Dylan Tweney

25 things I learned in 25 years of newsletter publishing

A newsletter is the single most powerful tool I know of for building and maintaining a network.
Dylan Tweney 6 min read
abstract painting showing white marks on a black field, with a few white marks on a black field some lines and squiggles
Are these story lines? Untitled (Undated) - Álvaro Lapa (1939 - 2006), via Pedro Ribeiro Simões. CC BY 2.0

In today’s writing circle, fellow writer Alicia asked me if I had just recently launched my newsletter. 

“No,” I said, “I’ve been publishing it in one form or another for about 20 years.”

In fact, when I looked at the archive, I realized that I’ve been publishing a newsletter for over 25 years.

When I first started sending emails to a few friends and family, back in 1998, I had no idea that the practice would turn into a career-transforming newsletter. In fact, it was sort of an accident.

I had started writing a column for InfoWorld, the tech newsweekly where I worked as an editor. Subscribing to InfoWorld in print was expensive, and I knew most of my family and friends would never visit the relatively new InfoWorld website. So, in March 1998, I started emailing my weekly columns just to keep them in the loop. It was one step up from “Hey Mom, look at this thing I did!”

At first, I managed the mailing list in Excel and sent mail out via my work email, using Lotus Notes. (Kids: Lotus Notes was one of the worst email programs ever designed. Clunky, standards-violating, massive, slow … it was a nightmare. But it’s what we had.) It was only later that I realized I had tapped into an emerging new publishing format: the email newsletter.

The following year, I published my first blog post (using Blogger — then a brand-new platform for another brand-new publishing format). That post appeared on Nov. 4, 1999. By then, my mailing list had grown to a few hundred email addresses, and I was using it to keep in touch with key industry sources as well as my family and friends.

Since its launch, my newsletter has gone through many permutations. It went from being managed on an Excel spreadsheet to a list in Pegasus Mail, to Topica (RIP), then Tinyletter (RIP), Revue (RIP), Substack, and now Ghost Pro. Its name evolved from The Tweney Report (blunt but effective) to Dylan’s Desk (cute and direct) and then Postcards From the Waterline (which no one understood). Subscribers peaked at over 3,000 in the early 2000s. The subject matter started being about the growth of the internet and e-commerce, before widening the scope to cover tech and business strategy more broadly.

Over that time, the newsletter has been instrumental in helping me raise and maintain my profile as a writer and thought leader. It has led to work (both full-time and contract jobs), and it’s given me a valuable, ongoing audience that has helped shape my thinking and provided me with frequent feedback. I am grateful to everyone who has subscribed and everyone who has written back to me for helping to encourage and support me on this journey.

Turning to a new chapter: storytelling

Nowadays my newsletter is focused (as I am) on narrative development and content creation for businesses, mostly in tech. 

Given the new focus, I’ve got a new name for it: Storylines.

I chose this name after polling my friends on LinkedIn. They let me know that it was their favorite of the choices I was considering (by quite a margin). Thank you, friends.

The list is considerably smaller. I’m taking a bit of a risk in shifting the focus (and the name), stretching out in a new direction. I don’t know how this chapter will turn out yet.

But the new name is necessary. “Storylines” reflects the core of what I’m doing now: Finding the stories embedded in companies’ products and services, teasing out the throughlines that make for compelling narratives, and figuring out how to tell stories that will resonate with the target audience.

The name “Storylines” also gives me some encouragement to share not just writing and storytelling techniques, but stories — and that’s what I plan to do a lot more of in the coming months. 

I’m going to start by sharing stories of content creators I know, but I’m open to other examples of great stories as well. If you have a story that you’d like to tell (whether it’s a story about how you write or not), please get in touch and let’s talk.

Are you thinking of starting a newsletter? Don’t be afraid to start just because you haven’t been doing it for 25 years. As the old proverb goes, the best time to plant a tree was 25 years ago, but the second best time is today. 

“On the last day of the world, I would want to plant a tree,”  W. S. Merwin once wrote.

If it were the last day of the world, I’d probably want to write a newsletter.

Until then, here’s a list for you. If you’re thinking of starting a newsletter, maybe these things will be helpful. Take what works, discard the rest, and please let me know how it goes for you.

Almost everything I know about newsletters

  1. A newsletter is the single most powerful tool I know of for building and maintaining a network of connections across the course of a career.
  2. Although I haven’t tried to monetize my newsletter yet, it’s definitely led to work, both contract gigs and (arguably) full-time employment.
  3. Writing regularly for an audience (one that occasionally gives you feedback) is probably the most effective way I know to learn how to write better.
  4. Publishing regularly is a discipline that requires a lot of effort.
  5. It’s impossible to sustain a high level of effort indefinitely, so there will be gaps and fallow periods. 
  6. When you return from an absence, try not to apologize too much. Readers don’t care about your apologies — they care about what you have to say.
  7. The key to reducing the stress of coming up with new issues is to create a big list of topics you’d like to write about. Add ideas and notes about each idea to this list whenever you can, and every few weeks, schedule an hour to brainstorm and build out the list. Then, when it’s time to write a newsletter, you can just pick something from this list.
  8. Don’t rush to publish. It’s almost always worthwhile to let a draft sit for at least half a day, and then give it one last read/edit before sending it out.
  9. Sometimes, you’ll find yourself redesigning your blog, picking a new theme, and tweaking its options. It’s okay to do that occasionally, but if it continues too long, it’s probably a sign that something else is wrong — something about the content or your inspiration — and you don’t want to face it.
  10. Moving platforms is part of life. No platform lives forever.
  11. When switching platforms, try not to change the URLs for your popular posts. A long time ago I had a post that ranked really high in Google on searches for Eminem (The Real Slim Shady). It brought me a ton of traffic I didn’t deserve, but it was nice. In a platform change, I stupidly moved the URL of that post, and all that traffic went away.
  12. Don’t sweat the audience size. If your words aren’t resonating with folks, you may need to find a new audience. If you’re authentic and consistent, the audience will come.
  13. Unsubs are part of the cycle of life. People will leave because their interests have changed, because your focus has shifted, or just because their old email address no longer works.
  14. If you haven’t published in a while, you’ll get a lot of unsubs at once. Don’t panic: you’ve just concentrated them into one day because you weren’t publishing for a while.
  15. Recommendations by other newsletters are the key to newsletter growth, especially in the early stages. I benefited a lot from recommendations by Seidman’s Online Insider, The Internet Tourbus, List-A-Day, and Strom’s Web Informant (the last of which is still going strong).
  16. Consistency of publication is the key to retaining subscribers. I don’t mean cadence, but consistency of quality.
  17. Open rates are always lower than you think they should be. Click rates are really low, especially lately.
  18. Don’t assume anyone you know actually reads your newsletter, even if you know they’re a subscriber. We’ve all got busy lives.
  19. Even your spouse!
  20. If someone volunteers a comment about a recent issue, take it for the unexpected gift that it is.
  21. It’s worth getting editing help occasionally, especially for posts you feel are a bit risky. Ask a friend or join a writing circle for feedback.
  22. Your focus will change over time. If you’ve outgrown it, don’t box yourself into a restrictive definition of what your newsletter should be.
  23. Be brave. Readers will reward honesty and forthrightness.
  24. Email is still an open standard, it’s still free, and it’s not controlled by any company or government. Let’s keep it that way.
  25. Be yourself; everyone else is already taken.

Thank you for the editing help: Sara Campbell, Jude Klinger, Melanie Keath

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