Entrepreneurs

How the 10 Masks You’re Still Wearing Hurt You and Your Business


9 min read

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Wearing a mask started with Covid and will end, hopefully, with Covid.

Right? 

Wrong!

We’ve worn a mask that impacts our careers, relationships and sense of self long before a global pandemic forced us to learn how to smile with our eyes. But if I’m not talking about the non-breathable cloth prisons my friend refers to as “face panties,” which masks am I talking about? 

More importantly, how do we take them off?

What is a mask?

No one gets out of childhood without the battle scars of living in an imperfect world with imperfect caregivers. Growing up, we find ways to control the ways others experience us to reduce the chances of getting hurt. A mask is a defense mechanism or coping strategy we develop to ensure security, safety and love. 

Masks have an energetic quality to them; they’re our attempt to force people to feel a certain way about us or treat us in a particular way. Often masks are so deeply ingrained that we refer to them as our personality.

Confusing a mask for a personality trait is a slippery slope that can leave us feeling inauthentic, guarded and even a little desperate. How could we not feel like a fraud? We’re acting a role because, at the core, we don’t believe that being ourselves is safe or enough.

Think about masks from an entrepreneurial perspective; if a defense mechanism you developed at age seven to make sure your dad loved you affects how you operate in business, you’re not a brave and thriving adult. You’re a surviving wounded child. That’s something you want to be aware of so you can move beyond fear in the way you approach your work and other people.

Related: How a Childhood Incident Created His Unhealthy Drive for Success

Here are ten common masks. The big question is which mask, or masks, are you wearing? 

1. The Sled Dog

Some people guarantee their survival by making their value visible and undeniable. At work, the Sled Dog is the first to arrive and last to leave. She is positively reinforced for her work ethic, but her effort isn’t generous; it’s desperate. Working “the hardest” is a smart way to impress people, and validated by our societal definition of success, but the extreme effort is rooted in feeling unworthy, unloveable or even like a disappointment. Acting like a Sled Dog can also have severe health implications.

Real-world example: The Sled Dog lets everyone in the Slack general channel know she’s clocking in on a Sunday for three hours. Wait, seven! 

2. The Perfectionist

The Perfectionist doesn’t care about doing good work. He cares about doing perfect work, a common response to the fear of annihilation. Trying to be perfect manufactures a false sense of dominance, safety and control; it’s a way to mitigate the anxiety of what might happen if we don’t cover all bases. Some Perfectionists grow up in households where love and attention are held ransom and exchanged for achievement. Some grow up gifted where success is assumed, creating a huge amount of pressure to appear perfect. Most Perfectionists are allergic to vulnerability. Perfectionism creates a rigid, fearful life that is often painful to inhabit. Joy isn’t common.

Real-world example: The Perfectionist pours hours into a presentation, refuses help, rehearses endlessly, notices a spelling mistake on a slide mid-meeting, spirals and goes home feeling humiliated and scared.

3. The Martyr

Unfortunately, many people grew up with a model Martyr: their mother. Traditionally, a woman’s worth was defined by serving others, regardless of personal cost; martyrdom runs in a woman’s blood. Selfless actions are underpinned by the exaggerated and loud vocalization of sacrifice. The Martyr has the ability to make herself indispensable. Everyone around her feels indebted and uncomfortable. Don’t think for a moment this is a woman-only thing.

Real-world example: The Martyr picks up all the terrible jobs no one else wants to do, then subtly tells everyone how she didn’t sleep or eat all week. 

4. The Bully

The playground definition of the Bully holds; those who were made to feel powerless become the ones who pin others down. The Bully controls his environment and other people through dominance, a response to deep-seated fragility or fear. At some point, all Bullies have felt powerless. They can be as subtle as they are overt in their flexing of power and might bend the rules to get what they need. The common thread is fear.

Real-world example: The Bully talks down, over and about his co-worker in a meeting. His colleagues witness the power move and adjust their behavior to avoid being publicly shamed in the next Zoom call.

