1 » THE TWO JOBS Take Off Your Leadership Costume

Everything worthwhile in life is won through surmounting the associated negative experience. Any attempt to escape the negative, to avoid it or squash it or silence it, only backfires. The avoidance of suffering is a form of suffering. The avoidance of struggle is a struggle. The denial of failure is failure. Hiding what is shameful is itself a form of shame.

MARK MANSON, The Subtle Art of Not Giving a F*ck

“Mass, you’re the best facilitator we’ve ever seen.” As the head of global leadership development at Slalom Consulting, an international business and technology consulting firm, I traveled across the United States, collaborating with some of the brightest leaders in our organization. Many people praised my facilitation skills, often referring to me as a “sage on the stage.” I was privileged to witness their growth and development firsthand. It was easy to get caught up in the admiration and mistakenly claim their progress as my own.

In my pursuit to enhance my skills, I voluntarily participated in a 360 assessment just like Dan Harris, whose story I shared in the introduction. This evaluation tool is well known for its harsh but honest feedback. Despite the accolades and recognition I received while on the job, the assessment painted a starkly different picture. The results clearly labeled me as an ineffective manager. The person responsible for growing all the leaders in the organization was objectively a bad leader. The irony was (almost) funny. Feedback highlighted my controlling and defensive demeanor, with one courageous employee even describing me as a bully.

I was devastated. The feedback felt like a savage punch to the gut, making me feel like I was about to throw up. So I did what any logical person would do—I defended myself: I’m not defensive. You’re defensive for saying that I’m defensive. I was completely oblivious to how incredibly defensive my defense sounded. That’s how shockingly unaware I was. At some level, I knew they were right, but it seemed almost impossible for me to process. I struggled to reconcile the image people had of me with my self-perception. Immediately, I went into problem-solving mode. I was a leadership expert. I could fix this!

I was committed to leveraging the skills and tools I used to help others grow and apply them to myself. I had the best intentions. I tried so hard. For months. When I was called in for a follow-up conversation with my manager six months later, I was cautiously hopeful. I thought she was going to say: “You’ve made a lot of progress. We’re really proud of you.” She didn’t. My manager acknowledged my genuine attempts to change but emphasized that it hadn’t translated into a perceptible improvement in the team dynamics. Instead, she told me the team felt the same way about me as they had six months before. I felt crushed all over again. I was trying as hard as I could without making significant progress.

Even if our backgrounds and specific situations are different, maybe you can relate. Have you ever felt like this?

• » I’m the only one struggling with this challenge.
• » I need to be the smartest or most dominant person in the meeting.
• » Nothing I do is ever good enough.
• » I feel overwhelmed by constant to-do lists and overly organized fun.
• » I have to compensate for other people (finish what they started, get people to make progress, clean up after everyone).
• » I constantly have to prove myself at work or in my personal life.
• » I can rarely focus on anything for too long.
• » I feel lonely despite being surrounded by people I love and care about.
• » I expect things to go wrong and anticipate having to fix them.
• » I believe, deep down, that the world is against me.
• » I tend to put people into boxes and attach rigid labels.

The stories and beliefs we unquestioningly accept as true speak to our deepest fears of not being good enough. Core to our identity, they are so ingrained that it’s hard to question their validity. In a threat situation—big or small, real or imagined—these core beliefs come to the “rescue” to keep us safe (or employed). But these fears and stories also cause many leaders to take on a second full-time job in addition to the already challenging position listed in their job title.

THE SECOND FULL-TIME JOB: THE SINGLE BIGGEST WASTE OF ORGANIZATIONAL RESOURCES

According to developmental psychologists Robert Kegan and Lisa Lahey, all of us are working two jobs instead of one.5 The first job is the one we’re hired to do. It’s the job our companies pay us for, consisting of our duties and responsibilities, the targets and objectives we’re expected to meet, and the official role we perform. But on top of that, every one of us holds a secret second job. This second job consists of the energy and time we spend hiding, masking, and pretending in an effort to cover our weaknesses and manage other people’s impressions of us. It entails showing only our best side, playing politics, and hiding uncertainties, inadequacies, and limitations.

