How to not feel like sh*t sending a newsletter

Summary: My goal here is showing you a different blueprint for what newsletters can be, with examples of terrible vs great newsletters and tips to succeed with your own. 

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Publishing an article online is accepting vulnerability. It’s feeling like shit for a while: you're judged, you're an imposter and an annoyance. A newsletter is worse: it’s knowingly annoying hundreds of people at the same time. Feeling like spam doesn't feel good, so we don’t do it. 

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I started a newsletter a year ago. I added a signup box to the first landing page of this website as an afterthought, "Put your email, get updates". I forgot about it. But people have been signing up and now I have a few hundred emails. But I didn’t send any newsletter because I was afraid, I felt like spam. 

Over the last months I've been receiving newsletters that feel like nice conversations, packages in the mail stuffed with interesting treats. I now use the same model and my subscribers love it. I actually look forward to sending the next one.

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We associate newsletters to bad marketing, bragging, promoting, annoyance. Yes, most newsletters suck. Great newsletters exist though. Some people even pay for a lot for them. What makes them good?

Changing your view

Let me try changing your perception of what a newsletter can be. By the end, you hopefully have enough reasons to overcome your fears and hit send. 

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First, think of a newsletter as similar to a letter for a friend. You're trying to share some things that you recently found interesting and want to bring value into their life and your relationship with them. Keep this in mind with you write and imagine that you're writing a letter to your friend. Your relationship with your subscribers shouldn't be transactional. People don't want "updates" from you. They want to cultivate a relationship with you. They may be past or potential clients, friends, family or just curious people. Newsletters are the best way for building 1-to-1 ongoing relationships with hundreds of people, simultaneously. Take advantage of that.

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Second, don’t be afraid to share things you haven’t made yourself. People come from your version of content as much as the content itself. There are thousands of newsletters and countless ways to get new information today. And it's precisely this abundance of information that pronounces our need to bond with some people. People who signed up to your newsletter chose to find meaning in your curation of information. When you give a peek into your life, sharing selfies or the book you’re reading, you’re breaking this company newsletter model and allowing your subscribers to feel an emotional attachment to you. You’re the medium.

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Third, don’t copy brands. Almost all company newsletters make you feel being sold to and insignificant. This is the opposite of receiving an email from a good friend. We automatically, unconsciously categorize templated emails as spam, not the type of email you'd receive from someone you love. Instead, take inspiration from emails sent by independent creators. They use plain text. 

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Newsletters are what we make out of them. They don’t have to be something. They can be anything! They’re just emails sent on a regular basis. Imagine all of us had our own "party talk" email lists, a place to find out about what each person is thinking about, like what Robin Hanson imagined in 1994. A future where everyone has their private salons. You can just sign up to a conversation or leave it. Social media without big brother. 

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Finally (and only finally), these email relationships create incredible leverage to find new clients, sell your courses or get new users for your product (or the three at the same time). If you see it rationally, not sending a newsletter is a big opportunity cost. Take note though: selling is a consequence of the first two points. Maintaining strong relationships with people who find your work useful is worthwhile by itself. You don’t have to be selling anything, a newsletter just helps. 

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Some examples

Let’s compare:

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Other tips for sending newsletters

• The best days to send a weekly newsletter are Tuesdays and Wednesday mornings. Choose Friday if you want to be associated with fun, relaxing stuff. Monday for more serious stuff.

• You don’t even have to use Mailchimp to send newsletters! You can just include everyone as BCC. Works well for smaller newsletters with a few hundred subscribers. Over this threshold I’d suggest the easy-to-use ConvertKit. 

• Champion subscribers who reply and share screenshots of recent positive conversations. This will set the stage to what others can do if they appreciate your newsletter. 

• Publish newsletters consistently, make it a ritual in your week. If it's too hard, set up an accountability deal where you give your friend money if you don't send the weekly newsletter (and vice versa).

• Use bullet points :)

I'm on a quest to send the best newsletter ever. How do I measure that? By the amount of answers I get vs number of total subscribers. I encourage my subscribers to reply with questions and share their own discoveries. Here's a preview of the one I sent last week:

Now... Hit send!

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Let's keep in touch 👇