Principles and pragmatism

An excerpt from a post I wrote last week for Substack employees.

Are we idealists or pragmatists? Do we have principles we hold dear, and a vision for the future we want to create? Or are we fumbling along, tinkering, finding what works, and forever allowing contact with reality to rearrange our mental furniture, make a mess on our conceptual floor, and occasionally punch so many holes in the walls that need to strip our whole idea-house down to the studs before we can renovate?

To me the only answer that can possibly be satisfying is: both.

If you have ideals but you don't take responsibility for making a change in the world, you are working on your self-image, not a product for other people. If all you have is pragmatism, then you have speed but not a direction and the purpose of your work will get set by default to, at best, the same conventional things that everyone else is chasing.

Putting the idealism and pragmatism together is forever uncomfortable. Frequently the direction set by ideals means not taking the clearest practical path. More subtly, often as you go to put principles into practice, you realize that the ideal is not quite as simple as you thought when you started. You might not be able to get an ought from an is, but we are fallible creatures and if our oughts wander too far from what is, we can get very lost indeed.

The compensation for choosing to take this fraught, ambiguous, uncomfortable path is that only such paths lead to greatness. Not all of them, certainly—grappling with this tension is no guarantee that you will make something that matters. But failing to grapple with it does, in my view, doom you to mediocrity.

Pursuing an ideal opens up practical avenues that you would never otherwise find. Building things that work leads you discover ideal truths that are stranger and more wonderful than the fiction that you started with. The hard way is the only way.

As usual,

Mills Baker

said it best [in a footnote in a weekly design update]

We all know “startups are hard,” but I think we tend to imagine that this difficulty is bounded, contained, modelable, a bit like running a marathon: yes, legs and lungs hurt, but that’s normal and appropriate, and we know the route, the distance, and that there’s a finish line. This is a kind of difficulty we can contend with without losing ourselves. But I think “startups are hard” more in the sense that “life is hard” or “relationships are hard”: there is no real route; there is no real finish line; and the difficulty of it all will overwhelm you; it will seep into the deeper parts of yourself, catalyzing existential anxieties and all kinds of psychological instability. This is a “normal” thing that cannot feel “normal,” and indeed I’d argue that anything truly hard has this property: that it stresses you to the point where you can lose your orientation, ability to calmly react to challenges, and capacity to plan effectively. But of course: many things worth doing are hard in this way —like living life or being in a relationship— and as ever, all we can hope to do is be aware of it and support one another. My own experience has been that it’s definitely worth it.