We invited Lenny Rachitsky, author of Lenny’s Newsletter, to share his insights on creating a consistent writing habit during our 2021 Substack On! Conference.
Lenny writes one of the most popular technology newsletters on Substack, where he writes about product, growth, and people management. If you want to hear more from Lenny, check out his workshop about how to launch a paid newsletter.
This transcript has been lightly edited for readability.
Commit publicly. Tell people that you’re riting a newsletter. When others are aware of your goals, you’ll feel a stronger sense of accountability.
Follow what excites you. Writing is hard enough, so make sure you write about topics you’re genuinely excited by and curious about. If you’re not feeling strongly about a certain topic, then give yourself permission to change course and go where your energy takes you.
Maintain a sustainable pace. Working on your newsletter should feel like a marathon, not a sprint. Consider the long term and don’t burn yourself out.
Carve out deep work time. In order to create valuable writing, you need to avoid constant distractions. Try blocking out a few hours where no one can schedule meetings with you and turn on “Do Not Disturb” mode on your computer and phone.
Keep a backlog of ideas. You never want to start writing and feel like you are out of things to say. Whenever a thought comes up, write it down so you have a constant list of ideas to keep you going.
Commit publicly to your writing
I launched Lenny’s Newsletter in June 2019 and added paid subscriptions in April 2020. I've got about 45,000 free subscribers, 3,500 paid. I'm about to hit 100 posts and it's generating a six figure income. I've been doing this for a year and a half now, every week, and haven't missed a single week.
When I created my Substack, I just tweeted out, "Hey, I'm going to do a newsletter. Maybe you should subscribe if it's useful." This didn't do anything, because I didn't actually commit to anything. I tweeted this and then three months went by and nothing happened.
Then, in September 2019, I had a much more committed-oriented tweet where I implied I'm going to do a weekly newsletter: “This is week zero. It's an advice column. You should subscribe.” I still couched it as an experiment. If you're ever worried about committing publicly, my advice is just think of it as,"Hey, this is an experiment. I'm going to see how it goes. There's no pressure. We'll see what happens. Don't worry about it." No one's ever going to be upset if you stop, but it gives you something that you're committed to and puts it out there.
After that tweet, I started writing and kept at it for nine months before I launched paid. It actually worked really well, because I started getting positive feedback and I didn't want to miss a week. I decided this commitment was going to be weekly, so it kept me going. It also got me my first batch of subscribers. If you have an audience in any form, people will subscribe.
But it doesn't have to be public. Before that tweet, I had a sprint set up with my friends, where I emailed them every two weeks with updates on my work and personal goals, because I had recently left my job and I had no structure. That setup alone gave me motivation to do things because I wanted to feel good about the end of the two weeks.
If you don’t want to announce publicly, just pick three friends and tell them, "Hey, I'm going to work on this post in the next two weeks," and then summarize how it went. It becomes a fun way to keep your friends updated about what you're doing.
One of my goals was to write a newsletter. So if you don’t want to announce publicly, then just pick three friends and tell them, "Hey, I'm going to work on this post in the next two weeks," and then summarize how it went at the end of the two weeks. It becomes a fun way to keep your friends updated about what you're doing. Eventually this email grew to 30 or 40 subscribers just because I ended up finding it useful to update my friends.
If you really want motivation to write, you should charge people money for your writing. Because once I went paid, that's a whole new game. People are paying you money for your content. And it's very hard to not write when they're paying you money.
If you really want motivation to write, you should charge people money for your writing. Because once I went paid, that's a whole new game.
To be transparent, when you’re charging money for a newsletter, it feels like there’s this boulder always chasing you, that you always have to get the next post out. But the motivation is there because people are paying you.
Find a place to just tell people you’re going to write. And that alone is going to create some serious motivation. It helped me a lot.
Stay close to what you're excited to write about
Writing is hard enough. If you're writing about things you're not interested in or not energized by, you're just not going to do it. If you're trying to write consistently, think about what topics pull you in and make you want to write about them.
What topics make you want to scratch your curiosity itch and dive into research? And what are things that you just want to get out of your head? That's how I started writing. I was just like, "I need to get this out of my head before I forget it."
