7 Things I've Learned About Writing and Creativity In 6 Months of Publishing on Substack

It’s been about six months since I started a ladder to the stars, and I wanted to take some time to reflect and share what I’ve learned about writing and growing a Substack publication.

Before we dig in, let me provide a little background. I’ve been a professional writer for 10+ years, and at the end of last year decided that I needed to reclaim my writing voice and share some of the work I’ve written that has never seen the light of day. It’s fair to say that I was out of the cycle of sharing regularly, and I was used to hiding behind my clients and the work I needed to do for them. There was never enough time to do my own work until I stepped back from professional writing. This newsletter is an attempt to grapple with creativity, writing, spirituality, life, and finding your voice.

Below are 7 lessons I’ve learned about creativity, writing, sharing, and (slowly) growing a newsletter. Hopefully, they help you, whether you plan to start a Substack or you just want to get into the habit of sharing your work regularly.

1. Writing and sharing work regularly is not just about building the muscle of consistency. It is also about building trust with yourself.

If you’re like me and many other creators, consistency is the often-insisted-upon thing we need to gain traction. And yet consistency is hard to come by when we experience the constraints of time and motivation, as well as all of our other obligations. Newsletters can easily take a backseat in the face of family time.

At first, I didn’t trust myself to stay consistent because, frankly, I had never done so with my own creative work. The stakes were always too low, and everything else was too pressing. So, I had doubts about committing to a weekly schedule, even though I was clear that I wanted to build a practice of writing and sharing work. To ease into it, here’s what I did:

1. I took a large subsection of my “old” work (more on what “old” work means in a moment), no matter what I thought of its quality, and scheduled them as posts.

2. I didn’t send out emails for two months, meaning I never sent anyone on my list an email. Instead, I got into the rhythm of sharing each piece as a post, writing for two months, and I let each post populate on my Substack homepage so that when random folks came across it, the publication wouldn’t be barren. This had the effect of feeling like a rehearsal for a play. The stakes felt lower, and I could find a rhythm that worked for me without pressure. If I missed a week, no one knew but me. If I posted three or four times in a week, no one knew but me.

3. I let myself be moved by what was going on around me to the point where I could write spontaneously. Then I could either choose to interrupt the flow of scheduled posts or add it to the end of the line.

At some point in January, I was ready to start sharing. Sharing felt fun and low pressure because I’d “practiced” before.

As I continued to post, share, and experiment, I noticed that I no longer had that question in the back of my mind: “What if I drop the ball?” I now have a level of trust in myself that I will continue working on this, even if I send out someone else’s poem, or share work that I think is less-than-complete because that’s what I’ve committed to.

In the last six months, I’ve learned to trust that I will follow through on my creative commitments to myself. I’ve also learned what it takes to build a sustainable commitment. And that in itself is worth every bit of time and effort I’ve spent on this endeavor.

2. What you work hard on does not always equate to what people like, and what feels “old” to you does not feel old to other people.

When I’m out of ideas, I turn to my bank of “old” articles and post one of those, feeling as though I’ve phoned it in. By “old” work I mean things I wrote months or years ago that no longer feel pressing or have the power of immediacy, or that represent moments in time that I’ve moved beyond. Then that post gets more interaction than anything I’ve written lately, and people say things like “I really needed to hear this today!”

Sometimes I feel like it’s a cop-out when a post feels easy and takes less than 30 minutes—and yet the posts I spend hours on, and that I work to tie in lots of ideas and references, get the equivalent of crickets.

All of that to say is that, so far, there does not seem to be any correlation between the effort of the writer and the response of the reader. Killing myself over a post doesn’t seem to equate to more thoughtful interaction. It also seems like a fool’s errand to try and guess what readers will like and write to that.

So far, I’ve gained nothing from that kind of exercise except this realization: Sometimes the easiest writing is the most impactful.

3. Curation is important.

I had a string of calamities over the last four weeks. Small calamities—school canceled, moving deadlines, weather emergencies, sicknesses, long weekend trips, and a round of COVID for the adults in the house. It all had the result of backing everything up and making everything … just … harder. And, my newsletter took an unintended hit: I accidentally scheduled several gloomier posts in a row. How that happened is comical but not important, but what I noticed is that people have slowly responded less to each successive post, with the exception of one: where readers seemed to think I needed to be rescued from my own judgment of myself (more on why that’s not a good thing in the next point).

This experience taught me something: paying attention to careful curation, or in other words, the way each article rolls out and what it’s situated next to, is important to keep people engaged. One gloomier, or more pensive post might be good to read in a string of other posts that touch on different themes, but three in a row = a major decline in reading.

Now, the caveat is that this particular newsletter does not serve any particular kind of niche, other than the very vague description of “spirituality” and “life.” If you were writing a newsletter about a very specific niche topic, this bit of advice might not apply. But I daresay people are still interested in a variety of angles of any given topic—they get bored when the feel or the tenor is the same piece after piece.

4. Real, raw writing is good. But avoid unintentionally burdening your reader.

With one of my recent gloomy posts (On Feeling Insignificant), I realized that I had represented a certain place and time in which I worked through feelings of insignificance. By the time I shared it (six months after writing it), I no longer identified with the place from which I’d written it. And although I had worked through that pain, it did not seem to appear that way to the people reading it.

