Getting Comfortable in My Own Skin

I use this image as my Twitter cover photo for a reason, but not what you may think.

I have been a “fearless girl” all of my life. When people would tell me something couldn’t (or shouldn’t) be done, I would ignore them. When an opportunity knocked, I never stopped to think about the risk, I would just seize it. I’m incredibly outspoken (even where I should pick my battles). Some people even consider(ed) me reckless.

Which is why most people would be surprised to hear that I was afraid of everything I was doing (and especially what I was not doing) all of my life. Fear drove me to take risks. I seized opportunities because the thing I have always been most afraid of was that I wouldn’t make an impact. For me, being “regular” and fading into the crowd felt like a death sentence.

And yet, for so many years, I spent oodles of time and energy trying to fit in. While I feared being regular, I was also highly susceptible to external pressures.

While attending the Personal Democracy Forum in 2009 — where I was a speaker on stage (in conversation with Douglas Rushkoff nonetheless!) — a male colleague approached me and made a comment that would impact me way more deeply than it should have. He said:

“There are people who are saying that you are too self-promotional. I thought I should let you know.”

I scoffed at him — I spend the majority of my time trying to lift others up! And what about Gary Vee and other men in my position who are self-promotional engines and who are celebrated for their bravado?!— but the comment cut deep. I spent the following years questioning myself on multiple levels. If I was about to publish a post, I would heavily edit it for anything that smacked of self-promotion. I would stop myself from posting an accomplishment (award or media mention or the like) on Twitter or Facebook because I worried about “those people” who were talking.

It harkened back to my youth, when influential adults in my life (teachers, family members, etc) would take me aside and tell me to: “be humble”, “stop showing off”, “tone it down” or give me warnings like, “young ladies who are outspoken are not considered attractive.”

So even as I endeavoured to stand out and be adventurous, the message coming back to my attempts was always, “you will be punished for standing out.”

And perhaps I could have taken these message as a loving warning that would be given to any person. I mean, my colleague at PDF framed his advice with “I really like you and want to see you succeed.” But the thing is that not everyone gets this ‘loving’ advice. This advice is reserved for those who aren’t welcome or encouraged to be outspoken, risk-taking, adventure-seeking, brash, or brazen. This advice is reserved for those not in power. Because to seek power as a woman is an anti-social act.

[To note here, I acknowledge that as a white, middle-class woman, I have it easy. I can take risks that a person of colour could never even dream of without risk of bodily harm and even death.]

Beyond my own experience, there are plenty of studies that show that women who exhibit too much confidence or certainty are punished by both men and women. “Uppity” women are only now being depicted in popular culture as heroes, and not villains, but the discomfort I see (and have even felt myself — which shows me how deep-seeded this is in our culture) when a real-life uppity woman appears is palpable.

I just turned 44 and, though I am a long way from getting to that “I don’t give a f*&% what other people think” phase of my life (which, I am told is coming and is glorious), I have gotten to that “I’ve earned my right to be me” phase of my life. In the past year, I’ve cut my hair into a rather brazen faux-hawk, which I love, started building that tattoo sleeve I’ve always wanted, been less apologetic for my strong opinions, and cared a lot less about whether I’m ‘regular’, because I’ve realized that there is no such thing. Nobody is regular, just trying to get by.

The photo my husband took of me at my birthday dinner and I’m not afraid to say that I think I look rad.

All of this is happening for me at a time when the startup world is in a bit of an uproar about the sexism in tech. My response to that is, “D’uh.” And something that myself and my fellow OG tech women have been talking about for years. Or, I should say, we’ve talked about as much as we could as the retribution for speaking out in the past years was incredibly career damaging.

Even now, I’m holding my breath for the brave women stepping forward. Sure, there is lots of public kudos for their bravery, but I see just as much for the men and organizations accused. The truth as to how far we’ve come will come out in how they fare versus their predators.

As I find myself getting more comfortable in my own skin, I really hope our culture will follow suit. I don’t think any of us can celebrate until young women are celebrated for their brashness as much as young men, women are being hired and promoted for their potential as much as men*, when we make as many excuses for women’s bad behaviour as we do for men, when there are as many mediocre female speakers as there are currently male at conferences, when VC’s and angels write as many cheques to women-led startups as they do man-led, when all of the above happens for people of colour, people with disabilities, and the LGBTQ+ community as well, and, most of all, when there is no such thing as ‘regular’ or ‘normal’.

Fear is a liar, but it’s also a sign of very real threats around us. It’s time we all grow up and get comfortable in our own skin.

— — — — — — —

*studies have shown that men are hired and promoted based on potential, versus women, who are hired based on proof (and they need a lot more of it even then).