Just over two years ago, on April 12, 2020, I sent out the first issue of this newsletter.

I’d attempted to write several newsletters in the past, but they had always fizzled after a few months at most.

Something about this one felt different however, and now, 100 issues later, it seems that hunch was true.

Over those 100 issues the newsletter has nearly tripled in size, almost all of that growth coming in the past 12 months, and I’ve learned a lot about creating and growing creative projects like newsletters.

And while a lot of what I’ve learned corresponds with the standard advice you can find all over Twitter, for this milestone issue, I wanted to share 10 of the more unconventional learnings I’ve had about growing creative projects, several of which fly in the face of standard audience building advice.

Let’s jump in.

1 // Feed Yourself First

We’re often told to serve our audience above all else.

But in my experience, creative projects have a much higher chance of succeeding when the act of creating them gets us something personally, before anyone else ever interacts with them.

Ironically (or maybe not), this was the topic of the very first issue of this newsletter, which I titled, Focus on What Fuels You.

Feeding yourself first is about structuring your projects in a way that first & foremost scratches an itch you have. Then finding a way to adapt & package it in a way that overlaps with an existing audience’s interests & desires.

This isn’t to say that every project that scratches one of your own itches will have an opportunity to build an audience around it. You need both project-market and project-creator fits to be successful.

But in my experience, it’s easier to find an audience for a project that feeds you than the other way around.

2 // Pay Attention to Signals of Progress

Almost any creative project is going to take several years to grow a significant audience around. But if your work has the potential for growth, you should be getting at least small bits of positive feedback fairly quickly.

Five issues in, I received my first email response from a reader (shoutout to Jason Perrier!) about how they resonated with the issue.

That email encouraged me to lean further into what I was doing, and since then, I’ve received at least 1 similar email almost every week.

If you’re getting your work in front of even a small number of your ideal audience members and you’re not getting any positive reinforcement, it’s a sign you need to make some tweaks.

And if you’re not regularly getting it in front of even a small number of your ideal audience… well you need to start there.

3 // The First Version Won’t be the Final Version

We all want to launch our projects as their fully realized & perfected versions.

But most of the time, we, ourselves don’t know what they’ll morph into once we launch them. Better to get a first draft out and then iterate on it from there, a process I call Thinking in Drafts which I covered in Issue 27.

I wrote the first 56 issues of my newsletter under what was essentially a placeholder name, The Listen Up Newsletter.

I named it with a vaguely audio-related name before I ever wrote the first issue and wholeheartedly believed I was going to be writing about podcasting… which never ended up happening even one time.

It was only after those 56 issues over more than a year that I started to see the through-line in the newsletter & rebranded to the more aligned Creative Wayfinding Newsletter.

If you’re creating a long-term body of work like a newsletter or podcast, you should expect it to go through significant shifts over its lifecycle, none of which you can predict before you start.

Understanding this reduces the pressure you put on the first (or current) iteration to be perfect.

Ship it & then have the faith to keep moving through the fog and follow where it leads you.

4 // Being Unable to Describe What You do Might Mean You’re Onto Something

I often feel sheepish that after 100 issues of my newsletter, I still can’t really describe what it’s about.

But recently, I’ve discovered that this is a common trait of successful creators’ platforms.

The reason, I think is that successful creative platforms are often a blend of ideas that haven’t been paired before. This is what makes them novel and interesting. But it also makes it hard to develop messaging around them because the vocabulary doesn’t yet exist.

Creating that vocabulary is a huge part of our job as creators.

5 // The Things that Work Best Don’t Always Make Sense

We all love frameworks, templates & archetypes that promise to shortcut our way to success.

But the things that work best usually don’t fit neatly into the existing boxes. And they often break all the rules you’re supposed to follow.

My audience is almost entirely made up of podcast creators, many of whom receieve the newsletter after having signed up for one of my podcast-related offerings.

My newsletter, however, has almost nothing to do with podcasting and is about finding your way as a creator of any kind.

This goes against a lot of marketing advice.

There’s a significant disconnect between my top of funnel (podcasting), middle of funnel (Creative Wayfinding) & paid offerings (podcasting).

And yet, based on anecdotal feedback from customers and subscribers, I have a suspicion that this franken-funnel somehow works better than if all my content was tightly aligned around podcasting.

I think there’s a reason…

A highly aligned funnel probably would do a better job converting cold traffic into one-time sales.

But my current creative platform allows people to really get to know a much deeper more nuanced version of me without feeling like I’m just buttering them up to make a pitch (which I’m not).

In the short term, this is likely a less financially successful strategy. But the long-term upside is huge.

For one, it leads to more perfect-fit customers & clients who buy into my philosophy around creative work which leads to better outcomes for everyone involved.

It also moves my product offerings away from being commodities which can be easily compared to other products designed to help people achieve similar outcomes. I’ve heard time and time again from PMA students that the biggest reason they enrolled was because of me.

I don’t know that that would have happened if I was more focused with outcome-oriented, purely instructional podcast content.

Most important of all, however, this approach leads to friends, partnerships, collaborators & deep personal connections that I have a hard time believing would have come from a super-specific, topic-aligned funnel.

I regularly get comments from readers along the lines of, “I found Jeremy through his podcast content, but actually stuck around for his ideas around creative work which I don’t get anywhere else.”