A 2014 Harvard Business Review article explains “covering” as behavior employees use to mask or hide certain parts of their identities, personalities, or struggles. While this behavior disproportionately affects minority groups, it impacts everyone. Authors Dorie Clark and Christie Smith report that 61 percent of employees admit to covering: “A gay person might be technically out, but not display pictures of their partner at work. A working mom might never talk about her kids, so as to appear ‘serious’ about her career. A straight white man—45% of whom also report covering—might keep quiet about a mental health issue he’s facing.”

Our drive to belong to a family, community, crew, or organization often overrides our desire to be true to ourselves. “Covering” or hiding our true identity and self is shockingly common and adversely impacts us, our peers, and our employees.

This second job was exactly what I was doing. Before the inevitable confrontation with the feedback, I’d spent years of my life and massive amounts of energy attempting to hide my challenges. The silly thing is I was doing it in plain sight. Everyone else could see it. We can often spot this behavior in others while being blind to our own charade.

Kegan and Lahey explain that people expend vast efforts “covering up their weaknesses, managing other people’s impressions of them, showing themselves to their best advantage, playing politics, hiding their inadequacies, hiding their uncertainties, hiding their limitations. Hiding. We regard this as the single biggest loss of resources that organizations suffer every day. Is anything more valuable to a company than how its people spend their energies? The total cost of this waste is simple to state and staggering to contemplate: it prevents organizations and the people who work in them, from reaching their full potential.”6

Covering is a lose-lose proposition for employees and employers alike. As an employee, you may feel as if you’re living the life of a double agent, always stressed about doing the job you were hired for plus your second job of hiding your true self. Think about this: the single biggest cause of burnout is not overload but a work environment that forces a prolonged lack of personal growth. As an employer, you’re missing out on the full contribution and impact your employees could make while simultaneously having to absorb the cost of their secret limitations. Kegan and Lahey remind us that we humans are just as wired for self-protection as we are for psychological growth and development. Often this urge to protect ourselves leads to rigidity and an unwillingness to change, even if our current approach causes significant damage.

If you relate to this and think you and your team are engaged in this form of hiding and self-protection, it’s essential to recognize that this pattern may be a manifestation of a lack of trust and psychological safety in the work environment. It’s natural to want to hide our weaknesses, and acknowledging this behavior is the first step to emerging from the shadows. We all replay outdated stories and limiting beliefs about ourselves in our heads. We listen to these inner critics, even when they’re brutally judgmental, and these voices and fear-based thoughts can cause real damage. However, we often forget that they’re based on good intentions and attempts to keep us safe. That’s why I’ve coined the term “well-intentioned, misinformed protectors,” or WIMPs.

WELL-INTENTIONED, MISINFORMED PROTECTORS: YOUR LEADERSHIP KRYPTONITE

We often expect leaders to be heroes with superpowers: X-ray vision to foresee problems, telepathy to understand every team member’s needs, flexibility to adapt to diverse challenges, and stamina to endure relentless demands. This idealized view of leadership creates an unrealistic expectation of infallibility and invulnerability.

In the face of these expectations, our WIMPs play a critical and often misunderstood role by serving as a sort of armor, or leadership costume. I’ve identified six main types of WIMPs: the perfectionist, the hard-ass, the achiever, the people pleaser, the imposter, and the contrarian.

These protectors, though well intentioned, are informed by the fears and limited understanding of our younger selves. While WIMPs intend to safeguard us, their strategies are based on misconceptions about what effective leadership entails. WIMPs urge leaders to maintain a facade of perfection, seek relentless validation, and hide any sign of weakness or uncertainty to avoid perceived dangers like vulnerability, criticism, and failure. They push for an unattainable standard of superhuman performance, forcing us to stretch ourselves in unsustainable ways.

This pursuit can become our leadership kryptonite, not because human fallibility is inherently detrimental, but because denying our own limitations cuts us off from our greatest strength—our authentic humanity. WIMPs, in their effort to protect, inadvertently encourage a leadership style disconnected from the very qualities that make us relatable and effective. They foster a culture of invulnerability that undermines genuine connection and empathy, shielding leaders from embracing their true power.

GET TO KNOW YOUR WIMPS

You may have met one or several of the six WIMP personas as they emerged from your formative experiences. As complex humans, we don’t fall neatly into one, or even several, of these categories of WIMPs. However, they can help us understand some of our most prominent tendencies in context.

