Just over a year ago, I sent out the very first issue of the Listen Up Newsletter.

The subject line of that first issue was, “Focus On What Fuels You,” and was, at least in some part about coming back to writing newsletters, something I’d tried multiple times in the past, but had never been able to stick with.

While those past attempts at writing a consistent newsletter had always felt like chores, this one felt different. A year ago, starting the LU Newsletter felt like something that actually energized me, an additive force rather than a draining one.

A year later, I’m grateful that I still experience that energy when I sit down to write each issue.

The past year has brought a lot of trial, error, and learning when it comes to the newsletter, and in this issue, I want to break down some of my personal takeaways from one year and 50 issues of newsletter writing.

But before we do, let’s look at why I started it in the first place.

Why I Started A Newsletter

When I started the newsletter in April, 2020, the pandemic had recently shut the world down. Like most everyone else, I found myself stuck at home with more time to fill, especially during the weekends.

It was during the initial lockdown that I started discovering some truly fantastic email newsletters that completely changed my idea of what a newsletter could be.

These newsletters from people like Khe Hy, Jay Clouse, Ann Handley, and The DO Lectures showed me that a newsletter was not the same as email marketing. It wasn’t about simply summarizing your latest blog post or podcast episode or blasting your list.

I learned that a good newsletter could (and should) stand on its own, as a unique product, valuable in its own right. What’s more, like a podcast, if presented the right way, it’s something people would choose to subscribe to willingly without the need for a lead magnet, freebie, bribe, etc.

What I especially liked about the newsletters I read was the sense of intimacy and familiarity that was lacking from a lot of blogs, including mine. As a writer, I wanted to speak more personally and directly to a community of like-minded people, and I didn’t feel that was happening through my current blogs. A newsletter, however, felt like the perfect fit.

My motivations for starting the newsletter has always been personal first, business second, which is one of the reasons why I think I’ve been able to main the energy and excitement behind it for this long

The primary reason I started was to give me a forum to experiment with and improve my long-form writing, particularly as it related to storytelling and teaching. What I liked about that goal is that it could be worked toward and achieved even if no one ever read a single issue.

That said, I did have a number of audience-facing goals related to the newsletter as well.

Audience-Facing Goals

I saw the newsletter as becoming what I refer to as my flagship content, the primary content channel that I poured the bulk of my focus and creative energy into, and which would drive the rest of my content marketing.

Like most flagship content, my primary audience-facing goals were to grow my email list, and nurture the subscribers on it with regular insight and communication that they (hopefully) found valuable.

I’d built up an email list of around 900 people in the past, but had let my communication lapse multiple times. At the time I started the LU Newsletter, I hadn’t sent a single email to my list in over a year.

Starting a newsletter as a dedicated content channel was a way to avoid falling back into that situation again.

So with those goals in mind, let’s have a look at some of the results of publishing the newsletter weekly over the past year.

Outcomes

Writing Improvement

The biggest and most obvious benefit of writing the newsletter for a year has been the improvement of my writing.

As mentioned, this was one of my biggest goals when I started the newsletter so I’m glad to see that there has, in fact, been growth and improvement.

There have been a few issues of the newsletter in particular that stand out to me as being notable leaps forward in my writing, where everything just clicked for me. Two of the issues that stand out most as big steps forward are #10: Directing Your Energy Wisely and #43: What Pinky Toes Teach Us About Strong Foundations.

That said, after a year of writing, I’m starting to realize that my writing has a long way to go to be at the level I want it to be, and that I’m reaching the limits of how much I can improve my writing on my own. With that in mind, I plan on taking one or more writing courses over the next year to take a more active approach to continued improvement.

List Nurturing & Engagement

After the improvement of my writing, the list engagement has been the biggest positive outcome for me a year into the newsletter.

I’ve had a number of people reach out either privately or publicly on social media and say that the Listen Up Newsletter is their very favourite newsletter. As you might imagine, this means a lot to me. I’ve written before about how our goal as creators needs to be to make work that has the potential to be someone’s favourite, an idea I borrowed from Jay Acunzo.

While the growth of the newsletter has been slower than I’d hoped, the fact that it’s resonating with people and has achieved that coveted “favourite” status for at least a handful of them is a strong sign to me that I’m on the right track, and that it’s worth continuing.

Beyond the compliments and the positive feedback, I’ve also run three launches for Podcast Marketing Academy, as well as some other mini-promotions and the majority of the sales have come from the list.

There’s no way to know for certain, but given that I hadn’t sent an email in over a year before starting the newsletter, I’m guessing all of those launches would have fallen flat if not for the regular contact with my subscribers and in many cases, back and forth interaction that email allows for.

Unexpected Benefits

Aside from some of the goals and expectations I had in mind when I started the newsletter, there have been some unexpected side benefits of publishing it consistently as well.

The first has been some of the relationships I’ve both made and deepened through back and forth conversations with subscribers who’ve replied to my emails. In many cases we’ve actually ended up getting on Zoom calls to connect and chat. These connections weren’t something I anticipated when I started out, but I’m really grateful that the newsletter has facilitated them.

The second big unexpected benefit has come as a result of the curated section of each newsletter.

In each issue, I include a list of “5 Things You Might Dig” based on my own content consumption and findings each week. The unexpected byproduct of doing this section is that I now have a reason to always be on the lookout for interesting content that is helpful to the creators, marketers, and entrepreneurs in my audience. In seeking out and consuming this content myself, I’ve learned a lot when it comes to marketing, content creation, and more.

