Last week in the newsletter, you might have noticed that I switched things up a bit.
While the subject matter was more or less the same as my usual–how to navigate the Creative Wilderness–the format was different, in that, I opted for a poem rather than my typical weekly essay.
I wasn’t entirely satisfied with the finished version of the poem I sent.
And yet, within a few hours of publishing the newsletter, I was surprised to see a number of emails from readers hitting my inbox, telling me how much they appreciated the poem, as well as a couple of shares on social media.
Compared to the average newsletter, this was a significant positive response.
It also meant that two of my five most resonant newsletter issues featured poems instead of essays.
So what’s going on here?
Do people like you who read this newsletter prefer poetry to essays?
Somehow, I didn’t think so.
Curious, I looked back at the issues that had received the most positive feedback from readers and discovered a through-line between them.
What surprised me, however, was that the common thread wasn’t related to a specific topic or format of the writing, but to my personal experience and approach to creating them.
It turns out, there’s a lesson here for all of us seeking to create work that resonates more deeply with our audiences.
But first, back to the poem.
Poetry Is Hard
This wasn’t the first time I’d included a poem in the newsletter.
Issue #35 is not only one of my very favourite issues of this newsletter, but the poem I wrote for it is one of the things I’m most proud to have ever created.
Ever.
It’s also the issue I received the greatest positive response for to date.
And yet despite the precedent and the positive feedback, I was nervous all week as I wrote the poem and prepped the newsletter.
The reason?
Writing poetry is hard.
Compared to an essay, poetry has a less-forgiving structure.
Each line (and perhaps word) needs to earn its place and flow from and into those around it. These factors, combined with rhythm and pacing, can undermine a poem with otherwise interesting content if not executed well.
While I’ve written several dozen poems in my life (most of them of the teenage angst variety), I’m certainly no expert.
From the moment I sit down to write a poem, it feels as though its future is in doubt, like I may give up on it halfway through when it feels too hard to complete.
Unlike the average essay I write, writing poetry stretches me in an uncomfortable way.
And it’s this stretching that turned out to be the through-line in my own most resonant work.
Stretching Past Your Natural Resting State
Much like our muscles naturally come to rest in a state of comfortable relaxation, so too does our creative work.
In both cases, in order to experience any positive benefits, we need to actively and intentionally stretch.
Whether it’s writing a blog post, producing a podcast, or rolling out a new product, or service, when we’re entirely comfortable with the work we’re doing, chances are, it’s not that interesting.
This is because that feeling of safety can only really exist when we know going in that we’re not saying something that our audience might take issue with, push back on, on fail to understand.
When you think about it, the only way to have that kind of confidence before you hit publish is to (consciously or unconsciously) be rehashing an existing, broadly accepted idea.
No stretch.
No risk.
No resonance.
If we want to create work that truly resonates with others, that hooks them and keeps them coming back to see what we’ll do next, we need to stretch past the edge of our comfort zone and into discomfort.
I think David Bowie said it best:
If you feel safe in the area you’re working in, you’re not working in the right area. Always go a little further into the water than you feel you’re capable of being in. Go a little bit out of your depth. And when you don’t feel that your feet are quite touching the bottom, you’re just about in the right place to do something exciting.
– David Bowie
So what does this type of stretching look (or more accurately, feel) like?
The Challenge Zone
We’ve talked before in this newsletter about the value of Marathon Projects.
These ambitious, time-bound projects go above and beyond our typical creative output and stretch us to improve our skills and conception of what we’re capable of achieving.
Marathon Projects, along with micro-challenges we might impose on our daily or weekly creative output (eg. write a 1,000 word blog post in only 30 minutes or record a podcast working the word “chicken” in every 5 minutes…) are certainly one type of stretch.
These stretches push us out of our safe, resting mode and into what I think of as the Challenge Zone.
Work done in the Challenge Zone engages our creative muscles, tests our skills and capabilities, and expands our conception of what we’re able to achieve.
This type of stretch is important in developing our creative skills and building confidence in ourselves.
But to create deeply resonant work, we need to perform a deeper kind of stretch, extending ourselves past the Challenge Zone, and into the Discomfort Zone.
The Discomfort Zone
The Discomfort Zone is what Bowie was talking about in regards to wading out into the water to the point where your feet can’t quite touch the bottom.
In practical terms, the gap between our feet and the seabed is doubt.
And while it might seem like inviting doubt into our work is the last thing we would want to do, the presence of doubt is a clear indication that we’re doing something interesting.
In my experience, there are two ways to stretch into this level of discomfort.
1. Stretching Into Vulnerability
On the last Creative Wayfinding Friday Fireside call a few weeks ago, we got talking about the work that had been best received by our audiences.
