A speech is like a love affair. Any fool can start it, but to end it requires considerable skill.

~ Lord Mancroft


Conversations are difficult to end well. I’ve spent considerable time thinking about how to end them, and talking to people about how to end them. (I am aware it’s awfully meta to have conversations with people about how to end conversations.) As with anything (making toast for example), it’s good to first figure out common ways to horribly muck it up (try burning the toast), and learning to consistently not muck it up.

Here are three ways to muck up a conversation so as to avoid having a good ending.

First: Drag the conversation on until your conversation partner is exhausted. One might think it could make for a good ending—just the sheer relief of it ending! But alas (poor Yorick), it’s just an ending and not a good one.

Second: Get the last word in. If you’re the host (of the podcast, the dinner party, etc.), insisting on being the last one to touch the conversation baton is guaranteed to make a bad ending.

Third: If it’s going well, always keep going. That way, you only end when it’s not going well. In other words: Actively choose a bad place to end.



Via negativa

Like nature, which removes mistakes to progress, you can remove things to not only survive but thrive. (This is one of the ways we can apply via negativa, an important mental model.)

~ Shane Parrish from, https://fs.blog/what-holds-people-back/

It’s a semi-interesting, but short, article. But this bit about via negativa made me down-shift. Because I’d never heard that little latin phrase. I wrote a blog post about how not to mess up endings of conversations… and then went directly to a bookmark on that Parrish article and realized that via negativa was exactly what I had just been writing about.

Via negativa is simply the idea of improving by studying what one should not do. Addition by subtracting one might even say.