Creative Wayfinding For Ambitious Optimists.

Are Your Creative Heroes Leading You to Failure?

July, 9, 2022

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

It’s hard to walk around the town centres of many major cities these days without noticing a conspicuous array of empty stone pedestals.

These pedestals, of course, were at one point occupied by statues of historically significant figures who, in the past few years, have had their legacies re-examined through a modern lens.

Statues, we’re realizing, celebrate, honour, and uphold more than just the person depicted.

In many cases, a statue might be better thought of as a personification of a set of values. Its presence is not only a reminder of those values, but a reinforcement, and in many cases an aspirational ideal.

This is true for every stone-carved general, sword drawn, horse reared, eternally charging into battle to defend his homeland.

It’s true for every bronze-molded sports icon revelling in the moment of victory over seemingly insurmountable odds.

And it’s true for the statues we’ve erected internally for our personal creative idols.

Much like physical statues reflect and reinforce the values and aspirations of a given society, the heroes we place on our internal pedestals reflect and reinforce our personal values and aspirations.

Our choice of heroes, then, is one of the most impactful choices we as creators make, as they have a heavy influence on both the outcomes we seek and the routes we choose to get there.

And yet, so often we unwittingly follow our heroes down paths that have no hope of delivering us to the destination we seek.

Choosing Heroes for the Wrong Reasons

Like most statues, we tend to erect internal statues based on our heroes’ accomplishments alone.

Maybe they’ve built the type of business or creative platform we aspire to build. Maybe they’ve won awards, accolades, and honours we dream of winning. Or maybe we simply aspire to lead the same day-to-day life they do.

Accomplishments are both easy to observe and easy to aspire to.

But they don’t tell the whole story.

We don’t need to look further than any of the real-world statues that have been torn down in recent years to see that many people who’ve made significant accomplishments have done so while also wreaking pain and destruction on those around them.

While it’s (hopefully) unlikely that our creative heroes’ journeys involved slavery, colonization or mass degradation of other people, there are plenty of other problematic narratives we may be subconsciously internalizing from them.

In some cases, the lessons we internalize from these narratives may be outright sleazy or unethical.

But more common (and perhaps the more dangerous) are the banal variety of implied directives that are simply unpractical, unrealistic, or misaligned with our personal circumstances, skills, and dispositions.

When internalized, these takeaways send us happily off in the wrong direction, thinking we’re making progress toward our goals, when they are in fact keeping us in stuck in place.

Problematic Origin Stories

My partner, Kelly, and I were talking about this idea recently and she immediately referenced two of her own former heroes who she’d soured on after learning more about their backstories.

The two women in question are full-time humour writers and for a long time, served as proof to Kelly that humour writing was a viable career path.

Each of them are supremely talented (and funny) writers, and have built huge followings through their popular blogs, written several books, and are living what appears to be the picture-perfect writer’s life.

As Kelly started researching their backstories and deconstructing her heroes’ journeys, however, another common thread emerged.

It turns out that they both had wealthy husbands that had allowed them to work full-time on their writing for multiple years without any pressure for their writing to support them.

What’s more, in getting to know one of these heroes at a conference, Kelly discovered that even as a published author of multiple books, her hero was still not making enough from her writing for it to actually be considered a viable career option.

The realization was crushing.

These statues which had formerly represented hope and possibility were now monuments to what now felt like an all but impossible goal.

The Tortured Artist

Another common example of a problematic hero’s journey is that of the tortured artist.

Yes, there’s something poetically compelling about a person who produces transcendent work but can’t bear to live with themselves or the world they inhabit. This inherent tension and drama is often exactly the thing that draws us to these people and their stories.

But if we’re honest, do any of us actually want to live those lives?

Personally, I’d rather make great work and live a happy, rich, fulfilling life while doing so.

While these examples are each problematic in their own ways, there’s another origin story that is more pervasive, and perhaps more destructive.

This is the origin story where our hero got to where they are by being picked or discovered.

Pick Me! Pick Me!

Maybe it’s the movie star who was randomly spotted on the street by a director and cast into the role that changed their life.

Or the writer who was able to land a publishing deal because they knew the right people.

Or perhaps the creator who was picked, not by a person, but by an algorithm, that for some unknown reason caused them to go viral and delivered their big break.

There are countless stories of successful creators who broke through based on being discovered by being in just the right place at just the right time and essentially being delivered a heaping serving of luck.

And to some extent, we all benefit from luck at some point in our creative careers.

Indeed, I’m convinced that a massive part of creative success is simply producing good work long enough for luck to catch up with us.

But erecting statues to heroes who got where they are based on a singularly lucky (and perhaps unrepeatable) event is a dangerous practice. They reinforce the idea we already desperately want to believe that some day, we might get picked as well.

And when we hold out for getting picked, we tend to cut corners with our creative practice.

Why learn to market ourselves effectively when one day someone, once we’ve been discovered, someone else will do it for us?

Why focus on learning the ins and outs of audio and video production, web design, and copywriting? We’re just the talent after all, and soon enough that talent will get noticed and amplified by someone with all the resources we currently lack.

Except…

The odds simply aren’t in our favour.

In all likelihood, neither you nor I are going to get picked.

And with that in mind, we’re better off erecting statues to more realistic heroes. The type of heroes whose paths to success are actually possible for us to follow.

Empowering Origin Stories

My biggest personal creative hero is Seth Godin.

I admire the deeply personal impact his work has had on countless creators, entrepreneurs, and marketers and aspire one day to leave a similar legacy of positive change on the people who’ve interacted with my work.

But while I admire Seth’s achievements, what I admire most is the path he’s taken to get there.

See, Seth is notorious for his publishing habit.

In addition to 30+ books, over the course of his career, he’s published more than 7000 blog posts. The vast majority of those have come in a daily publishing streak that has stretched for almost two decades

His persistence isn’t limited to his blog, however.

While working as a book packager, Seth sold his first book only to follow it up with 900 straight rejection letters from publishers.

While we all might hope for better luck for ourselves, there’s something comforting to me in Seth’s origin story.

It conveys the idea that if all else fails, we as creators can win through sheer attrition. By outlasting and wearing down all the forces aligned against us until it becomes impossible for us not to succeed.

To me, it’s these stories of mundane persistence that are most worthy of our statues.

Audit (& Tear Down) Your Statues

Whether you’re aware of it or not, you’ve likely got your own array of internal statues you’ve erected to your various heroes.

Some of these may have been intentionally constructed while others may slowly and subtly taken form over time.

Regardless of how they got there, these statues influence how you show up in the world as a creator and a human. They influence the goals you set, the paths you choose to reach them, and how you choose to view your progress along the journey.

Every so often, it’s worth re-examining them, questioning the values they embody and the messages they send, and considering whether or not those messages are aligned with where you’re currently looking to go and how you’re looking to get there.

Many of your statues won’t be.

In these cases, don’t think twice about tearing them down.

Then, atop the empty pedestals, consider erecting new statues to replace them.

Perhaps your statues will honour those who persisted through countless rejections until they could no longer be ignored.

Perhaps it will be those who discovered their gifts and and created meaningful work late in life.

Or perhaps it will be those who created in their spare time, who never achieved fame or fortune but who found enormous personal fulfillment or community impact through their work.

Whoever you choose to choose to build up in your mind, remember that our heroes, and the statues we erect to honour them matter.

Choose them wisely.


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.