May 6, 2025, 9 a.m.

The steps of (re)positioning

Draft's Letters

As a humble reminder, we’re out at a conference this week. We’ll be back the week of May 19.

We’re aware that our positioning towards software is the most important technological event of the past century, and as a result, some people have questions about how we did it. We’ve undertaken a few initiatives, some done, some still in progress:

  • Rework our website to reflect our new focus on software, which we wrapped up last week.

  • Start from basics. Paid members have already received a couple of lessons on pricing & onboarding, with more to come.

  • Outline a few years of new lessons on increasingly granular topics. Hoping to do this on the plane in a couple of days.

  • Relationship building. Figure out where to speak next, who to talk to, etc.

Let’s talk about lesson planning. Content ideas are shockingly easy to brainstorm; you just need to make the writing prompts to get you going when you’re in front of a blank screen. I got this idea from Naomi Dunford at IttyBiz and have adapted it for our use.

First, come up with a few primary topics that fit your positioning. For us, that involves:

  • Marketing sites

  • Pricing

  • Onboarding & retention

  • Design research

  • Experimentation

  • Project management & planning

Three of these are pages or areas of focus in the businesses we serve; the other three are activities.

Then, come up with some subtopics. For marketing sites, for example, you can go deeper:

  • Home pages

  • Landing pages

  • Social proof

  • Business positioning

  • Branding & style guides

  • The seam between marketing & app

Home pages can go even deeper:

  • Headlines

  • Mastheads

  • Calls to action

  • Layout

  • Copy

  • Features (where and what)

  • Long-form pages

  • Pain-dream-fix models

  • Contemporary design trends

And gosh, you can do this with just headlines, too, can’t you?

  • The role of humor in headlines

  • Using testimonial quotes for headlines

  • Headlines as positioning (how narrow to go?)

  • Animated headlines (“[tool type] for [rotating cast of industries]”, e.g.)

  • Imagery in headlines

That list there looks like a good set of lessons to write about, doesn’t it?

Now imagine doing that for every single branch of the tree that I just listed. You get thousands of ideas in minutes. Some are short, some aren’t worth keeping around, but you always get enough that the whole thing works.

That’s how I’ve made content for the past ten years or so. Might be helpful!

One small announcement

I’ll be in Mexico for a conference at the end of this week, so we’ll be back in a couple of weeks. If you’re in Playa del Carmen, say hello.

You just read issue #197 of Draft's Letters. You can also browse the full archives of this newsletter.

Draft