Comments like this are a sign to me that I’m on the right track to building the kind of creative platform I aspire to. One that is nuanced, real, and human.

There’s no way I could have (or would have) planned this strategy in advance, but somehow I stumbled on to it, and it works.

6 // Track the Right Metrics

We all want to see our subscriber counts go up.

But total subscribers/views/downloads/etc aren’t a great way to measure the true impact of quality of our work. Plus, by measuring the wrong thing we’re likely to optimize for it, which is a big mistake.

While I certainly track my subscriber count, my North Star metric has always been reader responses.

These responses, to me, are a signal of resonance, which is the target I’m aiming at with each issue.

With every issue, I hope to get at least 2-3 meaningful emails from subscribers who resonated with the article. When I don’t get any, I have a closer look at why that might be.

I also use the Reactions feature from Sparkloop (which you can see below this essay) and track how many responses I get for each issue using the scale:

👍 Above Average
👊 Average
👎 Below Average

Each issue averages between 5-10 total reactions. Any more or less than that is an interesting data point to look into.

7 // Know Why You’re Doing It

Hand in hand with tracking the right metrics is knowing why you’re creating the project in the first place.

Chances are, it’s not all about audience growth (although that might certainly be one reason). Remembering the true purpose of the project will help keep you on track & avoid distractions.

This newsletter’s primary purpose for me has always been as a sandbox to:

• Hash out ideas that later find their way into other parts of my work
• Experiment with marketing strategies & tactics
• Hone my writing
• Get to know myself better

Reminding myself regularly of the non-audience-growth-related outcomes helps me avoid feeling frustrated when growth is slow as the project is still achieving its other purposes.

It also keeps me focused on creating work that’s aligned with my internal compass rather than trying to guess what other people want.

8 // Release the Handbrake

Last year I took a writing course from The DO Lectures.

In one lesson, David, the instructor, said something I haven’t been able to shake:

“You don’t need to find your voice. You already have it, you just need to release the handbrake.”

Since starting my newsletter, I’ve consistently discovered that the more I release the handbrake & lean into the ideas, quirks & traits that make me unique, the more my work resonates.

This runs counter to a lot of entrepreneurial advice, however.

One of the first rules of building a company is building it so that it can run just as well without you.

But perhaps the first rule of creative work is that the work should seek to fully reflect & embody you as the creator.

Release the handbrake & remove the barriers to resonance.

9 // Define & Reinforce Structure

Creatives are notorious for hating the idea of structure & constraints.

But the more structure you build into your work the easier it is to create while also providing a frame around which to explore your topic w/ more depth & clarity.

Structure for me started with defining the general format of the newsletter:

1. Welcome
2. Announcement
3. Community Shoutouts
4. Feature Essay
5. 5 Currated Links
6. Twitter Feature
7. Sign Off
8. Gratitude/Wins/Excitement

After implementing this structure, it immediately made the newsletter easier to put together each week.

And after my first structural experiment, I decided to take it further by bringing more structure to the 5 Things You Might Dig section of curated links.

As you might have noticed, those links now fall into one of five consistent buckets:

1. Thought
2. Tool
3. Tactic
4. Podcasting Resource
5. Wildcard

Much like more structure made it easier to put together the newsletter as a whole, more strucuture around the links made it easier to source & curate links for each issue while also reinforcing the “brand” of the newsletter by bringing more consistency to the offering.

So far, every time I’ve added more structure, the newsletter has gotten better & creating it has become easier & faster.

Chances are, structure will have the same effect on your work.

10 // You Can’t Do it Alone (Cliche but True)

Find your people who will inspire, motivate & support you.

It’s a long road to building a life around meaningful creative work and you’re going to need all the help you can get.

We all need a steady supply of inspiration, motivation, support, accountability and commiseration in order to keep moving forward with our creative work. There is a long list of people who’ve played one or more of those roles for me and this newsletter whom I referenced in Issue #47 about Acknowledgments & Accompaniment.

In my experience, perhaps more important early on than finding your audience is finding what I call your Creator Cohort, the group of people at roughly the same stage as you, with whom you’ll “grow up” together.

These people will not only help you gain clarity on your audience but also on how you, your work, and your voice fit into the larger conversation taking place in your space.

11 // You’re Not Going to Figure Out What the Hell You’re Doing for a While. And That’s Fine.

Big ideas rarely come fully formed.

In fact, they often take years of steady, persistent excavation.

But the real purpose of a creative practice isn’t to grow now. It’s to slowly and persistently chip away and excavate the big ideas that will lead to bigger things in the future.

I’ve been creating in one form or another for over a decade.

But I’ve got at least 4 more decades of creative work yet to come.

I’m at the beginning, just finding my feet. My best work is so far off in the future I can’t even imagine it yet, let alone see it on the horizon.

The same is true for you.

This work is not for the faint of heart.

It will wear (if not outright beat) you down.

It will make you deeply question your self and your worth.

It will disappoint and frustrate and shatter you more times than you feel you can bear.

It takes a special kind of person to not only put up with all that, but choose to walk further into the Creative Wilderness without a map, following only the subtle tug of your internal compass and the belief that there’s something out there for you.

If you’re here, I think you’re probably that type of special person.

And I’m honoured to be navigating the wilderness alongside you.

Here’s to the next 100 🍻

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Explore how to navigate a creative life that matters

This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

It’s something I’m proud to create and I’d be honoured to share it with you.

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