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In a quest to fail, if you fail, is it considered a failure or a success?

Posted on June 25, 2022June 25, 2022 by Surya

On constraint, chaos and confusion in the creative process and life

If you fail to plan, you plan to fail. Someone must have told this to me when I was quite young, for I have adhered to it for a large part of my life – I planned, so that I could succeed at whatever I set out to do. Avoiding failure seemed the logical and desirable byproduct.

Lately, people have been telling me that I need to fail. In my previous job, my boss told me. My boss’ boss told me. Then my best friend told me. I ignored the first, the second and even the third – I am generally good at taking advice only when I agree with it. However, the pattern of three – same message from three different people under difference contexts (though there is probably a correlation between first and second. My boss’s boss wanted me to fail, or try failing, and when I didn’t seem to be heeding it, she asked my boss to tell me). But still two data points seems like I need to at least consider the concept of failing in a different light.

Check out this article, I liked it. It is written by Brandon Stosuy, who has a book called “How to fail successfully.” I haven’t read the book, but the article has made me ponder the title, and perhaps I will at some point get hold of a copy too.

I am a stickler for using precise terms, and tracing the line of thought and reason. I respond badly to people who just share conclusions and end actions without their path to it, and since none of the three characters above (boss, boss’ boss and BFF) really shared their full thinking (or perhaps I was too chuffed to listen when they did), let me attempt to understand it further.

First of all, let me assume good intent. It’s all for my eventual benefit, even failure (even though in corporate world, who knows.) But why? Why should I fail? It could be that I take too little risk, and they want me to push boundaries. I like to understand and manage risk, sure, I was a risk manager in one of my earlier careers after all. But I also think if you take my timeline of life, I have made some bold audacious moves that most people would consider insane. Risk and I have a complicated relationship, and I have thrown caution to the wind plenty of times. But I am also not an idiot, if I am going to jump off from an airplane, I will check my parachute. Twice. But I will get on that plane, and jump without too much of a fuss. And I do that sort of thing over and over again. So pushing me to take more risks seems a little unnecessary.

Going to the old adage. – plan and you won’t fail. So by reverse logic, if you don’t plan, you will fail. So don’t plan. Essentially what they are trying to say is – don’t plan. Which is rather weird. I hate planning, and I am chaotic and unstructured by my inherent nature. A lifetime of learning structure and order has got me to where I am. To slip to chaos is easy, sure it makes me uneasy too, but that flowy chaos is home turf. Perhaps I should just learn to accept that flowy chaos. Or perhaps by now, both are equally home. So I just need to learn to oscillate better between the two.

Over the years, the reason I try so hard to put structure in my life is consideration for others around me. Living with chaos is not easy for anyone (myself included), so then how do I manage this.

I need to do two things – externalise structure, so I am allowed to flow in my chaotic creative abandon internally (in the mind). And then, get comfortable with it, it might be mental home, but it’s been a long time since I have been here, so it does take some getting used to. Last thought on this, it has to be aesthetic chaos. There is a difference between chaos and clutter. Clutter doesn’t work for me, and I need to understand how the chaos does not disintegrate into clutter or confusion.

So next steps: 1) figure out how exactly to externalize structure 2) get comfortable with it, and as a bonus stretch goal – learn to enjoy it 3) understand/articulate the spectrum of (i) creativity under structured constraint (ii) diffused creative confusion (where it diverges so much there is no hope of convergence) (iii) creative chaos (the aesthetically and emotionally pleasing kind).

Will that lead me to failure? Oh well, whatever. It leads where it leads to. I hope to enjoy the ride, however which way it goes.

I am grateful to Brandon Stosuy, that his writing provided me the impetus and inspiration to think this through. I really should get that book. While I am at it, a book about creativity that I have enjoyed and a podcast I subscribe to (but rarely listen, I am just not a podcast person) is Todd Henry’s Louder than Words (book) and The Daily Creative (podcast).

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