The Masks We Wear

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Authors: Kimberly & Alisha

The idea for this podcast came from a conversation that Alisha, CFO at SOS and Naomi the CEO and Founder of JobJar, had about being female entrepreneurs and the insecurities that they sometimes feel as leaders and business owners trying to navigate an ever changing world.  The third voice in the conversation comes from Kimberly, who is part of the SOS team but also runs two businesses in the event space.

Imposter Syndrome

The conversation started here…because we’ve all been there.

According to Harvard Business Review Imposter Syndrome can be defined as - a collection of feelings of inadequacy that persist despite evident success. 'Imposters' suffer from chronic self-doubt and a sense of intellectual fraudulence that override any feelings of success or external proof of their competence. 

This definition resonated with all three because in their own ways they all have had challenges seeing themselves as successful, being confident as leaders and accepting compliments.  Why is that?  Is it because they are women and that’s the way that they were brought up? Is it that they are TOO Canadian?  We don’t know... but it’s real. Kimberly likened it to a little green demon sitting on her shoulder whispering in her ear that she’s not worthy even though intellectually she knows that she has the requisite skills, experience and smarts to complete the task at hand. Alisha acknowledged that she has a tendency to brush off compliments and even respond with self-deprecating statements rather than taking it as a good thing and actually allowing herself to feel a moment of pride. Everyone could relate to that because they all had done the exact same thing...as if pride was a four letter word...which it is not.

The world is evolving but women are still far from being treated as true equals in many circumstances and that adds to this feeling of insecurity. It was 1960 when the last province in Canada gave women the right to vote. Let that sink in...1960. (see a timeline HERE) It’s no wonder that some women are finding it hard to lead with confidence when many were raised with the stereotypical gender roles perpetuated in media, advertising, government and the workplace. Challenging those norms and presenting as a strong, intelligent and worthy leader requires some reprogramming of those gender roles...for all parties involved.

Both Naomi and Kimberly shared that at various points in their lives and careers, these feelings of self doubt have not only manifested themselves emotionally but also physically. For Naomi it was panic attacks and for Kimberly it led to ulcers and stomach issues. They both have learned to manage these moments of self-doubt so their effect isn’t as deeply felt, but it doesn’t mean they don't still happen.  Sometimes you just need to put on a brave face. 

Behind the Mask

In order to determine what is actually going on behind our mask, we need to define what our masks are. Within the context of this conversation, our masks are our “work personas”. Our masks say “leader” across them; leading within our teams, our industries, and our communities. So as women who lead, what is going on behind the masks? There seems to be a lot of ‘fake it till you make it’ and some guilt around that. As the conversation progressed, the trio recognized that in actuality, everyone is faking it until they make it, to some extent. With the exception of those who have had a similar role for a number of years. And I do believe those folks, with the experience, are looking at the rest of us with a measure of grace. Behind our masks, we may not understand deeply, that the ones who have learned the hard lessons won’t begrudge the rest of us the opportunity to learn from our mistakes as well.

Behind our masks we also seem to be focusing on the gaps. We discussed the fact that men will apply for a job having 4 or 6 of the 10 required skills, knowing full well that they can learn the remaining skills. Women are more likely to see the gaps as a reason not to move forward. So I think that is a key learning, a key take away - it’s not over confident or hubristic to assume we can learn new skills as well. It’s not a gap so much as an opportunity.

We talked about how women do, at the end of the day, just need to get the job done - to execute efficiently. So where does the idea of authentic leadership come into play? Do we show up and lead in a way that moves the organization forward - because that is what our employees, vendors, shareholders, and stakeholders need from us? Or do we draw a line in the sand. Take off our masks and show up as “Alisha” or “Kim” or “Naomi” - a person, not only a “leader”, and hope that as others adjust to the resulting new dynamics - a more authentic style of leadership follows?

Naomi noticed that in her organization, the majority of the concerns were being put on her. Although this is part and parcel of business ownership, there were opportunities to ease the pressure she was feeling. A pressure that was to an extent, self imposed. Once she admitted where she was struggling, it became a group effort to figure things out. They became more of a team, and with that pressure eased, she could show up in a more authentic way. Leading as Naomi and not as ‘the boss’. 


We ended this amazing conversation agreeing that the levels at which we remove our masks was individual to each person and what felt right for each leader. There is also an opportunity to optimize on gender roles. Alisha, painting with broad strokes, noted that many men genuinely like to help and fix. It could be as simply asking for what we need, so we may lead more authentically. As impostor syndrome is linked to many other physical and mental illnesses, we may be overdue in embracing authentic leadership, even though the vulnerability required can feel uncomfortable. 

We hope that this conversation sparks a bit of introspection. And maybe a willingness to be more open and authentic with the people around us, especially when in a leadership position. With a little practice and patience, we can peel those masks off one by one.


Joel Olandesca