Today I want to share my thoughts and experiences after sending out 1,000 weekly email newsletters for 20 years. It’s funny to see those numbers added up, because the reality of it was just me writing, clicking ‘publish,’ and engaging with readers. Then, doing it again.
If you have followed me for awhile, you may know that I have been excited about the ways that Substack has helped make newsletters cool again, encouraging more writers to share their unique creative voices, and more readers to discover writers they resonate with. So this post will also be a reflection on Substack.
Social media and online platforms have changed so much in recent years, I wanted to pause to consider the ways I do appreciate newsletters. This is my story of starting and sustaining my newsletter, and some of what I recommend if you are looking to launch or grow your own.
Okay, let’s dig in…
Starting My Newsletter
This is a story I have told before, but is central to why I am such a big advocate for email newsletters. I worked for a decade at a large publisher of trade magazines. My days were spent with writers, including journalists, reporters, editors, and the many other roles in magazines such as Publishers Weekly, Library Journal, School Library Journal, Variety, Interior Design, and dozens of others.
I worked there during the huge transition that publishers were making from print to digital. I ended up helping to launch the company’s blog initiative, training 300 bloggers, as well as helping to establish the social media strategies for dozens of brands. Of course, I assisted with newsletter strategies too.
This is where my own newsletter began, back in 2005. It started with me needing to ask permission. I asked my boss if I could share a small weekly newsletter that helped the writers and business leaders in our company embrace how to connect with readers online. Thankfully, she gave me permission. Communications in the company were tightly controlled, and she was in charge of the formal company newsletter. It felt like a big step that she would approve a smaller one, run entirely by me.
I walked around to the desks of nine people I knew and asked if I could send them the first issue.
What happened next was unexpected, and a little harrowing. This is the moment that everything changed for me, when it became possible for me to work full-time on my own, spending my days doing creative work that I love. (Though that wouldn’t happen until years later.)
One of the nine people I sent the first newsletter to was a lawyer for our company. He replied back that he thought I should send it to our CEO, and that he would appreciate it. I resisted. Emailing the CEO seemed like the type of thing that a guy sitting in a gray cubical didn’t do. Too often, in corporate culture, you don’t raise your hand in order to stand out. You simply try to fit in.
My colleague gave me an ultimatum: if I didn’t email it to the CEO, he would. My cube was near all of the executive offices, and this was the chain of events:
I asked my boss permission to forward the newsletter to the CEO. She approved.
I forwarded the first newsletter to the CEO saying that it was suggested I forward it to him, and that he may appreciate it.
A few minutes later, I saw the CEO walk out of his office, past my cube, and into my boss’s office. He shut the door. Welcome to the longest five minutes of my life.
Five minutes later he went back to his office.
Thirty seconds later, my phone rang and my boss called me into her office.
When I arrived, she asked me to close the door and sit down.
At this point, I was 100% convinced that I was about to be fired. Why? Not only because I had spoken up within a corporation, but because the topic I was writing about (how digital media will affect writers, readers, and impact our revenue with print media) represented a huge threat to the company’s core business model, and to many of its employees.
Then she said something unexpected: “The CEO would like to forward your email to the entire company, suggesting that everyone subscribe.”
That instantly boosted my subscriber base to well more than nine people. Within the company, I became well-known. I had advocates, but I’m also well aware that I had detractors — those who did not like what I had to say, and were not supportive of my ability to share so easily within the company.
This experience taught me so much about the power of sharing your voice, but also about the importance of advocating for others. When my colleague gave me the ultimatum, “I think you should share this with the CEO. If you don’t, I will,” he became a staunch advocate for me and what I believed in. His involvement was not passive — a simple “like” on a social media post. He focused on amplifying my voice.
Through what he did, what my boss allowed, and what the CEO insisted on, a chain of events happened that has lead me to where I am today. In many ways, I got lucky. In other ways, what I did with that luck shaped what was to come next. If I had just sent 10 newsletters and then stopped, nothing would have changed. But I kept going, sending newsletters week after week, and in the process I learned more about who I was and who my readers were. This journey continues today with this very newsletter, and you reading these words. (Thank you!!!)
Sustaining My Newsletter
How did I send out a newsletter every week for twenty years? It was by finding my deeper motivation. I grew up as the art kid, and my entire life has been surrounded by creative pursuits and creative people. A weekly deadline for writing and publishing has been a huge motivator for me.
To write and publish is both an opportunity and a risk. When I was young, I took loads of creative risks with one project or another. What I found as I got older was that the newsletter is my way of sustaining that feeling: to be both excited and terrified to write and publish each week.
Right now, I am 52 years old. I am infinitely thankful that every week I feel that sense of opportunity and fear in using my unique creative voice. That each Friday, I will click “publish,” and I never have any idea which posts will deeply resonate, and which will fall flat. I love living in that space. That I don’t look back on “when I used to be creative,” or “I used to take creative risks.” Having the opportunity to write this newsletter each week is a gift.