Write as much as you can about things that you want to learn about. I know this is strange to hear, because often the advice is, "Give the customer what they want. Give people what they're asking for." But I find the opposite is best. Think about what's interesting to you. One, it keeps you going, and two, the content ends up being better, because you're excited about it and you're going to go deeper. Oftentimes, the things that I find interesting are interesting to other people, versus what I think they're going to find interesting.
Often the advice is, "Give the customer what they want. Give people what they're asking for." But I find the opposite is best. Think about what's interesting to you.
Don't feel like you have to write about things that people tell you you should write about, or that you think are going to generate clicks. Instead, index towards things that energize you as much as you can.
My newsletter is this hodgepodge of things. Usually, the advice you get is to pick one niche and focus on that and become the best person at that one thing.
To me, I just couldn't get excited about spending all my time on just product management, or just growth, or just startups. I didn't feel like I'd be excited about that for a long time. So I ignored that advice and found this broader combination of things that I felt was going to keep me interested. Don't focus too much on things you're just going to get bored by in a year.
Maintain a sustainable writing pace
A lot of people start a newsletter real fast and with a lot of energy – and then they burn out. The way I would think about writing a newsletter is this pace where it's moving forward, you're making progress, and it's feeling good, but you're not sprinting. It’s more like a marathon.
In my experience, weekly is a really great pace because it gives you time to think. It gives you time to relax. It gives you a life buffer. If things come up, you don't have to feel bad not delivering many times a week.
My advice is to just keep it sustainable. Think long-term, think about what's going to allow you to keep doing this for a long time. Even if you have 30 great ideas, just space them out, because you'll need more ideas down the road.
I also find that people don't often want more email. You might think, "I need to deliver more value to my readers. I'm going to do more emails." But people want quality emails. So my advice is to focus on quality over quantity. What really wins is this combination of consistent quality.
People don't often want more email. You might think, "I need to deliver more value to my readers. I'm going to do more emails." But people want quality emails.
As an example, I added a second email for my paid subscribers, where I summarize the best conversations in a private community for paid subscribers and send that out. It's anecdotal, but it feels like I had a higher unsubscribe rate once I added a second email. It just reminds me that every time you send an email, people unsubscribe. If nothing else, there's just a trigger of, "I don't need this thing," and then you unsubscribe.
Bottom line, don't feel like you need to deliver more and more content. People value high quality stuff that they don't have to read every day. But if you can deliver amazing stuff every day, like many writers do, that's also great.
In terms of word count, I never count what I'm writing. But honestly, I think people prefer shorter newsletters. People just don't have time. They don't want more work. And if you're creating more work for them, or they're like, "Oh no, I’ve got to read all this stuff," that's not how you want your readers to feel.
To figure out your cadence, ask yourself how long you plan to do your newsletter. If you're like, "I'm just going to do this for a year and I'll stop," then pick up the pace. If your goals are just to have fun, it doesn't matter. Just pick a cadence that's consistent. If your content is timely, then daily or biweekly makes sense. If your content is evergreen and useful anytime, you don't need to do it that regularly.
Protect your deep work time
I highly recommend the book Deep Work. It goes through the importance of deep work time, which is essentially distraction-free, long stretches of time where you focus on knowledge work. This book teaches you that the things that have any value, that are creative, that are new, and that are useful to people all come from deep work.
For me, I don't let any meetings get booked before 3:00 PM. I keep my entire day open for writing as much as I can. When I had a full-time job, I had three hours blocked out on Mondays, Wednesdays, and Fridays that no one else could schedule over. And it actually worked really well. My advice to you is find a time in your workday to block out a few hours of time. It ends up being a game-changer.
Find time in your workday to block out a few hours of time. It ends up being a game-changer.
If you wonder if you can even write when you have a full-time job, know this: the number one highest grossing Substack writer, Heather Cox Richardson, does it part-time. She's a history professor and she does it every day, which blows my mind. So it's possible, even if you have other things to do, to write consistently and to create time to write. So let her inspire you, because she inspires me.
There's a really simple trick that helps a ton. It’s turning on “Do Not Disturb” mode on your phone. In this mode, your phone doesn't buzz, doesn't make sounds, and doesn't vibrate, which is the dream. Similarly, on your computer, “Do Not Disturb” mode shuts off all notifications from popping up, like from Slack, iMessage, and WhatsApp.
