Category: Email GuidanceCategory: Email Guidance

Someone emailed me how they would paywall their work after 90 days, and was looking for some thoughts and ideas on growth and such.

First — are you “married” to the paywall? Is this paying your rent right now? I don’t want to say anything flippant if it’s keeping the lights on. But since you mention wanting to ditch it, I get the feeling you’re still figuring it out, just like we all are.

I experimented with a paywall for a while, and I hated sending my newsletter to five people at a time. I appreciated the money and support, but I didn’t appreciate that my best work was only being seen by a few people. What if the post that deeply resonated with one paid member could have attracted 100 new readers?

Every piece we put out into the world is a chance for the right person to find it. Especially when you’re just getting started. You’re coming up on a year on Substack. There are people who have just discovered you, maybe told their friends, and a large part of your work is inaccessible until they pay.

I fully believe we all need to get paid. But I think we need to build trust first. And we build trust when we’re our most comfortable selves, instead of worrying about paywalls, page counts, SEO, all of that. Get your work out there in ways you can sustain. A website and a newsletter, for example. When you start adding TikTok, long-form YouTube, and everything else, that’s where things get hectic.

The more of yourself you put out there, the more people can see and feel and read, the faster you’ll discover how they actually want to support you.

I started my Substack in 2021 and didn’t rebrand to until 2023. That’s when I started hosting Zoom calls, just kind of like, “I want to talk to more people about this stuff.” And that’s when I discovered people really wanted to talk about it, too. And that some of them would pay to be part of it. Not in some guru-funnel way, but genuinely: I had to try a bunch of different things before I found what worked for me.

Reduce friction. Get to the core of what you want to be doing, without giving yourself too many side gigs to make it work.

Sometimes I help people realize that building something is a lot of work. Here are two examples of that, where we arrived a few rounds into our Email Guidance sessions:

“Took some time to sit with it and realized that pursuing [REDACTED] isn’t realistic for me at this time. I really appreciate your insight and the clarity it helped bring me.”

“In the end, I was able to decide that I actually want to scale back and just have [REDACTED] as a “fun thing” for me and that my [main job] needs to be my sole focus for work. I don’t have the energy to do both and so your help also helped me figure that out too!”

It’s not “never,” it’s just not now. Sometimes things need to come into alignment, doors need to open, others need to shut. That can take time, even years. I didn’t set off years ago thinking I’d be helping people with this as I approach turning 50 years of age, but I know 25 years ago all of this would have been “not now.”

From a recent Email Guidance client:

Decided to go through my “General” IG mailbox and send a version of this note: [REDACTED]

Picked up two new free sub’s in the first five mins.

This writer reached out to people already in his DMs with a note saying they could subscribe to his newsletter, and two people did that just that in the first five minutes.

I’m not saying automated systems cheapen the exchange, but honest communication certainly can’t hurt.

I started all this as music blogger in 2001. I’ve been flown (all expenses paid) to a music festival in Norway. Interviewed Slayer. Met bands before they blew up.

Below is a lightly edited Email Guidance reply to someone in the midst of promoting their upcoming book:

One of my favorite promos over the years for bands and musicians was the holiday themed round-ups.

Valentine’s Day, tell us about your worst break ups.
Halloween, tell us your favorite horror movies.

Everyone involved had a new album coming up, or a tour to announce, but this was a fun way to learn more about the bands, beyond “hi I have an album coming out.” ZZzzzz.

Now, you don’t need to talk about your favorite horror movies of course (haha), but whatever you’re into, other people are into probably, too. Not everyone, but that’s okay. It’s a busy crowded world out there. Maybe you’ve got a book coming out. Well, lots of people have books coming out!

But only you can talk about the book and your work and your life in the way that you can, so capitalize on that.

While everyone else is screaming “pre-order my book” (boring!), you can talk about that adventure on the river back in 1999, the bookstore you visited that had a cat named Wizard, or the meal that changed your life in Italy (your own stories may vary). Things that nobody else gets to talk about because they’re not you, but they’re tiny glimpses into who you are, which is the first step towards someone thinking, “this story is amazing – oooh, and they have a whole book coming out!?”

From a recent Email Guidance exchange, helping someone clarify what their paid offering actually is. What’s the thing they want to put into the world and invite people to support?

The big thing I feel with a lot of us creative people is we think we have this OFFER than people will want, and if we just word it the right way, or promote it enough, people will flock to it and pay us for it. Even if we’re good at it! We can do this stuff, hire me!

What I’ve found is instead leaning into the thing that’s ridiculously easy for us that could be the beacon that shines for the right sort of people that need what we offer.

Rather than turn ourselves into round pegs to fit into square holes, what if we doubled down on what comes natural?

I believe when we work from a space of almost supernatural flow we’re bound to attract the right sort of clients, co-conspirators, and allies.