Hello! I’ve been learning a lot about business over the last few years (it’s possible to make a living by helping people learn! it’s amazing!). One of the things I’ve found hardest to get my head around was email marketing.

Like a lot of people, I get a lot of unwanted email, and at first I was really opposed to doing any kind of email marketing because I was worried I’d be the source of that unwanted email. But I’ve learned how to do it in a way that feels good to me, and where the replies to my marketing emails are usually along the lines of “wow, I love this, thank you so much!”. (literally: here are excerpts from the last 20 or so replies I’ve gotten)

I’m going to structure this as a series of beliefs I had about email marketing that turned out not to be universally true.

myth 1: selling things is an adversarial relationship

I used to think that selling things was a sort of adversarial relationship: the person selling the product wants to convince the buyer (by any means necessary) to spend as much money as possible, and that people buying things are usually kind of resentful of anyone asking them to spend money.

I’ve learned that actually a lot of people are happy (or even actively want) to spend money on something that will help them solve a problem they have.

Here’s a silly example of something illustrating this: 2 years ago, we’d hired someone to paint our new apartment. We decided to paint a lot of the walls white, and we were stuck with the impossible problem of deciding which of the 10 billion possible shades of white to paint the walls. I found a $27 ebook called white is complicated, and (long story short, this blog post is not about painting) it really helped me confidently choose a shade of white!! We spent thousands of dollars on painting, so $30 was a really good investment in making sure we’d be happy with the result.

So even though $27 for an ebook on how to choose a white seems silly at first, I was really happy to spend the money, and my guess is a lot of other people who bought that ebook are as well.

The bigger idea here is that it’s easier to run a business when you’re selling to people who are happy to buy things based on the value they’re getting from the product. In my case, I’ve found that there are lots of programmers who are happy to pay for clear, short, friendly explanations of concepts they need to understand for their jobs.

a quick note on how I learned these things: 30x500

I originally wrote this blog post about all these things I learned, and it kind of read like I figured out all of these things naturally over the course of running a business. But that’s not how it went at all! I’ve actually found it very hard to debug business problems on my own. A lot of the attitudes I had when I started out running a business were counterproductive (like thinking of selling something as an adversarial process), and I don’t know that many people who run similar businesses who I can get advice from.

I learned how to think about selling things as a non-adversarial process (and everything else in this blog post, and a lot more) from 30x500, a business class by Amy Hoy (her writing is here) and Alex Hillman that I bought a couple of years ago. 30x500 is about running a specific kind of business (very briefly: sell to people who buy based on value, decide what to build by researching your audience, market by teaching people helpful things), which happens to be the exact kind of business that I run. It’s been a really great way to learn how to run my business better.

Okay, back to my misconceptions about email marketing!

myth 2: sending email is inherently bad

The next thing I believed was that sending email from a business was somehow inherently bad and that all marketing email was unwanted.

I now realize this is untrue even for normal marketing emails – for example, lots of people subscribe to marketing newsletters for brands they like because they want to hear about new products when they come out & sales.

But marketing emails aren’t just “not inherently bad”, they can actually be really useful!

marketing is about building trust

When I started sending out business emails, I based them on the emails I was used to receiving – I’d announce new zines I’d written, and explain why the zine was useful.

But what I’ve learned is that (at least for me) marketing isn’t about describing your product to the audience, marketing is about building trust by helping people.

So, instead of just periodically emailing out “hey, here’s a new zine, here’s why it’s good”, my main marketing email list is called saturday comics, and it sends you 1 email a week with a programming comic.

What I like about this approach to marketing (“just help people learn things for free”) is that it’s literally just what I love doing anyway – I wrote this blog to help people learn things for free for years just because I think it’s fun to help people learn.

And people love the Saturday Comics! And it makes money – I announce new zines to that list as well, and lots of people buy them. It’s really simple and nice!

myth 3: you have to trick people into signing up for your email marketing list

One pattern I see a lot is that I sign up for some free service, and then I start getting deluged with marketing emails trying to convince me to upgrade to the paid tier or whatever. I used to think that this was how marketing emails had to work – you somehow get people’s email and then send them email, and hope that for some reason (???) they decide to buy things from you.

But, of course, this isn’t true! If your marketing list is actually just full of genuinely helpful emails, and you can describe who it’s intended for clearly (give people a link to the archive to see if they like what they see!), then a lot of people will be happy to sign up and receive the emails!

If you clearly communicate who your mailing list will help, then people can easily filter themselves in, and the only people on the list will be happy to be on the list. And then you don’t have to send any unwanted email at all! Hooray!

