Issue #021

What to do when you having nothing new to say

How do you come up with new content when your readers have heard it all from you before?

The other week, long-time friend and C&S customer Rob Fitzpatrick, sent in a great question...


There's no "news" in my space, and I've already written the core knowledge in a book that all of my subscribers have read, so I also struggle with finding meaningful content to share.

My understanding is that the normal solution here is a drip campaign that spreads the education over time, but in my case I feel like I've already written the canonical version as the book.

So I occasionally send emails when we have, e.g., a fun event coming up (or with the video highlights afterwards), but that's hardly valuable content and is more of an alert.

Do you have a mental framing for this sort of situation? Thanks :)

What I like so much about this question is it's something I've struggled with for the last ten years at Double Your Freelancing.

"Haven't I said enough already?"

How can I keep coming up with things to say about freelancing?

It really never changes: you get clients, you pitch them, you do the work.

Sure, different software might get released that helps freelancers. Or you take something like "get clients", and so you keep coming up with an articles du jour on how get clients with Facebook, and then another with LinkedIn, TikTok, etc. etc. etc.

But while that works super well when you have a strong SEO game and you're optimising for alllll the long tail searches, there's only so many ways you can spin and rehash the same old content... right?

Well, no.

At least I don't think so any longer.

Learning doesn't happen overnight

My daughter Lucy just learned how to crawl.

But she's been trying to crawl now for months. After so much struggle, grunting, and frustration, she finally figured out how to move herself forward!

Listening, learning, and trying rarely yields the results we want right away.

Instead, we typically need to hear the same thing again, and again, and again before we take action. And then scrape our knees quite a few times before we become decent at something. And even then, mastery is still so far away.

I'd often get feedback from readers who would say something like, "I've been on your list for a while, but it wasn't until today that XYZ finally clicked."

And what I sent that day might have been something that, to me at least, wasn't anything revolutionary. It was just another weekly email about something that, in my mind, I'd said so many times already.

But for that person, it was exactly what they needed to make everything fit together.

What I think Rob should be doing...

Rob writes books (they're great, btw.) And the majority of people on his email list are there because they read one of his books – with the majority, I'm guessing, having come via his Mom Test book, which I think is his most popular.

#1) I wouldn't assume most people on his list have actually internalised his teaching

I recently read Write Useful Books by Rob. I'm writing my first real book, and this was exactly the book I needed.

But have I internalised it? Has it become second-nature? Am I fully immersed in "the Rob way" of writing a book just yet?


And the best way to get me there would be to receive a bunch of messages from Rob over the months and years that continue to expand on what I already read in the book.

Maybe that means sharing some additional anecdotes that didn't make it into the book, or a great TED talk that relates to something he covered in Chapter 5, or just sharing the story of someone who struggled with applying something in the book – and how it finally ended up becoming clear, and what they did next.

Rob: Create a "Virtual Book Club"

Before I moved to England, my wife and I were involved in a really great local book club. What I liked so much about it (besides the wine) was that I was challenged in a structured way to think more deeply about a book. Rather than just reading something and putting it away, I had to actually think about what so-and-so character meant by this, and what implications that had for so-and-so other character.

If readers of Rob's book are primarily joining his list because of their purchase, I'd be sending those new subscribers a canned follow-up email drip that largely achieves what I just covered above, but in a way that's specific to what someone just read.

Think of it as a great way of onboarding someone onto the list and ensuring that buyers of his book aren't just having it collect physical/digital dust. (After all, unless someone both reads + acts the book is useless!)

#2) Write and send more diverse stories

A few years ago, I started regularly writing Student Success Stories at Double Your Freelancing.

The idea was to ultimately add social proof to the brand – "look at all the people I've helped" – but I also had another reason for doing this...

People ultimately want need confirmation that what you're saying can help THEM.

And, my God, have I struggled with this!

When I started creating my first courses, I made sure to intentionally make them non-technical. Double Your Freelancing Rate is a course on pitching and pricing yourself, and no matter what you do (assuming you sell to other businesses) the principles taught will work.

