Creative Wayfinding For Ambitious Optimists.

Work with What You Have

April, 15, 2023

🧭 This blog post is adapted from my Creative Wayfinding Newsletter.

While I have a wide variety of taste in music, my hands down favourite artist is Gregory Alan Isakov.

The first time I ever heard one of his songs was, was—believe it or not—in the background of a McDonald’s holiday commercial on TV (as a lifelong vegetarian and farmer, he donated the licensing fee to a sustainable farming non-profit).

Immediately, I was hooked.

Unable to get the Shazam app on my phone up in time, I did my best to memorize the lyrics I’d heard, ran to my computer, furiously typed them into Google, hit enter, and held my breath.

Big Black Car by Gregory Alan Isakov” came back as the top result.

A quick listen confirmed that this was the song that had captivated me and from that moment on, (what I can only imagine will be) a lifelong bond was formed.

Since then, I’ve probably listened to Gregory’s music more than anyone other artist. I’ve seen him perform live 5 times, in 4 countries (most recently in Paris, though the most memorable show was in Edinburgh). I know all the lyrics to every one of his songs and can play at least a dozen on guitar.

Most of all, however, I’ve spent considerable time and angst wishing I could write songs like him.

See, something about his music resonates with me in a way that feels like I could have written it, as though he’s put the perfect words to my experience of life in a way I never could.

What’s more, our vocal ranges overlap nearly identically, meaning the melodies I might write, align as closely as the lyrics.

Despite the overlap, however, the fact remains that when it comes to songwriting, the magic I find in Gregory’s music is something I simply can’t replicate.

During the time of my life when I still imagined my greatest creative contributions would be as a songwriter and musician, this was a bitter pill to swallow. As my creative identity has shifted from musician to writer and teacher, however, I’ve come to peace with it.

At this point, I can appreciate the magic Greg’s music holds over me and simply behold and appreciate it.

Of course, with the shift in identity, new comparisons have emerged.

As a writer, I now envy James Clear’s single-minded drive, the clarity, precision & background research of his writing, and his systematic approach to building a brand around his work.

I envy Ann Handley’s seemingly effortless injection of wit and humour into business writing.

I envy Robert Macfarlane’s masterful vocabulary, especially when it comes to his lucid descriptions of the natural world.

And I envy David Hiatt’s incredibly personal, story-driven, bordering-on-poetic sales copy.

The list of comparisons doesn’t end there.

And of course, when I think of all the fantastic writers whose work I’ve yet to read, I think it’s safe to say the list of comparisons is potentially limitless.

And yet, despite all the myriad ways in which I might feel my own writing doesn’t measure up, I still regularly get emails like this one.

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These emails remind me:

I can’t write songs like Gregory Alan Isakov.

I can’t write non-fiction like James Clear, Ann Handley, or Robert Macfarlane.

I can’t write sales copy like David Hieatt.

But I can do something.

I can work with what I have.

And do the best I can with it.

Because if I don’t do it, no one else will.

We often struggle to perceive our own creative magic.

But that doesn’t mean it doesn’t exist.

Don’t hide it.


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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    Hi, I'm Jeremy, I'm glad you're here.

    No matter what you create, I'm guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.

    So do I. And so does everyone doing creative work.

    This is the Creative Wilderness.

    Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.

    If you're building something that matters, but aren't quite sure how to take the next step forward, I'd be honoured to have you join us.