I’ve been writing online for over 25 years now, but it’s been only recently that I feel confident in answering this sort of question (asked during a recent live stream):

“I write sporadically here on Substack and would like more of a system. We’ll eventually move to my website. What do we think about consistency versus right when I feel like it?”

I think part of the consistency aspect is that writing a newsletter via Substack (or anywhere) is grand. It’s big. It’s “to everyone.”

Now think about something like Morning Pages, or writing in a journal. It’s private, staying close to home.

One is out there, sent directly to people’s inboxes, while the other never sees the light of day.

Since restarting my blog in 2018 (sethw.xyz), I didn’t know that getting back to writting a few posts every month would help with consistency (this from someone who managed a site that published 20+ posts a day in 2009).

See, when sitting down to write a newsletter on a regular basis, say every Friday, I’d start thinking about it on Wednesday. Write a draft, come back to it. Thursday night, write some more. Finish it up on Friday morning maybe, before hitting send.

But lately I just write a bunch on my blog, or here on this site. It’s not really “to everyone,” and it’s technically not private.

So I really think the sporadic, maybe “not consistent,” writing in a public space has helped, because a post I wrote last Tuesday informs the one I write a few days later, and maybe that post unlocks something in a conversation I have on a Zoom call, and a week later when it’s time to send a proper newsletter, I write the new thing here on this blog first, then send it to everyone via Substack.

That’s how I started to answer this question nine months ago, from this post “BLOGGING IS LOWER STAKES WRITING.

“One thing about Substack is every newsletter you send is a “launch.” It’s to everyone, your whole audience! It can be intimidating, knowing that everything you write will be seen by 40% of the people you send it to.

Since I’ve set up this site, I find myself posting sometimes twice a day. It feels like my music blogging days, when I found an interesting band or quote, I’d dive into WordPress and just get something posted. That’s exactly what I’ve done today with this post!”

In the last year this has worked better than “start a draft in Substack in solitude,” as hitting publish more often introduces some tension, and puts it out in the world, even though it’s not delivered to anyone’s inbox.

So for me, this solves the “consistency versus right when I feel like it” riddle. If I’m always writing when I feel like it, when it’s time to send a proper newsletter I’ve got a week’s worth of ideas to pull from.

This is a recap of our Monday call, “Finding Your Cozy Corner on YouTube,” to show why authenticity matters more than fancy equipment and how to use video as a trusted, discoverable extension of your own work.

I explain that a simple selfie‑camera walk in the woods can be effective, and that consistently publishing videos creates a catalog that the YouTube, Instagram, and Substack algorithms can surface over the years.

I use YouTube as free hosting, embed the videos on my own blog (like this one), and always link back to my site so viewers stay reachable (instead if sending readers to get lost on YouTube’s massive site). In this era of AI‑generated content, video conveys who we are and builds trust, so I encourage experimenting with short formats, directing traffic to your website or newsletter, and treating YouTube like a supportive platform rather than some big lottery you need to win.

Join one of our upcoming calls!

Thursday, Nov 12 at 2PM EST → https://luma.com/7ppu10a7
Monday, Nov 16 at 9AM EST → https://luma.com/4szvpb73

Google and Apple recently changed some rules on your photos.

​Apple will start checking photos you share by public link (iOS 27.3, coming in December), and say stuff shared that way is no longer end-to-end encrypted. (via MacRumors)

​Then Google quietly updated its privacy policy, saying that if you turn on Personal Intelligence, your Gmail, Drive, and Photos data can be used to target ads. (via 9to5Google)

​As Ente (a photo management alternative to those two big tech giants) said it in a recent email, “privacy is just a setting for them, and settings change.” Very true!

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​Ente Photos is a private, hosted home for your photos

• ​Download Ente Photos from https://ente.com/app
• ​Create an account
• ​Apply the referral code ESCAPECLUB in Settings -> Referrals
• ​Get extra 10 GB free

​Check out other photo management tools here.

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​So hey – come hang out and figure out what it takes to move your photo library somewhere else, why it feels so hard, and then do this with other people live on this 90 minute hang session.

​This isn’t a workshop, but a focused Zoom hang where we talk about alternatives, how to untangle ourselves from big tech, and work together in real time testing out services like Ente (or whichever tool you want to you) to manage our photo libraries!

Monday, November 30 from 9-10:30 AM EST → https://luma.com/ls3t8haw

Thursday, December 3 from 2:00 PM – 3:30 PM EST → https://luma.com/v8byzvkz

​You already send email for yourself. What if you sent it for someone else?

​On this 90 minute call (limited to 12 guests) we’ll talk about how to get comfortable enough in Mailchimp, Substack, Buttondown or Klaviyo to help a friend’s nonprofit, a small shop, or another artist who’s new to this whole ’email marketing’ thing.

​You’ll walk away knowing where to start, what the work looks like, and how to get to a point where maybe it can pay the rent (or the phone bill).

(more…)

If you’ve only got two subscribers, you’ve got more of an audience than 99% of the world who don’t even have a newsletter.

Looking at other people’s engagement and numbers and subscribers is only helpful if you want to feel bad about yourself, so it’s best to leave that off your daily to-do list.

Instead, pay attention to the people who signed up. Maybe they’re not paying your rent, or even your phone bill, but they show up, and what a honor that is. If you’d like those people to help pay the rent, well, that’s a whole other topic for another post, but for now, acknowledge the people who showed up.

Do you want to make a difference, or are you trying to compete in a game you don’t want to play?

On today’s Escape Pod Zoom call, I talked with Frederick Woodruff about his book, I Love You, Jeffrey Dahmer, and about what it takes to get the word out without social media, or with only a toe still in those waters.

One idea keeps coming up in my world comes from Michelle Warner, in an interview I heard her do with Jay Acunzo, another marketing person doing great work. She talked about getting awareness off your plate and onto other platforms.

What she meant is this: rather than posting on Substack Notes or Instagram, put yourself into someone else’s platform. That could be a popular podcast in the world you work in, or a YouTube channel that’s the right fit, one talking to an audience that would probably vibe with what you’re doing.

(more…)

A recent Dense Discovery newsletter came my way with a subject line that made my heart sing: “Breaking up with Gmail,” which is a familiar topic around here!

“I went with Fastmail, a small Melbourne company (represent!) with a solid reputation. Its migration tool pulled everything across via IMAP in a few hours and mirrored my Gmail labels. On my laptop I use the web interface and don’t miss a single feature. On my iPhone, I can still use the native Calendar and Contacts apps, and Fastmail’s own app for email (it’s good). When I made a mistake during my custom domain setup, an actual human replied to my support request within a day with an answer that helped. I’d forgotten that was possible.”

Yes, there’s definitely some friction to leaving an email platform that maybe you’ve used for decades. But if using a tool just doesn’t sit right with you anymore, it’s worth the effort.

And as Kai explains, it’s not always going to be a clean cut, saying “too many clients and collaborators live in Docs and Sheets.” I’m in the same boat. But the act of moving our main email inbox to another company that values privacy and actually providing customer support feels good.

Tired of Gmail?
Try Fastmail.
Try Proton (50% off deal right now for Black Friday).