Here’s one story that influenced how I think about this: once I sent an email to everyone who had bought a past zine saying “hey, I just released this other zine, maybe you want to buy it!”. And I got an angry reply from someone saying something like “why are you emailing me, I just bought that one thing from you, I don’t want you to keep emailing me about other things”. I decided that I agreed with that, and now I’m more careful about being clear about what kinds of emails people are opting into.

marketing is about communicating clearly & honestly

One insight (from Alex Hillman) that helped me a lot recently was – when someone is dissatisfied with something they bought, it doesn’t always mean that the product is “bad”. Maybe the product is helpful to many other people!

But it definitely means that the person’s expectations weren’t met. A tiny example: one of the few refund requests I’ve gotten for a zine was from someone from who expected there to be more information about sed in the zine, and they were disappointed there was only 1 page about sed.

So if I communicate clearly & accurately what problems a product solves, who it’s for, and how it solves those problems, people are much more likely to be delighted when they buy it and be happy to buy from me again in the future!. For my zines specifically, I like to make the table of contents very easy to find so that people can see that there’s 1 page about sed :)

myth 4: you have to constantly produce new emails

I’ve tried and failed to start a lot of mailing lists. the pattern I kept getting stuck in was:

I have an idea for a weekly mailing list I send 2 emails I give up forever

This was partly because I thought that to have a weekly/biweekly mailing list, you have to write new emails every week. And some people definitely do mailing lists this way, like Austin Kleon.

But I learned that there’s a different way to write a mailing list! Instead, you:

put together a list of your best articles / comics / whatever when someone subscribes to that list, send them 1 email a week (or every 2 weeks, or whatever) with one article from the List Of Your Best Articles

The point is most people in the world probably haven’t already read your best articles, and so if you just send them one article a week from that list, it’ll probably actually be MORE helpful to them than if you were writing a new article every week. And you don’t need to write any emails every week!

I think this is called a “drip marketing campaign”, but when I search for that term I don’t find the results super helpful – there’s a lot out there about tools to do this, but as with anything I think the actual content of the emails is the most important thing.

myth 5: unsubscribes are the end of the world

Another email marketing thing I used to get stressed out about was unsubscribes. It always feels a little sad to send an email about something I’m excited about and see 20 people unsubscribe immediately, even if it’s only 0.3% of people on the mailing list.

But I know that I subscribe to mailing lists very liberally, even on topics that I’m not that interested in, and 70% of the time I decide that I’m not that interested in the topic and unsubscribe eventually. A small percentage of people unsubscribing really just isn’t that big of a deal.

myth 6: you need to optimize your open rates

There are all kinds of analytics you can do with email marketing, like open rates. I love numbers and analyzing things, but so far I really haven’t found trying to A/B test or optimize my numbers to be that productive or healthy. I’d rather spend my energy on just writing more helpful things for people to read.

The most important thing I’ve learned about website analytics is that it’s unproductive to look at random statistics like “the open rate on this email is 43% but the last one was 47%” and wonder what they mean. What has been helpful has been coming up with a few specific questions that are important to me (“are people visiting this page from links on other sites, or only from my links?”) and keeping very rough track of the answers over time.

So far I’ve really never used any of the tracking features of my email marketing software. The only thing I’ve done that I’ve found helpful is: sometimes when I release a new zine I’ll send out a discount code to people on the list, and I can tell if people bought the thing from the mailing list because they used the discount code.

it’s important to remember there are people on the other side

The last thing that’s helped me is to remember that even though emailing thousands of people sometimes feels like a weird anonymous thing, there are a lot of very delightful people on the other side! So when I write emails, I usually try to imagine that I’m writing to some very nice person I met at a conference one time who told me that they like my blog. We’re not best friends, but they know my work to some extent, and they’re interested to hear what I have to say.

I often like to remind people why they’re getting the email, especially if I haven’t emailed that list for a long time – “you signed up to get announcements when I release a new zine, so here’s an announcement!”. I think the technical email marketing term for this is a list being “cold” and “warm”, like if you don’t email a list for too long it’s “cold” and your subscribers might have forgotten that they’re on it.

that’s all!

When I started, I was really convinced that email marketing was this terrible, awful thing that I could not do that mostly involved tricking people into getting emails they don’t want (ok, I’m exaggerating a bit, but I really struggled with it). But it’s possible to do it in a transparent way where I’m mostly just sending people helpful emails that they do want!

The big surprise for me was that email marketing is not a monolithic thing. I have a lot of choices about how to do it, and if I don’t like the way someone else does email marketing, I can just make different choices when doing it myself!