Leadership, Authenticity, and Shame

Rachel Happe
7 min readOct 26, 2020


Authenticity is Infectious — Me with business friends (and colleagues, partners, clients)

I have been thinking a lot about leadership. It took me decades to even think about what leadership meant — especially as it applies to me. I was raised in a world where acknowledged leaders neither looked like me nor had similar social positions and roles. Clearly, I could not be a leader — so why think about it?

Over the past decade, the denial of leadership became problematic — because more people, and more influential people, started to pay attention to what I said. Other people treated me like a leader well before I considered myself to be one — and that created conflict. My words had more impact than I ever imagined they would and in unexpected ways — and sometimes in ways that were hurtful. Others started to confess they felt intimidated by me. Internally I still felt like an awkward 20-year-old who was not taken seriously so I sometimes dismissed the feedback. It’s not that I had never had what might be considered leadership roles — I was a product executive at two start-ups — but I was always the only woman in management and board meetings and I rarely felt influential.

Recently, I ran across a thread about how a male and female switched names when dealing with customers and it gave me a perspective I had never considered — and grace in how I thought about myself. I have always felt like that I am argumentative and challenging — it has generally just been a given, part of an immutable piece of my personality. For the first time, I considered an alternate truth: Maybe the only reason I am challenging is because I am often challenged. For most of my career in technology and business, I have rarely offered an opinion that was readily accepted — I always had to prove it. In some ways, it is not surprising I became an analyst because it gave me data to justify my perspective. When I was a product executive I lost battles about product decisions to engineers and engineering team leaders (male… of course) when I knew I was right. I don’t say that with ego — I just knew I had more up-to-date experience about how to architect applications. It did not matter — if I wanted to be heard I had to push back, often repeatedly. The fascinating thing is that is sometimes, the engineers were so behind that they had no idea what they didn’t know — and yet were confident that they were right. Ignorance is bliss.

I got out of managing technology and while I did not do so explicitly because I wasn’t being listened to, in hindsight it may be what compounded in such a way that I decided I could no longer succeed in technology companies. It was a work environment where I couldn’t be authentic and respected. When I had a miscarriage, I quickly scheduled surgery so I could present at an important board meeting rather than ask to be excused. Looking back on that, it makes me angry but, at the time, faced with a group of ten 50–70-year-old white men it just didn’t feel comfortable. I did tell the CEO, my boss at the time, who should have insisted on covering for me but he was unsure of the right approach. For me adequately explaining my absence would have made things…. awkward. My colleagues would have avoided talking to me. However, in not excusing myself I robbed myself of authenticity. There were issues and stress that were impacting my work that I did not feel I could share. Being emotionally closed reduced my ability to connect with others, which then impacted my ability to lead and influence. My reduced ability to lead impacted my opportunities. It was a negative feedback loop that affected my potential and my career — in this situation and many others like it.

People from underrepresented groups of all kinds face similar dilemmas every day. I suspect this is a large part of what creates the ‘pipeline problem’ because women, BIPOC, gay, and transgendered people are all faced with a point in their careers where they have to decide to betray themselves in order to “succeed” in a mainstream career or they accept that most work cultures do not support them and find more creative careers where they have to compromise their financial success for authenticity.

The irony is that mainstream work cultures don’t work for white men either — because people are not machines. We are all gloriously unique. But our current model of organizational governance has no room for diversity — it treats everyone like a standardized part, boxing people in and enforcing conformity. White, straight men can more easily force themselves into the mold but they too have to conform and sacrifice or hide pieces of themselves or risk social unease to fit into mainstream work cultures.

For marginalized groups, mainstream work environments are much riskier. Because white men tend to be listened to, when they are vulnerable or caring it is seen as a strength. For others it is almost impossible to be vulnerable — because they are often not listened to in the first place, never mind given the benefit of the doubt — or support — when they falter. It makes the personal cost of authenticity much higher.

And yet, authenticity is also where we find our power as humans — because power is generated with we deeply connect with others. It is what drives engagement and trust. It is one of the greatest tools of influence. It is a critical element of leadership.

Tanmay Vora, who does lovely graphic renditions of leadership perspectives, recently created this graphic from some of Peter Drucker’s work on self-management.

My reaction to it was that it was 100% accurate and yet missed entirely this power differential that makes articulating and pursuing this easier for some than for others.

Without authenticity, it is also difficult to become more self-aware. You discover yourself through your interactions with others. Their reactions and feedback help you understand who you are, what your strengths and weaknesses are, how you perform, and where you belong. If you are not able to bring your full self to your relationships, you will not get accurate feedback — and you may completely miss some aspects of your unique value.

Growing up, I was too loud and had too much to say at home. At school I was bored, distracted, or daydreaming — I honestly don’t remember much of school. It didn’t engage me. Even leaving college, I had no idea what my unique strengths were. I discovered recently, that much of it was likely in large part due to pronounced ADHD, which makes me think differently and process more quickly. It wasn’t until I started working — and working with some amazing women in particular — that I started to better understand I was a great analyst, systems designer, technologist, and business strategist.

In a world where your perspective is discounted, and you are not often given the benefit of the doubt it is impossible to be modestly confident and deeply authentic — the two things that are absolute requirements for good leadership and relationships.

Like others in my position, I left mainstream work environments because I was not able to be myself. Being free to follow my strengths and interests for a decade has opened up immense opportunities and the more I can be myself, the more I connect with others. The more I connect with others, the more I see my own value, and the more I can be myself.

The impact of authenticity and it is both mundane and profound. It makes it much easier to share my thoughts, I am more aligned with my work, and I understand my strengths and weaknesses. More than anything, I am comfortable with myself. I am confident in spite of my weaknesses and I can openly admit to them — knowing that others will appreciate understanding what I can and cannot do. I am not as defensive or competitive as I once was. I can now compassionately accept my flaws and failures — waking up and starting new days anew and reaching out to collaborate with people who complement me in ways that make us both better.

People are drawn into that confidence and authenticity. I have a network of amazing individuals who I consider colleagues and friends. I have other women reach out to me because they feel the pull of my authenticity, wondering how they can get there too. I have more women who would like to work with me than I can ever hire. Potential clients are drawn to the power of that authenticity — because my purpose is clear without the frenetic need to prove myself and the latitude to appreciate and incorporate other perspectives without getting defensive.

The biggest lesson for me though is this: there are a lot of people and a lot of opportunities in this world. You can approach finding them in two ways; you can either try to fit yourself into what you think others want or you can be unapologetically yourself, which will draw in people who are excited by your vision and energy. Pursuing what gives you joy and meaning is contagious. People want what you are having.

In the end, being yourself is your only option.

For more reading on this, check out Nilofer Merchant’s book, The Power of Onlyness