When I first decided to leave the corporate world for self-employment, I prepared myself to face a lot of failure. Not because I’m bad at what I do, but because in all my reading and research about striking out on one’s own, the topic of failure was everywhere.

I was encouraged to redefine failure as an opportunity for growth and self reflection, to experiment, to take risks, and to even sometimes fail on purpose. I saw constant “mindset shift” posts on social media about “embracing failure”, and read in books that the only way to continually improve oneself was to try, fail, get up, and try again. 

I even recorded a Write Now podcast episode about failure back in 2015, in which I encouraged creators to release their fear of failure, and in fact to get out there and “fail a lot”.  

But in all of this talk of failure, I was left wondering — what exactly was “failure”? 

I knew what “success” meant, largely — in my preparations to run my own business, I had gone through a gauntlet of exercises designed to define realistic, measurable metrics for success. I needed to make $1200 per month, secure at least four speaking engagements per year, and not work more than 65 hours per week.

(My definition of success has changed since my early days of self-employment, as I have grown and learned and changed. Today, that definition includes mandatory time off and an exchange of client work for my own creative projects. But I digress.)

To me, at that time, “failure” appeared to encompass scenarios in which I did not meet my established success metrics. Making less than $1200 in a given month, securing only two speaking engagements instead of four, working more than 65 hours, etc. But… I began to wonder: was securing those two speaking engagements actually a failure? I didn’t have four gigs, but I did have two, which was (according to my math) more than zero.

And if I made $1200 in that month but worked more than 65 hours each week… what then? Was it half-success, half-failure? And what did that make me in turn? A successful business owner, a failed business owner, or something in between, which I graciously allowed myself to call “still learning”? Was a “failure” the same thing as a shortcoming, a loss, a disappointment?

And what about all those times I was technically “successful” in reaching my established objective(s), but still felt like a failure?

It became less and less clear to me what “failure” actually meant, and I began to question whether success/failure was even a binary system. Perhaps I wasn’t just one or the other, but somewhere in between, bouncing back and forth like the little dot in Pong, spending the majority of my time hovering in the liminal in-between. And who knew where I would finally land, and when (if ever)?

Yet if I couldn’t precisely define “failure”, how was I to fully embrace and learn from it? What was I to embrace, and what was I to learn? Was I failing to fail properly? Was I just getting hung up on semantics? (Answer to that last question: oh yeah, big time.)

Today, I’m not really sure I even believe in failure because so much of what we do and achieve is wrapped up in context, relativity, emotion, expectation, and the impossibility of knowing the full impact of everything we do. I think that, for me, the only real failure in life would be to give up on writing altogether — to stop one day and never try writing again, despite being of sound mind, body, etc.

What about you? What does failure mean for you as a creator? (Or do you end up overthinking it like I do?)