What I learned writing fifty issues without missing one

Fifty Tuesdays in a row is not a big number, but it is long enough to see which habits were real and which ones were only good intentions.

When I started, I had a system. A content calendar, a research database, a template for every kind of issue. Within three months most of it was gone. What was left is simple enough to fit on an index card.

What survived

A fixed day for drafting, a fixed day for cutting, and a rule that nothing goes out that I would not forward to a friend. Everything else, including most of my productivity tools, fell away.

The fixed days matter more than I expected. Drafting on Thursday means I always have a bad version by Friday. Cutting on Sunday means the bad version gets a cold read before anyone sees it. Separating the two jobs made both of them better.

The first draft is for me. The second draft is for you.

What did not

Batching issues weeks ahead never worked. By the time a stockpiled issue went out, I had changed my mind about half of it. Writing close to the deadline turned out to be a feature: the letter sounds like what I actually think this week.

Tracking open rates every day did not help either. It made me nervous without making me better. I look at them once a month now, next to the replies, which tell me far more.

The habit I wish I had started with

Keep a running list of questions readers ask. It has become the best source of topics I have, and it reminds me who the letter is for.

The list lives in a plain document. Every reply with a question goes in, in the reader’s own words. When I am stuck, I read it from the top, and something always jumps out.

If you lead a team, the same list works. The questions people ask you are a map of what you have not explained yet. Write them down for a month and you will have a better onboarding guide than most companies ever produce.