The Perfectionist

The perfectionist seeks external validation instead of intrinsic self-worth and sets unattainable goals and expectations for themselves and everyone else. Perfectionists strive to meet their personal standard of perfection, which isn’t clearly defined, so they’re doomed to failure from the start. They are always chasing an elusive ideal, never reaching it, then mercilessly judging themselves for being a failure.

Perfectionists tend to be black-and-white, right-or-wrong, binary thinkers. There are no grey areas. There is no room for errors or flawed humanity. They become defensive and critical when others don’t perceive them as perfect or when they judge someone else as lacking, because worth and value are tied to achieving perfection, not being human.

Core strength: The perfectionist is thorough, pays close attention to aesthetics, and produces excellence that inspires others.

Core fear: If I’m not the best, then I’m the worst and “not enough,” which means I’m unworthy.

Core drivers: Superiority and protection from the judgment of others.

Catch phrases:

• » I have to win.
• » I’m not good enough.
• » If it’s not perfect, then I failed.
• » If I’m not the best, then I’m the worst.
• » If it’s not perfect, then I didn’t try hard enough.
• » If it’s not perfect, then I’m not good enough to do this job.
• » When things are perfect, I’m in control and all is right in the world.
• » I’m not unrealistic; I just have high standards and expect the best.

Low self-worth that results in perfectionism isn’t always caused by extreme childhood trauma or abusive parents. You can experience critical mental chatter and perfectionism even when you’ve had a pretty good childhood and loving parents, as I did. Much of my personal “not-good-enough” trope originated with dyslexia in early childhood. The resources for dealing with my diagnosis were not as comprehensive and effective as they are today. For years, I struggled with feeling left out and left behind in school, and a consequent feeling of low self-worth.

As an adult, I realized the education system was not designed for my dyslexic mind and how I think and learn the best. It took me decades to understand I wasn’t flawed, just different. Self-compassion helped me see that what I (and society) considered a disability was actually cognitive diversity. Today we openly talk about and value neurodiversity, but back then I never heard it framed that way and thus felt shame for an innate part of who I was. I now see the gifts embodied in this difference rather than just the ways I fell short of perfection in traditional educational structures. I was great at problem solving, connecting disparate ideas to form a cohesive argument, and coming up with unique metaphors and illustrations to express and share my thoughts. Self-compassion allowed me to see myself as neither good nor bad but as a combination of strengths, weaknesses, and unique traits. I realized I wanted and deserved love and connection.

The “not-good-enough” story comes in many flavors. I’m a failure. I’m a fuck-up. I will never get it right. What’s the point? I might as well give up. Interestingly, it often affects leaders who have already achieved a measure of success—but that success is never enough. Instead, they continue performing with a chip on their shoulder, always feeling the urge to prove themselves, never asking for help, and refusing to show any weakness. Whatever your personal story and the specific words you hear in your head, you have probably noticed that they bleed into every aspect of your life, including your career.

We can get caught up in the idea that we, as leaders, must try to be more human, as if there are certain practices that make leaders more human. The irony is blatant. We are already human; we just forget that sometimes. We are humans first, leaders second. To be human is to be imperfect and fallible and still know that we deserve love and respect. Self-compassion gives us the peace of mind that we are enough exactly as we are. We don’t need to do or be anything else to access connection and kindness.

The Hard-Ass

The hard-ass is more concerned with being right than being perfect. The hard-ass has high standards, always knows best, and refuses to accept being wrong. A hard-ass is hardest on themselves and wouldn’t ask anyone to do anything they aren’t willing to do themselves. Relentlessly pushing their team to achieve their best, the hard-ass is focused on accomplishing tasks rather than considering how people feel in the workplace. It’s business, not personal.

The saying “It’s lonely at the top” resonates with the hard-ass, who sees their intensity and commitment as driving forces behind their success. The hard-ass fears losing everything they’ve achieved by showing their humanity, which they consider weakness. Their armor has become part of their identity. Nice guys, they believe, finish last. But at their core, hard-asses are self-protective and sensitive, with their defensiveness acting as the proverbial shell keeping the soft crab safe inside.

