The Newsletter Advice I Give Again and Again

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“What’s the biggest challenge you’re facing with your newsletter?”

Five years ago, I started asking every new reader of my newsletter that question. I reply to everyone who writes back to me — as of this moment, I’ve responded to 2,683 of you.

In the course of those 2,683 replies, I’ve answered many questions over and over again. Sometimes, people with very different newsletter strategies ask almost identical questions. I remember one afternoon when, in the space of about an hour, two different newsletter operators wrote back to tell me they were worried about their ability to grow their newsletter. One had launched their newsletter that week and had fewer than ten subscribers. The other was a bestselling author with more than a million readers on their list. They were two different newsletters at very different stages — but they both had the same big problem to solve. It turns out that no matter what type of newsletter you work on or what your goals are, everyone’s struggles are pretty similar.

A lot has changed over the past five years, but I keep returning to certain pieces of advice, which must mean that many people must be asking the same questions. Here’s the advice I’d give you.

The first version of your newsletter is never perfect. All the good stuff happens after you launch and start to get feedback from readers. So as soon as you can start, start.

If you’re thinking about launching a newsletter but aren’t sure what to write about, start with the thing you care most about — not the thing you think will be the most profitable. If you’re passionate about it, the audience will be able to tell. If you’re not, you’re going to get tired of writing about it before long, even if you’re getting paid for it.

The biggest newsletter red flag is when a newsletter operator tells me their newsletter is for “everybody.”

The best newsletters have a specific audience in mind. Every newsletter operator needs to be able to answer a few questions clearly:

• What does your ideal reader care about? 
• What are they motivated by?
• What are they inspired by?
• Where do they live? 
• What do they do for work?
• What do they like? (Besides your newsletter, of course.)

The more you understand about them, the better you can serve them.

It can feel scary to commit to a newsletter for the long haul. So, at the start, instead of committing to writing something every week in perpetuity, think about your newsletter more like a podcast, where there might be a season’s worth of content. Begin with a cadence you think you can stick with — the first season might be a newsletter per week for eight to ten weeks — and hold yourself accountable to that cadence. At the end of the season, give yourself time to re-evaluate. Was that cadence too much? Not enough? Then, you can set a new goal for whatever the next season of the newsletter should be.

Follow that process over and over, and you’ll soon find that you’ve written a weekly email or a whole year. And if you can do it for a year, you can do it for another and another.

Relationships — not format — make a newsletter.

It doesn’t matter if your newsletter keeps everyone inside the inbox or links readers to content elsewhere. It doesn’t matter if your newsletter is all text or has many design elements. It doesn’t matter what color your call-to-action buttons are, or how long your newsletter is, or how impressive your photography or artwork is.

Newsletters are for every type of strategy as long as you keep this rule in mind: The best newsletter operators are the ones that have the strongest relationships with their readers. The more you work to build trust with readers, the better your newsletter will be.

Whenever you’re not sure what to do next, ask your audience. Ask them to hit reply, answer a poll, or take a survey. Let their feedback guide your next steps.

Every time you send an email, a few readers will unsubscribe. I used to write a newsletter at BuzzFeed called This Week in Cats, which had a 60%+ open rate — at a time when being above 40% was rare — and we saw unsubscribes every week. (I still have no idea what those readers thought they were getting into.) If that newsletter lost readers every week, then every newsletter will lose readers.

In general, I recommend that your unsubscribe rate for the average newsletter should stay below 0.25%. If you’re below that, there’s not a lot to worry about. (If you’re above that, we should talk!)

The best deliverability advice is also the most boring: Send consistently amazing emails. If your readers love your content and always engage with it, their inboxes will ensure that your emails show up in the right place over time.

When a reader takes the time to reply to you, take time to write back to them. Even if it’s a short note, even if it’s just a few words — those replies matter.

I cannot tell you how many clients, speaking gigs, and opportunities I’ve gotten simply because I took the time to write back. Don’t ignore those emails. Hit “reply.”

A great newsletter isn’t about the what — it’s about the why.

What’s your newsletter about? You probably have a decent pitch for that already.

But why does it matter? Why will it create some sort of impact for your reader? Why should readers take the next step and subscribe? That’s something not enough newsletter writers have thought through.

Maybe your newsletter saves people time, or makes them money, or helps them make big decisions, or makes them happier. A newsletter can add value in all sorts of ways.