I have it on all the time now. It just makes your life much happier, not getting buzzed all day. You might think, "I’m smart. I can ignore messages and phone sounds. I'm just going to stay focused. I don't need this stuff."
But our brains are so bad at this stuff. If you know that there's something to look at that's going to give you an excuse to get away from the hard work of writing, you're just going to do it. Ignorance is bliss in this kind of situation. If you don't even know that there's something to look at, you're going to end up being a lot more successful. It's powerful, and it's free. Just a little feature on your phone.
Find the right tools to help you write
Find tools that help you stay focused, organized, and distraction free. You don't want to come back to writing and be like, "I don't know what I'm doing right now.” Here are tools that I find valuable:
To-do app: It’s important to have an app that gives you a clear set of priorities. I use Centered. (Disclaimer: I'm an investor, because I'm a huge fan.) It's a to-do app where you create a playlist for your day. You click play and it turns on music that helps you focus and gives you nudges like, "You're distracted. Maybe get back to work." I honestly can't even work now without this thing. There are a lot of to-do apps, so just pick one.
A doc tool to organize your content: You want to find something for organizing all of your thoughts. I use Coda, which gives me a place to store my writing plans and throw in notes, quotes, and writing advice. You just want to find a place to dump all of your ideas and keep track.
Nutrients to boost energy and focus: I need a little bit of caffeinated liquid energy. So I drink tea. And then there's this nootropic caffeine product called Magic Mind that I love. It’s all natural and helps my mind get in the zone. But even just coffee is probably enough for a lot of people.
Writing tools: There are a few I really like. First, Grammarly. I have typos all the time and I’m just very bad at spelling. People would not read anything I'm writing if not for Grammarly. They'd just be like, "Who's this joker?" Second, I use a free Chrome extension called Power Thesaurus, which lets you double click on a word to get all its synonyms. I use it all the time.
A platform for hosting and sending content: Substack, thumbs up.
Keep a backlog of ideas
Have a place to dump ideas as they come. You want to avoid the blank page syndrome of like, "Okay. I have time to write. But, oh man, I don't know what I'm going to write.”
Every time I have an idea that I think could be an interesting post, I just create a new page in Coda. This is a list of all these random ideas that I have, and then I just dump my raw thoughts into each of these pages. Over time, you start to build dozens of nuggets of ideas that you can come back to whenever you're excited to write about that piece.
Turn your idea backlog into a prioritized list of your upcoming content. I have a list of future posts over the next couple of months. And I go in every week and rearrange them based on what I'm feeling. This gives my brain a chance to marinate on what's coming up next, and let go of the things that are way out in the future.
Go where the energy takes you
A lot of people stick to a plan of, "Okay. I have to write about this thing this week." But sometimes I just don't feel it and I have something else I'm much more excited about.
Give yourself permission to write about the thing you're excited about and forget about what people are expecting and what you thought you had to do – just go with the energy that you have. Writing is so hard, so if you have energy to write on something, just go for it as much as you can. It's not always going to work. You can't always do whatever you want, but if you have the flexibility, you should feel comfortable moving things around.
Writing is so hard, so if you have energy to write on something, just go for it as much as you can.
You want to feel like,"Yes, I can't wait to write about this thing. It's going to be so great." What's cool is even if you don't end up publishing that piece that week or day, you have now all this content that you could bring the next week or whenever you get to it. Essentially, you want to avoid the feeling of, "Oh my God, I just don't want to do this thing." The way to do that is to give yourself permission to go with what's giving you energy.
Create a summary when you stop writing
I just learned this tip recently from David Perell, who has an amazing free email series on how to become a better writer. His advice that I love is when you're done writing for the day, stick a little summary at the top with where you left off. Before you're leaving the computer, just write, "Here's the next thing to do when I come back to this post. Finish this paragraph here, explore this topic, go in this direction.”
The next day, you want to avoid ramping up to the place that you stopped at. You want to zoom to that mental model and mental state as fast as possible. That's what this little summary does. It gives you a bit of a boost to restart it.