Show your work

Eight rules I follow when writing this newsletter

Photo by Clay Banks on Unsplash

I’m currently working on a couple of longer, more ambitious pieces of writing, so this week I’m deviating from the usual format. I hope this will be interesting not just to writers, but creatives of all kinds.

Writing advice is often viewed as low-hanging fruit, and rather cliché. But I think there is a good reason why writing advice is so compelling to so many people.

Writing is a method of paying attention to the experience of being alive. More than just putting words on the page, it is about engaging with the world in an attuned, open, and curious way. Whether it’s writing essays, painting, dancing, or cooking — it’s all variations of the same act: A way to show your work as you figure out how to be alive. 

I’ve done many different kinds of writing in my career, from longform feature journalism and business and lifestyle journalism to deeply personal writing and plenty of content or copywriting for clients. But the writing I do here is something different. Since 2021, when I quit my journalism job, it’s been the most authentic version of my voice. The things I write about here don’t require a news hook, peg, or timely reason for publishing. I just write what I feel compelled to say.

There is a lot of advice on Substack these days about how to grow your Substack. I find it strange that so little of this advice seems to address the writing part. In my opinion, sending stuff that people will consistently want to read is the long game you want to be playing. Below is a list of the various habits, practices, rules, and guardrails I follow to increase the odds that I do just that. 

1. Before you hit publish, sit with it 

I’ve said before that I only hit send when I have something to say, and following this rule keeps me honest about that. Clear writing is a process of distillation and even if you’re an incredibly clear thinker, it’s almost impossible to get things right in one go. 

When it comes to this newsletter, I almost never sit down to write something, edit it, and hit send all in one day. For the work I do for paying clients these days, I sometimes have to do this, but I strenuously avoid it, especially if it’s a new client or something that’s particularly challenging. When I was working in journalism and media, I did this all the time — sometimes going from idea to published piece in an hour — which is probably why I was very stressed out.

So after you write something, close the laptop, go for a walk, forget about it for a while. You’ll be amazed how new sentences, clarifications, mistakes, structural problems, and other blind spots reveal themselves when you’re away from the page. The thing starts to edit itself. 

Sometimes, the longer you sit with something you’ve written, the more uneasy you become about publishing it. This is actually useful information. Learn to pay attention to how something feels in your body after you’ve written it. Your dopamine-addicted brain will always want to hit publish (the clicks! the likes!) so you need to leave enough time for your nervous system to figure out how you feel about sharing a piece before you hit publish. The feeling of being able to really stand behind what you’ve written — regardless of how it’s received — is one that’s worth a lot. I’ve learned this the hard way.

2. You can get somewhere on 25 minutes a day

I’m not a write-every-day kind of person, nor do I often have long stretches of uninterrupted time to write when I feel like it. But I’ve learned that the trick to writing often is that you cannot wait for the perfect time to write. There is no such thing.

I am a big believer in the Pomodoro timer method — just 25 minutes a day on whatever creative (aka non-deadline driven) project I’m working on. At first, it will feel horrible and it may take you a few sessions to re-orient yourself in your draft. Then it will feel slightly less horrible. By the end of the week, it will even start to feel good. From there, 25 minutes may effortlessly stretch to 45 minutes or even a full hour without you noticing.

Whenever I get really off track with my writing practice, I always come back to this. The 25 minute increment is a sweet spot for me. It’s long enough to actually make some progress if I do it three to five times a week, and yet it’s short enough that I can realistically commit to it even when I think I have no time. It’s also funny how if you delete Instagram from your phone, you will magically find 25 minutes a day.

3. When the words come, drop everything 

Writers live for those moments when the words just write themselves, when the perfectly-formed opening sentence enters your brain. But it only works if you write those words down. I promise you will not remember that amazing sentence once you get out of the shower and dry your hair. You have to get out of the shower right now. (If you have small children and almost never have full use of your hands, ask Siri to send a text message to yourself. This is how I capture approximately 50% of my ideas.)

My experience of these downloads is that they suddenly arrive from somewhere, and if I manage to capture them, they leave a scent trail that guides the rest of the piece along. I don’t know where they come from, but I always defer to them when they do. 

4. Keep track of threads 

The things you read, the conversations you have, the podcasts you listen to, the films you watch, the things you overhear – these are all threads. If a passage, idea, or caption really strikes you, you have to capture it somehow. It doesn’t matter if your camera roll becomes a chaotic mess of screenshots, your Notes app reads like a teenager’s diary, and you amass a stack of notebooks you’re scared to throw away. The simple act of jotting it down it will help you remember it if you need it down the line.