Core strength: The hard-ass makes confident decisions in emergency situations and leads teams through uncertain times with conviction.

Core fear: If I don’t demand the best, we are at risk of worst-case scenarios. I have a fear of looking incompetent. My scarcity mindset leads me to fear losing it all, so I hold on to what has worked, which is to push myself and others relentlessly.

Core drivers: A need to control outcomes, even those outside their control; dominance; and winning at all costs.

Catch phrases:

• » It’s better to be respected than liked.
• » If I’m not driving for top performance, no one will.
• » If other people can’t do it right, I’ll just do it on my own.
• » I push people hard because I want what’s right for the company.
• » I’m not intimidating; I just have high standards and expect the very best from others.

One of my past coaching clients, Max, was the CEO of a rapidly growing Bay Area technology business. Max came to this position with a strong background as a sales executive and high standards that he would communicate by yelling and demanding excellence. There was one right way to do things: his way. He was respected for his outstanding technical skills but feared for his terrible people skills. He had a hard time understanding the weight and impact of his words and how intimidating his presence was.

Scared to look bad or incompetent, Max disliked surprises and hated being put on the spot to make decisions. He had a deep need for control, leading to a fixed rather than flexible approach to problems. He lacked the curiosity to consider other people’s opinions and the empathy to see anyone else’s perspective. So he pushed and bulldozed and white-knuckled it.

If fear is what turns a hard-ass into a bully or a jerk, self-compassion is what gives us the courage to explore the worst parts of ourselves instead of becoming defensive and recoiling in shame. Self-compassion can alleviate the scarcity mindset that drives hard-asses and makes every situation seem high stakes, every mistake critical, and every show of weakness lethal. Self-compassion doesn’t let us off the hook—it will not make a hard-ass feel better about mistreating others—but it will provide a nonjudgmental approach to discovering the root of the behavior. It teaches us how to balance self-kindness and accountability so we can call ourselves on our own shit and make lasting changes.

The Achiever

The achiever exhibits a perpetual sense of urgency, always asking, “Are we there yet?” Impatience characterizes their approach. Afflicted with an intense fear of missing out, they are constantly worried that if they’re not on their game 24/7, someone younger, hungrier, and better will surpass them. Achievers proudly exclaim that they can outwork anyone.

Achievers are constantly eyeing the next promotion, next award, next accolade, next title. Successes and achievements immediately get swallowed up in the black hole that is their need for external validation. No accomplishment can ever make them feel satisfied. They don’t pause to celebrate victories, instead finding temporary solace in constant productivity, industriousness, and the relentless pursuit of progress and improvement.

Core strength: The achiever will push through heavy workloads and demanding timelines to accomplish the goal.

Core fear: If I stop or slow down, I will be seen as lazy and judged as a failure.

Core drivers: The need for power and protection from the judgment of others; an insatiable black hole in need of external validation.

Catch phrases:

• » If I’m not winning, I’m losing.
• » Once this project is done, I’ll take a vacation.
• » If I just had X, I’d be satisfied.
• » I’m never satisfied with my success and achievement.
• » If I get this award, my boss will have to say yes to my request for a raise.
• » If I’m not progressing, I’m not worthy of the position I have.
• » If I got that promotion, people would finally respect me.

Achievers are programmed to believe that success is defined not only by their ability to lead but also by their attainment of constant progress and ever greater titles, authority, compensation, and accolades. They strive and fight and scrap and persevere to attain these markers of external validation—outward signs that they’ve been deemed worthy. Even when achievers reach the upper echelons of business, they can’t relax. They must constantly prove they deserve to be there. Rise and grind! Hustle! They can fall prey to the idea that their value lies in doing rather than being. The more they do, achieve, and perform, the higher they will rise in the regard of others.

Of course, with leadership comes the need to deliver results, meet performance metrics, and hit targets. There is nothing wrong with being bold and setting ambitious goals. The problem arises when we link our intrinsic self-worth to external validation and rewards. We all know this, but it’s challenging to remember when much of leadership culture encourages us to measure our value according to our job titles, the size of our teams, and our annual bonuses. Have you ever caught yourself comparing the size of your team or organization to that of a colleague or peer? Have you ever had a case of org chart envy?

