I Hate Oprah: Why We Need More Work-in-Progress Leaders
By: Leah Hunt
Tags: Personal Growth, Professional Development, Coaching, Leadership, Humour

Not a perfect replica of my jean jacket — but close enough (Licensed from Adobe Stock)p

Oprah has always hit a nerve with me. For my generation, especially women, Oprah was more than a successful role model and leader, she was a force to be reckoned with. Everyone loves Oprah and I kinda’ hate her and I never really understood why.

I inconsistently watched her show, heard a lot about her background and read all the books in her Book Club but I was never a ‘fan’. I have heard her very compelling story — a youth of struggle and abuse and her very real ongoing personal and professional struggles. I understand and appreciate her contributions to breaking down barriers for women. She has tackled sensitive issues and been transparent and vulnerable about her own experiences. She has enabled others development — authors, filmmakers and developing professionals, straight shooting rednecks (you’re the best Dr. Phil!) — paying her success forward in so many ways. Rationally, by my own argument above, she is someone to be lauded and admired. Yet I did not have that doe-eyed admiration and I am left asking the question I ask so often: What the hell is wrong with me?

At the ripe old age of 40, I am finally figuring somethings out. With life experience, confidence, two kids and a mortgage, I now wear floppy hats out the sun instead of Hawaiian Tropic, fall asleep on the couch before the 10 o’clock news is over and shout things like “Do you have underwear on?” and “Don’t put chocolate milk on your cereal!” At this point, the only thing that makes me feel young is the occasional outbreak of middle-aged acne (thanks universe) It isn’t all downside though. That little bit of experience and perspective means I can properly think about what I react to — positively or negatively — and why. I have always had such an intensely negative reaction to Oprah and, upon reflection, a handful of other super impressive women — so what’s my problem? Am I jealous and bitter? Do I feel inferior and like I have so far to go? Do I feel like I am so far behind and everyday others move forward and I’m standing still? Do I feel like they have faced so much more adversity while I have largely lived a life of advantage and that this fact alone makes me even pathetic? (pick 3…I can’t decide which one to cut but go with three thoughts)

In a word — Yes. All these things. When viewed as a race, they aren’t just beating me. They are kicking my ass.

If I back it up and frame it less like a race and more like an athletic competition — a competition where there are different weight classes and categories, where like athletes compete with like athletes and each person decides whether they want to go to the Olympics if the rec-league is okay — I start to feel differently. Suddenly, the women that I have looked at and indirectly compared myself to cease to be the ‘other’ and start to be a group of real people. People who are the culmination of choices they have made, the experiences they have endured and the effort they have invested. They are what they have done and I can admire and appreciate that regardless of the finished product.

At 38 I am clear and confident about my choices. I am letting go of the jealousy and resentment of others who are, at first glance, kicking my ass. The truth is they are not beating me — some of them aren’t in my weight class, some of them are ‘all-around-athletes’ which is not what I want to be, and some are killing it but in a domain that I don’t care about. I want to be able to appreciate what they contribute without becoming distracted or demotivated by it. They aren’t my competition — they are just other athletes trying to hone their skills. This is the distinction that I think many of us fail to make — and I continue to struggle with. Perspective sometimes arrives in a moment of grace. Retaining that perspective and applying it to your thoughts and daily life requires effort.

I think it took me 38 years to figure this out for a couple of reasons. First is that there is a culture of success and perception control and in the age of social media we have more and more influence our public persona. I call this the Facebook Family phenomenon. This is created by folks who post perfect family photos and use #blessed all the time; meanwhile I am in a full sweat trying to get out the door shouting “Put your boots on!” and trying to scrape the yogurt off my suit jacket. Not enough people are talking about their struggles and their screw-ups and when they really got it wrong. Ultimately, they will talk about it in their biographies but only if they make it and are successful enough to write a biography and now the failure is just an anecdote to an overall ‘leadership journey’. I want us to start talking about our failures now and not in self-congratulatory humble-brag kind of way. Stuff we screwed up in the last two years or, in my case, two days. We learn the most from the mistakes of others; hearing and learning those lessons without having to endure that pain or setback gives a kind of perspective that is priceless. Anyone with an effective and authentic mentoring relationship knows this deep in their bones. Here’s the rub — Not enough of us have those mentors because we are too intimidated by supposedly perfect leaders.

The second reason is that leaders are often presented as the finished product. They don’t pop up with a baseball card of stats outlining all the choices they have made, the mistakes and failures they have endured and the raw effort they have invested. They are held up as success stories, as examples of what is possible ‘if you really put your mind to it’ and ‘lean in’. The implication is that it is either brute-force effort and willpower and if we all just work harder, anything is within our grasp. The alternate implication is that leaders are pre-destined to greatness. I think that’s rubbish. I think it is far more strategic and a lot messier. I think making leaders is like making sausage and I want to see how the sausage is made. Young and aspiring leaders need to see how the sausage is made because it is gross and ugly and probably not all the sausages turn out. There are also lots of different kinds of sausage — spicy, mild, big BBQ versions and small delicate versions. Hell, I think there are even tofu sausages.

At 38 I am working to understand myself, make choices that work for me and then looking to see who has or is making similar choices. Then it becomes a case of finding others competing in our sport, our weight-class, our league or the league we aspire to. These are the people who should our inspiration and our mentors and our heroes. Lots of amazing people do amazing things but is that the amazing thing you want to do? It doesn’t mean you have to hate them or resent them or rip them down. Rather acknowledge it and move on; as Amy Poehler describes in her brilliant biography Yes, Please it’s okay to say “Good for you, not for me”.

What I need — what I think we can be to each other — are ‘Work-in-Progress’ leaders. Other people who are training hard, climbing up whatever hill and tripping and falling and getting muddy along the way. Elite athletes look to train with people who are like them and also better than them and leadership can be the same.

Oprah is still competing and while it might be in a different category, I can objectively appreciate she has always sought out competition to make her better. So my reaction was not to her as a person, it was frustration with having a two-dimensional understanding of what makes her successful. Not only was I competing with someone in a different sport and weight class than me, I was competing with a made-up cardboard cut-out of her, a caricature of a real person. At 38, I know how distracting and silly that is.

I don’t really hate Oprah. The truth is I don’t really hate anyone — except for the girl in high-school who came to the house party I threw (and got busted for) and took my acid-washed jean jacket. I will hate her until the day I die.

I just want to see the sausage. And get that jean jacket back