Leonard Cohen once appeared on a radio program and read one of his poems. When the host asked him to share what it meant, he read the poem again.

My whole creative life, people have been asking me what my art means, whether it’s a blog post, a song, or a business I’m creating. I sometimes try to come up with wise-sounding answers, but it never seems to work. What, then, is the point of art?

I think it’s an attempt to make meaning out of life. Of course, one might say life is full of meaning and purpose, and I would agree—if that is how you choose to see it. But there are plenty of people, and I have also been among them, who see life as lacking in meaning.

Viktor Frankl taught us that what we really want in this grand experiment of being human is a reason for existing. And it turns out that we have some say in what that is.

I never created because I wanted to say something. I created because I had to, because something wanted to find an expression through me. Maybe that sounds mystical. I don’t know.

All I know is that there is this compulsion in me to say everything, to express all the emotions one might ever feel, and the challenge of capturing it in a word or a phrase is more than a little frustrating.

Sometimes I feel like Ruth Stone, the poet whose work seemed to rush at her in a great gale of wind across the plains; all she had to do to write was get back home before the poem passed her by. Isn’t all creative work a little like that, like trying to capture lightning in a bottle? And doesn’t it all seem to fall a little short?

Maybe art is a proxy for life in that respect. We see something beautiful, and we want to contain it. But life cannot be contained. As soon as we grab hold of it, it evades us, like trying to pick up the water and take it with you. Once contained, it ceases to flow. Perhaps it is so with this thing we call creativity.

The meaning of art seems to be a timeless subject for many great artists. JRR Tolkien struggled with this when he was working on the stories that would become his epic tome The Lord of the Rings.

Since the success of The Hobbit, he likely felt some sort of pressure to continue the story and expand upon it; after all, he’d created an entire world and several languages around these characters and stories. So, he started writing; and, as was his way, he wrote slowly.

Now, this was all happening during World War II when the Germans were bombing London on a nightly basis in a “total war” attempt to destroy the morale of Londoners. As we all know now, the opposite happened, resulting in the “stiff upper lip” that has become typical of being British. Tolkien, however, was scared. He feared dying with his greatest story stuck inside him. What would his life mean then? What would have been the point? So, to process such a fear, he wrote a story (pretty meta, huh?).

The story was called “Leaf by Niggle” and was about an ambitious artist who loved to paint but, like Tolkien, was very particular about his work. His whole life, he worked on a single painting of a tree, often getting so caught up in the details that he fixated on a single leaf. He was also a man with other responsibilities, a life outside of his work that included a needy neighbor who was always asking for favors.

Being the good man he was, Niggle obliged and helped where he could, but ultimately died before he could finish his painting. This was not unlike Tolkien’s own story: he was a dedicated father and committed husband and would often take months at a time off of writing to focus on his family or his work as a professor. So what was he doing? He was telling himself a story to help make sense of the potential “emptiness of existence.”

The story ends with Niggle going to the afterlife and seeing not only his neighbor, but also the tree he’d spent his entire life painting. But there, it’s not a painting; it’s an actual tree, full of physical leaves and branches and bark. And not just the one tree—he finds an entire forest, filled with all kinds of mysteries he never could have imagined. And that is just the beginning of the story.

It seems to me we are all trying to create from the vastness of what could be and feeling the frustration of what could have been. We are the consciousness staring into the quantum void of potentialities, daring to pull something out. And this is hard, because there could always be something else, and it doesn’t take a genius to recognize it.

But it does take a critic. And I’ve seen my fair share of those while I continue to create, figuring out exactly what wants to come out. It is so interesting to me how many people have opinions about what they think I should do with my time and talents.

For the past ten years, I’ve written books and taught courses and played in the online marketing space. I’ve heard over and over again things like, “When are you going to be a real artist, Jeff? When are you going to create instead of just talking about creating?” This made me sad. I thought I was creating.

It reminds me of an interview with Lady Gaga I came across recently in which she says, “I’ve won Grammys now. I’ve written albums. I’ve toured the world four times. You’re telling me to look beautiful? It’s all back to tits and ass? That’s so sad.” I can relate to that. Granted, I’m no Gaga, but it lands; and what I love about her work is how intentional she’s been about sharing her process, the “why” behind her “what.” She’s taken care to inspire other creators.

