As you might imagine from the occasional poems I write and publish for the newsletter, I certainly have some interest in poetry.

But that interest is more closely tied to writing poems than reading them.

See, while I recognize the value of good poetry (is there another medium with more meaning-per-word?), I suffer from the same problem that keeps most people from reading, let alone enjoying it.

In short, it makes me feel dumb.

It probably stems from high school English class assignments to interpret a poem and write an essay on its themes and meanings, but I’ve internalized this belief that I’m supposed to understand absolutely what a poem is saying after reading it.

On the rare occasions I do read poetry, that understanding is conspicuously absent.

It’s surprising, then, that one of my favourite podcast discoveries from the past year is a show called Poetry Unbound.

Here’s the show’s description:

Your poetry ritual: An immersive reading of a single poem, guided by Pádraig Ó Tuama. Unhurried, contemplative and energizing. New episodes on Monday and Friday, about 15 minutes each. Two seasons per year, with occasional special offerings. Anchor your life with poetry.

I discovered the show through an interview the host, Pádraig Ó Tuama gave on one of my other favourite shows, On Being.

And despite some initial skepticism, my interest was piqued, and I decided to give it a shot.

I don’t remember which episode I listened to first. But what I do remember is that my whole conception of what it meant to read and consume poetry was immediately shattered and then reconstructed into something entirely different.

And with it, the way I viewed all sorts of creative puzzles and problems in my life and business.

You’re Not Supposed to Know

Pádraig opened that first episode as he always does, with a full, read-through of the poem.

As usual, I had no idea what it was trying to say.

But what stood out to me as Pádraig–an accomplished poet himself–finished reading and began talking through the poem, was that he clearly had no idea exactly what the poem was about either.

And yet that not knowing didn’t hamper his enjoyment of the poem.

If anything, it increased it.

His analysis of the poem was filled with suppositions, hunches, and personal reflections on what the piece was bringing up for him.

It was clear that for Pádraig, the value of poetry is not in the knowing exactly what the poet meant when they wrote the poem, but in the wondering about what it could mean, even–or perhaps especially–if that meaning is only true for you.

As I’ve been thinking about this approach to poetry over the past few months, it’s struck me that it’s the same approach the most successful creators and entrepreneurs bring to their work.

And yet, most of us have been ill-equipped to embrace this essential mindset.

First, You Have to Unlearn

Our culture places a high value on knowing.

Our education system spends over a decade ingraining in us the idea that there is not only a single definitive answer to any problem for us, but in fact a single definitive answer for everyone.

Armed with this worldview, we head off into the post-school world looking for singular answers and certainty.

As creators, this leads us to seek out the “one key strategy” or “secret growth hack” that will guarantee success. We feel as though there is some definitive right way to build a successful creative platform, product, business, or career, and that someone out there has the answer, we just need to find it.

But this desire for the right answer often limits both the quantity and quality of the work we publish.

We often feel as though our work must be airtight, impermeable to critique, and absolutely defensible in order to share it publicly.

We imagine the army of trolls waiting to tear us down for publishing anything less than codified fact, and so steer well clear of publishing ideas based on our flimsy feeling hunches, suppositions, and wonderings.

And yet, it’s those very wonderings that are at the heart of any original idea, business, content, product, or art.

Anything that can be definitively known must, by definition, be unoriginal.

And anything new, that hasn’t yet existed can’t possibly be known. It can only be imagined. Wondered at.

In our thirst for knowing, we’ve forgotten the value in this wondering.

The Value of Wonder(ing)

The value of wondering spans across every aspect of our work, from individual pieces of content, to the strategies we use to market and sell our work, to the arc of our careers.

Wondering About Content

At the micro, content-level, wondering is at the heart of both original and resonant work, both of which are required traits to grow a creative platform.

And at the heart of both originality and resonance is an element of surprise.

As Robert Frost succinctly put it, “No surprise for the writer, no surprise for the reader.”

Indeed, all of my very favourite essays and creative content I’ve produced are the ones that ended up in a place I couldn’t have predicted or imagined when I sat down and wrote the first line.

It turns out, those are typically the ones that resonate most with others as well.

If we want to create this type of surprising, original, resonant work, however, we need to leave room for that surprise. That room can only come from exploring topics and ideas about which we don’t have all the answers.

