As we go through life, we encounter situations from time to time where we need to make a decision about something complex. Planning a product development roadmap? Navigating a tricky interpersonal relationship? Trying to figure out your own personal goals?

Here’s one technique I use sometimes:

First, start by asking: what is the most important thing?

What is the one single thing you could do whereby: a) if you get this thing right, everything else is just an implementation detail, and b) if you don’t get this thing right, then nothing else will work no matter how good a job you do?

Sometimes people get stuck here: they see the situation as being many-sided, with many factors, and of course there can’t be one single thing that matters most, that’s silly – right?

Keith Rabois talks about this in his lecture at Sam Altman’s Startup Class at Stanford – quoting here from his talk,

“[Peter Thiel] used to insist at PayPal that every single person could only do exactly one thing. … He would say, I will not talk to you about anything else besides this one thing I assigned you. I don’t want to hear about how great you are doing over there, just shut up, and Peter would run away. And then focus until you conquer this one problem. And the insight behind this is that most people will solve problems that they know how to solve. Roughly speaking, they will solve B+ problems instead of A+ problems. A+ problems are high impact problems for your company but they are difficult. You don’t wake up in the morning with a solution, so you procrastinate them.”

So here’s an exercise to help expose those A+ problems, that single most important thing: Ask yourself, ‘What would be the WORST way for me to proceed? What would the worst possible outcome look like? And then ask: what is the opposite of that?

Here’s why this works: when we think about the worst way to do something, our brains all of a sudden get a lot more creative. It’s a way more fun exercise! We get out of our usual ruts and have some fun: “The worst way for me to design this particular product feature is to make it so that the user never has an idea what she’s supposed to do!” Then, flip it around: the most important thing, therefore, is to build the opposite of that: something where the user always understands what she is supposed to be doing. Or, “The worst way for me to navigate this personal conflict is to make this person I’m arguing with feel dumb & insecure, have them get defensive and lash out, and make us both look terrible.” Then flip it around: the best way for me to navigate this conflict, therefore, is to make the person I’m arguing with feel valued and recognized for their contributions, so we can respectfully discuss our disagreements.”

I suspect that this technique works because, at some level, we’ve all internalized this notion that “solutions are always multi-sided”, “complex situations demand complex approaches” and other shit like that. The funny thing is, in most situations that I can think of, there usually is in fact one thing you could do that is the single most important thing. It also often happens to be, ‘the thing that is really hard’, or ‘the thing that makes you cringe most at the thought of having to do it.’ So, naturally, we come up with all kinds of excuses for ourselves about why, in fact, there are many important things to consider, so we’re going to go work on those other things which aren’t so spiky and threatening. We avoid doing the most important thing, and instead do all of the other things in order to make ourselves feel better. But the most important thing never gets done, and the problem persists. Goal != accomplished.

The reason why we flip the problem around, to ‘what is the worst way we could solve this problem’, is because we haven’t been trained to think that way about problems. When we do the creative exercise, ‘what would be the worst way to solve this problem’, the answer usually comes to the top immediately. It’s quite striking. Flipping it around – asking, ‘okay, what is the opposite of that, and is that therefore the most important thing?’ – forces us to be honest about how, in fact, there is one thing we need to do that is the most important, and it’s also the hardest- so go do it, already!

I hope that this “Most important thing / What would be worst way to solve the problem” technique proves useful to you, even if you only use it once or twice. I am consistently surprised at how often it comes in handy for life situations, both at professionally and personally. And yet, as I write this, I know that I only force myself to go through this kind of thinking intermittently – and it’s often the hardest problems where I’m least likely to stop and think to use it. So, for those readers who know me personally, you have full permission to call me out on this in situations where I’m clearly ducking the most important thing. Better practice what you preach, right? Hope this is useful.