Fear in High Heels: Why I'm Trading in my Perfectionism for Courage

I really struggled to write this post for fear of how it would be received and therefore how it would make me look. At the end of the day, it was this quote from Neil Gaiman's University of the Arts commencement speech (which I borrowed from Timothy Ferris' book, Tools of Titans) that convinced me to push on:

The moment that you feel that, just possibly, you’re walking down the street naked, exposing too much of your heart and your mind and what exists inside, showing too much of yourself. That’s the moment you may be starting to get it right.

So here goes nothing.

Yesterday morning I picked up Elizabeth Gilbert’s book, Big Magic - Creative Living Beyond Fear, and on a whim of spontaneity, flipped it open hoping for some inspiration (yes, I do this often).

The fact that I randomly landed on the chapter in the book titled “Fear in High Heels” was oddly appropriate for two reasons. First, I have become somewhat of a poster child for diversity in the startup world and find myself speaking about spiky gender issues like equal pay, crying in the office and other “I-really-don’t-want-to-share-this-but-know-it’s-important-I-do” anecdotes.

Me (far right) on an "All Things Being Equal" panel at the World Capital Market Symposium, wondering if I'm being a little  too  honest in a room full of money market folk

Me (far right) on an "All Things Being Equal" panel at the World Capital Market Symposium, wondering if I'm being a little too honest in a room full of money market folk

Second, I have been personally struggling to find my authentic voice and share my uncensored thoughts with the world, whether it be through writing (a creative battle I am still fighting) or speaking out on stage about important but uncomfortable topics. Note this disgruntled comment from a male bystander in response to an audience member's tweet:

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For obvious reasons, I am deeply interested in why we as individuals hold ourselves back personally, professionally and my new obsession, creatively. Why do we never start that company? Write that book? Take those lessons? Voice our truth?

Gilbert's answer is perfectionism.

Perfection stops people from completing their work, yes – but even worse, it often stops people from beginning their work. Perfectionists often decide in advance that the end product is never going to be satisfactory, so they don’t even bother trying to be creative in the first place.

(Kind of explains why in the first year of starting my personal blog, I only ever released three safely industry-related articles while anything remotely heartfelt remained in perpetual 'draft mode'.)

Even now, I am still having to convince myself NOT to wait until next week to publish this post, once I've had time to re-read, re-edit and lose my nerve. That's the funny thing about doing what we love, the experience usually comes gift-wrapped with fear and self-doubt. But this isn't necessarily a bad thing. In his book, War of Art: Winning the Inner Creative Battle, Steven Pressfield explains it well:

Self-doubt can be an ally. This is because it serves as an indicator of aspiration. It reflects love, love of something we dream of doing, and desire, desire to do it. If you find yourself asking yourself (and your friends), "Am I really a writer? Am I really an artist?"  chances are you are. The counterfeit innovator is wildly self-confident. The real one is scared to death.

I found this to be true in starting companies well. The best founders I have ever met are usually humbly self-aware of their own limitations and ruthlessly pessimistic about the odds of survival. As a result, they're always trying to overcompensate with a great team, group of mentors and ferocious appetite for learning - regardless of any success they've achieved. This is because "imposter syndrome", as anyone who has attempted anything worthwhile will agree, never goes away. I still feel surprised (and quietly relieved) when the CEOs I look up to admit that they too face the same fear of failure and insecurities as the rest of us. The difference, according to billionaire entrepreneur, Elon Musk, is that they push through because the work is "important enough".

Gilbert says it another way: if we want to have any semblance of a happy, creative life we must learn how to become a "disciplined half-ass". That is,  don't be lazy but forget perfect:  "perfectionism is unachievable, a myth and a trap and a hamster wheel that will run you to death".

Truth be told, perfectionism did almost run me to death. I spent most of 2017 in a pit of utter despair and self-loathing despite working with amazing people, on projects that I genuinely cared about and receiving titles that my younger self would only dream about - my Linkedin caption currently reads, "MD at Artesian, Chair at JA Australia, Cofounder at Zookal, Forbes 30 under 30". (I suspect my internal caption might read something along the lines of, "Self-confessed overachiever and still seeking external validation but sincerely working on that").

