One of the most obvious observations about high upside events is that they are unlikely.
What do I mean by high upside events? 2 types come to mind. The first could be doing something uncomfortable, with a very low chance of success, something like applying for very prestigious schools or companies, incubators, etc. The second is doing great work.
I kind of cheated in putting great work under high upside events, but it follows the same principle that I’m about to get into, comfort.
When you’re doing great work, it’s tautologically uncomfortable. The work wouldn’t be great if you didn’t think the problem you were solving was hard. You might have to learn a lot of new things, or have to face the dreaded ‘am I good enough?’ question.
When you’re doing high-upside, application oriented events, you also get the same feeling. If we liked writing applications and selling, we would be in sales and no development.
Then it follows the limit to doing great work, or winning in a high upside event is bound by the level of uncertainty you can handle.
Take applying for excellent schools or companies. The excellent ones are the ones that are least likely to be particularily impressed by you.
This gets us to sell too quickly. In order to avoid the discomfort, you might be tempted to take the very first offer, or to choose an easier challenge that doesn’t quite make you work as hard.
And the thing about the level of discomfort you can handle is that the choice becomes an unconcious one. It’s not that we choose to settle early, or take on less challenging pursuits, but they become a default, rationalized behavior.
The way to get yourself out of it is by watching other people. If you see someone at your skill level is doing harder things, or getting better results, it most likely that he can just handle more discomfort and uncertainty.