than you’d realised. Maybe you’re happy to work on this problem for two hours, but as soon as you hit hour three you find that you’re completely bored with it.

It’s because of that uncertainty that you need to be willing to discard your plans when you realise that they relied upon incorrect assumptions and when you’ve gathered more information about the problem. At that point you will have a better understanding and can make a better plan.