From a technical level, I use the tools that I often help writers with: I maintain an editorial calendar, I am clear on my Key Messages, I try to engage with a lot of writers so I have a sense of what is important to them, and so much else. Some weeks I know exactly what to write, and some weeks I give myself total freedom to write whatever I want the day before I have to publish. It waxes and wanes, and not locking myself into one modality is part of what has helped sustain the newsletter.
I try to give myself a long leash to experiment. Some weeks, the newsletter was nearly entirely just photos. Sometimes it was a poem. Sometimes more of a personal letter. Others, a long case study.
My typical routine is this:
I do keep an editorial calendar, but I don’t always follow it. I have a daily habit of capturing any idea or inspiration I have into an “ideas” file in Dropbox. There are hundreds of ideas in here.
Usually on Monday or Tuesday, I will select the topic for that Friday’s newsletter. Sometimes it is already defined in the editorial calendar, other times I am obsessed with a topic and know I will write about it that week, and sometimes I have no idea, so I go fishing for ideas in the Dropbox folder.
Then on Tuesday or Wednesday I will create a sample headline for the post, an outline of the flow of it, and consider the introduction. Once I have that roadmap down, it is sooooooo much easier for me to write the post because I know the structure and where it is leading.
Wednesday, and especially Thursday, and Friday morning, I write the essay. Some days it is 95% done by the time I leave work on Thursday. Sometimes it is only 50% done. This may sound odd, but I still love waking up to the pressure to finish a post on Friday morning and click “publish” to thousands of people.
After I send it out, I collapse into a puddle of emotions and then take a walk. See — easy peasy!
On a technical level, my process is pretty simple. I’ve moved platforms a few times: the first was moving it from the platform the company I worked for used, once they shut down. Then I used Aweber for years, then Convertkit, and now Substack. Of course, with clients I have used loads of other platforms too.
What Feel Refreshing About Substack, Still
Writers have shared with me posts they have seen where others have discouraged people from using or staying on Substack. In general, many of these posts make excellent points. Some advice was tried-and-true wisdom that people have shared long before Substack even existed, such as "Build your platform in a place you own." Others are more specific to a decision that Substack has made, a way they operate, or how it has evolved.
My (hopefully non-controversial) reaction is this: Great! These people make wonderful points. I could not be happier that each person is finding the path that works best for them, and the platform that resonates most. If you don't like Substack, if you want to leave, have left, or never joined -- I totally love that you have made the right choice for you! I appreciate that you can advocate to others what you feel they should keep in mind. Yay!
One reason I still appreciate Substack is that it feels kinda like a social network focused on writing and reading. Are there other newsletter platforms? Yes! So many, and they are all good. But it’s been nice to see the celebration of writing and reading here. Is there the unintended side effect that this can be overwhelming? That you find too many newsletters you want to read? Well, like walking into an amazing bookstore, I find that to be a wonderful problem to have.
When I consider the things I have appreciated about Substack, it tends to include:
Recommendations — Substack has made it easy for writers to connect with each other, and recommend writers/writing they love. They made it easy for a reader to subscribe to these folks. Before Substack, the other newsletter platforms mostly seemed to focus on providing the technical tools to send a newsletter. But Substack focused way more on solving the challenge that most people faced: how to get subscribers. The ability for one person to recommend another has felt really nice. A nice change to the more algorithmic alternative that social media uses.
Making newsletters cool again. For so long, even when newsletters weren’t cool for writers, so many successful writers would say, “What would I have done differently? Started my newsletter sooner.” Why? Because having an email list is a central way to maintain contact with your readers, especially as your career as a writer evolves. It can have a significant impact on book preorders, getting reviews, etc. Plus: you can always back up or move your email list. I like that more writers have embraced this, and think Substack played a role in this.
No longer being an island. For so long, if someone had a newsletter, they were essentially an island. You couldn’t easily find newsletters/writers very easily on certain topics. Substack provided not just a newsletter platform, but they created a “Publication” for you that was connected to a network of other writers and readers. In logging into your account, you would see not just your newsletter — but those of other writers. It was easy to find like-minded people writing on topics you were interested in..
Normalized getting paid for your writing. For many years, I saw firsthand how magazines and newspapers struggled to find a model to collect revenue from readers, which was vital to sustaining themselves. It was even more complicated for an individual writer. But Substack normalized this for writers — the ability to get paid for their newsletter. They didn’t just provided the technical tools, but the ecosystem where this became completely unsurprising. That normalization has become a gateway for people —I have seen writers who started earning serious money on Substack. Then, they may stay on the platform, or move to a new one that fits them better as they grow.