Once you get religious about doing this, you’ll be amazed how often these threads coalesce into a cohesive idea or theme over time. This process is something like magic, and it’s honestly why I’ve written this newsletter for so many years. Having a place where I can tie all these threads together makes me pay closer attention to the world as I move through it. It just makes life more interesting.

I’m fond of the idea from the music producer Rick Rubin that ideas have lives and wills of their own. They want to find their expression in the world. As a creative, you have to be receptive and open to receiving them, or they’ll move onto someone else. Ideas are sneaky like that, so pay attention.

5. If it’s not coming together, it’s not a writing problem – it’s a research/reporting problem

Though I’m not strictly a reporter anymore, my time as a reporter definitely still informs how I write. When I had to file a big feature that I’d done tons of reporting and interviews for, there was always this moment where I wasn’t sure if I was going to be able to pull it off. Usually, I just needed to keep my butt in the chair long enough to get to the other side of the hill. But if I’d had my butt in that chair for hours or days and I was still climbing uphill, then a sickening realization would land: I didn’t have enough information to be writing this yet. Ugh.

The same thing happens to me now. But more often, instead of reporting and interviews, the thing I need to do is integrate and digest things a little bit more, which is ultimately a different kind of information-gathering. You can’t force your way through this problem and expect the writing to be good. Keep reading, keep talking, keep digging. You’ll know when you get there.

6. Don’t write about a personal thing while you’re going through it 

People often comment that my newsletter is very personal, but it doesn’t feel that way to me. That’s because I follow the old advice: Write from the scar, not the wound.

Writing about intensely personal and vulnerable things can be powerful, but it becomes less powerful and even a little destructive if you do so while you’re going through that thing. (Obviously, I’m talking about writing for an audience, not in a journal.) You may say too much, write things you regret, and the writing probably won’t be as clear-eyed as it would after you have had time to digest (and possibly speak to a therapist about) whatever you’re writing about.

When I use my personal life in my writing, I’m very intentional about the purpose it’s playing. I don’t want the reader to walk away thinking about the gory and sordid details of my life, but rather, of their own. What you leave out is as important as what you include.

7. Leave the house 

I’ve been writing from kitchen tables and beds and sofas for my entire professional life. But I can say with certainty that working from home does not result in my best writing. If I have five laptop-based tasks I need to get done in a day, I will always try to leave the house for the writing portion of the day. Boring cafes work best for me: Costa, Starbucks etc. (don’t cancel me, they just work better) or local public libraries (I listen to white noise to drown out the alluring librarian gossip). There is something about the energy shift of packing a bag, leaving the house, and limiting the temptation to clean the house or organize random piles that works for me. Even if I’m just going out for an hour, leaving the damn house is how I do my best writing. 

8. Don’t write for outcomes 

You don’t write essays or books that resonate with loads of people by trying to write essays or books that resonate with loads of people. You do it by showing up to your writing practice often enough that you begin to close the gap between the great ideas in your head and how they come out on the page. You can’t hack it or shortcut it. You just have to show up.

There is a sense on Substack that tight, branded niches are an essential component of success, but I’m not sure I buy that. Of course, having a clear focus or niche can be helpful, but tidy packaging is usually not why we love the writers we do. We love them because of the worldview and tone of voice they’ve developed. If you like a writer’s worldview, you’ll read their work matter if they’re writing about cake or war or sex. I’m convinced that distinctiveness comes from focusing on the process, not the outcome.

I’m amazed at people who start Substacks and ask for paying subscribers from the jump, promising weekly or even more frequent editions. It’s a kind of pressure and outcome-based thinking that would absolutely ruin my writing. It took me literal years of writing this thing for free to figure out if what I was writing about even had a theme. (Thanks to those of you who’ve been around for the whole time!) I’m not saying you can’t do it faster than I did, but you need to give yourself some space to breathe and experiment when you first start.

I’ll finish by saying that every time in my life I’ve written something that really took off or resonated with a surprisingly large amount of people — whether in journalism or this newsletter — I had no idea that was going to happen when I was writing it. I was just doing what I always do: writing as a way to stay connected to the world. It’s something I’ll continue doing whether my audience is small or enormous. Because the boring daily process is actually so much more nourishing than the shiny yet unpredictable outcome.

Thanks for reading. If you enjoy this newsletter, it helps a surprising amount if you forward it to a friend or two, or leave a like or comment below, or share it on Substack Notes. If you’d like to support me further, you can update your subscription to paid here. All content is free for all subs, but paying subscribers allow me the time and space (aka childcare!) to explore these themes. It means a lot.