Why I invested in Substack after a year against it

For a year I told anyone who would listen that newsletters were a phase. I had the numbers to back it up, and I was wrong about what the numbers meant.

My argument was simple. Open rates were falling, inboxes were crowded, and every writer I knew was launching one at the same time. It looked like a gold rush, and gold rushes end badly for most of the people who join late.

What changed my mind

It was not growth. Growth was real but uneven, and it mostly went to people who already had an audience somewhere else.

It was retention. Readers who paid in the first month were still paying two years later, at rates most software companies would envy. When I talked to a few of them, they did not describe a product. They described a person whose judgment they trusted, and whose letter they would miss if it stopped.

What I got wrong

I treated writing as content, something to be produced, consumed and replaced. The readers I talked to treated it as a relationship. They forgave a weak issue the way you forgive a friend for a dull dinner, because the next one would probably be good.

Relationships compound. Content decays. I had built my whole view on the second idea and ignored the first.

I was measuring the inbox. The readers were measuring the writer.

The habit I took from it

So I changed my position, wrote down why, and set a date to check whether I was wrong again. That last part is the habit I would recommend to anyone who makes decisions for a living.

When you reverse a view, write three things down:

1. What you believed before, in one sentence.

2. The specific evidence that changed your mind.

3. What would have to happen for you to change it back, and when you will look.

Most of us change our minds quietly and then forget we ever thought otherwise. Keeping reversals on paper, with a review date, is the cheapest way I know to get better at judgment. It also makes it much easier to admit when you were right the first time.