The Life of CreativeMornings’ Weekly Highlights: How to Create a Newsletter Your Community Loves

In January 2016, the Weekly Highlights was born as a fun campaign in collaboration with our global partner MailChimp. What was intended to be a finite project became an indispensable and beloved newsletter for the creative community.

It’s the first thing I work on when I come into the office on Monday, combing through dozens of links, sifting the debris of the Internet to uncover the gems. Since joining the team in June 2016, I’ve sent more newsletters to more people than I ever had in my lifetime. Even after many repetitions, my palms still get sweaty before I hit send.

I’ve learned that a newsletter can feel like a gift — like our free monthly events in 180+ cities — and can have a life of its own. The inbox is more sacred than any online space we engage with; to be able to send something frequently is truly a privilege. You’ve earned the most valuable assets: trust and permission. (You can dig into the archives here.)


Below is a list of guidelines I ascribe to when creating our newsletter: questions I ask myself, and principles I adhere to in creating a newsletter that people love. I hope they’re helpful for you, too.

What is it for?

Why am I sending an email?

With the Weekly Highlights, I’m providing the creatives in our community a must-watch talk from a CreativeMornings event, Fun Stuff to Click On — which is a diverse collection of links that aim to educate, empower, and of course, be fun — and cool job opportunities from all sorts of companies.

This can be challenging, of course. Defining what this newsletter is for and setting clear boundaries in what to include and not include is paramount; it shapes the content I curate for the readers.

If your newsletter is for curating a list of books that you’ve read, and folks are signing up because they trust your taste in books, then that’s exactly what your newsletter is for. Consistently providing great value in curation and thoughtfulness builds a loyal readership that is eager to hear from someone they trust.

When it’s time to advertise an event or sell a book, the trust earned throughout the years will be the greatest asset — not Instagram or Facebook ads. We’ll touch more on this idea below.

Who (and what) am I trying to change?

Whether I’m writing essays, interviewing people, taking photos, or creating newsletters, it’s helpful to ask myself: Who am I trying to change, and what change am I trying to create?

With our newsletter, I’m trying to change the global creative community by connecting them to diverse ideas, deep thinkers, and meaningful projects that will enrich and expand their creative endeavors. When I hear feedback that people don’t have the time to find links like these, I realize I’m creating a resource that they rely on to learn, grow, and become better. Knowing this, I am obligated to care about what I share and to taste test the links myself to ensure they’re worth consuming.

If I answered, “I am trying to change the people who attend our events,” then the newsletter would look, read, and feel different. Because people who receive our newsletter are not all attendees, it’s a smarter long-term strategy to cater toward a more general approach than just our events. The best is when someone says, “I don’t think I am creative, but I love your newsletters!”

Content is best when it deeply connects with the readers, not only meeting them where they are, but showing them the possibilities of the future. I remember thinking, If a newsletter is so good it inspires folks to attend an event, then everyone wins. And I did a good day’s work.

How do I want people to feel?

This is a simple question that has a profound impact on my work.

I try to think through the following questions:

Can I describe the emotions I want my readers to have? Can I imagine their reaction to the newsletter, and would they forward it to a coworker? “This link here, you have to read it!” What are the different puzzle pieces that combine to form this narrative? What imagery and language will I use to invoke these feelings?

When I took over the newsletter, I dug into the archives and studied every campaign to find a connecting thread that this community resonated with. Then I zoomed back out and imagined the possibilities ahead and devised a strategy for how to get there.

Start with the feelings, the story that you want readers to tell themselves, and work backwards.

What does success look like?

My knee-jerk reaction can be to compare the success of our newsletter to someone else’s.

What are our open rates? What are our click rates? How many new subscribers do we get a month?

This is fun to do (or excruciating to do!) but rarely gets me anywhere. Instead, I try to focus on the feedback that we receive and the love that people share on social media. That’s rewarding to think about: Our newsletter enters a person’s inbox and it’s so valuable that they’re compelled to share it with their friends.

Yes, open rates and click rates matter. But you decide what you want to measure and how much value you place on it. For my sanity, I check the number of unique people reading our Weekly Highlights and the number of clicks that a link gets. If our unique readership goes up, good, and if I can study 10 or 20 links through the course of a month, I can get a pulse on what kinds of topics resonate most.

Publish the best content

I either create the content or shine a light on others.

What is good content? I think it has to do with empathy and experience.

As a writer, I’ve devoured content for years, learning to understand the DNA of thoughtful work. I’ve also written many awful essays (and some decent) and shipped projects that fell flat on their face, which honed my ability to sniff out great work. It’s helpful to keep a pulse on makers who I admire and realize that they belong to a community of other makers whose work is equally fantastic.

The Fun Stuff to Click On are links that I personally study, dissect, and determine whether they make the cut. Here are some things I look at:

Headline: This is the first sentence we read and it determines whether we continue or not. If it’s link-baity, I’ll still give it a chance, but if it’s nutritiously sparse, like white bread versus wheat bread, I’ll question why I’m even subscribed to that person/publication.

Quality: Putting aside my irrationally high standard of quality, did this person understand what they were creating and who they were creating it for? Were they generous, thoughtful, and clear? Did they care about the work? Is there heart?

