7 Steps to Publish Weekly

A loose guide to maintaining a strict deadline

When I launched this newsletter two years ago, you would’ve thought I was sending rockets into space the way I nervously hit ‘publish’ each week. For the first couple of months, I massively overthought everything from what I wrote to how I formatted it. Ironically, I had ten subscribers at the time and most were fellow writer friends who had launched their newsletters in tandem—so god knows they were supportive as hell. But I still felt nervous.

I had just finished Write of Passage, a five-week intensive writing course, in which I’d published five peer-reviewed articles on a website I’d built in week one. But then came the extra assignment upon graduation. We were instructed to start a newsletter on Substack or ConvertKit. I opted for Substack because it was said to be simpler if you just wanted to write and weren’t trying to sell products. And I’m glad I did because two years later, the platform has evolved into a robust writing community that I’m proud to be a part of.

I can’t say for sure when I stopped feeling nervous about hitting ‘publish’. All I know is it took a few months for me to gain confidence, knowing full well that my writing wasn’t good yet—but each week it was getting better. My motto was “practice equals progress,” and I encourage anyone starting to write online to stick with it long enough to see some gains.

The Latest Write of Passage Cohort

I worked on the latest Write of Passage cohort (which wrapped up on November 8th) as an editor for five weeks. This was the fourth cohort I’ve partaken in since September 2021. Since then, I’ve been a student, a mentor (twice), and most recently, an editor. Needless to say, I’m well-versed in the course—though I’m impressed by the changes the team makes from one cohort to the next. They’re always levelling up the experience based on student feedback so it’s a nice blend of familiarity and fresh air each time I come back.

The latest Write of Passage cohort

But one thing that never changes is students’ eagerness to understand how those of us who have maintained our weekly publishing cadence did so once the course structure faded away. I usually start getting messages in the last week of the course asking for my advice. Here’s a perfect example:

Hey Alexandra! I’ve learned so much in [Write of Passage], including that I want to keep writing every week. I'd love to learn from others, like you, about how to continue to write after WOP. How do you keep writing every week outside of WOP? What's your weekly writing routine? How do you come up with topics? Thanks!

In the past, when I was a mentor, I’d direct students to a session I ran on “how to keep publishing beyond the course.” But since I opted for an editor role this time, I promised to share my advice in my newsletter. So here it is.

7 Steps to Publish Weekly

This may come as a surprise since I’ve been publishing my newsletter for 111 weeks, and in that time I’ve only missed two weeks based on a deliberate choice to take a break when I was feeling burnt out—but I don’t have a super tight routine for writing my newsletter. What I have had since my Write of Passage graduation is an unshakeable determination to keep writing.

The biggest thing for me was making the decision that I was going to continue shipping my newsletter every Wednesday. Because I thought, “I’ve come this far and I’m not giving up now.” From my perspective, knowing why you’re doing something is the root of everything.

Start With ‘WHY’

I’m taking a page out of author and inspirational speaker Simon Sinek’s book ‘Start With WHY’ because ultimately, unless you know why you’re doing something, you’re unlikely to stick with it—particularly when things get hard and you feel your motivation dipping. Here’s what I mean.

Simon Sinek explaining how ‘WHY’ is at the centre of everything (source)

In November 2021, a few weeks after I graduated from Write of Passage, I had the pleasure of meeting course instructor David Perell in Montreal. When he asked me why I started writing online, I told him I didn’t have a good answer. All I knew was, “I just had to start writing. I felt compelled to.”

Ironically, two years later, I realize my answer was sufficient. You don’t have to have a big, bold reason to write. Feeling compelled to do so is sufficient. The main thing I’ve learned since then is “trust your intuition.” Because often our intuition can sense things before we can make sense of them. So if you’re compelled to write—or do anything else for that matter—go for it. You don’t need a why beyond that. In fact, your why will emerge as you immerse yourself in your craft.

Here’s a great Tweet from author Rob Lennon on the subject:

So reflect on your why. Again, it can be as simple as “I intuitively feel the need to write for reasons unknown to me at present.”

Pick a Deadline & Work Backwards

Once you’re clear on your why, it’s time to get tactical. This is where it’s important to be outcome-driven. That means having a weekly publishing deadline. In my case, I picked Wednesdays, but you can pick any day you want.

Next, you need to identify the steps necessary to achieve your deadline. I used these 7 steps:

1. Pick your topics

2. Do a brain dump

3. Draft your newsletter

4. Get peer feedback (optional)

5. Edit and finalize your newsletter

6. Hit ‘publish’ or schedule your post

7. Engage with your peers’ newsletters

Before I elaborate on each step, I want to introduce a vital concept that’s helped me achieve each one.