Without fail, every single person on the call shared that the work that seemed to resonate most with their audiences was not the work that contained the most information (ie. the work that should have been most “helpful”), but the work where they themselves had gotten uncomfortably vulnerable.
As the conversation progressed, however, it became clear that while all of us on the call were aware of this correlation between vulnerability and resonance, few, if any of us made this type of vulnerability a regular part of our work.
This is because, when done right, it stretches us in an uncomfortable way.
It’s easier and safer to instead default to information-sharing, which, while potentially helpful, offers little opportunity for genuine emotional connection.
The connection that comes from this kind of uncomfortable vulnerability is an important ingredient for creating work that resonates deeply. But there’s a balance to be found somewhere between surface-level, faux-vulnerability, and oversharing.
In my experience, vulnerability that resonates needs to:
- Be relevant to the topic at hand, and
- Make you nervous to share
This type of stretch into vulnerability can work wonders for developing and strengthening your relationship with your existing audiences, turning casual engages into superfans.
But there’s another type of stretch into discomfort that is necessary if we want to become true leaders and innovators in our niches and community.
2. Stretching Into the Unknown
If there’s one thing that keeps us as creators stuck, it’s our default setting of producing content and work that’s more or less the same as what everyone else around us is creating.
We cover the same topics in the same formats, perhaps with a little personal flair thrown in here and there. On the whole, however, the work we create is a different recipe for the same dish many others are creating.
What separates the thought-leaders of any niche, however, is their willingness to explore new topics and start conversations that aren’t already happening.
Creating this type of work requires a major stretch into discomfort.
This type of work isn’t about simply sitting down and recording our existing knowledge. Instead, it’s about exploring and attempting to get our head around something new, finding a thread to pull on, and unraveling it to see where it leads.
Work that fits this category is more about the thinking than the writing, recording, or tangible creating, and consists of extensive detours, backtracking, deletions, edits, and amendments.
In short, this type of stretching is frustrating, time-consuming, uncertain work.
And this is exactly what keeps us from pursuing it.
I personally have a list of 20 or so of these ideas that I’ve been sitting on in some cases for more than a year.
These are ideas that I’m excited to write about, but feel too big and too important to start on just yet. If I’m going to commit to fleshing out these ideas, I know I’m going to need time, space, and focus that never feels readily available.
And so, for the most part, they sit on the shelf gathering dust.
The irony is I have a sense that all of these topics would be among my most resonant work if I were able to publish them, with potential to be shared and circulated within the creator community. This was the case with my article on the unasked questions guiding your creative work, the one big idea I’ve been able to develop so far, and one of my most popular articles to date.
Shipping work that stretches us into the unknown terrain of big, unexplored ideas requires extensive grappling with Resistance, impostor syndrome, and perfectionism, as it never feels ready to publish.
An inherent trait of this type of work is that we don’t have our heads around it yet. As such, the wording feels clunky, the ideas don’t feel cohesive, and we feel self-conscious about publishing such an unrefined mess.
And yet, once again, the discomfort at the thought of publishing is exactly the right place to be.
On the same recent Friday Fireside call, CW reader Sam Harris brought up the point that if the idea is novel and interesting, it doesn’t actually need to be perfectly articulated and fully developed in order to benefit our audiences.
In fact, when we’re stuck trying to tie all the loose ends of an idea like this together, it often helps to share it before it’s complete.
If all goes well, it will start a conversation that may open us up to additional perspectives and ideas we’d never have otherwise considered.
While time-consuming and frustrating, the potential upside of stretching into the unknown is significant.
Novel, relevant, big ideas are infinitely more likely to be shared throughout our niches than generic “how-tos”, listicles, and other safe, generic content that lies firmly within our comfort zones.
As We Stretch, So Do Our Audiences
Few of the big wins in life come from playing it safe, pursuing the same as usual, or perpetuating the status quo.
But pushing our boundaries and stretching into discomfort doesn’t need to mean grand gestures and wildly ambitious projects with a sprawling scope.
Instead, we can choose to stretch ourselves juuuuuuust a little bit into discomfort with each blog post, podcast, product, and anything else we create.
For you, it might be taking on a topic that’s been nagging at you but which you don’t quite feel ready to share publicly.
Maybe it’s asking every podcast guest at least one question that makes you as the host uncomfortable to ask.
Or maybe it’s leaning into vulnerability and sharing your own stories and experience more deeply and honestly than you have yet.
The most successful creators consistently create work that stretches their audience to think and perceive the world differently.
We might try to convince ourselves we can create this type of work without extending ourselves beyond our comfort zones.
But the truth is we have to lead by example, stretching into discomfort, and then inviting our audiences to join us.
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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