15 Lessons From Writing 30 Newsletters

Insights to help you get started (and keep up the momentum)

Hi friend!

9 months ago I was procrastinating and struggling just hit publish on the first issue of this newsletter.

Today, I’m hitting publish on my 30th issue of The Slow Digest newsletter.

There are so many lessons and insights I gained from publishing an almost weekly newsletter, that I want to share with you today.

Lets dive in.

💡 Today at a glance

  • 15 lessons from writing 30 issues of this newsletter

  • One big tip if you’re creating your first website or updating an existing one

I decided to do some Adventure Working and drafted this week’s newsletter at a local cafe. The change of scenery was refreshing and stopped me from being distracted by my home environment!

If you haven’t tried Adventure Working before, give it a shot!

When I sat down to draft this week’s newsletter, I wanted to share the 30 lessons I learned from publishing 30 newsletters. It got very long very quickly! So I decided to share the first 15 lessons focused on the getting started (and keeping up the momentum) phase of the early days.

Next week, I’ll share the 15 lessons I gain once I moved beyond the “just getting started” phase of my newsletter—The growth, collaboration and metrics phase.

15 Lessons I Learned Writing 30 Newsletters in 9 Months

1. Just get started

I wanted to start the newsletter in May 2024, but didn’t hit publish until September 2024.

I struggled to get started because I felt like I needed the perfect format, the right platform, know my exact niche and who I’m serving etc. before I could hit publish. Don’t get me wrong, you got to have a general idea, just don’t let it paralyse you from getting started because it’s not perfect in your eyes.

Once I started, I realised all of that actually evolves and improves with time and experience.

So you just need to get started.

2. Newsletters can be a curation of links or original content

You’ll find successful newsletters (and your favourite ones) do one or the other, or a mix of both.

Every newsletter expert has an opinion on this. I’ve come to realise there is no perfect format. It depends on your goals.

I ended up with mostly original content and thinking.

But I also share curated resources that I personally found valuable and that I think are relevant to my readers.

3. Writing takes a long time at the beginning, but stick with it!

I write mainly original content, so I find it takes a lot of thinking, writing and research time.

I was spending 8-10 hours on my first few newsletters! It was such a heavy lift. But after putting in the reps, I now spend around 4-5 hours each week drafting, editing, finalising and scheduling the newsletter.

The more your do something, the more efficient you become because you create routines, systems or workflows for it with more experience.

4. Focus on the quality of the your content by focusing on what gives value to your readers

In the early days, I didn’t want to be discouraged by the low subscriber count or slow growth (out of my direct control), so instead I tried to focus on the quality and making writing the newsletter a habit (within my control).

That means focusing on how to make each issue of the newsletter valuable to the reader.

As a result, I got a bunch of email replies from readers that were hugely motivating to keep me going. I’m so thankfor for them taking the time to hit reply.

But most importantly, I’m glad the content was resonating with the readers and was actually helping them in some way.

5. Start sooner rather than later, so you can experiment, experiment, experiment

The format you start with is unlikely to be the format you stick to.

I feel like the first few newsletter issues I tried to follow the “structure” of newsletters I liked out there. While it helped me write, it felt a bit boring and constraining after a while.

So over time, I just experimented with format, style, voice, length etc. to figure out the intersection between what I enjoyed writing and what readers enjoyed reading.

6. Start collecting emails before you’re ready to launch

To avoid sending your first newsletter out into the void, start collecting emails as soon as you can.

I started an email list when launching my first freebie back in April 2023, my guide to creating a digital writing system in Notion. That meant I sent my first newsletter in September 2023 to 162 readers (instead of zero). A few people unsubscribed, but the majority continue to be subscribers to this day.

7. Hit publish even if you feel imposter syndrome

Because that’s totally normal.

In fact if you’re feeling imposter syndrome, it’s probably because you feel like you’re doing something you care about and you’re afraid.