Deploying self-compassion reminds us that external validation is a finger trap—the children’s toy that catches your index fingers in a bamboo tube. The more you struggle and pull, the tighter you’re gripped in the trap. Similarly, the more we pursue external confirmation of our internal worth and let the world dictate whether we feel like “enough,” the harder it is to escape that trap. By helping us calibrate and balance the external and internal, the doing and being, self-compassion allows us to loosen our grip to escape the trap.

The People Pleaser

The people pleaser conforms, avoids conflict at all costs, manages other people’s emotions, and focuses on everyone else’s needs to uphold harmony. Driven by a fear of not being liked or included, upsetting others, or making situations worse, people pleasers are scared to rock the boat and tend to go along to get along. They often say “yes” when they want to say “no” and find it challenging to establish clear boundaries. They prefer to absorb any underlying tensions and stress rather than face direct conflict. Labeled as peacekeepers, servant leaders, or doormats, people pleasers place a priority on being liked rather than respected for delivering hard truths or practicing candor.

Core strength: The people pleaser creates harmony in a team fraught with conflict, naturally empathizes, and reduces friction to accomplish work.

Core fear: I fear that showing my true self or inserting my own needs or agenda will lead to rejection and abandonment.

Core drivers: Acceptance from others and the need to be liked.

Catch phrases:

• » Leaders eat last.
• » It’s better to be liked than respected.
• » Servant leadership requires self-sacrifice.
• » When I know people like me, I feel safe.
• » If I upset someone, I assume they no longer like me.
• » If I’m not liked by everyone, my job may be at risk.
• » I’m not meek; I just like harmony and try to avoid conflict.

Although we still have some outdated ideas on hard-nosed, large-and-in-charge executive leaders, recently there’s been a movement toward “people-first” leadership. The people-first approach prioritizes the unique needs, strengths, and goals of employees. Not only is this approach the right thing to do but it is also necessary to successfully compete for talent. Employees have easy access to LinkedIn and Glassdoor to learn about company culture, benefits, and opportunities for promotion within their industry. Companies must attract top-level talent by focusing not simply on retention but on customized growth opportunities.

However, we’re now at risk of overcorrecting. Leadership problems can afflict not only the drill sergeant but also the complacent people pleaser who always puts the needs of others first. We don’t need self-aggrandizing leaders, but neither do we benefit from leaders who deny their own limitations and care for everyone else at the expense of their own health and sanity. The servant leader who says yes to all requests will eventually burn out. Have you noticed that when you’re extra efficient and respond rapidly to emails, the result is never more time or space, but simply more emails? Limitless tasks, piles of work, and urgent requests will flood into any space you create, so you must set boundaries or eventually be buried under the avalanche.

Leaders who embrace their humanity with self-compassion are showing up with their armor off. Such leaders have a deep understanding of their strengths, gifts, and talents and a keen awareness of their flaws and weaknesses. Because they accept their humanity, they don’t feel the need to hide any part of their whole selves, even if that means they won’t be liked by everyone, will disappoint some people, or will cause occasional friction and conflict on their team. They don’t bury their excellence under false humility or conceal their limitations with fake bravado. They allow themselves to be fully human, giving permission to everyone around them to do the same.

Self-compassion also protects recovering people pleasers from burnout and compassion fatigue, according to a 2020 study of healthcare professionals by Zeena Hashem and Pia Zeinoun.7 Leadership positions in helping professions (such as therapists, medical personnel, and social workers) are often expected to constantly serve others while forgetting themselves almost entirely. Hashem and Zeinoun found that “self-compassion practices explained 22 percent of the variance in burnout” among the nurses who participated in the study. The study showed that participants who practiced self-compassion by not judging their high level of emotional exhaustion were less likely to experience burnout. Self-compassion can be the antidote to compassion fatigue because it requires us to put on our own oxygen mask first.

The Imposter

The imposter feels undeserving of any success they’ve earned. Always worried about being found out for “who they really are,” imposters feel like they’ve somehow cheated their way into whatever position they hold. They constantly minimize their abilities, lack self-confidence, and are notoriously bad at taking compliments. Their default response is self-deprecation. Because they feel inferior to other people, they rarely engage as equals with peers. Imposters often think of themselves as misfits who are missing a key ingredient or are broken in some unfixable way. Their low self-worth can hold them back from reaching bigger goals and, worse, prevent them from imagining and defining their purpose.

