Speaking to another respectable flesh and blood person forces you to think more clearly.

This week, I handed Holloway's CEO reins over to my co-founder, Josh Levy. As we built Holloway over the last four years, I got the chance to explore the depths of my love for research, writing, and sharing stories. My belief in the purpose and mission of this company hasn’t wavered, but over the last six months I found myself wishing I could be a full-time independent creator. And at the end of July Josh and I came up with a way for me to do that.

And it’s here where I made the crucial mistake – I prioritized winning over improving. do I do something that’s uncomfortable that will eventually push me to be better? Or do I prioritize winning right now, even if it doesn’t help me later? I chose the latter, to my detriment. It’s strange to say it, but for me, it’s far more comfortable being uncomfortable, than it is to be content on a seemingly endless plateau.

Supercompensation theory states that when an appropriate training load is applied to an athlete, followed by an appropriate recovery, the athlete’s body not only returns to the previous baseline, but supercompensates in order to be prepared for a greater future training load. The hardest person to coach is usually yourself.

On Volitional Philanthropy (a short essay!) T. E. Lawrence, the English soldier, diplomat and writer, possessed what one of his biographers called a capacity for enablement: he enabled others to make use of abilities they had always possessed but, until their acquaintance with him, had failed to realize. People would come into contact with Lawrence, sometimes for just a few minutes, and their lives would change, often dramatically, as they activated talents they did not know they had. Most of us have had similar experiences. A wise friend or acquaintance will look deeply into us, and see some latent aspiration, perhaps more clearly than we do ourselves. And they will see that we are capable of taking action to achieve that aspiration, and hold up a mirror showing us that capability in crystalline form. The usual self-doubts are silenced, and we realize with conviction: “yes, I can do this”. This is an instance of volitional philanthropy: helping expand the range of ways people can act on the world. I am fascinated by institutions which scale up this act of volitional philanthropy. Y Combinator is known as a startup incubator. When friends began participating in early batches, I noticed they often came back changed. Even if their company failed, they were more themselves, more confident, more capable of acting on the world. This was a gift of the program to participants [1]. And so I think of Y Combinator as volitional philanthropists. For a year I worked as a Research Fellow at the Recurse Center. It's a three-month long “writer's retreat for programmers”. It's unstructured: participants are not told what to do. Rather, they must pick projects for themselves, and structure their own path. This is challenging. But the floundering around and difficulty in picking a path is essential for growing one's sense of choice, and of responsibility for choice. And so creating that space is, again, a form of volitional philanthropy. There are institutions which think they're in the volitional philanthropy game, but which are not. Many educators believe they are. In non-compulsory education that's often true. But compulsory education is built around fundamental denials of volition: the student is denied choice about where they are, what they are doing, and who they are doing it with. With these choices denied, compulsory education shrinks and constrains a student's sense of volition, no matter how progressive it may appear in other ways. There is something paradoxical in the notion of helping someone develop their volition. By its nature, volition is not something which can be given; it must be taken. Nor do I think “rah-rah” encouragement helps much, since it does nothing to permanently expand the recipient's sense of self. Rather, I suspect the key lies in a kind of listening-for-enablement, as a way of helping people discover what they perhaps do not already know is in themselves. And then explaining honestly and realistically (and with an understanding that one may be in error) what it is one sees. It is interesting to ask both how to develop that ability in ourselves, and in institutions which can scale it up. [1] It is a median effect. I know people who start companies who become first consumed and then eventually diminished by the role. But most people I've known have been enlarged. Note, by the way, that I work at Y Combinator Research, which perhaps colours my impression. On the other hand, I've used YC as an example of volitional philanthropy since (I think) 2010, years before I started working for YCR.