For as long as I can remember, I’ve wanted to write a book.

As a kid, I’m told, I was prolific to the point my mom was sure I’d grow up to be a writer. It took some time, but if this newsletter is any indication, she’s been proven right. And while writing blogs, newsletters, and podcasts has always come easily to me, the idea of a book has felt entirely unapproachable.

It’s not the scale of a book-writing project that’s deterred me thus far.

I wrote more than 100,000 words last year alone across my blogs and newsletter, more than enough for a book.

Instead, it’s the level of experience, knowledge, and vision I felt were required to write a meaningful, useful, coherent book. I felt I couldn’t possibly have enough to share on any one topic. And so I pushed the idea of writing a book to the back of my mind.

“When I’m ready, I’ll know,” I thought.

But then six months ago, in a single moment, my perspective changed.

While listening to a podcast, one tiny comment by the guest shifted my entire perspective of what it meant to “be ready” to take on a big, scary, ambitious creative project of any kind.

In that moment, not only did my perspective around readiness shift, but I realized with stark clarity the common thread among all creative work that really matters. The type of work that fulfills our potential as creators. The type of elusive work we’re all striving to create.

This approach has nothing to do with having all (or any) of the answers, and everything to do with asking the right questions.

Why Write a Book in the First Place?

The shift happened while listening to an episode of Krista Tippett’s On Being podcast.

But despite the impact of the revelation, I’ve completely forgotten who the guest was and what they were talking about.

What I do remember about the guest is that he was impressively (even intimidatingly) credentialed. One of those people who seems to contain within themselves the knowledge of multiple lifetimes. Someone for whom writing a book was surely as simple as sitting down, turning on the tap, and letting it flow out of them onto the page.

Or so I thought.

Because as soon as he was asked about his motivation to write the book in question, he responded with, “I wanted to learn about [whatever the hell the book was about] so I decided to write a book on it.”

Wait. What?

I was so stunned by the comment I replayed the comment to make sure I had heard correctly.

Sure enough, upon second listen, he reiterated that his process for writing a book was not built on knowledge, experience, or a predefined vision for the finished product.

Instead, it was built on a single, nagging question, and the curiosity to explore it.

The conversation on the podcast moved on. If I heard any of it, I didn’t take it in. My mind was off on another plane, ruminating on the repercussions of this new information.

Creative Work Should Explore, Not Explain

In the months since, this quote has haunted me.

It suggests that writing a book is first and foremost an act of exploration and discovery. The sharing, explaining, and educating of the audience are secondary considerations.

This mindset highlights a gap in the way a certain type of creator approaches their work and the way the rest of us do.

Most of us view books (or courses, or podcasts, etc.) as Capstone Projects.

Viewed from the outside, these projects appear to be the culmination of years of research and experience, concisely and compellingly packaged for broader consumption. But when we carry this approach to our own projects, we start down a slippery slope.

The Capstone Project view demands that we spend years, if not decades, gathering information and experience before we ever sit down to put pen to paper and share.

No matter how much knowledge we build up over the years, however, the feeling of impostor syndrome will persist. It may even increase. The longer we put off writing the book, the greater the pressure, after all. If this is to be our magnum opus, it can be nothing short of perfection, we think.

And so the longer we wait, the harder it is to start, and the harder it is to start, the longer we wait. Kicking the can down the road to a “someday” buried safely in the future.

How Fear Creates Generic Content

Our reluctance to commit pen to paper and start before we know where we’re going is based largely on our fear of being wrong in public.

By publishing our work–and with it, our ideas–we’re putting ourselves out on a limb.

When we do, we open ourselves up to being challenged. What if my information is wrong or incomplete, we wonder? What if my perspective is flawed? What if new information comes to light tomorrow that changes the way I think about this topic? What if someone smarter than me reads this and calls me out publicly?

This fear of being found out and exposed causes us to delay publishing anything about which we are anything less than absolutely 100% certain. Most often, that means settling for recycling tried and true ideas that are already in common supply.

While this feels like the safer bet, it categorically precludes us from reaching our potential as creators or ever doing anything really interesting.

We don’t need to look farther than our Twitter feeds full of endlessly repeated advice on how to improve our writing, Instagram feeds with thousands of accounts offering subtle variations on the same fitness tips, and countless business podcasts sharing the exact same marketing, mindset, and entrepreneurship advice to see the result of this fear of going out on a limb.

Generic Work Can Only Take Us So Far

This approach to publishing presents a convenient place to hide.

Much of this endlessly repeated content is, in fact, useful after all. It’s tried, true, proven, verified. We’ve found it helpful ourselves and are confident it will be helpful to our audiences as well.

The problem is that sooner or later, we reach a limit of how far this type of regurgitated content can take us. While it’s hard to be called out for publishing content that fits into the conventional wisdom and worldview of the pack, it’s also hard to stand out from the pack when everything we publish can be found a dozen times over elsewhere.