Core strength: The imposter is unlikely to overestimate their abilities, which makes them conscientious and prudent when taking on challenges that require new skills.

Core fear: I’ll probably fail, so what’s the point in trying in the first place? Failure avoided by complacency is better than failure resulting from ambition.

Core drivers: The need for protection from the judgment and rejection of others.

Catch phrases:

• » I’m a fraud and will be found out eventually.
• » If people really knew me . . .
• » I don’t belong here and don’t fit in.
• » If they knew how incompetent and useless I was, I would be fired.
• » I can’t do this and don’t understand why other people think I can.
• » If I try and fail, I’m worse off than I would be if I never tried at all.
• » There’s something wrong with me.

When we persistently doubt our abilities and talents, feel as though we don’t deserve our accolades, or haven’t earned our achievements, we may experience a constant fear of being exposed for lacking talent or skill. It’s easy to see how low intrinsic self-worth and the need to garner outside validation make us prone to doubt whether we really deserve praise. We quietly ask ourselves if we’re just really good at faking it and dread the day everyone will finally find out who we really are—a fraud. Wondering if you belong and identifying as a misfit can lead to feeling like you’re the odd one out or will never be part of the group. Once everyone else finds out who you truly are, they will reject you.

I experienced imposter syndrome while writing this book. Let’s just say I had daily opportunities to practice self-compassion, which didn’t erase my imposter syndrome but helped me put it in perspective. The more I practice self-compassion, the less imposter syndrome I experience. Throughout my life, I’ve often feared being exposed as a fraud. My résumé is proof of all the jobs I started and quit and the educational programs and universities I attended and dropped out of. My twenties were littered with false starts and career changes. I spent years trying to figure out where I belonged, where I would feel right. Self-compassion helped me understand that no external circumstances would give me the feeling of belonging.

Having dyslexia was one of the main drivers of my imposter syndrome. I was privileged to have loving parents who had the means to help me with tutors and support me through academic and career ups and downs. I got chance after chance. Where I am today is due to hard work and undoubtedly a lot of luck. Many people with language-based learning differences are not as fortunate. While self-compassion can help us personally, it is also essential to remember that once we apply it to ourselves, we have greater capacity to extend it to others. We may start advocating for systemic changes that alleviate collective suffering and offer people the support they need to thrive. Because of my experience with dyslexia in the educational system and my passion for improving outcomes for the next generation, I’m deeply grateful for the opportunity to serve on the board of a Seattle-area school for students with dyslexia and other language-based learning differences, where I get to help shape supportive school policies and educational frameworks. I also had the honor of speaking to a class of eighth graders. Struggling with imposter syndrome myself, I found it meaningful to encourage them to trust their abilities and creativity while validating their struggles and inviting them to see the gifts within. Self-compassion allowed me to show up for these kids as my whole self and model that they can find their own path and make a beautiful life for themselves. It remains one of the most moving moments of my life and career.

The Contrarian

The contrarian goes against the grain, frequently playing devil’s advocate and challenging norms. Contrarians habitually zig when everyone else zags. They “think differently” from everyone else—and “different,” in their estimation, means “better.” They’re overconfident in their ideas and perspectives, considering anything new or norm-defying superior to established practices.

Contrarians seldom have the patience to advocate for their big ideas beyond initial discussions to gain consensus. Even when they express verbal agreement with others, they may hold onto contradicting viewpoints internally. If outcomes deviate from expectations, the contrarian’s go-to response is “I told you so.” They’re quick to point out when they’re right but ready to redirect focus or shift blame when proven wrong. Contrarians can be indecisive and uneasy when held accountable for specific decisions.

Core strength: The contrarian offers a big-picture vision and innovative ideas to challenge the status quo and make impossible breakthroughs possible.

Core fear: If I don’t come up with exceptional ideas all the time, I will be perceived as average, which is unacceptable.

Core drivers: The need to be perceived as different, special, and visionary.