Sacred Hours

Before I took Write of Passage, I took another, lighter writing course called Ship 30 for 30. And my key takeaway from it was that you have to carve out “sacred hours” in your schedule to write and edit. Ultimately, that means blocking off specific hours in your schedule to get them done.

In my case, I carve out those “sacred hours” early in the morning so I can focus without distractions. But figure out when is ideal for you based on how your energy and concentration fluctuate throughout the day.

Now, back to steps 1-7.

Steps 1-7 Explained

Here’s a detailed overview of steps 1-7 for more context.

1. Pick your topics

When you’re starting out and you don’t have a big audience to appease, you have the gift of freedom. So take advantage. Write about what you feel compelled to write about—and note this may differ from what you had planned to write about. Take me, for example. When I started my newsletter in October 2021, I was adamant I was going to write exclusively about online courses because I wanted to raise my profile within my industry to attract and retain clients. But by week two I was veering. I started opening up about leaving my 9-5 to freelance and the journey I was undergoing in that respect.

As weeks and months went by, I alternated between course-related content and more personal professional development stuff. I also played around with different formats, like having three specific sections on different things versus one common thread woven throughout—in the end, I’ve stuck with the latter.

A cautionary tale

I want to share a “cautionary tale” regarding a friend and former Write of Passage student who like me, launched his newsletter in October 2021, but then abandoned it a few months later. The reason? He got stuck in his head. He had added a mix of peers and former clients to his newsletter when he launched it, and he immediately started getting mixed feedback. Some readers wanted less about X, and more about Y. Others felt the complete opposite, and so on. So my friend got stumped and decided to take time to think about what he wanted to focus on going forward. The problem with that is you won’t figure out what you enjoy writing about just by thinking about it. You have to write. And to improve your writing in the meantime, you have to write. But don’t take my word for it.

Here’s a text message from my friend in response to a newsletter I sent a few weeks ago (roughly two years after we simultaneously launched ours):

The takeaway is don’t let feedback derail you. Chances are you’re going to be a bit all over the place initially and that’s OK. You’re experimenting and that’s a vital part of hitting your stride. Be compassionate with yourself in the process and have as much fun as you can.

Picking high-level topics

To keep it simple, limit the topics you plan to write about to three at most (this is a best practice from the Ship 30 for 30 co-founders, both of whom are prolific writers). For example, I used to write about courses, solopreneurship, and online teaching. But having recently pivoted, now I’ll be writing about professional development, online teaching, and well-being. Those three buckets give me an ideal bandwidth.

The next order of business is to pick your subtopics from week to week.

Picking weekly subtopics

I don’t look for weekly topics, they tend to find me. In other words, I write about whatever’s top of mind—things I feel a need to get out there. That can include:

• A recent challenge I’ve overcome (ex. this post on burnout)

• A big project I’m working on (ex. this post on launching a course)

• Expanding on concepts that resonate with others (ex. this post on speaking last)

Like your high-level topics, you can plan your weekly topics in advance. But if, when the comes to write about them, you feel pulled in another direction, go with your gut. Pivot as much as you like. Because ultimately, you have to enjoy what you’re writing about. Otherwise, you’ll never stick with it.

2. Do a brain dump

Another thing I learned from Ship 30 for 30 is the value of brain-dumping your thoughts before writing a draft—even if it’s just a few bullet points. So the day before I was scheduled to write a draft, I would drop some notes onto the page with links, graphics, quotes, or other sources of inspiration that I planned to draw on. Often I’d end up with a messy heap of ideas. But when I came back to said heap the next day, I was brimming with inspiration and could start writing stat.

3. Draft your newsletter

Back when I started my newsletter two years ago, I’d easily spend 15+ hours over 3-5 days going from idea to published. I tried to be strict about sticking to specific time blocks but I always found myself needing more time. It was slow going. And I’d seize extra time where I could (between meetings, deep work, etc.). But that’s to be expected early on. I’ve gotten faster through putting in the reps and now I publish in a fraction of the time.

My advice is to determine what a reasonable amount of time is to go from idea to published, and then allocate 10% of that time to drafting and the other 90% to editing. Rewriting tends to be where the magic happens as you develop and refine your draft.

4. Get peer feedback (optional)

When you’re first starting out, peer feedback is helpful in two ways: first, it keeps you accountable to send your draft to someone by X deadline, and second, you’ll get a confidence boost by having someone vet your draft. The easiest way to do this is to pick one or two people you can reciprocate with. That way it’s win-win and you don’t feel like you’re pestering someone for a favour.

