The Worst That Could Happen

Almost everything that is worth doing is risky. So, if you’re not failing regularly, you should probably be spending more time doing interesting and challenging things.

I’ve found a simple trick that helps me to keep failing on a regular basis. I call it learned pessimism¹.

Everyone talks about their unhealthy #FOMO. Until recently that #FOMO was very necessary for your survival. You needed to get out there and hunt that wooly mammoth with the rest of your tribe if you wanted to have something to eat.

Our problem is that we’re also programmed to avoid failure. Until very recently the cost of failure was very likely death. If you’re hunting wooly mammoths, messing up means that you’re going to be either hungry or flat. So we developed an equally unhealthy #FOFU².

But in the context of our safe and sheltered modern lives, our #FOFU tends to harm us more than it helps us.

When I’m thinking about trying something scary and new, I think quite hard and quite graphically about all the things that could go wrong. If I’m surfing, I think about sharks, drowning, wiping out, bruises, bleeding, pain and broken bones. If I’m working, I think about embarrassment, losing clients, losing money, going bankrupt and feeling stupid.

Then I spend some time pondering the worst possible realistic outcome ³. The realistic part is important. It takes some time and practise to figure out what is plausible and what is simply melodrama. Your mind is able to effortlessly conjure up a smorgasbord of ghastly but highly improbable outcomes. So you need to focus quite hard to discard the ones which are unlikely, unrealistic or just plain silly.

Once I’ve found the worst thing that is likely to actually happen, I think about how serious it is likely to be. Generally, I can get a pretty good sense of whether that worst possible outcome is likely to kill me (either literally or figuratively). ⁴

If I’m about to set up a tricky meeting with someone and there is a chance that things might go pear-shaped: we might end up embarrassed or losing a good opportunity. But would it sink the company? Very, very unlikely. We have cash runway, a variety of possible pivots, a good network, a great team.⁵

And after that, it generally seems a lot easier.

When the worst thing that could happen is not actually that bad, I feel much happier to try (and fail at) new and interesting things.⁶.