#056 Insights on building a newsletter

Read this if you’re contemplating starting a newsletter or recently did.

Oct 10, 2023

(01) REFLECT

Since sending my first newsletter on Substack on April 5, 2022, my personal creative practice has been filled with both learning opportunities and continued excitement for this project. Between The B&W started as an outlet to share my thoughts, findings, and interests with you. During a time when many creative business owners were leaning into education, it was clear to me that I wasn’t the course creator type. However, I have always been a fan of knowledge-sharing, so I made it a goal to find a way to build collective knowledge within my community.

That is when I realized a newsletter could be more than a tool to hit sales numbers or book more clients. I didn’t have to sell anything or make complicated automation flows to build a successful newsletter. It could serve as a resource, an open invitation, and a safe space. This distinction sparked something in me, and 56 newsletters later, I want to share with you some lessons I’ve picked up along the way:

Customization has its time and place. Earlier this year, I made a brief switch to Mailchimp. The main reason I made this decision was to have more creative freedom regarding the newsletter’s design. I started to feel quite limited on Substack and wanted to be able to implement some more custom design elements. However, I quickly learned that heavy customization shouldn't always take precedence. Some readers reached out, letting me know they had issues reading the newsletter because the fonts weren’t rendering correctly. I found that setting up the newsletter every week became more time-consuming, and I definitely got carried away trying to implement features that didn’t serve the core purpose of the newsletter. Designing a newsletter is a lot like building a website. It might look beautiful on your end, but ultimately, it will land in inboxes across various applications. If readers can't easily access and read your content due to compatibility issues, all the beautiful design becomes useless.
Building a newsletter takes time. When people subscribe to your newsletter, they share their personal contact information with you. It’s not like following someone on social media and forgetting they exist — they’ll be receiving your emails directly to their inbox. For this reason, it takes time for people to decide whether subscribing to your newsletter is a worthy trade-off. While freebies can serve as incentives, it isn’t always so straightforward since some will subscribe for immediate gratification and will likely not want to stay around in the long run. The positive side is that it's much simpler to identify patterns because no mysterious algorithm is working against you, leading to increased audience retention over time. Either way, it’s still a slow process. Some creators have run newsletters for a decade before experiencing substantial growth, so be patient and definitely don’t get discouraged.
Planning is your best friend. I’ve had my share of late nights scrambling to figure out what to write just hours before I have to hit “send,” so take it from me: planning your newsletters in advance is crucial. Creating any form of content is an active practice that relies on consistency, which is why skipping newsletters is so often discouraged. If you skip one, then two, and eventually three, you may find yourself with a month-long gap. When you finally gather the motivation to send a newsletter again, you’ll have your audience thinking one of two things: “Where were you?” or “Who are you?” Think of it as journaling or working out — following a consistent routine is what makes both of these habits effective. Since writing a newsletter might not be your full-time job, pulling it off every week might require some planning, so figure out a schedule that works for you and stick to it.
Get comfortable with first drafts. I recently wrote a newsletter about how I’ve never considered myself to be a writer, and it’s likely that many of you also don’t. In my experience, building a newsletter doesn’t necessarily require you to be an extremely skilled writer, but it does require getting comfortable with putting your thoughts on paper as they are. Even best-selling authors didn’t write the perfect novel on the first try. Articles, books, magazines, etc., go through numerous rounds of edits before they see the light of day. That said, making a habit of always writing a first draft is not only easier but leads to better, more articulate entries. It doesn’t have to be perfect, well-structured, or even make sense at all. You can always go back and edit it. I’ve made the mistake before of trying to write a final draft on my first try, and it would take me almost a full day to finish writing. Now, it takes me about 2-4 hours on average. The more I have to work with, the easier it is to edit into its final stage. During the weekend, I sit down and write without the pressure of having to hit send. Then, on Monday, I can edit it one final time once I set it up in Substack.
Structure is key. The structure of your newsletter is an important aspect that's easily overlooked. When I first started sending emails, they were very spontaneous. Readers didn’t know exactly what to expect every week, and sometimes, I didn’t even know what to write about. The first thing almost everyone does before making a commitment to anything is research. For example, if you’re planning a trip and are interested in spending a day sightseeing, you’re not just going to go to every spot you find online; you’re likely to do the specific activities that stand out to you. Maybe you are an outdoor enthusiast and want to go on the hikes with the best views, while some might prefer to visit museums and plan their day around dinner. Similarly, there are thousands of newsletters readers can subscribe to, so you need to make it clear exactly what they will receive when they subscribe. I’d say BTBW is a hybrid — it starts out as long-form, but I also made sure to include a roundup of things to pick from. Some weeks, you might not be able to read the journal entry, but you can still browse through all of the links and pick the one that stands out to you. This makes it digestible, which is exactly what I wanted the newsletter to be: a weekly creative diet. In your case, you might prefer only to do long-form entries or a compilation of lists. Both can be extremely successful, but whatever you choose, be consistent with it.
Monetization is not a bad guy. This was a big one for me to overcome because I’ve always wanted this newsletter to be completely free. Although it still is, a few months in, I began to understand why creators monetize their content. Sending out a weekly newsletter demands a considerable amount of time every week. I need to choose a topic, research, and write something of value while ensuring it is factually accurate. It’s more than just recycling the same content that’s widely available online. It’s about understanding different perspectives, uncovering hidden gems, and identifying trends — all of which require constantly exposing myself to new content and communities. Then comes the process of setting up the newsletter, creating graphics for social media, and studying engagement patterns so I can continue to write newsletters you’re interested in. This entire workflow occupies anywhere from 6-12 hours every week. Since February, Courtney has been helping me manage high-level tasks since I still have clients to prioritize. Regardless, I still write every newsletter myself, dedicating around 4-6 hours weekly, in addition to compensating her for her time. It’s clear that the long-term sustainability of free content is questionable. This is why some newsletters incorporate ad slots or brand partnerships to sustain their work. I still haven’t figured out what makes sense for me yet, but it’s no longer something completely out of the cards.

Overall, I’m so grateful I’ve found something that allows me to explore my creativity in non-traditional ways. I am always learning new things about this world (like finding out that a newsletter is actually considered a news & media business), so I cannot wait to write an updated version of this in the future. If you’re contemplating starting a newsletter or recently did, I’d love to hear from you! Whether you’re seeking advice, have questions, or just want to connect, I'm always just a message, email, or comment away.