For my part, I’ve written books and launched businesses; I’ve taught courses and reached millions of people. I’ve toured with music groups and spoken on stages in front of thousands of people. I’ve been published and paid for my work. I’ve made a living at this work for over a decade, while sharing what I’m learning in hopes of inspiring someone else. I’ve tried to tell the truth and share what I learn as I go. I’ve challenged myself to stay true to my art and care enough about it to not starve. I’ve written poems and songs and shared them with the world.

If you didn’t notice, that’s fine; but it’s not really my job to convince you that I’m doing real work. Most days, I don’t believe it myself, so I don’t need anyone to give me extra shit about it.

And then, I wonder if this is just how it goes. The artist is constantly vying with the expectations of others, in some ways needing them and also kind of despising them as they do. We are all so confused about what it means to be a “real artist,” and most of the pros I know struggle to believe it about themselves.

As Hemingway once said of writers, “We are all apprentices in a craft nobody masters.” And if the great Papa (who was anything but humble) would admit that, such a revelation is quite telling.

Maybe the art is the approach but never the arrival. Maybe it means what it means and all attempts to explain it are not “it” but another art form entirely. As David Whyte says of poetry, it is a way of hearing yourself say things that you didn’t know you knew.

What does it all mean?

Hell, I don’t know.

Confusedly,

Jeff

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This week's HC podcast is all about the creative question, and the answers we're always trying to find with our work. Make sure to also check out the issue that matches up with this week's newsletter: What does it all mean?​

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📖 Read: For some creators, death isn’t the end of their art. (One recent example is Anthony Bourdain’s latest book, which was supposed to be a collaborative project, but ended up being largely the piecemeal creation of his editor.)

🎙️ Buy: The Career Author Summit is happening this month. Tickets are sold out, but we managed to reserve some just for our subscribers. Grab yours here before they’re gone, and join us virtually for a powerhouse of sessions about making a career of your writing. Jeff speaks on Day 1!

🧥 Wear: “So go ahead, get a baggy pair of pleated chinos and toss a t-shirt and blazer on.” Bistro Vibes is the look every creator in their 30s or 40s is sporting these days. (Don’t forget the dad hat.)

🚴‍♂️ Consider: Buried in an article about Peloton fitness influencers comes this gem from Anne Helen Peterson: “These celebrity instructors, like all celebrities, are texts. Their primary ‘meaning’ is located in their status as ‘coaches,’ inflected with whatever coaching personality they’ve adopted and refined. (Ally, oscillates between a murderer (her Tabata classes) and a cool church praise leader (Sundays with Love)). As consumers, we can be influenced and swayed into certain ways of reading those texts, but the reading practice itself is never static. What matters is that we’re invested, even if we don’t admit it.” We want your thoughts, creators. At what point does a creator become a creation, and when is what they “mean” up to consumers?

🏠 Peek: Famous authors’ houses worth seeing. (Chantel once posted a whole Instagram essay about the first house featured here—it’s where Fitzgerald wrote This Side of Paradise.)

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When I Have Fears

By John Keats

When I have fears that I may cease to be

Before my pen has gleaned my teeming brain,

Before high-pilèd books, in charactery,

Hold like rich garners the full ripened grain;

When I behold, upon the night’s starred face,

Huge cloudy symbols of a high romance,

And think that I may never live to trace

Their shadows with the magic hand of chance;

And when I feel, fair creature of an hour,

That I shall never look upon thee more,

Never have relish in the faery power

Of unreflecting love—then on the shore

Of the wide world I stand alone, and think

Till love and fame to nothingness do sink.

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Jeff, whose name means "God Peace." While he hasn't always felt at peace, he knows he can bring peace to others, often through his connection to the deep and spiritual.

Chantel, whose name translates literally from the French as "singing girl." She heard this week that your name defines the journey of your life, and while she doesn't sing, she is forever learning to use her voice.

Matt, whose name means "gift of God." Left to his own work, Matt says this can feel like pressure. When he realizes the gift is already given (and it is good), life is much lighter and more free.