Diversity: I’ll have the serious reads like insights on psychology or hourlong interviews, but I also mix in easily digestible content. Having ten links only about design doesn’t serve the community we’ve built.

Constraints: I could easily curate 50 links, but that won’t do anyone any good. Constraints champion creativity. If I tell myself 12 links max, then my mind is pushed to be even more thoughtful about what I’m including and why.

Picking a talk: Every Weekly Highlights features one talk from a CreativeMornings chapter. My criteria is simple and I ask myself: Is this talk from the heart? Is the speaker exercising humility? Are they telling a story that connects with the audience? Are they being open about their process, failures, and successes?

A/B test the work

In October 2016, we created a gentle sign-up bar at the bottom of the screen because the process for signing up wasn’t clear and many of the existing forms were hidden. It was a quick and effective solution that was on-brand.

And then the open rates on the Weekly Highlights dropped nearly 10%. Adding tens of thousands of new subscribers will do that, and I was committed to getting the number back up.

I A/B tested subject lines to start. If you’re an old subscriber, you might remember the former subject lines beginning with “Weekly Highlights #X: [copy].”

I remember dissecting our campaigns, looking at each element, and asking myself, “What is it for?” To simply tell someone the edition of the email? So what? Unless it’s the 100th anniversary, no one cares. The first thing people read is the subject line and I was losing attention before the email was fully baked.

So I kept one email with the old copy and the second email with a clear, simple sentence. For two months — a total of nine newsletters — the data was obvious: Clear subject lines are better than clutter.

When you test your campaigns, start small and be intentional with your experiments. I wrote documents about the process, ensuring that I wouldn’t be tempted to add something else on top of what was already being done — that’s a recipe for thrashing and failing.

It’s easy to want to rush these experimentation phases, but that’s the short-term game.

Remember that your greatest asset is your newsletter

What would you rather have: a million followers on Instagram or a million subscribers to your newsletter?

It would be nice — and possible — to have both, but in the long-term game of building your business, a newsletter is less likely to be tainted by algorithms and changes outside of your control. Email is direct contact with people who want to hear from you.

Growing a newsletter list is a commitment to a long-term game. Writers like Seth Godin and Maria Popova committed to the game over a decade ago, and through consistently showing up and giving value, they’ve earned trust. Through their work, they represent their values and communicate what they stand for. When it comes time to sell a product like a book or a course, the likelihood of it selling is far greater through a newsletter rather than a post on Instagram or ads on Facebook.

Indeed, the future of freelancing and online businesses will depend on one’s newsletter list and the platform where they share their work. The more trust you have, the better off you’ll be.

I look at people like Paul Jarvis and Jocelyn Glei who are generous with their insights and work, own their platforms, grow their email newsletter lists, and connect with their tribes. It’s no wonder why they lead fruitful creative careers — they have the support of real people who believe in their art. Amanda Palmer understood the value of trust and permission. So did Nipsey Hussle.

It’s also a great responsibility of power

When I took over the newsletter, it was daunting at first — I had never sent an email to over 100,000 people at once; now it’s double the size. My personal newsletter is 2% that size. It was like playing wall ball by myself and then suddenly playing against Roger Federer without warming up.

I soon realized how much power I was wielding when my colleague Sally forwarded me a project by her friend Sarah, founder of Make a Mark — a 12-hour design and development marathon for humanitarian causes.

Sally asked for me to look at it — that’s it, not to feature or share it, just check it out. The decision for me was obvious: The project was generous, thoughtful, and focused on social good; the mission was clear; and the people who subscribe to our newsletter and are part of our global community believe in things like this. Featuring it was a no-brainer. Good work like this deserves to be noticed.

Little did I know that bringing attention to this project helped Sarah scale to seven cities in a year. It’s pleasantly shocking how much wonderful work is happening in our world and we have no idea until some huge media outlet talks about it. I realized this was the power of our newsletter and ultimately a core value of CreativeMornings — shining a light on others.

Which game are you playing?

It’s strange for me to look back 10-15 years ago and see how marketers raved about the importance of growing your email list, for whatever you do online.

Then there was a period where that shifted: Everyone glorified social media, video content, drones, live video, and more recently, influencers and branded content.

That’s not to say that these platforms aren’t important; it’s to realize that there are timeless assets that exist in the realm of building something that lasts, and right now it’s email.

Many of us woke up today stressed out about invisible things like algorithms. We never used to care about them, and now they’re the bane of our existence. We’ve put trust in companies that don’t care about creativity, but rather, commerce. I don’t know much, but I doubt this is a smart strategy for leading a creative career.

Instead, it’s better to focus on the timeless, the scalable: Earning trust, building your reputation, practicing your craft, working well with others, improving the quality of your work, being generous with what you learn, and shipping even when you’re scared to fail.

The catch is this: Every day, we choose to either play the short game or the long game. Every day, it’s our choice.

Thanks to our global partner MailChimp, which allows us to do work like this. CreativeMornings/HQ and our 180+ chapters send over 1.5m+ e-mails every month using MailChimp. We wouldn’t recommend any other platform for building your list.

Photo credit: Stacy Keck.

Further reading and resources:

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