But I'd inevitably get loads of pre-sales emails from people asking, "I'm a vegan web designer who loves CrossFit and owns 2 cats, will this work for me?"

(ok, slight exaggeration there...)

Before adopting my way of selling freelancing, they first wanted to see that others like them have successfully crossed the chasm. And while we can sit around and poke fun at people for thinking that they're so unique that what we're teaching probably won't work for them... we all do this.

I do this. You do this.

We want to take the easy way out and think "this won't work for me" because learning and doing something new is hard work. And the easy thing is to maintain business-as-usual and clinging to whatever inherited ideas we hold.

Rob: Share stories from your readers – both "I shipped a book!" and those who are still a work-in-progress

I'd start talking to the people on my list and encouraging them to share what they've done with what I've taught them.

A big objection will be "I'm not ready. I'm still a work-in-progress (WIP)" because many of us think that you need to have it all figured out in order to be a "success story."

But imagine you want to learn web programming...

Who do you think is going to be more helpful: someone who's been doing it for a decade, or someone who recently learned? Who is able to help you more?

Rob, I'd be highlighting the trials, tribulations, and wins (big and small) from your readers.

Because there's likely a lot of people on your email list who are just waiting to hear from someone who used your book to help them self-publish a nonfiction book on, eh, Creating Crypto Web Apps because they too want to write about cryptocurrencies, and it wasn't until they read that story that enough F.O.M.O. set in to kick them into action.

#3) Facilitate Rob <> reader dialogue

I didn't think of this email, Rob did.

And while getting questions like this help me tremendously (yay, one less newsletter idea to come up with!) it ultimately is rooted in reality. If Rob had this question, chances are others do too.

By creating flywheels that capture key moments in the lifecycle of a subscriber – why did they join your list? why did they buy The Mom Test? what have they done +1 month after reading the book? – you can systematically collect questions, frustrations, and doubts that your readers have with the subject matter you tackle.

I don't want to be the oracle at the top of Delphi telling people how to think about email marketing.

Rather, my job is to set up the right links that allow me to collect a lot of great data, and then deliver shared experiences (mine and yours) to the Create & Sell list.

I don't see myself as a "creator". Sure, I make tangible stuff like email newsletters and courses. But ultimately, I'm researching & trying & failing & learning & cleaning it all up to share with you all.

Rob: Systematically capture what your readers are struggling with and share what you learn

There's a lot of similarities between this recommendation and the previous one, but there's still plenty of nuance.

I think you need a combination of "learn from how I struggled to apply what Rob's taught" to "here's the frontier of what Rob covered in his book, exposed as reader questions."

While your books undoubtedly cover a lot of, nothing is ever exhaustive.

For example, at the end of Write Useful Books you cover a bunch of marketing ideas for promoting your book. But you can't fit "marketing" into a single chapter in a single book. I'm sure there are a lot of great ideas and questions from readers that could be captured, researched, written about, and then shared.

Definitely look into setting up some automation that captures this sort of stuff from your readers. Some ideas here.

Many-to-Many > One-to-Many

I think a lot of what Rob asked in his question could be solved by thinking more about your email list as community vs. "notes from Rob."

He mentioned sending emails about upcoming events and such – which are great – but announcements are inherently one-to-many. Rob has something to say or announce, and so he says it.

While us creators are absolutely at the centre of our respective lists, the single best thing I've done for both solving the "what to write" question and for truly delivering better ideas to my audience has been shifting my thinking to many-to-many.

A few quick ideas to sum things up:

  • Truly internalising ideas takes time and repetition

  • People resist new ideas if they can't figure out how it can help them specifically

  • Therefore, don't be afraid to send the same ideas, described and positioned differently

  • Share stories from your list, both success stories and works-in-progress

  • Facilitate dialogue with your list. Expand the frontiers of your thinking & subject matter by getting your readers to "fill in the blanks"