Lessons from Emma Gannon’s Success on Substack

Emma Gannon has a powerful story of how writing has not only become central to her life, but the primary way she earns a living. To me, her story embodies the ways that newsletters (and Substack) have empowered writers. Today I want to share some lessons I have been considering as I watch her find more fulfillment, growth, and connection with others through her newsletter.

Recently I ran a workshop focused on helping writers get started on and grow their Substack newsletters, (you can purchase access to the recording here) and I wanted to fill the presentation with real-life examples. In the end, I included more than 50 of them. But one name came up again and again: Emma Gannon.

Back in 2021, I interviewed Emma for my podcast and it was an amazing conversation. She talked about how she was “rejected once a day” from magazines she submitted work to, only to find that people loved her writing that she shared on her blog. Now that work has extended to her Substack.

If you are a writer who is looking to:

  • Find a way to share what you write and why, without the unending pressure of social media
  • Be a part of a platform that has huge growth at the moment specifically for writers
  • Focus on writing first, and be known primarily for that
  • Be engaged in a community of writers/readers
  • Earn money from your writing

Then please keep reading!

Show Up For Your Writing (and Readers) Consistently

Sorry to begin with a bummer, but Emma didn’t just start her newsletter (called The Hyphen) a month ago. In fact, she started her blog back in 2009. I’m not sure the exact date of her newsletter launch, but she has said that by March 2022 she had 8,000 subscribers on another platform, which she then moved to Substack.

A year later, her list had grown to 20,000 free subscribers and 1,000 paid subscribers. Today, she seems to have around 30,000 subscribers overall, with enough paid subscribers to make this her full time job, earning six figures just from Substack.

This is a series of Instagram Stories she shared back in 2021, long before she moved her newsletter to Substack:

Emma Gannon

Here she is encouraging people to sign up for a newsletter that is about to go out. Then a few hours later, she shares a link to newsletter itself. After that, a reminder to subscribe if you want to see future issues. Why do these screenshots matter? So many reasons:

  • They illustrate that she has been slowly honing the craft of communicating what she writes and why, and how to get involved.
  • She has become comfortable encouraging readers to join others in her readership, and not miss out. So many writers worry about this, calling it “self promotion.” But it’s so much more meaningful than that. I love seeing when a writer shares their work in a way that feels genuine and welcoming.
  • To give you an opportunity to engage with her around her writing.
  • The before/during/after of the three images above show the many opportunities we have to share our work.

It’s so easy to look at Emma’s success today on Substack and try to refine it to simple questions of: “Emma, what is your best trick for getting more subscribers?” Or “Emma, if you were to start again today, how would you get your first 1,000 subscribers?” These are all good questions, but often queries like this are trying to distill years worth of work down into a simple action or two.

One of the most common challenges writers tell me about when it comes to newsletters is being consistent. They fear committing to any schedule at all, and the schedule they tend to envision is sending a newsletter infrequently.

If you want to share your writing and connect with people, commit to showing up for that writing and your readers. Not only may it lead to the growth you seek, but it will fill your life with writing and readers!

When I help writers with this, we get clear on the themes they write about, and create a practical editorial system whereby they plan some newsletters ahead of time, while also keeping the process loose enough so that they can write in the moment.

When you zoom out from Emma’s newsletter, what else do you see? The myriad of other ways that she has been creating and sharing over the years: her incredibly successful podcast, her many published books, her essays published in a variety of well-known publications, and so much more. I don’t say this to overwhelm you, where the only rational conclusion is, “Oh, I can’t do all that.” You can do your own version of what feels authentic to you. I share this because I want to honor that this work takes time. It is about showing up to create. It is about sharing your voice. It is about connecting with readers in meaningful ways.

You can start small. But as best you can, try to show up consistently.

Go All-In

Earlier this year, Emma ended her podcast, which was called Ctrl Alt Delete. Why is that a big deal? Because she had published 400 episodes over six years, reaching 12 million downloads, interviewing incredible writers and creators in the process, and she has said, it “made [her] really good money.”

Later in the year, she doubled down on Substack further, putting almost all of her content behind a paywall. She explains:

“The main thing for me is putting everything behind a paywall. Then it is clear that paying subscribers get access to everything… I made a decision after a year of Substack, that I wouldn’t write for free anymore. I have spent years writing for free at this point, and so I made the choice to focus only on my members. (I also offer a small handful of complimentary subscriptions to those who genuinely cannot afford it.)”

This sounds super empowering, right? A writer who is making a bold decision to get paid for their writing, and to deeply connect with readers? But that doesn’t mean it is easy to go all-in like this. This is a Substack Note she shared not long ago:

Emma Gannon

Wrapped up in all of this are decisions around what she creates, where she shows up, how accessible she is, how she earns a living, and how she is known. That is a lot! These decisions aren’t easy. And so often (as Emma writes so deeply about), they can impact our sense of identity in unexpected ways.

What can “going all-in” look like for you? So many writers I speak to feel that they are on a hamster wheel of trying to keep up with it all. They have read enough advice on the internet to try to do a million things at once. Perhaps that means trying to post to Instagram, LinkedIn, Facebook, Threads, Bluesky, and 3 other places all the time. And they are feeling diminishing returns on that effort, as if the more they put in, the less they get out of it.

But what if you picked one or two primary channels, and went all-in on those? Instead of trying to become amazing at 5 or 10 things at once, you focused all of your energy on just 1 or 2 places? How would that feel? How does that allow you more time and attention to experiment, to learn what works, to connect with others, and to — dare I say — have fun in the process?

