How to be Bold: A Guide

For most of history, Anonymous was a woman.”

– Virginia Wolfe

Women cannot afford to be invisible any longer. We should not shrink nor make our voices small and meek in the face of adversity. We should stop being silent when that guy from the office who thinks he knows best begins to mansplain the way things are, as if we misplaced our brains at the bottom of our purse.

Accomplishing a great shift in consciousness requires courage and a wee bit of sass.

1. Set Yourself Apart  


When I was 23, before I became so damn enlightened *giggle* I was a waitress at a pub in Liberty Village. Where I come from being a server isn’t highly regarded, but I confess, I enjoyed it more than many of the career paths I’ve sampled.

The greatest moments of serving people are the opportunities to share stories and brief moments in time with those you’d never normally meet. No matter how brief or seemingly insignificant these moments are, they are precious and life altering.

It was a blustery day in Toronto when I received a vital lesson on boldness that surprisingly came from a much much older man.

I remember him as if it were yesterday. Early eighties, handsome, kind eyes, wide grin, gentlemanly and full of life. We shared stories, jokes and laughs while he and his chum drank their beers.

His hat story is what I remember most.

“Three women are walking down the street. One is wearing a hat, one has no hat, and one is wearing a scarf,” he riddled.

I nodded.

He continued, “Which woman do you remember?”

I considered the options, smiled, then said, “the one with the hat.”

“Why?” he questioned, raising an eyebrow.

“Because she stood out,” I replied, succumbing to a vision in my head of a stunningly confidant woman in a red dress and a large brimmed hat sauntering down Avenue Road.

A photo by Lechon Kirb.

This wonderfully insightful man gave me one of the most timeless and influential pieces of advice I will never forget. So much so that when I feel insignificant or anxious around others I imagine myself as my lady with the hat.

What he meant was,

A woman should always be bold.


“Well-behaved women seldom make history.” 

Laurel Thatcher Ulrich.


2. Model Behaviour of Those You Admire 


Who are the women you admire? You may have more than one. I bet they are audacious.

Do you ever wish to be more like them?

One of my secret lady crushes is Kate Winslet. She’s an incredibly talented actress, stands up for her beliefs and other women, doesn’t succumb to pressure, yet remains poised and respectful. She’s also classically beautiful, which is totally my thing.

Others I’ll include are Sheryl Sandberg, Brené Brown, Lavern Cox, and Brittany Spears.

Laugh all you’d like at my love for Brittany. Have you seen her Instagram? The woman is real. She’s battled with her mind and media and won #LikeALadyBoss. She looks healthy, happy and continues to be a positive role model for young women.

hat old lady

These women are bold and fearless, but that does not mean they never feel fear or fail. When dark shadows creep across their hearts they raise their chins, set their shoulders and scream,



3. Speak Up and Out Without Regret


Women who never give up, expose their true selves and speak up and out often are the ones we remember.  These are the astonishing ladies who make waves invoking change. These are the sassy offbeat broads who take the high road when the other side plays dirty. These are the victorious damsels, in distress no more.

As Michelle Obama says to her daughters, “When they go low, we go high.” And we keep aiming higher than ever before. Higher than the glass ceiling, because it’s not enough to ‘fit into a man’s world’and the traditional western female archetype. Why keep fighting for something we didn’t create and would probably change if we could.

By being bold we design a brave new world with the vibrant colours only our imaginations can behold. In this new world we have a chance to reshape our identities and become the people we want to know and love.

When you discover the truth inside yourself, the tiny voice whispering, “you can!”, believe that you are good enough to make the world a better place. You can make miracles happen by putting yourself out there, shutting up the fear inside you, and facing your challenges head on.


“Woman must not accept; she must challenge.” 

Margaret Sanger

4. Accept Challenges, Push Forward 


Challenges may be painful, but are the necessary devilish parts of growth. And in order to challenge the status quo, we must be bold.

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