Why the press never got Kathleen Wynne: Because they never understood the secret problem with women in power.

When I was in j-school, as part of one of my classes, I did a documentary that aired on the local television station about women who smoked cigars. I did a lot of research, but it was different than the research I had done in the past. I had interviewed a professor who specialized in the topic, and interviewed one woman who frequented the cigar shop as well as that store's manager who was also a cigar-smoking woman as well. The manager was sharp, insightful, comely, young, elegant, articulate, lively, and made for a very good interview, and I was not surprised that a couple of months after my documentary aired, that she ended up being on the cover of the city's business magazine, smoking a cigar, of course. As an interview subject, she was a find and a get.

And strangely, the city's best kept secret until my interview. It was her store's backroom parlour where people in power didn't just smoke stogies: they did business deals in there. It was an unspoken power centre -- and you wouldn't think a small cigar shop in a downtown shopping mall would fit that bill.

I had even managed to get permission and the cover slide from the magazine Aficionado for my piece -- in was the days where email wasn't an option, and they couldn't just email me the image: they had to mail the slide to me, and I had to mail it back.

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But back to the manager.

She seemed to have been invisible. It is hard to imagine that someone who ran an unlikely hub wouldn't be the talk of the town long before a young and ambitious j-school student with her ear to the ground got an idea in her head to explore the topic that would bring her to an unknown trailblazer.

You'd think she would have gotten a lot of publicity, even outside of the city. Women smoking cigars was the rage back then, and there was a reason: it was a way to tweak those in power who had made-up rules to keep their clubhouse an elite one. Turn over the rule, prove it to be trivial, and then push to cross another line.

The hypothetical and untested truisms get knocked down one by one, as you prove that the false list of what makes successful people superior to others is just a feint and a ruse, and you take away their fortresses and defences one by one as you gain equality.

But not before you gain experience first. Without experience, you have no map on how to deal with confines and obstacles. You get tripped up by simple tricks. You think invisible walls are real, and you become your own enemy who stops you from pushing ahead.

Challenging the trivial gets you thinking on how to challenge the bigger threats once you reach them.

But always gaining experience and devising your maps as you hone your own natural thought processes, experience, and emotions to work with you and not against you.

I am a tweaker and challenger by nature. I learned the value of the left hook -- the probe jab -- and the howling reactions they get, always revealing the strategies of those who seek to keep me back: how they think they can try to impose a false pecking order, what made up garbage they will throw in my face as "proof" of something, and the like.

Over the years, I created my own war manual to help me combat the various war strategies used against people like me. I have read The Art of War and other manuals of the sort in order to gain an understanding of how to fight.

Except those manuals were made for men to be used by men. They are not in tune with women's thought processes, confines, strengths, weaknesses, or experiences.

I realized this problem when I was doing that fateful documentary.

Here were women tweaking the noses of those powerful white men by smoking cigars in the same clubhouse where big deals were being made -- it was a subtle political defiance, but it was often turned in such a way as to sexualize the women thumbing their nose at convention.

At first, it was seen as a threat until a counterpunch of downplaying and trivializing the act seemingly neutralized its symbolic impact. 

Except it did break down a subtle barrier, and did its job.

I know the cigar stench got me thinking about how women had to struggle, especially if they didn't fit some puritanical and Victorian mold. Women were never allowed to be focussed: she had to "have it all": get married, have kids, be perky, and work without ever complaining. She had to smile and be bubbly as she expressed gratitude how lucky she was that some man gave her the time of day, that her children were all perfectly behaved geniuses, and had the best career ever as she looked like a toothpick and injected her face so she never looked her age -- because getting older was a bad thing.

She could drown her sorrows in her wine because at least that looked chic and glamorous with her girl posse who all competed to try to make herself be the most envious of the group.

As a misdirection, it still works extremely well. Any natural bumps or troubles were to be internalized as the woman's failure.

I always said women's greatest strength was also her greatest sin: women have an ability to turn any hell to feel like a paradise, meaning she is enabling every bad thing and taking that burden herself.

If you are in Hell, you do not reward it. If Hell wants to be paradise, it shouldn't be banking on women do to the dirty work.

No wonder there is perpetual trouble in paradise: there is always a hell being hidden if you scratch the surface.

This problem dawned on me very early in my life, and the genesis of my realization began in that smoky, but posh room where I did my filming and interviewing.

Women would push for rights, break a rule or two, and then had no idea what to do once she reached the next level. There are always too many distractions, and so very little guidance.

That has never been the case for men who had centuries to study each other, clinically look at how their forefathers succeeded and failed, and then improve on their methods.

I keep meticulous notes on women in power: I see how they succeeded and broke down a barrier, but then, having no road map, get lost along the way, and then fail.

I do it in order to find a better way -- not to knock or dismiss a woman who worked hard and paved a path. Men have no shortage of books that speak to their own natural and evolutionary rhythms. Women have none -- or they are like me, they have the manual, but don't have it published.

Sometimes women get livid when you collect failures -- but in order not to repeat failures, you have to collect them, analyze them, and see where all the rigs were.

Or else you end up like Hillary Clinton -- a woman who had more supports than any presidential candidate in US history -- and then lose to a man who never ran for public office in his entire life.

She made serious tactical errors: she focussed on the wrong things and ignored the critical ones because she thought she was cunning, never seeing how blind she was to her own self-entitled narrative.

But her rival saw how blind she was and took full advantage of it.

Covering women in power is something journalists never learned to do properly. They either go for the fluffy cheerleader patronizing drivel, or they turn the woman into a dangerous monster who must be stopped.

It is unscientific, childish, and completely uninformative.

Kathleen Wynne is a premier who the press never understood. They didn't understand how she broke barriers to become premier -- and they certainly don't get how she lost power.