Catch phrases:

• » It’s better to be different than conform to what I don’t understand or agree with.
• » By regularly changing my opinion, I avoid being held accountable for the outcome.
• » By challenging other people’s ideas, I look smart.
• » New is always better.
• » By questioning other people’s work, I don’t have to come up with my own solutions.

Some highly successful entrepreneurs and company CEOs could be considered contrarians. These can be highly intelligent visionaries with eccentric streaks whose appetite for risk and novelty can skyrocket a company to a billion-dollar valuation one year and bankrupt it the next.

This impulsivity can lead companies to expedite product launches to outpace competitors while compromising quality and security. The rush often backfires, causing delays and damaging reputations. Rapid growth requires rapid recruitment, which can destabilize an organization’s culture and core values, leading to increased human resources issues and costly employee training and turnover. When a charismatic contrarian heads a company or a team, it can lead to unilateral decisions that exclude key stakeholders and disregard the nuances of organizational politics, restricting future opportunities.

Self-compassion helps contrarians take a pause, making it less likely they’ll break something irreparable. It helps them remember that they are both special and yet connected to others, so they’ll feel less like they need to set themselves apart from the rest to maintain their uniqueness. Self-compassion can help contrarians be who they are rather than just trying to be different from the mainstream.

Comedian Jon Stewart was asked in an interview with radio host Howard Stern how long it took him to get good at stand-up. During his early career, Stewart worked at the Comedy Cellar in New York City and was regularly assigned to the last spot at 2 a.m.: “You learn how to be yourself, and once you learn how to be yourself, that’s when it opens up. You learn how to channel what you actually care about, and then you find your voice.”8 Self-compassion can help leaders learn who they are at their core and what lights them up so they’ll see big ideas and projects through to the end instead of abandoning them after the initial excitement wears off and the first obstacles appear. Self-compassion can alleviate the contrarian’s need to be “the next big thing” and instead be their truest selves.

Our WIMPs Are Trying to Tell Us Something

If you see yourself in one or more of these well-intentioned, misinformed protectors, you may have already started mercilessly judging yourself. Our goal is to change our relationship with the WIMPs. We may think of them as our shadow or dark side, but there is no need to vilify them. Our WIMPs are a part of us that serves an important function. When we remember that they’re designed to protect us, we can respond with kindness rather than disdain. We can turn them into an asset, because they offer data about something important that needs our attention. The WIMP wants to be seen, heard, and appreciated just like you, because it is you.

The transformative moment in leadership comes when we recognize the role our WIMPs play: trying and failing to offer us a cheap sense of safety that no longer serves us. By acknowledging and integrating the human aspects of vulnerability, uncertainty, and imperfection, leaders can turn what was once their kryptonite into their strongest asset.

This paradigm shift involves redefining strength not as the absence of vulnerability but as the courage to face it head on. Giving up on the illusion of superhuman prowess allows leaders to step into the power of being profoundly human. In doing so, leaders not only liberate themselves from the unrealistic expectations set by their WIMPs but also foster a more authentic, empathetic, and resilient leadership style throughout their organizations.

Self-compassion helps us see that we are not alone and that we share these insecurities and fears of rejection with almost every other human on earth. This feeling of shared humanity in self-compassion can curb the shame that often keeps us from seeking help, asking for what we need, and setting healthy boundaries. Self-compassion permits us to gently redirect our WIMPs and instead tell ourselves that we are allowed to feel bad and to focus on our physical, emotional, and mental needs and that we deserve to surround ourselves with supportive people. Accepting difficult feelings without trying to push them away actually lessens their impact and frequency and helps create psychological safety at work so everyone can more fully express themselves. Leaders, however, must pave the way.

Self-compassionate leadership transcends the quest for superhuman perfection by embracing the full spectrum of the human experience, including the well-intentioned, yet misinformed, protective instincts of our WIMPs. We finally recognize that our greatest strength is not invulnerability but our shared humanity and the courage to be authentically ourselves.

Another way to learn how to appreciate our WIMPs for their service is to understand the Internal Family Systems Model, which is an integrative approach to individual psychotherapy developed by Richard C. Schwartz in the 1980s.9 It combines systems thinking with the view that the mind is made up of relatively discrete subpersonalities, each with its own unique viewpoint and qualities. Everyone has a Self to lead the individual’s internal system, and each subpersonality has the potential to contribute positively to the Self, unless carried to extremes. Similarly, each WIMP has a beneficial side—a core strength that serves us well in moderation—which is often the reason why adopting this persona has led to success. It becomes a problem only when one of the WIMPs turns extreme or takes over completely.