List Growth

Alright, finally we get to list growth, the goal where the least progress has been made.

As you might expect, after not having emailed my list for over a year, I experience a large drop off in subscribers when I started sending emails again. I had 50 unsubscribes from the first email alone, and over the first two months of publishing the newsletter, I dropped from a high of 1,094 subscribers down to a low of 955.

From there, the list started growing, but if I’m honest, it hasn’t grown at nearly the rate I would’ve hoped.

In the year of publishing, I’ve been able to grow it from the low point of 955 subscribers up to 1,186 where it’s currently at, a net gain of 231 over the course of a year. I hadn’t set any measurable goals around list growth when I started out, but I think I would have hoped or expected to grow the newsletter by at least 1,000 subscribers in a year of publishing.

The growth that has come has mainly been driven by speaking at virtual summits, participating in a handful of collaborative promotions, and most recently by running a free 5-day workshop related to podcast sponsorship, which was promoted by a number of affiliate partners as well.

While the results have been somewhat discouraging, as I mentioned earlier, the fact that I’m getting positive feedback and engagement from readers is a much stronger indicator for me to double down and keep going than the number of subscribers is.

Lessons Learned From A Year Of Newsletter Writing

While there’s a lot to think and sort through when it comes to what’s working and what’s not, there have been a few lessons that clearly stand out from this first year of the newsletter.

1. It’s Hard To Have More Than One Flagship Content Channel at a Time

Shortly after starting the newsletter, I also started a podcast, Build A Better Wellness Biz. The show was a fairly ambitious endeavour with high production value, and each episode of the weekly show ended up taking between 15-20 hours of my time to produce on top of the time my team put into it.

On top of that, I also maintained my practice of writing and publishing a new blog post every day. This ended up being way too much content to produce at the level I wanted it to be at, and so, after 30 episodes, I decided to end the podcast.

In the end, the newsletter felt much more aligned with the direction I wanted to be heading in, and the topics were more focused around where I thought I could bring unique insight and perspective to the world.

Going forward, while I will almost certainly experiment with adding more content channels again in the future, none of those endeavours will be as ambitious or time-consuming as Build A Better Wellness Biz. Ultimately, the one thing I want to be known for is the newsletter, so I’m going to make sure I’m allocating the time and attention to making it the best it can be, with everything else being secondary.

2. The Secret to a Successful Newsletter Is Thinking About It as a Product

This is true for all content, but I think it’s especially worth mentioning for newsletters. It’s easy for the line to blur between email marketing and a newsletter, when they are not, in fact, the same thing.

To me, each issue of a newsletter needs to be approached as a discrete product, something that your subscribers look forward to and are excited to read, much like the latest issue of a print magazine. It should be tight, cohesive, and nicely packaged.

Unlike email marketing the point of the newsletter should never be sales, but value. There should be a clear line drawn between the two types of emails.

3. I Need To Bring More Clarity to the Newsletter if I Want It To Grow More Quickly

To market anything effectively, it’s essential to be able to concisely summarize who it’s for and what it’s for. One of my current frustrations with the newsletter is that I’m not quite sure how to actually articulate this in a concise and compelling way.

The best I can come up with right now is that this is a newsletter helping creators find the clues to navigating a meaningful creative life that are hidden in plain sight. Kinda clunky but it’s the best I’ve got right now.

I feel like gaining clarity on both the topics I write about and how I talk about the newsletter is a piece that needs to fall into place before the newsletter can really start growing.

On that note, I’d love to hear how you would describe this newsletter. Feel free to hit reply to this email or even better, fill out this reader survey and let me know.

4. I Need To Create More on-Ramps to the Newsletter

Lastly, I’ve realized that while I have one or two solid lead magnets leading people to the newsletter, I need to create more diversified, high-quality on-ramps to appeal to more people.

My big focus over the next six months or so is going to be list growth. I’ve already got a number of ideas on how to create valuable free or low-cost resources to grow my list, and I’m excited to start building them.

I’ll be sharing updates both through the newsletter a well as on Twitter as to how Project List Growth is progressing, including what I’m trying, what’s working and what’s not.

Bring On Year Two

If I had any doubt a year ago about the newsletter as a long-term content medium, it’s long since dissipated. I still have just as much excitement to sit down and write each new issue and as the momentum continues to slowly build, I imagine that excitement is only going to grow.

I see this newsletter as being the compass needle of all the work I do going forward, where ideas are started, explored, and eventually developed into something bigger. I’m honoured that you’ve signed up to follow along and will do my best to keep sharing insight that you find valuable in developing your own creative work.

That said, I can’t make this newsletter the best it can be on my own.

How You Can Help

The first and most helpful thing you can do is to fill out this subscriber survey. It will only take a few of minutes and will help me understand what you like about the newsletter, what you don’t, and give me ideas on how to improve the content and your experience as a reader.

The second thing you can do is to reach out at any time. My inbox is always open, so please hit reply to any (or every) newsletter issue you enjoy and let me know what you took away. Also, feel free to reach out on Twitter.

Lastly, if you find value in the newsletter, I would be beyond grateful if you would send it to someone else who you think might enjoy it as well. I’m convinced all good things grow by word of mouth, and this newsletter will be no different.

Thank you so much for being a reader, it means the world to me. Now let’s get on to year two, shall we?

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Explore how to navigate a creative life that matters

This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”

It’s something I’m proud to create and I’d be honoured to share it with you.

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