Focus on the Community That Fuels You

This feeling of trying to keep up with social media, only to have it sap you of creative energy is common. I mean, we call it “social” media because it should be filled with a real sense of actual connection to others, right? For Emma, she seems to be fueled not only by her writing, but a meaningful connection to readers. Here she explains why moving most of her content behind the paywall is a powerful way to connect with others:

“I feel it fosters a real sense of community when it’s not accessible to just anyone (i.e. random strangers/trolls who just want to be annoying lol). If you become a member, you get access to entire hub and back catalogue and you’re ‘part’ of something… This has increased my paying subscribers, because otherwise there’s not much point in subscribing to The Hyphen tbh, it’s all about what you get as a fully-fledged member. (Giveaways, personal posts, threads, link round-ups, the comment section, everything!)”

She does exactly what she says: she makes her subscribers feel like a community. Her welcome email to me says: “You are now part of the community! This means a lot; you are supporting my work and enabling me to bring people together during a time that feels rather uncertain. Please do say hello & introduce yourself here (if you feel comfortable doing so)” … and she provides a link.

If you feel spread thin about what you share and where you share it, Emma is an incredible inspiration for focusing on what matters most to you, and focusing only on that. She says:

“Substack is not only a place not to freely write, but a place to build community. That is what was lacking, for me. A place to bring everyone together.”

Be Clear About Your Values

When I work with writers, I take them through a process of defining their values and messaging, which I call Key Messages. In following Emma for so many years, I have seen her resist being pigeonholed by one monicker or identity. Yet she always seems absolutely clear about her values and mission as a writer.

This means she can evolve and change as a human being, and that allows her work to evolve in a manner that feels authentic.

So many people try to shove themselves into a box creatively. Sometimes we justify this as “branding” so that marketing somehow seems easier. I grew up as an artist, my wife is an artist, and something I have always loved and celebrated is how those who create can — and should — change and evolve over time.

Emma shifts as she feels she needs to. From nonfiction to a novelist. From a podcaster to not. She is many things all at once, and honestly, aren’t we all? How she describes her process:

“Stick to your themes. I write about careers, books, creativity, wellbeing and digital themes. I don’t really go outside of this. It’s not necessarily about having ‘a niche’ but it is about sticking to your themes, otherwise it’s difficult to attract your audience and have them stick around.”

I encourage you to define your values to help you write and share in a way that feels meaningful. I shared a tutorial on how to do this a few months back. You can read it here.

Be a Narrator of Your Own Journey

Emma is an incredible narrator of her own journey. So often, she says things out loud that resonate with others in a powerful way. This is not easy — not by a long shot. In the process, not only is she able to present herself as she is, but she can shape how she is known, and inspire others to find the path that is right for them.

Emma is honest in sharing the different paths her journey as a writer takes, and why she makes the decisions she does. In doing so, she is taking us behind-the-scenes in a way that is rare and nuanced.

So often, a writer will tell me a version of: “Oh, I was raised that it is not polite to talk about yourself.” Yet, I find that when we share what we create and why, we not only make people’s lives better, but we are able to represent and advocate for ourselves in beautiful ways. Emma says of her focus on Substack:

“I feel fed and nourished on Substack (from both writing and reading) — I didn’t realise how starving I was for this sort of content back in my life.”

She has been embracing not only her newsletter, but being an advocate for Substack itself. I mean, that is the very position I find myself in right now, and in so many conversations with writers. Even though email newsletters have existed for decades, Substack has reframed them — and expanded them — in unique ways. A lot of people don’t say, “I’m launching a newsletter on Substack,” but rather, “I’m launching a Substack.” For her part, Emma has become something of a Substack celebrity for her success on the platform. And that story — that narrative — is one that reflects so much of who she is.

This isn’t “promotion,” it is more of an authentic reflection of finding a path that feels right. As she describes it:

“I no longer scroll through social media because my inbox is now an incredible place to read things. “

Don’t Be Afraid to Get Paid

Many writers tell me that they don’t have a desire to get paid for their newsletter, they simply want subscribers. Substack — and Emma’s success there — has been changing that narrative. Within 18 months of moving to Substack, she earns a six figure income through it. She talks about it as her full-time job now.

In the past, she has talked about how much less risky it was to have a multi-faceted career (and income streams) than a day job, because at the day job you can get laid off at any time. Today, she has more than a thousand people who pay her, and each of those people is making a clear choice to support her.

I see her taking a lot of actions to encourage growth, including promotions and discounts, and providing limited time access to some articles, or putting up a paywall midway through an article. I think this is actually how I converted to a paid subscriber, the intro to her post was so good, I just had to read the rest of it!

You don’t have to start a newsletter with the goal of getting paid, but I want to encourage you to be open to the concept. You may be surprised to find that people want to support your writing in this manner.

Of course, Emma shares a lot of advice about Substack, and I encourage you to check out her work!

It has been so inspiring to follow her writing and see the decisions she’s made over the years. This is why I have embraced Substack and teaching writers how to find success on it. If you want a guide to help you either start or grow your Substack newsletter, you can purchase access to my workshop here: Launch and Grow Your Email Newsletter On Substack.

What writers have been saying about the workshop:

“Goodness, I took pages and pages of notes! I appreciated the insights about frequency, content, and making it sustainable.”
– Barb Mayes Boustead

“This workshop was very informative! Dan shared his 18+ years worth of knowledge and experience writing newsletters.”
– Colleen Olle

“Overflowing with practical information, but also inspiring and encouraging. He always makes me believe I can do this stuff. I’m full of excitement for my newsletter!”
– Judy Reeves