Email courses for newsletter writers

The first week is where a newsletter loses people

A newsletter is a continuing argument. By the time somebody subscribes you have a vocabulary, a set of positions, three or four things you keep coming back to, and a tone your regulars read as friendly and a stranger reads as odd. The new subscriber gets none of that. They get issue 147, which assumes all of it.

This is the quietest failure in the format, because the list keeps growing while the people on it keep going quiet, and neither number tells you which is happening. A subscriber who never opens is indistinguishable from a subscriber who opens on a device that hides it, and both of them look exactly like growth.

A five-day course put in front of the newsletter fixes one specific thing: it gives the new reader the context your regulars have, in their first week, before they have decided what you are. It is the only part of a newsletter that can be written once and improve every week for years, because every new subscriber goes through it and you never touch it again.

What the five days should teach

Teach the reader how to read you. That means the vocabulary you use without explaining it, the recurring argument you make in different clothes every few weeks, and the one position that would surprise a newcomer. By Friday they should be able to predict roughly what you would say about a story they just saw, which is the moment somebody becomes a reader rather than a subscriber.

The obvious approach is a greatest hits: the five most-read pieces from the archive. It is better than nothing and it is not a course, because those five were written for people who already had the context, and the reason they did well is usually that context. Use the archive as material and write the connective tissue new.

Day one has to be genuinely useful on its own, for the same reason it does anywhere: a reader who got something on Monday opens Tuesday. Take the single most practically useful thing you know, the one you assume everybody knows because you wrote it in 2023, and give it away properly on the first morning.

The middle days each take one recurring subject and explain why you keep returning to it. Day four is the position most new readers disagree with on first hearing, argued properly. Putting it on day four matters: by then you have been useful three times, and disagreement with somebody useful is interesting rather than disqualifying.

The objection your readers arrive with

They already get too much email, and they know it. The objection is not about you and it is not about quality. It is a straightforward capacity problem, and the reader has learned that every sign-up form understates what it will cost them.

Daily makes it worse, which is the part newsletter writers underestimate. "One a day for five days" reads to a tired reader as "daily", and daily is what they have specifically stopped agreeing to. The fix is one sentence: the number of emails, that it stops, and the ordinary cadence afterwards. A bounded ask is a different proposition from an open-ended one.

The second objection is that a course sounds like homework. You are not a teacher and they are not a student; they were looking for something to read. Call it something else if "course" is wrong for you, and keep the voice of the newsletter rather than switching into a lesson register.

What your sign-up page has to say

Separate the two things clearly. The course is five emails and it ends. The newsletter is what arrives afterwards, at a stated cadence, indefinitely. A reader who agreed to the first and discovered the second is a complaint waiting to be filed.

Say what the newsletter is actually about in the words a newcomer would use, not the words your regulars use. The internal shorthand that makes your subject line work every week is exactly what makes your sign-up page unreadable to somebody who has never read you.

Then write the confirmation email in your own voice rather than leaving whatever your sending tool generates. It is the first thing a new reader ever receives from you, it decides whether the rest of the list ever hears from you at all, and a subject line reading "Confirm your subscription" from a sender they do not recognise is where a measurable share of a newsletter's sign-ups quietly stop.

The lines a newsletter front door has to carry:

• What the newsletter is about, said without any of the vocabulary the course is going to teach.
• Five emails, one a day, and then the course is over.
• That one confirmation email arrives immediately and the course starts once the link inside it is clicked.
• The ordinary cadence afterwards, as a number: weekly on Thursday, or twice a month, or whatever is true.
• That the two are one subscription and one unsubscribe link, so leaving is a single action.
• One sample sentence or paragraph in your actual voice, because voice is what they are deciding about.

What the day-six email asks for

Almost nothing. Day six is the first ordinary issue, arriving on the ordinary day, in the ordinary shape, with one sentence at the top saying the course has ended and this is what the newsletter looks like. The transition is the payoff of the whole sequence and the most common way it is wasted is by making day six an event.

The one thing worth asking for is a reply. Not a survey and not a form: one question at the end of the sixth email that somebody could answer in a sentence from their phone. What made you subscribe, or what subject you want more of. Replies are the only qualitative data a small publication gets, and a mailbox that sees a reader answering your mail treats the next one differently.

Resist the referral ask on day six. The reader has read five things; they do not yet know whether they will still be reading in a month, and asking them to stake their own credibility on you at that point gets a low rate and slightly cheapens what came before. If you want to ask, ask somebody who has been opening for six months.