The Art Of Hitting the Wall

Dear Readers,

When I started The Branding Habit, my intention was to offer a much wider and more generous lens through which to understand branding. I’ve always believed that different people need different aspects of the branding process, depending on where they are in their journey and what stage of growth they’re in. That’s why I broke branding into seven distinct areas — so that anyone, no matter their starting point, could begin from where they are and find a meaningful path forward.

The first series I created was called Tend. It was written for the early, fragile stages of a project — those moments where your idea is still new, still vulnerable, and your inner critic is loud. I wrote about overthinking, self-doubt, and the gentle courage it takes to simply begin.

I wanted to give you a bone-deep kind of permission from my heart to yours.

But something happened after I published that series.

I had given you permission to nurture your idea, but what I didn’t realise was that I was also extending that same permission to myself.

I soon started writing what I thought would be a short essay about the Impressionists, about creativity, and technology and change. But the story grew and became something else entirely.

The Art of Hitting the Wall

Coming Soon: The Art of Hitting the Wall

A Memoir.

What begins as a simple essay about the relationship between art and technology quickly unravels into something more personal — a reckoning with midlife, memory and meaning.

If this sounds like something that would interest you, you are welcome to subscribe to The Art of Hitting the Wall.

I am publishing it chapter by chapter, and I’d love to have you along for the ride.

The Art of Hitting the Wall

This morning, the best thing happened. I was on my way to a doctor’s appointment when — by happy happenstance — I caught Andrew Bird launching on Substack in real time, playing some tunes & chatting with Substack’s Hamish McKenzie.

There I was, cheering like a very happy kid. Or maybe a slightly unhinged middle-aged woman? Either way, I was thrilled, and I’m a big enough fan to require a full page to express my deep appreciation for the wonderful music of Andrew Bird.

…not to brag, but Andrew Bird was my most-listened-to artist of 2024 on Spotify, (and I have proof)… so to catch him launching live just before I had to don a gown and walk across the cold tiled floors under fluorescent lights? — It made my morning. I wrote this article frantically in the waiting room with a ridiculous grin on my face.

Andrew Bird’s music makes me think about artistry at its finest — about brave, authentic, creative work.

His music is inventive, expressive, unusual. It’s not trying to be palatable or perfect or viral. It’s just true. And that’s something I want more of in this world.

His music doesn’t try to appease everyone. He’s not trying to reach the widest audience. He doesn’t smooth out the edges to make it more digestible.

But for his people?

It goes straight to the heart.

I think of this as artistic courage.

It’s so tempting to overwork an idea until it becomes pop — polished, catchy, and safe. But in the process, we shave off all the things that make it special in the first place. Artistic courage resists that urge. It pushes away the impulse to flatten it to make it more palatable and more certain. That kind of trust is generous & brings the artist forward.

That’s what Andrew Bird does so beautifully. He leaves the edges in. He makes space for the work to be itself.

And it reminds me of something Seth Godin writes in The Practice, about shipping your work. Not shipping because you’re sure it’ll be well received — not because it’s perfect, but because it’s time. Because showing up for the work is the real commitment.

“The work is the work. The reaction to the work is a gift.”

Andrew Bird feels like someone who deeply understands that.

One of my favourite aspects of Bird’s music is how his songs evolve over time. Threads of melody and lyric reappear like old friends across different albums.1

As a listener, it makes me feel invested in the creation process. That piece I loved didn’t stop breathing when it was recorded onto the album — it kept growing. It came back, evolved, shifted shape, and became part of something new.

And Bird invites us into the creative process in ways I haven’t seen any other musician do.

He has a series of live albums called Echolocations, set in wild, resonant spaces like a canyon, or by a river — letting the acoustics of that environment shape the music. The space becomes a collaborator.

Then there’s the Fingerlings albums — a series of live recordings, imperfect & raw, featuring half-formed songs and ideas that might never make it to a studio album. They’re glimpses of the work mid-gesture. Still forming.

And it makes me think: in a world edging toward polished, AI-generated everything, there’s something radical about that kind of transparency.

In a time when machines are learning to mimic creativity, that kind of openness matters more than ever — But that’s a thought for another upcoming piece.

Substack feels exactly right for Andrew Bird.

It’s a place full of people who care about nuance. About craft. It’s not about being the loudest voice — it’s about being a true one.

And his music is just that.
It’s cerebral. Playful. Odd and lovely and layered — the kind of music that doesn’t shout for everyone’s attention, but stays with you.

And maybe that’s why I wanted to write about it here, on The Branding Habit.

Because creative work lives and breathes when we stop asking “Do you think people will like this?” and start saying: “This feels true to me!”

Andrew Bird’s music reminds me of that.

His music is a masterclass in artistic integrity.

So, Andrew Bird,
Welcome to Substack.

We’re so lucky to have you here!

And for the Substack reader who’s just discovered a new artist — here are my top 5 tips for where to start:

1. Wear good headphones.
Bird’s music is for active listening — headphones on. All those delicious little details get lost in open space if you’re listening in your car — you’ve got to funnel all that good shit directly into your ears.

2. Listen by album, not playlist.
His style shifts a lot across albums, but each one holds together as its own world. If you jump around too soon, it might feel chaotic.

I would start with:

• Inside Problems

• My Finest Work Yet

• Are You Serious

• Armchair Apocrypha

• The Mysterious Production of Eggs

Once you’ve found your favourites, then go wandering.

3. Savour the details.
Start with ‘Skin Is, My’ from the 2005 album The Mysterious Production of Eggs. The pizzicato violin bounces between your ears like champagne bubbles — it feels like a massage for your brain. You’ll understand what I mean immediately.

4. There’s so much to explore: ‘The NPR, Tiny Desk concert’, ‘Live From The Great Room’, ‘Song Exploder: Roma Fade’.

5. Still here?
Go follow Andrew Bird’s ‘Ahem’ on Substack.