Blogs and comments are back! Before Substack, even when you found someone you liked who had a newsletter, you would subscribe, and then… wait. Maybe you would receive an issue in a week. Or two. Or four. Or 12. Maybe not. But with Substack creating a Publication for you, they essentially brought back the old-fashioned blog. Which I love. Where, when people discover your writing, they can immediately read your recent posts and dive into your archives. Years ago when I had a blog, the comments section would be a way to engage with readers. But social media killed blog comments. It’s nice to have them back on Substack, to where you feel you can engage with readers outside of other social media channels.
Are other platforms doing some of these things too? Yes, which is great! Again, I’m sharing my personal experience here. All of this has felt very refreshing.
All Newsletter Platforms Are Fine. Running a Business is Hard.
Whatever newsletter platform you choose will be fine. Go with the one you like most.
For those who have been able to earn serious revenue on Substack, and use it to help establish or grow their business, that has been incredible to see. One thing I try to keep in mind as I observe this: running a business is difficult. And there is no one size fits all advice.
Going back to the good business advice I mentioned earlier — “Build your platform on a platform you own” — the idea here is so smart. Ensure the foundation for your business is not something that someone else can easily take away.
Except for the many businesses that is difficult. Where their entire business is on YouTube or Instagram or Etsy. Can they try to diversify? Absolutely. I see people create a Patreon, sell direct, and branch out to other social media channels. But businesses are often built in spaces they rent. Literal storefronts they rent, collaborations or partnerships, franchises, being beholden to suppliers or partners, etc. They also have to deal with a host of fees with partners, many of which they don’t have a lot of control over. These are normal business practices that mean someone doesn’t own/control a core aspect of their business. Yet, their business still thrives and is sustainable.
Years ago, when I interviewed my friend Andrea Lekberg about starting her bakery The Artist Baker, she said, “Sign the longest lease they will give you.” Here is her full quote:
“People would sign a year lease, and I thought they weren’t preparing themselves for success. They were first looking for a way out. Sign the longest lease they will give you. You can always get out of it, if you are smart about it. When you setup a business with lawyers, everybody is protected. It is key to have lawyers and contracts.”
Why does she recommend this? Another story from her when she was looking to rent a space in another town:
“I signed a lease on one property, and the person was just using it to get another person to sign the lease. I was used, but I didn’t know. Another time, I almost signed on a property, and the lease was a triple net, which means you are responsible for everything below the roof. Before I signed the lease, I had an inspection done, which I was paying for. I found all these problems, so I didn’t sign the lease. It was interesting learning about what could happen — what you are responsible for.”
The idea of signing the longest lease you can is the reality of trying to build a solid foundation when you can’t always control everything.
Likewise, finding growth and sustaining it is difficult. It takes a lot of effort. For example, I watched Emily Oster move her newsletter from Substack to another platform. I was so happy that she and her team were actively growing their business in a way that makes the most sense for them. But I’m also reminded that it’s not easy. Below are the emails I have received in the past 2 months with various ways they are encouraging me to become a paid subscriber:
Some messages are essentially saying, “This is it: the sale ends soon.” But then, the sale doesn’t end. Now, I don’t want you to take the wrong message here, I think this is 100% fine! When I receive these emails I am reminded, “Running a business is hard. Finding growth is hard. Emily and her team are trying to make this sustainable because they truly believe in their mission.”
I’m so happy that she and her team are able to run their business the way they want, with the platforms they want, and reach out to their audience whenever and however they like. I share this as a reminder that growth is not easy. Not on Substack. Not anywhere. It takes intention and work.
If You Are Overwhelmed…
I was texting with a friend not long ago about their newsletter. They expressed a feeling of being overwhelmed, and I suggested this: “Just focus 100% on your subscribers.”
I think on whichever platform you choose — newsletters, social media, or otherwise — it is easy to feel overwhelmed by all the things you can do. What I encourage you to focus on are the essentials:
Sharing your unique creative voice.
Bringing joy to your subscribers, however you define that.
How do I manage this? Well, there is so much of the Substack platform that I ignore. I focus on my writing deadline, on what I want to say this week, and on engaging with my subscribers. Everything else is extra.
Let me know in the comments: what do you find joyful or challenging about email newsletters?
If you want to explore working with me, there are two ways I collaborate with writers and creators:
As always, thank you for being here with me.
-Dan
Kids of the Week: The little guy had his first Zoom class ever! It was for his Hebrew lesson, and it was adorable to see how nervous he was beforehand (not knowing what to expect), and how much he loved it afterwards:
His outfit for school picture day!
You’re an inspiration. I pre-prepared six Substack posts before launching so I could have an on-ramp. I could not sustain weekly posts, so I did not paywall ANY of my content, because I did not want to disappoint subscribers. Nevertheless I posted consistently for at least a year, but then fell off. I’d like to return to regular posting. But I’m afraid I can’t sustain it.
Me, the friend overwhelmed!
Few words help so much tho: focus only on this group…
Amazing your story and history of your weekly newsletter. Have you taken weeks off?