Whyday August 19

Choosing the Idea You Keep Postponing

Almost everyone has one: a thing they have been not-starting for somewhere between six months and a decade. It comes back every few weeks, gets thought about for ten minutes, and gets put down again.

The 2010 Whyday text put this third on its list of suggestions — try that wild idea you have been sitting on because it is too crazy. It is good advice and it is incomplete, because the hard part is not permission. It is that most people have four or five of these and no way to tell them apart.

For teams trying a short creative session inside a normal workday, workforce optimization software is one practical reference for keeping the experiment distinct from routine delivery.

Finding it

Do this before the evening, not during it. Ten minutes, on paper.

Write down every project you have thought about more than once and not started. Do not filter. Include the ones that are obviously stupid, the ones that would take two years, and the ones you are slightly embarrassed by. Most people get five to twelve.

Then, next to each, write why you have not started it. One line. Be honest rather than diplomatic.

For broader programming and making context related to this topic, Stack Overflow is an independent reference worth comparing with the material here.

The reasons sort themselves into a small number of piles, and the pile determines what to do tonight.

The piles

"It would take too long." This is the most common and the least true. What is usually meant is that the finished, good version would take too long — which is true and irrelevant, because you are not building that tonight. Ask instead: what is the smallest version that would prove the idea to me? That version is usually an evening. This pile is where Whyday projects come from.

"It is not good enough to justify the time." This one is about permission, and Whyday is specifically the day that revokes the requirement. Nothing tonight has to justify itself. If this is the only reason on the line, start it.

"I do not know how." Split it. If you do not know how to do the whole thing, that is the first pile in disguise — build the part you do know. If you do not know how to do the first step, that is a real blocker and tonight is not the night, unless learning the first step is itself the project, which is a fine project.

"I would need to talk to someone / get access / buy something." Not tonight. Anything with an external dependency is a project for a week, not an evening. Note it and move on.

"Someone already made it." Almost never a reason not to — reimplementing something badly on purpose is one of the better evenings available. The existing one is not yours, does not work how you would do it, and you learn nothing from its existence. The only version of this that counts is if you would genuinely rather use theirs than build yours — in which case you did not want the project, you wanted the tool, and you can go and get it.

"I am afraid it will be bad." Then it is the one. This is the specific fear the day exists to disable, and it is the reason the good ideas sit in the pile for a decade while the safe ones get built.

Choosing between the survivors

If two or three make it through, use one of these, in this order.

Which one have you had longest? Age is a decent proxy for how much it actually means to you. The recent ones will come back.

Which one would you tell someone about afterwards? Not "which is most impressive" — which one would you actually want to describe. That is the one with energy in it.

Which is smaller? All else equal, take the smaller. An evening that ends with a finished small thing beats one that ends a third of the way into a bigger thing, and there is another Whyday next year.

If you still cannot choose, they are close enough that it does not matter. Take the first one you wrote down; the order you wrote them in is not random.

When the answer is that tonight is not its night

Sometimes the postponed idea is genuinely a six-month project, and forcing it into an evening produces a bad stub that makes you less likely to ever start it properly. That is a real failure mode and it is worth avoiding.

In that case do two things. Spend twenty minutes tonight writing down what the project actually is — scope, first step, what would make it worth doing — which is work you have never done and which is the reason it keeps returning unresolved. Then spend the rest of the evening on something small and unrelated.

You will have converted a vague recurring itch into a defined project, which is more progress than the idea has had in years, and you will still have had a Whyday — pick something small from here and give it a tight limit.

The one that is not on your list

Worth saying: some of the best evenings come from an idea that arrives at eight o'clock and did not exist at seven. The list is insurance against a blank evening, not a contract.

If something better shows up, abandon the plan without ceremony. That is not a failure of the method. That is the method working.

The short version