In fact, the unraveling and discovery of a subject should be the driving motivator behind everything we create.

One of the most perspective-shifting quotes I’ve ever heard came from a non-fiction author being interviewed about his latest book.

When asked about what inspired him to write this book in particular he replied, “I realized I didn’t know as much as I wanted to about the topic so I decided to write a book on it.”

This dynamic plays out abundantly across the arts.

Few songs flow fully formed from a songwriter’s mouth, nor paintings from the brushes of painters nor poems from the pen of poets.

Most often, original creative work starts as a small nagging thread of an idea that is then pulled and unraveled inch by inch.

All of this is driven by the process of wondering.

Great content follows the same process.

If we want to set our work apart, our best bet is not to share what we already know to be true.

Instead, it’s to start with a question about what we don’t know, and then follow its twists and turns and surprises to its logical conclusion.

One that no one else has likely yet arrived at.

Wondering About Strategy

Wondering is as much at the core of any successful marketing or audience growth strategy as it is of creating the content that strategy is designed to spread.

This is because no matter how successful a given tactic or strategy has been for someone else, it’s unlikely to give us the same results straight off the shelf.

Experimentation is at the heart of all successful marketing, and wondering is at the heart of all experimentation.

We might wonder:

• What would happen if we committed to Tweeting every day for a year?
• What if we started sending out a weekly newsletter?
• What if we focused on leveraging other people’s audiences to grow our own?
• What if the strategy we’re following right now isn’t actually the best fit for our personal disposition?

When we’re feeling stuck, instead of seeking out another off-the-shelf solution, the most productive action we can take might just be to start wondering. To start asking questions of ourselves and our current approach, and then following them where they lead.

In my experience, this wondering often opens up new ways to approach strategies to which we’d previously felt resistance, as well as entirely new strategies, that shouldn’t work… but for us, somehow do.

To find them, however, we need to get curious.

Wondering About Career

Finally, there’s the wondering that drives our careers.

This is the wondering that drives all great storytelling. The wondering that comes from knowing the beginning but not the ending.

It’s the tension that keeps us engaged, wanting to find out what will happen next.

We often think we want clarity and certainty in our work, but clarity and certainty have the same effect on our careers and lives as knowing how a magic trick was performed.

Once we know the answers, the magic is lost.

How many people do you know whose days, weeks, and careers follow the same rote pattern?

Day in, day out, season by season the work remains more or less the same, knowing each day what the next will bring. Predictable, repetitive, known.

And most often, boring and unfulfilling.

Is that what we really want for our careers?

How much creativity and inspiration can exist in such a sterile environment?

Because a state of absolute knowing and certainty can only exist as long as no new ideas or opportunities are permitted to enter.

Wondering at the level of our lives and careers allows us to imagine a version of our life beyond the one we currently occupy.

More importantly, wondering allows us to imagine a version of ourselves beyond who we currently are and what we’re currently capable of.

And only once this destination is established can we plot a course to get there.

Nothing Is as It Seems (If We Approach It That Way)

There are few more widely read and quoted poems than Robert Frost’s, The Road Not Taken.

I was first introduced to it in one of the aforementioned high school English classes and was delighted to find for once a delightfully simple and straightforward poem that required little in the way of interpretive genius.

I was surprised then, years later, to find that even this simple, seemingly obvious poem has multiple suggested interpretations, chief among that the poem’s commonly understood directive to “follow your own path” is actually ironic in nature.

On the one hand, it’s frustrating to realize that even this most accessible of poems with a clear and encouraging directive is not as clear-cut as it seems.

On the other hand, however, I can’t help but feel some delight.

The delight of finding a treasure chest buried just beneath the sod in your back yard.

Of realizing that the mundane world you thought you knew so well contains some hidden magic.

What if that were true for every aspect of our work?

What if every idea, strategy, project, medium, offer, and career path had hidden depths, and alternative interpretations beyond how they were initially presented to us?

Waiting to be discovered.

Waiting to be questioned.

Waiting to be wondered at.

I’d like to think that’s true.

And perhaps all we need to do to make it true is to approach our work, and our lives, with the assumption that it is.

Knowing is finite. Wondering is infinite.

---

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.

Subscribe

---