Category: Email MarketingCategory: Email Marketing

I’m working with a client who writes magnificent 3,000 word essays. They’re well researched, beautifully arranged, and they’re starting to gain traction and getting paid subscribers.

The problem is; they write a 3,000 word essays every week.

If this were their full time job, this would be great. But it’s a side thing, and side things can easily start to crowd into other areas of our lives if we let them. And when it’s work we love doing, it happens quick, before we even realize it.

Your newsletter writing shouldn’t be a prison sentence. It shouldn’t feel like digging ditches. It shouldn’t be fraught with stress, or like dealing with a horrible boss. None of these things are desirable, and yet so many times we create these situations for ourself.

We get so wrapped up in the moment, in the performance, and we see a sliver of it working, and we lean in.

Before we know it, we’ve painted ourselves into a corner.

But I have good news: you’re the artist. You’re the conductor. You’re the band leader. You’re the director, the captain of the ship.

You got yourself into this situation, and you can get yourself out. Otherwise you burn out, resentment builds, and you’re working this new job for yourself that doesn’t pay the rent.

It’s okay to take your foot off the gas. It’s okay to write one 3,000 word essay 12 times a year.

If you need the extra day of travel time to show up bright and refreshed for a talk or a performance, take it, because otherwise you’re putting on a different kind of show, trying to impress everyone else except yourself.

We’re trying to be our own boss, so don’t be a bad one.

Believe that your true fans will probably stick around. Let the other people leave, that’s okay. There are thousands of people out there today who’ve never heard or seen your work, who have no idea exist.

What then?

What happens when they do find your writing, or your music, or your artwork, but your latest output was from seven years ago?

You crashed and burned because you piled up too many expectations of yourself, trying to meet some un-said protocol, trusting gurus instead of your gut.

The saying “it’s a marathon, not a sprint” doesn’t even apply here because marathons hurt, too, but in a different way.

Writing is still hard work, yes, but it shouldn’t leave you sore.

From ‘Where does blogging fit in your newsletter strategy?’

First, publish freely on your own site. When stuck, employ constraints. Follow-up anywhere else you want. This keeps you healthy, curious, and prolific.

Remember, anything can be a blog post. Not everything can be YouTube video, a podcast, or pithy quote for social media.

The full post is gold, really.

I’ve been saying for awhile now, your subscribers eat first (a play on the old “Instagram eats first” saying). They deserve your gold, your finest work, your biggest news.

But really – “publish freeling on your own site.”

Do this for years and see what happens.

(via Rhoneisms)

Sarah Fay and I focused on how people are using Substack right now, especially the temptation to treat Notes like another social feed to optimize and post constantly.

We talked about slowing that reflex down and prioritizing email subscribers instead—saving strong ideas for newsletters, reposting things from Notes into emails so subscribers actually see them, and measuring success by retention rather than public subscriber counts. The emphasis was on engagement, keeping people on the list, and treating email as the primary channel rather than chasing visibility inside Substack itself. 

We also covered practical approaches to writing, video, and business models on Substack. That included writing in a way that feels natural, publishing without waiting for perfection, and getting comfortable sending work to small groups before larger audiences.

On the business side, we talked about proximity, like keeping most work public while charging for closer access through Zoom calls or live discussions, and using Substack as a tool that supports existing goals rather than becoming another platform to manage. We also discussed live video formats, replays, YouTube workarounds, and treating Substack as a professional practice without overcomplicating the model. 

Mario’s been shipping The Morning Shakeout every Tuesday for almost a decade, and the through-line is simple: doing the work every week is the “trick. It’s not hacks, not social reach, not “growth systems.”

We talked about how having your own website isn’t optional if you want staying power, how platforms come and go but archives and backlinks keep paying dividends, and why consistency beats trying to manufacture viral hits.

Mario’s approach is boring in the best way: show up, write, publish, repeat, and do it long enough that people can’t ignore you, and long enough that you actually figure out what you’re here to say.

Here’s a bit of some Email Guidance I wrote someone recently, about launching a newsletter. They were wondering if they should plan out what to write, and I started riffing on stories:

But think of three stories you like telling people. Or even three stories that involve the wonderful people in your orbit. It all comes back to you, right?

The people you’ve worked with. Recorded with. Performed with. So many people!

BECAUSE then you can send that newsletter to those people! Re-connect, catch up, laugh together about it.

Maybe follow that energy. Instead of thinking about what you’ll write, think about who. Who lights you up? Who made you happy? Who’d you make memories with?

Because if you’re writing from a place of joy and good memories, it’ll probably be easier for your audience to connect with, you know? I mean, you gotta write the music for yourself first, right? Same could be said for a newsletter – write around the good energy of the people you’ve met, and the stories you’ve created with those people.

For artists of all types, it’s very easy to get stuck in this broadcast mode of talking the things we do, and who we are. We are interesting people, of course, but writing about ourselves is HARD. It never feels good, right?

Which is why I suggest writing about other folks in your creative orbit. Weave that into your newsletter, and see what unfolds.