Just as surely as products and services can easily be commoditized, their value steadily driven down as their ubiquity increases, so too can ideas.

The thing about commodities is this.

While you can be confident about the existence of a market for your product or idea, your ability to capture more than a tiny fraction of that market is severely limited. Competition is fierce, and audience loyalty is low. There’s always someone willing and able to offer more value for less time, money, or in a lower word count. A classic race to the bottom.

As creators, we face a choice.

We can continue to take shelter in the pack, doing work and creating content that is acceptable, if unremarkable.

Or we can make a radical shift in how we approach our work in the first place. An approach that doesn’t start with an answer, but a question.

A question that hasn’t been asked or answered a hundred times over.

A question that might not even have an answer.

And it’s here, once we find, ask, and begin to unravel that question, that we find ourselves in position to do something new, unique, and interesting.

Behind All Work That Matters Is a Question to Be Unraveled

Questions break the status quo, create progress, and seek to understand what we don’t already know.

Questions like “How?” and “Why?” seek to understand more deeply. “Why not?” and “What if?” seek to expand on what’s possible.

Questions form the basis of all interesting work, from innovation in sustainable business models ( “How can we produce better products while also lessening our environmental impact?”) to books-turned-Hollywood-blockbusters (“What would a vampire-human-werewolf love triangle look like?”)

We might think it’s the lack of budget, skill, or experience that keeps us from growing our audiences as creators.

But our biggest lack is in the ambition in our questions.

Innovation Comes From Unraveling Big Questions

James Clear asked and unraveled the question of how to best build habits.

Brené Brown continues to ask and unravel the question of how to negotiate our relationship with shame and vulnerability.

Krista Tippett, and her podcast that kicked off this whole revelation, has been asking and unraveling perhaps the biggest question of all for almost 20 years and over 400 episodes: “What does it mean to be human?”

Big questions inspire, excite, and rouse curiosity. And yet, these aren’t the questions most of us find ourselves addressing through our work.

We more often find ourselves asking “How do I do this right?” than “How might I do this best?”

And “What should I do?” rather than “What could I do?”

These are the questions of implementors rather than innovators, explorers, and creators.

This timid approach to questioning isn’t entirely our fault, however.

Breaking Our Answer-Centric Conditioning

Our education system has conditioned us to believe that it’s having the answer that really matters.

When a question comes to mind for which the answer isn’t immediately available, frustrated though we may be, we move on. Sooner or later, we think, someone else with more skill, experience, and credentials will come along and solve it.

The problem is, when we rely on others to ask and answer the questions, not only do we consign ourselves to always be at least one step behind those willing to go out on a limb and break new ground, we also miss out on the opportunity to discover the best possible solutions to the problems we and our audiences face.

Our greatest opportunity to stand out as creators, then, is to be the ones asking, exploring, and unraveling the questions. To take our existing knowledge and the current best practices and use them as the foundation to push into the unknown.

The first step is to break our reliance on other people to discover the answers for us and realize that the very thing that qualifies us (or anyone) to tackle a big question is our curiosity and willingness to follow where it leads.

Choosing to follow a question instead of the well-worn path takes courage. But if we’re able to muster it, we open ourselves up to significant upside that’s hard to come by on more well-traveled routes.

How Unraveling a Question Makes You a More Confident Creator

Audiences gravitate toward big questions and fresh takes on old problems.

But while unraveling an ambitious question can certainly help to attract an audience, the greatest benefits of unraveling a question yourself, versus relying on the conclusion of others are internal.

Perhaps the most significant is the solid ground it gives you to stand on.

In unraveling a question, your opinions form based on your own research, interviews, and experiments. The information you’re working with comes directly from the source, rather than being co-opted and absorbed second (or third or fourth) hand.

This takes the pressure off.

Because now, your work isn’t about you and your beliefs about the topic at hand. It’s about answering and unraveling the question as fully and truthfully as you can, without bias for where it will lead.

The confidence that comes from this foundation is significant. It destroys impostor syndrome and empowers you to show up bigger in every aspect of your work and life.

While the increase in confidence might be reward enough, the products, content, and opportunities that come from unraveling an interesting question are also significant.

The Best Products Are Not Made but Unraveled

My course, Podcast Marketing Academy, emerged entirely from a question that nagged me for months regarding our clients’ shows: “Why do some shows grow effortlessly while others stall and plateau?”

After reading dozens of blog posts on podcast marketing and growth and being frustrated by the incomplete suggestions they provided, I resigned myself to the fact that if I wanted to answer the question, I was going to have to do so myself.

I took the question to interviews with my clients and dozens of other podcasters, observing, dissecting, and taking notes on many more in an attempt to suss out the ingredients for sustainable podcast growth.

The result was a very different framework than the one I would have created before I asked and unraveled the question.

