Plan for the best

The Philosopher Developer

June 10, 2023

One Friday night recently, some friends of mine dropped off their daughter for an evening play date with three other girls. Their daughter hadn't met two of the other girls, so they hoped she would get along with them but figured most likely she would still want to come home before bedtime. When they returned later that evening, the girls had become fast friends and were already making plans for what they would do the next morning. But since the parents had assumed their daughter would want to go home, they hadn't brought a change of clothes, her toothbrush, or anything she would need for a sleepover; so they found themselves driving home with a deeply disappointed and frustrated child.

This story reminds me of something I have seen many times in the workplace. The members of a product team will chat often about an idea: a vision, a strategy, or just a cool feature they'd like to build. These discussions happen in bits and pieces over Slack, during meetings on Zoom, in social gatherings—but never "on paper". No one ever takes the time to really put the idea into writing or flesh out all the details, because "We'll never get time to work on that." And then one day, some SVP or other senior leader comes along and asks, "Have we ever thought about..." and the team has nothing to show. They assumed they would never get the time of day from any senior leadership, and they were unprepared when the moment came.

We've all heard the expression: Hope for the best, plan for the worst. It sounds so sensible. And of course, it comes from a sensible place. We should not simply hope that good things will happen and assume all of our dreams will come true. Bad things do happen, challenges do arise; and if we don't invest any effort in preparing for them, they can knock us down.

Here's another expression, from President Dwight D. Eisenhower:

Plans are nothing; planning is everything.

The existence of a plan is one thing. But it is really the act of planning that forces you to think through the details of what might happen and equips you to handle different scenarios. This simple act makes a huge difference in determining whether we are prepared to respond appropriately to different situations, to take advantage of new information and choose promising new paths when they emerge from the fog.

One of the most common mistakes I see people make is spending all of their effort planning for the worst, and only hoping for the best. When you only hope for something, you aren't thinking through the details. You aren't asking yourself, "What if I get it done in 2 days instead of 2 weeks?" or "What if they actually say yes?" And then when something like that happens, you have no plan, and the moment passes you by like a wave passing a surfer without their board.

By planning exclusively for the worst, we render ourselves unable to seize those opportunities that could lead to the best—and then the worst just happens by default.

I'm not saying we should not plan for the worst. None of us has complete control over our environment or the obstacles we will encounter. This is why we should spend a portion of our energy preparing for those obstacles so that we're ready to deal with them.

But sometimes the universe smiles upon you, and you find yourself on a surprisingly smooth path. To spend all of our energy planning for the worst leaves nothing left to actually make plans for when things might go better than expected: when solving a technical problem turns out to be easier than we thought, when we're able to complete our work ahead of schedule, when all of our dependencies actually fall into place (it can happen!), when our executive leaders love what we're doing and want to give us more funding or support.

My point here is simple. Let's be done with "Hope for the best, plan for the worst".

Plan for the best, and plan for the worst.