I felt a lot of imposter syndrome. A key way to overcome that feeling is simply hitting publish despite the fear. The more I hit publish the easier it became.

Repetition is what builds your experience, confidence and efficiency for doing the thing.

8. Just pick a platform

I have analytical tendencies, and easily fall prey to analysis paralysis (which I did when it came to picking my newsletter platform).

Don’t do what I did and spend hours researching the “best platform”.

ConvertKit, Beehiiv, Substack etc. they are all great platforms that will do the job perfectly well, especially if you’re just getting started.

In fact, since I started each platform has evolved and tried to one-up each other (great for users). So the reason I might have chosen one platform over the other is kind of a moot point now.

All that time could have been spent writing and researching my articles instead!

Worse case scenario, you can migrate to a different platform in the future if your needs change. A hassle, but not impossible. So don’t let it stop you from getting started.

9. Community support was super helpful in starting (and continuing)

I've been fortunate to make a bunch of fantastic friends online in the last 20 months.

Conversations with them have pushed me outside of my comfort zone to launch this newsletter. Peers have responded with encouraging words, and a few who haven’t launched their newsletter even asked me for some tips on how I got started!

Writing online can feel lonely.

So find peers (or private community spaces) to talk shop about newsletters to help you get started and keep the publishing momentum alive.

10. Get clear on why you’re starting a newsletter

There are lots of reasons to start a newsletter. Get more clients, get sponsors to fund your writing, sell your products, for the pure joy of writing, as a tool to help you grow through “learning in public” etc.

Know your why and goal from the get-go will help you pick the right metric to measure your progress.

Subscriber numbers isn’t always the right metric to measure, as I’ve learned from experts like Josh Spector.

11. Focus on consistency (not subscriber numbers)

Starting a new habit or long term project is hard.

There are no two ways about it.

Instead of newsletter growth, I focused on just hitting publish weekly (I did that for the first 12 weeks… more on what happened after that in next week’s issue!) and making the quality of the content as good as I could make it in the time I had.

12. Choose a niche or group of topics you genuinely care about and you’ve tested it on social media for resonance

This intersection is key to helping you with #11 Focus on consistency.

If you care about a topic, you’ll be excited to research, write and share ideas on that topic for months and years to come.

If you’re tested some of these topic ideas on social media platforms like X and find there is an audience for that topic, then it increases the chance that you’ll get readers for your newsletter. I do this all the time on X.

13. Leverage Social Media

I’m still a total newbie when it comes to newsletter growth (something I’ll need to work on in the next phase).

One strategy I see experts do is to move people from social to their newsletter. A teaser tweet like this has been a helpful in slowly getting a trickle of new subscribers to The Slow Digest each week.

14. Growing a newsletter audience is not easy

Right now my X/Twitter content and my guide to creating a digital writing system in Notion are the main ways that I’ve gained my 283 newsletter subscribers.

But I’ve got a lot of work to do to make it compelling for someone to become a reader of this newsletter. An obvious next step is to make a valuable and compelling freebie that helps solve a specific problem for my potential subscribers, that ties into what I share in the newsletter.

15. Decide on the publishing cadence

This sets the expectations for you and your readers.

Decide ahead of time how often you want to publish and what kind of content you’ll share. It makes it clear to your readers how often they’ll get an email from you and why they might get value from giving your content.

Stay tuned for part 2 next week. The next 15 unexpected insights and lessons from publishing 30 newsletters.

🛠️ Website Progress Update!

I finally launched version 1 of the slowisbetter.co website this week. There’s still some work to do, but done is better than perfect, as I like to remind myself.

My 1 big tip if you’re creating your first website or updating an existing one… get feedback!

I’ve been so grateful for all the feedback I’ve received from peers, experts and clients, because it’s helped me refine my copywriting and design.

slowisbetter.co

That’s it! Thanks for reading.

If you found any of these 15 lessons helpful to you, I would love to hear from you!

See you next week,

Janice CK

📌 Noteworthy

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