Confidence walks into a bar like it owns the place.

What are we really enamoured with?

Confidence is the same as New Year’s Eve.

It’s got its feet up on the coffee table, childhood trophies on display, and a business card that says something excruciating (eg: Wielder of the Magic¹). Confidence has zero investment in what you care about; it’s too busy working on its golf swing. Confidence listens to Diary of a CEO and secretly dreams of being on The Apprentice and becoming best friends with Alan Sugar Daddy. Crossfit and Keto? Duh. Of course it’s invested in BitCoin.

Confidence is a bit of an arsehole, actually. My Gran would say: ‘all mouth, no trousers’.

Is it just me, or do words have complete personalities?!

IS CONFIDENCE CALLED DAVID??!

Call me Dave.

Let’s call this kind of confidence what it is: privileged entitlement. And this matters because privilege and entitlement literally run Britain.

A 2013 report into why more students from Wales weren’t getting to Oxford said they ‘lacked Oxbridge confidence’.

While more recent stats suggest some aspects are improving (almost 30% of places in 2023 went to BAME students), real change is agonisingly slow: 80% of offers went to the top two social groups, with most going to residents in London and southeast England.

This matters because Oxbridge graduates are in charge of an incalculable number of decisions that affect every single one of us. In particular, those with an Oxford PPE (Philosophy, Politics, and Economics) degree hold leadership roles across all conceivable industries in the United Kingdom. 

It’s jarring to consider how this plays out behind the scenes of everyday working life.

(Sidenote: a quick scan of the Googler suggests this pattern is largely true for every Western country, but my research is primarily based in the UK, so I’m on much more comfortable ground discussing Team GB).

In my mid-thirties, I worked at a central government department.

There were PPEs up the wazoo. Working there was a bit like being on the set of a dramatised Evelyn Waugh novel: the cut-glass accents, traditions and language, and because it was the mid-2000s, many loooong lunches in restaurants with white tablecloths.

It was one of those contracts where ‘a short piece of consulting’ led to increasingly complex problems to solve, and difficult conversations the actual leadership team didn’t want to have. (Confidence does not do its own dirty work).

(Sidenote: At the time, it was thrilling to be in board meetings that always had one eye on a Daily Mail/Private Eye front page. Plus, back then, I was fuelled by an Olympic-sized thirst for validation, so I kept saying, ‘Of course!’ and overworked to the point of catastrophic burnout and eventually had to leave the actual country to recover).

I was often shoulder-tapped for ‘a cup of tea offsite?’ and found myself with a ring-side seat into the inner worlds of the confident, privileged and entitled (more than one was named David).

They confided in me about office politics (THE GOSSIP!), the extreme politeness that hid the seething hatred of colleagues they’d known since school. I was privy to the details of an astonishing number of affairs and divorces. (Confidence is always looking to ‘trade up’).

I once asked a colleague - in a rare moment of vulnerability - why I was the one they turned to. He took a gulp of red wine, dabbed his lip on a linen napkin, looked me directly in the breasts and said: ‘You, my delightful creature - you are quite a rare thing. An Antipodean - utterly unable to be boxed! You may as well be Scottish’.²

And then he chuckled at his little joke. (Confidence laughs at its own jokes).

My sense now (after almost twenty years) is that most of my colleagues were quite lonely and a bit resigned to the class system of traditional expectations and a predictable path. I can see how calcifying privilege and entitlement was for them.

Given that so many were sent to boarding school before the age of ten, it’s' not quantum physics to see how this horrific separation echoed well into adulthood. A good show of confidence was likely a long-established and effective armour against vulnerability, emotional turmoil, and doubt.

When everything on the outside suggests you have ‘made it’, understanding why life doesn’t feel meaningful, fulfilling, or even joyful can be tricky. I suspect just the idea of giving up any of the benefits they hadn't earned in order to pursue their heart desires would have seemed unthinkable.

I'm left wondering if we can ever really connect with someone when they are wearing a mask of confidence.

The one question I am repeatedly asked is: How can I feel more confident?!

I completely understand why the answer feels so important, but I think this might be the wrong question to ask.

After researching self-doubt and coaching with hundreds of women over the years, I’ve found that so many of our experiences of self-doubt, imposter syndrome, and a lack of professional confidence are symptoms of the systems, institutions and organisations we work in.

Like, maybe it’s not you?!

Here are some findings that can help:

We are qualified enough. Across the Western world, women out-educate men across all learning environments,³ from workplace skills training to graduate degrees⁴, but these qualifications have not resulted in a comparable rise in access to positions of power.

We are capable enough. Despite our qualifications, skills and experience, people of colour, women and other marginalised groups are not only systematically deprived of access to power, but actively encouraged by those systems to judge our own abilities or each other and never the systems themselves. Hello Tools of the HR Sausage Machine that rank, spank and yank us.

We work hard enough. Collectivism is actively discouraged in the working world. This is evidenced in subtle and overt ways, including zero-hours contracts, the gig economy, unpaid internships, and the derision of Unions. It’s also wildly pronounced in side-hustle culture. For those not in work, it’s embedded in the often humiliating assessment process for benefit suitability. We are encouraged to remain in a self-identified loop of competition, individualism, and never-enoughness. 

It’s not that you aren’t doing enough to feel worthy of a seat at the table - it’s that the table was never built with someone like you in mind.

In the UK Civil Service, this used to be known as The Peter Principle, where ‘every employee rises to his level of incompetence’. A few years ago, I had a lush podcast conversation with Professor Tom Schuller about the consistent opposite pattern for women.

While researching for his book ‘The Paula Principle’, Tom found that regardless of our experience, skill, educational attainment, or the organisation’s stated values – women work BELOW their competence.

We understandably prize confidence as the panacea for our doubts and worries - especially at work.

I’ve seen first-hand that having a lot of natural confidence and the entitlement and privilege that comes with it often does not guarantee satisfaction.

So what are we actually enamoured with? What is it we think confidence will bring us? What if that was a lie?

By the way, I do think there is somewhere in between the blitheness of confidence and the defeat of self-doubt.

More on that in the next one x

1. Actually worked with this guy.

2. According to my journal from the time, this is exactly what happened. Those decades before #metoo. Vom.

3. Has Higher Education Solved the Problem? Examining the Gender Wage Gap of Recent College Graduates Entering the Workplace

4. OECD Report: The Persistence of Gender Gaps on Education and Skills.