Accepting The Worst

There’s an exhilarating freedom and motivation in having nothing to lose. History is full of amazing tales of underdog ingenuity. Likewise, stereotypes abound of the mighty falling flat, trying desperately to protect what they’ve got.

But even more insidious than actively trying to protect what you have, is frequent fretting about how to do so in your mind. It’s so easy to fall into an endless churn of worries about how your precious gains could vanish tomorrow.

This is known as loss aversion. It’s the default routing of our evolutionary brains, and it can lead to unnecessary stress, lost opportunities, and poor decision-making. But it doesn’t have to be your destiny – it is indeed possible to reroute.

The stoic practice of negative visualization is one way to do this. If you imagine, clearly and frequently, the worst case scenario, you can work on coming to terms with its consequences. Usually they’re far less dire than your worries would lead you to believe.

I’ve employed this technique from the get-go with everything I hold dear in my life. As an example, here’s how I’ve applied this to the thought that a terrible end could prematurely doom Basecamp.


We’re not running Intel, and I don’t want to have Grove’s “only the paranoid survive” as my modus operandi. I want to retain the underdog sense of having nothing to lose, even when conventional thought might say I (and the company) have everything to lose.

That’s the tranquil freedom of the stoic way.

As we get ready to officially launch, I’ve been thinking about exactly this same topic. And I’ve learned this: when you recognize what you are thankful for, you also realize that you have so much you could lose.

I think the biggest sense of fear comes from the feeling that if you deviate from a path that you have to an end that you hold dear, that you may never get around to getting back on the path. It leads to a fixation on the path, and worse still a fixation on the end.

That fixation is what I have been trying to remove myself from, and which I think I have managed to remove myself from. I’m focusing on making Data McFly great, and not on ways it may fail.

And the feedback from the community has helped stay on that path, as we get suggestions on ways to make things work in ways that work well for everyone.

This article provides some hints. Focus on the unchangeable, both about the path and end. The skills, the relationships, the learnings.