If you’re not sure what your why is, ask 10 readers what they love about your newsletter. If two or three give the same answer, that’s your why.

We live in an age of copycats. When someone has success in a particular way, there’s a rush for others to copy that model.

But the best newsletters find ways to take what others are doing and put their own spin on it.

Only you can do what you can do. So don’t be content to copy and paste — learn from others, but find a way to make things your own.

If you’re trying to attract new advertisers for your newsletter, start by looking for advertisers who sponsor similar newsletters or publications. Take note of who you see advertising in public places, like billboards, bus stops, or podcasts. Those advertisers are already spending money to reach audiences like yours. 

Put together a spreadsheet of those potential advertisers, and reach out to introduce yourself. (LinkedIn is your best friend for this sort of thing!) If they already advertise to reach similar audiences, they might be willing to advertise in your newsletter, too.

Many email metrics, like open or click rates, are directionally accurate. They’re not precise measurements — just because your email platform says you have a 50% open rate doesn’t mean that exactly 50% of people opened your latest newsletter. But they’ll still point you in the right direction, so there’s some value there. 

Use those metrics alongside a few other metrics, like revenue, growth, and feedback from readers, to understand how your newsletter is really doing.

Making money off your newsletter takes time. I often find that it takes two years — or more! — to grow an independent newsletter and start to monetize it in a meaningful way. If it hasn’t happened yet, it doesn’t mean your strategy isn’t working. It may just mean that you need to be patient.

I often talk with newsletter operators who tell me they want to launch another product, another course, another ebook, or another service.

The question I always ask is: Have you gotten everything you can out of the stuff that’s already out there?

I’ll see newsletters with great engagement missing obvious monetization opportunities, like running ads or affiliate content. Or operators with a paid membership who don’t promote it nearly as much as they could — even though with every new member they get, they’re getting more value out of a thing they’re already working on.

Forget about launching new stuff for a second. Is there an opportunity to get more out of the work you’re already doing?

If you make a mistake in your newsletter, correct it quickly, and make sure you do it in your own voice. This apology shouldn’t sound like it was written by a lawyer — it should sound like you. Own the mistake, and do your best to make things right for your readers. If your apology is sincere, you can turn a mistake into an opportunity to build trust with your audience.

Whatever you choose to do next with your newsletter, make it work for you.

There isn’t a single way forward that applies to all newsletters. 

Maybe that means, as I told one newsletter writer, telling their readers that they’d be taking a month off to get ahead and pre-write the next few months of newsletters. 

“I’m allowed to do that?” they asked me.

“You are,” I told them, “because this is all about making it work for you.”

Another writer told me that they’d been trying to push forward with a paid subscription, but it wasn’t working as well as they hoped. Advertising was likely a better path forward for them.

“Can I just cancel the paid offering and switch business models?” they asked me.

“You can,” I said, “because if you’re going to make this work, it first needs to work for you.”

If your revenue strategy feels forced, you can change it. If your newsletter cadence is too challenging, you can adjust it. If your growth tactics are stressing you out, you can change them.

Make it work for you.

Newsletters tend to move slowly. Yes, there are examples out there of newsletters who launched and immediately grew into million-dollar products within a matter of months. But those are exceptions, not the rule.

Most of us take small steps. It doesn’t matter how fast you get there — small steps can still get you where you want to go.

Make time to review, reflect, and iterate with your newsletter.

I like to make space to review things once every three months. I look back through my numbers and the feedback from readers. I think about what’s worked and what hasn’t. And then, I set some goals for the next few months. 

Put this sort of regular review on your calendar. It’s a great way to hold yourself accountable and make sure you’re always pushing your newsletter forward.

Don’t be too precious with your newsletter. The best thing about newsletters is that there’s always going to be another newsletter, whether you send the next one tomorrow, next week, or next month. They’re not all going to be perfect. Some will be better than others. The good news is that you’ll get another chance to do better.

Don’t worry about trying to make this newsletter exactly right. Just hit “send.”

Thanks to our sponsor

The stories you’re reading on inboxcollective.com are made possible thanks to the generous support of our summer sponsor, GetResponse. They’re an email marketing and automation platform with comprehensive, affordable, and easy-to-use tools to grow, engage, and convert your audience. If you’re looking for a platform with powerful automation and monetization tools, give GetResponse a try — and if you’re a non-profit, get a 50% discount on any of their plans.