Writing, Riffs & Relationships

Enter the riff.

The Anatomy of a Riff

Here are the basic ingredients for a riff:

• An inquisitive title, something that is not “the ultimate guide” but more “some notes on…”
• A few references - connecting the dots between some links, quotes from other sources
• An anecdote from your own work that provides rich texture and context for what you do
• Some open questions that invite people to respond
• A deliberate small list of 3-5 people you can send the post to

Here’s an example from me: Some Notes on Executive Dashboards (though this has 6 references - typically 2 or 3 is enough for a riff)

Here’s an example from my buddy Howard: Why tension in learning can be magic (I love the way he casually drops in the Dig kitchen arcade experience as the sawdust of his own consulting work)

Why This Structure Works

This structure works primarily because it’s easy to write, it exposes your thinking and it invites response. It means you can rely on it as a bedrock of outreach, instead of waiting for lightning to strike for big-C content marketing pieces.

Let’s break it down:

1. Riffs make your writing small 👐

People’s first instinct with content is to try and make it polished and closed. To be useful by solving something or creating the ultimate guide to something. Those pieces of content can be good - but they’re very hard to write, and even harder to write well!

Instead I prefer to take a more inquisitive and open-ended approach. I call this small-b blogging:

Instead - I think most people would be better served by subscribing to small b blogging. What you want is something with YOUR personality. Writing and ideas that are addressable (i.e. you can find and link to them easily in the future) and archived (i.e. you have a list of things you’ve written all in one place rather than spread across publications and URLs) and memorable (i.e. has your own design, logo or style). Writing that can live and breathe in small networks. Scale be damned.

When you write for someone else’s publication your writing becomes disparate and UN-networked. By chasing scale and pageviews you lose identity and the ability to create meaningful, memorable connections within the network.

This kind of small writing is great for creating connection because it sets up a natural peer relationship. It isn’t that I know more than you and I’m blasting it in your face. “HERE, ALLOW ME TO BLAST MY EXPERTISE IN YOUR FACE”. No, instead it’s saying “Hey, here’s something I find interesting and it made me think of you”.

You’re not writing from a place of authority, you’re writing from a place of curiosity. Open writing, not closed writing.

2. Riffs expose the sawdust of your work 🪚

If you’re planning on using riffs to generate work as an indie consultant, agency owner or founder then it’s really useful to embed in the riff a little anecdote from your work. Imagine you’re a carpenter, you want to show the sawdust. The “proof of expertise”. It’s not about giving a full case study, but rather giving a little vignette from your own work. Here’s an example quote I used in my “notes on executive dashboards” riff:

But, there’s something deeper here. Over the last few years I basically only work with the C-suite of organizations. Supposedly the “people in charge”. But time and time again my point of contact is frustrated at the state of reporting internally, while also not doing anything about it. So why not fix it?

It’s this kind of writing and example that situates your work in the mind of the reader. It allows someone to create a strong mental model of the kind of work you’re doing, the kind of seniority of the work, the kind of context in which they might hire you (or, the kind of context where they might make a warm referral for you).

3. Riffs expose threads to pull on 🧶

Closed writing is boring writing. If you’ve fully explored and put to bed the topic you’re writing about then there’s very little left for someone to react to. “Nice post” someone might say.

But if you deliberately leave some rough edges, some threads that the reader can pull on, then you’re inviting the reader into the conversation. You’re saying (possibly explicitly!) - “Hey, what are your thoughts on this topic? How do you think about it?”

4. Riffs are gifts 🎁

Listen, sales sucks. I hate doing any kind of outreach, so mostly I don’t do any of it. But… you know, I gotta eat. And outreach can be a very effective way of generating leads and work. So how do you create a habit of outreach without vomiting inside your own mouth?

The trick (for me at least) is to recognize that content can be a gift. A good riff is like a little present. Slide into someone’s DMs and say “Hey I wrote this and thought of you…”.

If you think back to the last time someone did this for you - I bet you loved it! I love it when people do this for me. Slide into my DMs anytime with a riff that you think I’ll like.

This completely reverses the dynamic of “sales” and “outreach” - no longer is it about me imposing on you, but rather it’s about me providing value. Here, have a gift.

5. Riffs are for relationships 💬

Forget about “visibility” for your post. The unit of blogging isn’t pageviews, it’s conversations. Don’t worry about how many people will see it - sure you might post it in your feeds (why not) but the REAL MAGIC of the riff is deliberately sending it to people.

This idea is deeply internalized in riffs - so much that I typically write a riff with one specific person in mind. My homie Steinbeck does the same thing - it makes your writing much easier:

Forget your generalized audience. In the first place, the nameless, faceless audience will scare you to death and in the second place, unlike the theater, it doesn’t exist. In writing, your audience is one single reader. I have found that sometimes it helps to pick out one person—a real person you know, or an imagined person and write to that one.

This means that you’re guaranteed to have at least one person to send the post to in their DMs. And if it’s relevant for that one person, chances are you’ve made it interesting to 3-5 others too.

I find there’s typically two ways to start. Either:

• You think of the types of people you know and say “I’ll write something for my friends who are agency owners” and then you pick one specific person as an archetype and write the riff. Or,
• You scan down your list of drafts (keeping a list of drafts, headlines and ideas makes writing riffs much easier), find an idea that’s half decent and think “who could I write this for?”. Again - create the archetype and get writing.

When I’m writing, I’ll keep a little list at the bottom of the post of people I’m going to send the post to.

Here’s my list of people I’m gonna DM this post to:

• Howard
• Elan
• Jim
• Brian
• https://twitter.com/jakobgreenfeld
• Sari

How do YOU riff?

Ok, so since this post is a riff. Here’s some provocations and open questions for you:

• Do you need a system like a personal CRM? Khe does and he walks the walk. Does this make it easier to riff consistently?
• It doesn’t feel to me like you can do this without hosting the writing on a URL - I default to my blog but I’m betting Notion / Google Docs would work just as well. Does anyone do this on a platform that’s not public? Whatever format it is, just make sure someone can FW it easily.
• Maybe this whole idea is easier from a warm start - I already have a blog and a presence all set up. This might be harder for someone who doesn’t have an active blog. What’s the minimum viable scaffolding needed to start riffing?

If you are having a hard time creating riffs, drop me a line. What do you find hard or challenging?