Newsletter Lessons

Note: "David's Dispatches" was meant to be a tag for LinkedIn posts and articles until I launched a newsletter here by accident.

But before I knew it, LinkedIn's software had invited everyone in my network to subscribe to "David's Dispatches."

It felt like hitting "reply all" to the entire company by mistake. Except it went out to my entire professional network.

I already had a separate email newsletter called Beyond the Cove, which is the subject of this post. And I certainly didn't need a second newsletter.

Initially, I intended to cross-post here any "Beyond the Cove" essays that felt appropriate for a broader LinkedIn audience, but then my best intentions hit the wall of reality. Writing and managing one newsletter was plenty.

I figured this was a good opportunity to clarify the difference (and possible confusion), and may be of help to readers contemplating a consistent writing practice.

I may post here from time to time, but you're always welcome to read past editions and subscribe to Beyond the Cove here. It's free and arrives in your inbox every other Tuesday morning.

Now back to the essay...

A little over two years ago, I hit the restart button on Beyond the Cove, committing to a bi-weekly writing schedule that has since become an integral part of my life.

As I reflect on this journey, I’m struck by how my measures of success diverge from traditional metrics.

Sure, I guess it’s nice to have an open rate that’s consistently in the low 70s - currently 73% over the past 90 days - a number that would make many newsletter writers envious.

But I’m not about to let stats like that go to my head. We’re talking about relatively small numbers here. There are roughly 300 of you out there, growing slowly, which is just fine by me.

The stuff that matters to me is more qualitative.

Nothing beats an unexpected reply from readers who tell me a particular essay resonated with them. Similarly, when someone I haven’t seen in years mentions they read my work regularly and feel more connected through my words, it reminds me why I started this writing journey - to write consistently and maintain genuine connections with my audience.

Along the way, I’ve learned a lot from this experience. Whether you’re considering launching your own newsletter (or wonder why I bother), I hope you’ll enjoy these seven learnings from my two-year writing adventure through Beyond the Cove:

1. Imperfect action > perfect inaction: Publishing something good is better than endlessly refining it towards perfection. Based on feedback, readers appreciate consistency and authenticity more than flawless prose. Plus, even if I spend every waking minute on an essay, it’ll never be perfect. It might even get worse! Just do good work and publish.
2. Carry a notebook: Since I started writing regularly, I’m much more aware of the world around me. I see essay topics everywhere. And the more you write, the more ideas you’ll see. I always carry a pen and small notebook ?? to jot down ideas from conversations, podcasts, books, or random observations. In my case, I’ve been unexpectedly inspired to write while visiting Austin with my son, walking past a statue of Longfellow in Portland, and sitting by the estuarine middle ground where the Royal River meets Casco Bay.
3. Consistency breeds creativity: Regular writing sessions often lead to unexpected ideas and insights. I’ve found that some of my favorite essays emerged when I didn’t want to write but did it anyway. Others meandered along one path, found their footing, and launched in a different direction altogether. Show up regularly and remain open to where your writing practice might take you.
4. Writing clarifies thinking: Yes, this point has been made countless times by myself and others, and for good reason. It’s true. Author Flannery O’Connor is known to have said, “I write because I don’t know what I think until I read what I say,” which sums it up well. Often, I think I understand something until my writing exposes flaws in logic or weak arguments, which, fortunately, the writing process can also help fix.
5. Quality and quantity can coexist: With practice, you can produce good work more quickly. Regular writing has improved both my speed and the quality of my output. When I first started, I spent too much time laboring through drafts, often avoiding other higher-priority work in the process! I’ve since found that imposing arbitrary time constraints is a tactic that has worked well. I’ll give myself 45 minutes to write a draft. Knowing there’s a limited amount of time and that I’ll be able to edit the draft later seems to relieve pressure.
6. Vulnerability connects: Sharing personal experiences and challenges resonates deeply with readers. Some of my most well-received pieces have been those where I opened up about struggles or uncertainties. For example, writing "Running with Doug" helped me process my feelings of loss as I remembered a close friend who took his own life. The essay generated a meaningful response from several readers who faced similar experiences.
7. The struggle often signals resonance: I’ve learned that the pieces I struggle with most, the ones I’m tempted to abandon, often resonate most strongly with readers. This unpredictability has taught me to trust the process, push through the doubt, and let my audience be the judge.

These lessons have not only improved my writing but have also enriched my life in unexpected ways. Consistently showing up through writing has taught me much about persistence, creativity, and the power of genuine connection.

As I look forward to the next two years of Beyond the Cove, I’m considering a few experiments, but I don’t expect too much change. I’m thinking about shorter formats, testing a weekly cadence, and whether I should try to drive growth authentically (or whether subscriber growth even matters).

Stay tuned. I hope you’ll stick around for the ride.

What has your experience with consistent writing or creative pursuits been like? I’d love to hear your thoughts and lessons learned.