That post got lots of interaction, including lots of emails or messages saying the equivalent of “You okay?” or “You’re awesome.” (I’m summing up to keep it short.) ALL of which I appreciate, by the way, but it was a sobering moment—the way I wrote the post made it hard for the reader to discern where I was on the journey.

For me, there was a giant disconnect between the events and feelings that spurred that post and where I am now.

But not for the reader. And it seemed to leave the reader feeling as though it is their responsibility to lift me up or tend to my emotions.

This is a tricky one to address: as a human who happens to know many—but not all—of the people subscribed to this newsletter list, it’s nice to know that the people reading my work care about my emotional well-being. It’s clear I’m not lacking community. On the other hand, as a writer, it was never my intention to cause anyone to feel that they needed to comfort me.

There is some balance to be struck between writing from the wound and writing from the scar; writing from rawness and writing from the place of healing. Of writing from one place and sharing from another.

It’s a balance I haven’t struck yet, so I have no actionable advice to others who might be thinking about sharing their writing—just a call to pay attention to the place from which you write and share, and to be mindful of the burdens you might unintentionally place on your reader.

5. Writing and sharing regularly will reveal your bad writing habits.

Writing regularly will reveal your tendencies and bad habits. Among mine: I write too much (case in point, this post is already far longer than I intended). Mark Twain said “I didn’t have time to write a short letter, so I wrote you a long one instead,” pointing to the fact that brevity is harder than it seems.

A couple of weeks ago, another bad habit became apparent: I felt compelled to turn something into a “lessons learned” post. It was a story, and as I sat there and toyed with the ending, I realized I do this with nearly every post. It didn’t feel like a choice. I viscerally felt like the piece would be incomplete if I did not add a section where I shared the lessons learned. Thus, another bad habit was revealed: the compulsion to teach.

Also, I’m a typically neurotic writer with a tendency for navel-gazing. That means my work can border on being too self-reflective and/or revealing, and at times can come off as self-centered.

There are definitely more, but those are the three main problems I’ve spotted and wrestled with so far. It was frustrating to see those. Embarrassing, too. But awareness is the first step to improvement.

Those problems take time to address—it takes time to rewire bad writing habits, to think about how to change up your pattern, especially when writing for catharsis or expression usually means writing in a certain way that you’ve grown accustomed to.

Be open to what you see and what gets revealed in the course of sharing your writing. It’s all part of the process, and only by seeing what you may not want to see do you have the opportunity to get better.

6. Keep the main goal the main goal. Don’t get sidetracked by things like “growing the list” unless that is the main goal.

When I started this, the main goal was to flex my creative voice and get into the habit of sharing work instead of hiding it like some kind of literary hoarder. Somewhere around month four, I got more interested in growing the list, as in reaching more people. This being Substack, there are dozens (really, dozens) of posts that come out every day telling you how to grow your Substack list. At first, I read a few to understand the platform. Then I tried some things, some of which worked and some of which didn’t. Then I read some more posts. Then a few more.

It wasn’t long before I could feel my focus shifting from flexing my creative voice to building a list. Those are not the same thing. The tools and tips used to grow a list are far more restrictive (if you’re using normative, generally accepted methods of marketing) than practicing the habit of saying what you want to say when you want to say it. The former narrows. The latter expands. Both are valid pursuits, but my original goal was more important to me, and I finally had to put aside my attempts to grow to focus on developing the writing and sharing habit.

Now that I feel fairly secure in my writing habit, I’m starting to consider how I will shift the goal, but I won’t be changing course until I make a conscious decision about what’s best for the creative work.

If you’re starting out, set a primary focus and stick to it for a pre-determined amount of time. Decide on the overarching goal of your work, and make sure that any decision—including decisions to grow or get in front of more people—align with that creative goal.

7. It feels good to put your writing out there. If you’re thinking about it, do it.

This has been worth it. The small moments have made all of the time put into this newsletter worth every minute of effort. Here are some of the big and small ways this has been soul-affirming:

There is now consistency between saying I’m a writer and actually being a writer whose work sees the light of day under her own name (as a former ghostwriter, much of my work is under someone else’s name, which is a disembodying creative experience). There is a newfound alignment between how I see myself and how I move about in in the world.

Having friends pledge money to this newsletter meant the world to me. I don’t currently have paid subscriptions, but the moment four friends said “I believe in your work” felt so gratifying. The total was a very small amount of money compared to what I’ve made in my business, but it honestly felt like an enormous sum because it was for work I created from my stories, thoughts, and experiences—not as part of a client contract. It was a new experience and redefined what it meant to be paid for my work.

Having friends comment “I needed to see this today” or “This really made me think/cry/laugh” always feels good.

Having friends add their thoughts to things I’ve shared is always wonderful and makes me feel like I’m starting a conversation that will hopefully impact everyone in the convo in a good way.

The catharsis of sharing so much work is real. There’s a sense of letting some of it go as I put it out there.

There is more to say, but if you’re thinking about sharing your writing, whether via Substack or some other platform, my advice is to do it. Set your own goals—goals that will keep you motivated and give you the emotional pay off you want—and stick to them. Experiment. Throw things out there. Write well and write badly and see what sticks. But above all, have fun while you do it.