When I first started writing my newsletter, I asked fellow Write of Passage graduates for their feedback and gave them mine in return. But then, within a month or so, it became harder for us to coordinate. Since then, I’ve been self-editing (except for the odd occasion where I ask someone for a sense check on something I’m unsure of).

My main advice is this: get peer feedback if you have access to it. But don’t let a lack of feedback become an “excuse” not to publish. I get that it’s scary to send something out that hasn’t been “vetted”—especially after five weeks of robust feedback on your drafts during Write of Passage, but the training wheels have to come off eventually. In an ideal world, we’d all get feedback on every newsletter draft but realistically, unless you have time to reciprocate or money to pay an editor, your best bet is to fly solo and leverage feedback in the forms of questions, replies, comments, etc. to assess and adjust what’s working and what’s not. Apply that knowledge to future newsletters. That’s how you learn and improve.

I was nervous when I started publishing my newsletter without peer feedback. But I did it anyway and I’ve learned a lot since. Now, I have no qualms about hitting ‘publish’ without “reassurance”. Because I know whatever I write is good enough. So as long as you’re writing for yourself (and not a company—which is different), don’t rely on peer feedback to hit ‘publish.’

5. Edit and finalize your newsletter

This part is pretty simple—though of course, not necessarily easy. My advice is to set aside two blocks of time to edit and then finalize your newsletter, respectively. Editing involves reworking the structure and wording of your draft. This is where 90% of your effort will go (which is why you don’t want to spend too much time drafting).

Then, I like to come back to the edited version with fresh eyes to do a final pass and make minor tweaks to feel confident “it’s ready to go out.”

Here are two additional tips to help you edit and finalize:

1. Change the format of your draft. Sometimes when you’ve been staring at your screen for too long, you start to miss minor things like typos or other issues with flow. That’s when it’s helpful to change up the format. You can give yourself a “fresh perspective” by looking at your draft on your phone or another device. Other examples include PDF-ing a Google Doc, sending yourself a “Test” email on Substack, etc.

2. Read aloud to spot logic gaps and other issues with flow. Sometimes you think something flows when you’re reading silently, but then once you read it aloud you realize it doesn’t. So read your piece aloud and if you get tripped up on something, fix it. Smooth it out until it flows.

At a certain point, nitpicking becomes excessive (I’m guilty of wasting hours in the past obsessing over minor things that didn’t really matter). So know where to draw the line and declare “good enough” to meet your deadline.

6. Hit ‘publish’ or schedule your post

This step is both minimal and monumental in that all you have to do is hit ‘publish’ (or ‘schedule post’) but it takes guts to do so. Like I said earlier, my fellow Write of Passage graduates and I used to laugh about how “you’d think we were sending rockets into space” the way we nervously hit the buttons (shoutout to Cohort 7). But as I also said, “practice makes progress” and it gets easier the more you do it. I don’t feel nervous at all anymore.

7. Engage with your peers’ newsletters

I mentioned earlier that my reason for writing was simple, “I felt compelled to.” And as one of my childhood friends has told me throughout my life, when I set my mind to something, I make it happen. I can’t be derailed, least of all by a lack of discipline. So while I know I would’ve stuck with my writing practice even if I was the only one to do so after Write of Passage ended in October 2021, I found it immensely motivating to have others publishing alongside me.

Week after week, I’d see newsletters from

Simone Silverstein

,

Christin Chong, PhD

,

Karena

,

Louie Bacaj

, and

Charlie Bleecker

hit my inbox like a bullseye. Each one, even if I didn’t have a chance to read it, served as a reminder to keep going. I was inspired by my peers and that amplified my motivation to keep publishing.

Another thing that helped was making the time (as much as possible) to read other newsletters and engage with them through replies and comments. And in turn, my early readers did the same for me. Again, all of this amplified my motivation to keep publishing.

Additional Tips

Create a Writing Ritual

To make writing as enjoyable as possible, I encourage you to create a writing “ritual.” I use the term “ritual” versus “habit” because rituals signal more depth and fulfillment. For example, my morning writing ritual entails hot coffee, and a calm and cozy set up next to big windows overlooking the nature beyond them. It’s an experience I look forward to, not something I have to do.