I guess I didn't see the true source of my suffering because I always viewed perfectionism as a virtue and therefore, tended to wear it like a badge of honour, something my former startup-COO self would certainly be proud of.

Gilbert's perspective on the matter debunked this false thinking with such articulate clarity that I feel compelled to share it with you, despite the risk of bringing my own deeply personal battles to the limelight:

Perfectionism is just a high-end, haute couture version of fear. I think perfectionism is just fear in fancy shoes and a mink coat, pretending to be elegant when actually it’s just terrified. Because underneath that shiny veneer, perfectionism is nothing more than a deep existential angst that says, again and again, “I am not good enough and I will never be good enough."

I read that last line, sat back and said one word: "shit."

I then promptly proceeded to unpack my life and kept seeing that insidious storyline everywhere. It was like that children's book, Where's Wally? (except Wally was my self-worth and he had two black eyes and a pair of crutches). I realised all the drama in my life - the invisible wall I put up in my relationships, my tendency to self-sabotage and the long list of passions I promised to pursue "someday" - were all just symptoms of the same root cause, a common kryptonite, the why behind the why (or more aptly, the wound behind the why).

Perfectionism is nothing more than a deep existential angst that says, again and again, “I am not good enough and I will never be good enough."

It was, however, the way Gilbert tied perfectionism to why we women hold ourselves back that really moved me (as only those moments do when we see our own truth staring back up from the pages of someone else's book):

Perfectionism is a particularly evil lure for women, who, hold themselves to an even higher standard of performance than do men. There are many reasons why women’s voices and visions are not more widely represented today in creative fields.

(And in entrepreneurial, corporate or any other fields for that matter!)

Some of that exclusion is due to regular old misogyny, but it’s also true that – all too often – women are the ones holding themselves back from participating in the first place. Holding back their ideas, holding back their contributions, holding back their leadership and their talents. Too many women still seem to believe that they are not allowed to put themselves forward at all, until both they and their work are perfect and beyond criticism.

Meanwhile, putting forth work that is far from perfect rarely stops men from participating in the global cultural conversation. Just sayin’. And I don’t say this as a criticism of men, by the way. I like that feature in men – their absurd overconfidence, the way they will casually decide, “Well, I’m 41 percent qualified for this task, so give me the job!" Yes, sometimes the results are ridiculous and disastrous, but sometimes, strangely enough, it works - a man who seems not ready for the task, not good enough for the task, somehow grows immediately into his potential through the wild leap of faith itself. I only wish more women would risk these same kinds of wild leaps.

So do I!

But I’ve watched too many women do the opposite. I’ve watched far too many brilliant and gifted female creators say, “I am 99.8 percent qualified for this task, but until I master the last smidgen of ability, I will hold myself back, just to be on the safe side.”

Now, I cannot imagine where women ever got the idea that they must be perfect in order to be loved or successful. (Ha ha ha! Just kidding! I can totally imagine: We got it from every single message society has ever sent us! Thanks, all of human history!)

Hence my life-long love affair with educating future leaders - get 'em while they're young, I say!

We women must break the habit in ourselves – and we are the only ones who can break it. We must understand that the drive from perfectionism is a corrosive waste of time, because nothing is ever beyond criticism. No matter how many hours you spend attempting to render something flawless, somebody will always be able to find fault with it. (There are people out there who still consider Beethoven’s symphonies a little bit too, you know, loud.)

Or, put another way:

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At some point, you really just have to finish your work and release it as is – if only so that you can go on to make other things with a glad and determined heart.

Which is the entire point.
Or should be. 

[SIDE NOTE: in the 24 hours prior to publicly releasing this blog, I:
1) Started three separate arguments with my fiancé after he didn't "respond appropriately" to my first draft (he was tired from work and I was a big ball of quivering self-doubt)
2) Spent the rest of the evening nursing a bad mood/wounded ego and worrying about the general direction of my life
3) Wrote a list of all the reasons why exposing myself on any public platform was a terrible idea
4) Recognised the same "I am not good enough" storyline at around midnight and then quietly resolved to finish/publish this post - unready as I was and imperfect as it seemed
5) Finally sat down to write and to my complete surprise, found joy in that simple act, in and of itself]

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Here's to more of us taking "wild leaps of faith" in ourselves.