But it was one that I now had 100% confidence in teaching and selling. I absolutely knew it would work and I absolutely knew it was the very best solution for a podcaster who had found themselves in the plateau that sparked the question in the first place.

What’s more, because the course is based on my firsthand research, there’s nothing else like it. It’s not the result of taking someone else’s podcast marketing course and then replicating it with some subtle tweaks thrown in. It truly is the one and only of its kind.

The unique program, however, is just one product of the unique perspective I’ve gained by unraveling the question.

That perspective has resulted in podcast guesting, speaking, and writing opportunities, new relationships, and a near-endless supply of content.

Developing a unique perspective and creating work that is truly singular should always be our goal as creators. Singular work is the polar opposite of commoditized work, and as such, is inherently more interesting and valuable.

The most reliable way of creating something singular starts with the question you choose to unravel with your work.

Picking Your Question

There are an infinite number of questions each of us could choose to focus on with our work.

Like my experience with Podcast Marketing Academy, or James Clear with Atomic Habits, we can choose to focus on a practical problem facing us, our audience, or our industry and work to figure out the best solution. These questions often start with a “Why?” and over the course of the unraveling turn into a “Why not?”

Unraveling these questions can lead to innovation, new products, services, businesses, business models, and even entire industries (the fast-growing private space industry comes to mind).

These questions are practical, helpful, and worthy of our time and energy.

But for many of us, there’s another, level of deeper, murkier Meta-Questions waiting to be unraveled. Questions that have unknowingly shaped our entire lives, and–once acknowledged–are the gateway to achieving our greatest potential.

The Meta-Questions That Shape Our Lives

In fiction, great characters are driven by one or more unanswered questions they spend their lives exploring.

“Well-drawn characters have a spine,” shares Andrew Stanton, the writer behind Toy Story and WALL-E In his TED talk. “The idea is that the character has an inner motor, a dominant, unconscious goal that they’re striving for, an itch that they can’t scratch.”

These Meta Questions don’t just apply to Pixar characters.

Stanton goes on to share how he became aware of the Meta-Question driving his own work and life.

“When I was four years old, I have a vivid memory of finding two pinpoint scars on my ankle and asking my dad what they were. And he said I had a matching pair like that on my head, but I couldn’t see them because of my hair. And he explained that when I was born, I was born premature, that I came out much too early, and I wasn’t fully baked; I was very, very sick. And when the doctor took a look at this yellow kid with black teeth, he looked straight at my mom and said, ‘He’s not going to live.’ And I was in the hospital for months. And many blood transfusions later, I lived, and that made me special.

“I don’t know if I really believe that. I don’t know if my parents really believe that, but I didn’t want to prove them wrong. Whatever I ended up being good at, I would strive to be worthy of the second chance I was given.”

Though we’re rarely, if ever, aware of them, we each have a series of questions that drive our goals, dreams, and motivations–and with them, our careers, relationships, and lives as a whole.

It’s in bringing awareness to and unraveling these Meta-Questions that our greatest opportunity and potential as creators (and humans) lies.

These are the questions that drive our life’s work. For which we have endless patience and motivation. For which the journey is truly more important than the destination. These are the types of questions that I suspect drive the work of Brené Brown and Krista Tippett.

Marrying Your Meta-Questions with Your Work

After watching Stanton’s TED talk, I started thinking about the Meta-Questions driving me.

Months passed without an answer. But over time, a question around the idea of “potential” started to take form.

Since childhood, I’ve ruminated on the idea of my own potential and the opportunities and burdens that come with it. My greatest fear playing on a loop in the background has always been that I would come up short. That I would waste my privilege, opportunities, and potential on things that didn’t make a difference.

I realized the question of what my potential really was and how I could possibly fulfill it had, in fact been the subtle driver behind all my major life decisions. From bicycling across Europe to starting an online business to the compulsion to create–whether through music, photography, or writing.

All of it, I realize, has been a part of the unraveling of that Meta-Question.

More recently, I’ve become aware that this newsletter has become the purest expression of that question yet.

Now more than a year in, I’m realizing that, at its core, this newsletter explores how each of us can fulfil our potential as creators and perhaps, even humans.

This is the question and the work I have endless patience for. Endless motivation. Endless curiosity. Regardless of any external success or validation. In this question, I see the potential for a book that, through this newsletter has seemingly begun to write itself, regardless of the fact that I have no expertise, no credentials, and no idea where it’s going.

That work exists for you too, buried somewhere inside a question.

It takes reflection to find the question, and courage to ask it, leaving the paved road and the signposts and the company it provides.

But it’s the work that has the greatest potential for impact. The work that will fulfill you unlike anything else. The work that, if you don’t do it, no one else will.

You don’t need more knowledge to pursue it. You don’t need more skill or experience or answers.

You simply need to ask the question, and follow its lead.

Big thanks to June Lin, Sean Stewart and Maxim Bos who gave incredible feedback on the initial draft of this essay and improved it massively.

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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?”

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