Be Adaptable

Another tip I’d offer is to be adaptable—meaning stick to your deadline as long as it makes sense. Here are three examples of how I’ve embraced adaptability in the course of maintaining my weekly publishing schedule:

• Improvising to beat the clock: Back in December 2021, I arrived home in Montreal on a Wednesday evening after a trip to New York, and I was determined to get my newsletter out by midnight (despite having done no prep and feeling exhausted after a non-stop few days). But because I was only two months into my publishing streak and didn’t want to break it, I got a second wind (I also turned to ice cream for a sugar high) as I wrote late into the night. I ended up writing about how “I’d just gotten in from New York” and shared a brief update with a promise to share more in my next edition (and I followed through on that promise a week later). Voilà.

• Better late than never: The second case of struggling to meet my deadline was back in April 2023 when a wicked ice storm plunged a million Quebecers into darkness. It was a Wednesday—my publishing day—and ironically, I had just written this first sentence for my post: “I’ve spent the past two weeks in the early 1800s.” It seemed almost poetic that my power went out at that moment. Anyway, my initial instinct was, “Oh my god, I need to find one of the few places that still has Internet to get this written and sent out before midnight.” But then I realized I was being neurotic. By that point, I’d been on an eighteen-month streak and I needed to focus on more important things as people dealt with damaged property and cars, no power, and worst of all no heat. Fast forward a couple of days, and I ended up writing and sending my newsletter out on the Friday once my power came back. I could’ve skipped that edition but ironically the chaotic events of the week gave me plenty to write about. So the lesson there is to embrace disruptions as writing prompts.

• Taking deliberate breaks: I mentioned earlier that the sole time I broke my weekly publishing streak in the past two years was for a two-week period this past summer. I was burnt out in general and I needed to disconnect from work and technology. So I did. At first, I was anxious about pausing my newsletter. I feared I might lose momentum once I fully “let go” and felt the extent of my injuries. But that was a risk I had to take to prioritize my well-being. Funnily enough, a couple of weeks was just what I needed to re-energize and I ended up being compelled to write about overcoming burnout when I got back into writing two weeks later. Again, the lesson there is pain can be a writing prompt.

How to Get Unstuck

Feeling “stuck” is one of the worst feelings as a writer. You have so much to share but can’t figure out what your next step is. I’ve been there. And I’ve learned staring at your computer overthinking things only prolongs your pain. So here are three tips I suggest to avoid this.

(Source)

1. Timeboxing: If you’re stuck searching for words (whether you’re starting a new draft, trying to clarify something or smooth out a transition), set a timer for 10 minutes, and write down whatever comes to mind. Go FAST and write as much as you can. Don’t question what comes to mind, just get it down. And don’t use ‘backspace’. You'll be surprised at the breakthroughs you have. From there, it’s just a question of refining what you’ve jotted down. The important thing is the faster you get words out of your head and onto the page, the sooner your piece will take shape.

2. Go for a walk: Sometimes the best thing to do when you’re stuck (especially if you’ve been at something for a while), is to take a break. Close the tabs in your browser to mentally disconnect from the task at hand. And then go for a walk outside (even if it’s a short stroll) to relax and reenergize. I guarantee when you come back, you’ll be in a better position to move forward.

3. Step away for a day or two: If you’re really stuck and a short walk isn’t going to cut it, that’s okay too. You don’t have to write every day to become a good writer. Sometimes stepping away for a day or two is all you need to come back fresh. So rather than apply brute force to get something written and published in one go, consider how you could be kinder to yourself by showing yourself patience and compassion as you’re learning.

Benefits of Sticking With It

My newsletter has been an undeniable catalyst of personal and professional development since I started it back in 2021. It’s become both a weekly reflection prompt and a picture window to share my journey with you. That said, here are three reasons why I encourage you to maintain a writing ritual going forward:

• You’ll get better at processing your thoughts. Publishing weekly has been a forcing function to converge on my biggest takeaways each week.

• You’ll become more articulate. The practice of refining my thoughts through writing and editing has made me more articulate in every aspect of my work.

• You’ll feel calmer. Writing is a form of meditation. It’s an opportunity to process a jumble of thoughts into a cohesive whole and create space for new thoughts to emerge with clarity.

Most importantly, you’ll raise your standards for reading and writing. When you start writing consistently, you get better at distinguishing good writing from bad writing. The more you devour good writing, the better you’ll write—and think.

And there you have it—my elaborate summary of how I’ve maintained a weekly publishing cadence for over two years now. I hope these tips help you maintain one of your own. And I’d love to know in the comments, what resonates as well as what tips you would add.

Thanks for reading and have a wonder-full week,

Alexandra

P.S. If you enjoyed this edition, please like, comment, or reply to let me know.

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