Doug Ford shook her confidence with a single question.

But she is a very good strategist, better than the average woman who chases narratives that work against her.

Wynne was focussed. She understood that she didn't have to be everyone's best friend to win: she focussed on several key alliances, and wasn't distracted by the men who were threatened by her because she was breaking their codes one by one.

When she was first elected, I had written to her because I had an issue that was of great interest to me as a writer, and I asked a question about it to her.

To me surprise, she wrote back to me personally, with a very direct, polite answer with a long list of various resources. The problem was none of those remotely touched the actual problem, but she didn't rudely dismiss me, have an underling send me a form letter, or ignore me.

On the other hand, my mother contacted her MPP Andrea Horwath a couple of years ago with a serious issue regarding a problem for the severely disabled. Horwath never spoke directly to her, had an underling call and admit they knew nothing about this issue, but would look into it. He called back a few days later, expressed surprise that yes, this was true and a big problem...and then hung up on her.

My mother's question was a critical one of life and death, and the apathy was horrendous. My question was important, but not in the same league, and Wynne took it seriously and directly, with her response being a couple of pages long. It was more than obvious that someone took the time to research and come up with the best the province had at the time.

Wynne was not like the other politicians. It's easy to see why she succeeded against all odds: she is involved. She has no problem dealing directly with people. She is willing to walk into the eye of the storm and face it.

But she faltered in this campaign, but it is not her doing.

First, she, like many women, had to clean up a mess of a man's making. In this case, her predecessor who jumped ship and abandoned the province when the going got tough. That she could get elected at all five years ago is a real and commendable feat.

That she was a visionary and managed to put her own imprint on policy without merely phoning in is also extraordinary.

We don't have too may female visionaries, particularly not in politics, and especially not in Canadian politics, but Wynne (and Christie Clark) are it.

So what went wrong this time around?

It is the second element that was not in her control: she was in unchartered territory for a woman, and she hedged her bets wrong.

In order to keep the Liberal ship afloat after Dalton McGuinty's chaotic turn as captain, Wynne made strategic alliances with certain groups, who, by theory, should have been grateful. It is often said that campaigns are the time where politicians bribe the electorate with their own tax money, but the tax base was such where the province had to borrow other people's money in order to do it. Those who benefitted the most from the Wynne regime should have understood the nature of the balance, and have sided with the premier who delivered on their unreasonable demands.

But they jumped ship and ran to someone who made bigger promises, even though there will be no way to deliver.

That's the precise trap that ensnared Wynne. If she had been prepared for those predictable and ungrateful defections, she could have been better prepared for it.

Those groups are asking, not thinking. Wynne increased the minimum wage, angering the business sector who would happily chain employees to their desks if they could. They were pleading poverty as they made full-time use of unpaid interns -- including many publications, such as The Walrus. Howling at having to pay employees a decent wage made them livid.

But those who benefitted from that increase didn't bother thanking Wynne. They just went to the NDP who parsed words to imply free dental care, even if that was not what was actually promised. You are not going to get free root canals and bridges. That would bankrupt the province.

What you will get is a vague promise that one of seven dental buses may come to your neighbourhood and do some basic work, like pulling out a bad tooth...but not with a free implant or denture.

Because the idea that you may end up with wages and benefits that would allow you to get your own dental work never crossed the minds of those who got a raise -- and those who also saw a bump in their salaries as a result.

Wynne arrived, delivered...and then got thrown off the stage.

But the news media was blind to it all.

Some saw she was betrayed by her alliances (as I have mentioned as well), but not why this betrayal was significant. Some took pity on her, but she didn't deserve that kind of patronizing abuse. She broke barriers and was focussed, but her troubles began having to try to make a paradise out of a hell -- and when you do that, you start to lose focus.

There are observations about female premiers getting turfed out after one term, but it is not about sex per se: it is about not having the deep roots in governing. It is easy to make money when you come from money: daddy gives you the seed money and connections, and you can lie to yourself that it is your ability, not your family's help, meddling, and legacy.

But when you are an orphan, you do not have people telling you what schools to go to or what Shibboleths to know to be accepted -- or what precise barriers you actually need to break.

We see this with Justin Trudeau: he had daddy Pierre's legacy and operatives to guide him -- and he glided all the way to 22 Sussex -- but once he tried to go toe-to-toe with the US president, he fell flat on his face.

He had the unspoken manual of how to be Prime Minister, but not how to deal with someone who isn't impressed with his cheats, hacks, tricks, and stunts.

But he still has other male leaders to refer to as a guide, even if this scenario is rare. Wynne doesn't.

But she has no shortage of frightened little boys to chastise her in the funny pages. The National Post is doing it, not seeing the big picture because that would require not being a petty little soul. The Hill Times sounds like a jealous little brat not seeing why Wynne's preemptive move was brave -- why would she just go away because her vision is not in tune with the little cowardly boys who think their made-up rules are there to keep their delusions in place?

Wynne was smart enough to get elected. She was brave enough to admit defeat and take control, unlike Clinton who never anticipated that sometimes you are going to lose even when you are blinded by a confirmation bias, missing all of the signs warning you to take a more humble and realistic attitude so you can make workable counter-plans.

It is easy to knock people who dare to bring change and be different, even when it is not convenient or what a passive majority are comfortable with as they never see the obvious storms ahead of them.

Wynne isn't perfect, but neither are you -- or me, but she broke barriers and made it to a level no woman in Ontario ever did.

But for the next woman, she had better be wise enough to take the lessons of the past in order not to make the same mistake -- and bring women back as they are then painted as unteachable and limited.

It will be a lie, of course, but the lessons are there -- and if journalism refuses to chronicle reality, it is up to others to pick up the slack...