Related: Effectively Addressing a Workplace Bully

5. The Robot

A Robot doesn’t allow herself to show any emotion at all. While this “strength” is often applauded, stoicism to this degree is toxic, a response to having feelings invalidated or shamed. To those watching, the Robot appears unflappable. Below the surface, she’s endlessly swallowing, sitting on and fermenting unprocessed emotions with no safe place to detonate the bomb. Steeling up to this extent is deeply dehumanizing. Poison starts to leak.

Real-world example: The Robot is the star performer at work, but goes home and binges on food until she passes out. Finally, the pressure is released.

6. The Control Freak

There are spreadsheets. And then there are spreadsheets. While organization is a useful skill, the Control Freak weaponizes it in a bid to manage her environment and control all outcomes. Rigidity is often a trauma response to feelings of chaos and instability growing up. By organizing the outside world, the Control Freak manufactures an illusion of security, but will quickly dissolve into panic when her system starts to break.

Real-world example: The Control Freak appoints herself to redesign the social strategy for the startup. She hands over the design templates and content plan, but people start going off-script. She gets so worked up she makes herself ill and has to take two days off to recover.

7. The Doormat

The horizontal description of this mask is intentional and hierarchy is implied. The Doormat is a relentless people-pleaser. He abandons his thoughts, beliefs, values and needs to make sure someone else is happy, which is often a response to having his needs systematically ignored or invalidated. The throughline: If I’m adaptable and no-drama, they won’t hate me, or leave. Trampling can get very painful.

Real-world example: The Doormat asks to meet at 9 a.m. for 60 minutes. His colleague says, “Make it 8am for 90.” The Doormat says “Ok, sure” even though that involves cancelling a doctor’s appointment, calling to see if his dog walker is available and missing breakfast.

8. The Sour Skittle

The Sour Skittle is endlessly cynical and doesn’t trust anyone or anything. It’s her job to poke holes and find fault. The Sour Skittle relentlessly voices reasons why something won’t work to avoid disappointment or rejection, or to maintain a status quo she is comfortable with. She’s most comfortable assuming the worst, which is often a response to being denied the chance to dream and play.

Real-world example: A freelancer writes some really creative copy for the new website. The Sour Skittle shoots it down, finds 17 reasons why it’s off brand and makes sure to point out the incorrect use of a semicolon.

9. The Drama King

The Drama King gets attention by making mountains out of molehills and uses drama to get attention or validation. He wants eyes on him. The Drama King sometimes manufactures chaos so he can ride in on his stallion and save the day, proving his worth and ensuring others notice his talents. Doing flashy things to get noticed is often a response to not feeling seen or important growing up.

Real-world example: The Drama King notices his colleague getting a lot of praise. He creates a fire with a client, escalates it, then miraculously puts the fire out. The Drama King gets publicly applauded for his heroics.

Related: 4 Messaging Techniques to Help Defuse Workplace Drama

10. The Comedian

Humor is both a fun way to connect with others and a powerful weapon to reduce the importance, relevance, or depth of an idea, conversation, or relationship. The Comedian always wants to stay light because she’s terrified of anyone penetrating her shield. She’s often hiding something deep, dark or shameful. While the Comedian might be popular and a masterful avoider of conflict, she’s often the person no one knows anything about. 

Real-world example: At a writing workshop, the Comedian is asked what she’s most scared of when it comes to sharing her work. She laughs, sticks out her bottom lip, and in a baby voice says, “My dog won’t love me.” 

How do you take a mask off?

Start with awareness. Imagine you’re watching a movie of your life and observe how you act in situations where things like worth, respect, success and love are on the line. Reflect on how you got attention or were validated growing up; you’re applying this same success blueprint through the masks you’re most commonly wearing.

Start noticing the masks other people wear. This can help build compassion for others and personal insight, especially if their masks activate you!

At the end of the day, a mask is a well-worn tool we used to get our needs met when we were young. But continuing to wear a mask without challenging it, especially when it’s causing personal disconnection and pain, is the equivalent of bringing our favorite childhood snake toy called Sammy to meetings for emotional support. It’s time to evolve. Once you’re aware of which masks you wear, you can practice moving beyond the limitations of defense mechanisms to give yourself a chance to gather evidence that you don’t have to perform or sacrifice yourself in order to be successful, liked and respected.

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