The Art of Iteration & The Alchemy of Fear

Making art means pursuing and engaging in meaningful work.

I’ve recently been reading the Icarus Deception by Seth Godin and it has been resonating with me. What really helped me unlock the sometimes-nebulous concepts and helped me own the message was replacing the word ‘art’ with ‘meaningful work.’

Thus I’ve concluded that I am an artist. And as an artist, I gravitate to where the work is meaningful. As I am sure you do too.

As Seth Godin lays out, art and this journey in creating meaningful work is scary.

It flies in the face of the Industrialist’s notion of “safe.”

It requires tolerance of the ambiguous and the uncertain.

It requires pursuing people and connection over productivity and eking out incremental efficiencies.

It requires reevaluating and realigning one’s comfort zone (and corresponding safety zone).

It requires being vulnerable, and speaking up, and owning a message and cause.

Art (meaningful work) requires owning and embracing “this might not work” and going anyway.

The journey is messy and scary and isn’t all unicorns and rainbows. We all know this, yet it often takes time to internalize it. To let that head knowledge permeate our being.

This journey, this process, this gauntlet, is wrought with iteration. Anyone familiar with the tech startup world knows the importance of iteration –

Launch the minimum viable product you can; get it into users hands.

Watch it hiccup, and fail.

These hiccups provide data points, benchmarks and information to get feedback, find the kinks and the bugs.


Launch again.

Rinse and repeat until you’re thing is rockin’.

The thought leadership is pretty clear at this point – we need to embrace the fear of failure. Or as Jonathan Fields puts it in his 10 Commandments of Epic Business that blew up in the lifestyle/entrepreneur niche – “Thou shalt train thy mind in the Alchemy of Fear.” And they’ll all tell you that it’s about learning to be comfortable with failing (and failing often).

Which it is.

The Unsexy Failure

But I’m not sure these thought leaders take it far enough, because failure, in and of itself, isn’t that scary. We all know in our heads that failure is part of the journey to making ourselves and our work better. Let’s all agree that’s a given at this point in our post-industrialist age.

Our fear goes deeper than just failure; we are afraid of a specific type or flavor of failure (at least when it comes to the meaningful work we care about). I think Jonathan Fields called it an “alchemy” because our fear is a complex and potent cocktail of many different strains of fears and flavors of failures. I think most anyone who has started recognizes and acknowledges, at the macro-level, that there is risk of failure – it’s part of the game.

We know that if our venture fails, we still have breath in our lungs, our rainy day emergency savings is still there (hopefully), and mom and dad’s basement – in all it’s dankness – is waiting with open arms. But it’s the expectation of how failure should look, that we get hung up on. 

We tell ourselves: for failure to be successful (oxymoron?) it needs to look like this or that. We try to fit failure into a box of our expectations.

We tell ourselves: Failure needs to have these tangible leftovers and pieces for me to show off and build on and boast about.

We tell ourselves: Failure needs to have sex appeal. And the the scariest thing – the thing I’m (we?) most afraid of – is an unsexy failure. 

The Unsexy Failure: A failure that can’t be leveraged, or spun into a compelling blog post, or turned into an ebook, or humble-bragged about in a job interview at Warby Parker or Zappos or Google.

What if our thing fails and all we have to show for it is an un-sticky idea and a false start?

What if all that’s left to show is no users, a broken co-founder relationship, some unanswered cold emails to potential investors and partners, and a half-renovated office space with a termite and rat problem.

What then?

The unsexy failure. God forbid.

Jerry Colonna talks about the importance of separating your feeling of worth from the thing(s) that you do – no matter how amazing or unsexy they turn out to be. One tactic he encourages to achieve this separation is by replacing expectation with gratitude. Practically, this may look like keeping a gratitude journal. Or pausing throughout the day to meditate or thank God for the small gifts along the way and focusing on wanting what you already have. Or a slew of other ways to cultivate gratefulness. 

A matter of selfishness.

I also think this fear of the unsexy failure is a matter of selfishness. And meaningful work, by definition, is not about us – it’s about serving others in a dignified way. This fear (and fear in general?) is selfish and shows our limited understanding of failure and its role on the journey.

It’s selfish because it means my failure needs to look a certain way, all the work needing to be done needs to be tangle and quantifiable to have something sexy to serve me and my contingency plan if it all goes to hell.

We all know that the process of failing and iterating is wildly important to make the best possible thing and serve the right audience. We know that this art of learning how to iterate well is key to learning, developing, and succeeding in our ventures (and life).

Therefore, we must recognize, name, and admonish the fear of the unsexy or the ‘wrong-type’ of failure. We do this by refocusing on the people we are serving. We double-down on the community and connections we are building. Our refocus suffocates this fear. And even if we experience the unsexy failure – not all is lost.

Failures – all shapes, sizes, and flavors – are an essential part of fortifying the strong and gritty emotional foundation required for being an artists/entrepreneur/change-maker/doer of meaningful work.

Big takeaway: 1) Identify and name the specific type of failure that you’re afraid of. This is the first step to punching that fear in the jugular. 2) The second step is to refocus on the human elements – the people you are serving.

Don’t discriminate against failure.

[Meaningful work] might scare you.
[Meaningful work] might bust you.
But [meaningful work] is who we are and what we do and what we need…
[Meaningful work] isn’t a result; it’s a journey.

I would add that meaningful work – work you are called to – will be a result of failure and iteration.

A snapshot from the back cover of Seth Godin's The Icarus Deception. (It helps to replace 'art' with 'meaningful work')

A snapshot from the back cover of Seth Godin’s The Icarus Deception. (It helps to replace ‘art’ with ‘meaningful work’)

And we must train ourselves for the emotional rodeo of not discriminating against which type of failures we fear and the ones we don’t.

So let’s drop our expectations of how failure (and successes) should look and feel, and learn (re-learn, and re-re-learn) to be content with living the questions and the adventure at hand.

Sure it’s generally better to strike out swinging for the fences than watching one hum in over the plate, but the moment we try to force failure into a predefined box is the moment that creates an environment primed for fear to take root.

Meaningful work is an art – the art of iteration and of training in the alchemy of fear.

Happy hunting.

Dan LeMoine


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