If we’re unaware of these parts of ourselves, and the way our fears manifest themselves as one or several WIMPs, we may slide toward an extreme where the negatives of a WIMP far outweigh the positives.

WHO TRULY BRINGS THEIR “WHOLE SELF” TO WORK?

As kids, most of us experienced the desire to fit in and not stand out. Anything that made us different could become a cause for rejection, abandonment, or even bullying and violence. I spent my childhood years thinking I was stupid. A vague feeling of uncertainty followed me everywhere. I was out of step with everyone else, always behind, and seemingly unable to catch up. Being different often made me feel “less than” or “not good enough.” I made up for it by being the class clown. I overcompensated by turning up the volume, being gregarious, and getting into trouble. I spent lots of time in the principal’s office for doing dumb stuff. At times, I came off as apathetic about school. The truth is I cared so much about what others thought of me that I found it extremely painful when I couldn’t figure out how to fit in. I was labeled a troublemaker, when I was just trying to survive in an environment where I struggled to thrive.

As adults, we can learn to embrace our differences and celebrate what makes us unique. In fact, we’re encouraged to consider our differences a competitive advantage or unique value proposition. However, that programming from long ago is still in our coding, and we can fall back into the grown-up version of hiding and protecting ourselves. These self-protecting behaviors are a massive waste of time and energy and prevent us from truly testing the limits of what is possible.

Yet authenticity is a double-edged sword. We want to be authentic in organizations, but we don’t want to show our weaknesses, uncertainty, fears, and limitations. To say we want to bring our authentic selves to work means not just wearing the clothes we like, showing our tattoos, or speaking freely. It requires us to accept our doubts and disappointments and to be honest without oversharing, so we can get as close to the truth as possible instead of becoming unreliable narrators of our own lives.

DON’T JUDGE YOURSELF FOR JUDGING YOURSELF

Most people, especially high-achieving individuals in leadership roles, are prone to believing their WIMPs’ constant judgments. And it makes sense. The reasons you are a successful high achiever are varied, but one of them might very well be that you’re overcompensating for the erroneous beliefs your WIMP subscribes to, always trying to prove yourself. Maybe you’ve got a chip on your shoulder. Perhaps you’re still trying to convince your second-grade teacher, first boss, parent, or ex-spouse of your worth and value.

In her book Trusting the Gold, psychologist and meditation teacher Tara Brach explains that when emotions are strong, it’s important to recognize they belong to us, but they are not us. I have an emotion, but I’m not the emotion itself.11 There’s nothing wrong with the rising anxiety, irritability, or aggression. They are our limbic caretakers, our survival brain’s primitive way of trying to protect us and promote our well-being. Even self-judgment can be well intended because it tries to improve us to ensure our acceptance by loved ones, families, or communities.

Self-compassion can feel like an uphill battle because it goes against our biological wiring. An essential part of practicing self-compassionate leadership is reckoning with how much of our brain development, evolutionary conditioning, and biological urges may have been indispensable for physical survival in the distant past but is less useful for thriving in the modern world.

Humans lived in tribes for 150,000 years of our existence; we have learned there is security and survival in the tribe, in belonging to a family or group.12 Banding together to compete for resources and engage in warfare with outsiders was an effective survival mechanism, but it was also the best way to meet our other needs—for belonging, family, and social interaction. Any action that threatens isolation or expulsion from the tribe is automatically considered risky. That’s one reason we avoid seeking need fulfillment outside of our family or peer groups, even if it’s much more likely that that’s where we’d find it.

Our biological drive for survival and belonging to a tribe can override self-compassion, which requires conscious effort and can threaten evolutionary need fulfillment. As Yuval Harari explains in his revelatory book Sapiens, evolution selected for tribalism because people who were more predisposed to adapting to a group and getting along within its hierarchy were more likely to survive and pass down their genes to the next generation.13 It takes a tribe to raise a human, and evolution therefore favors those capable of forming strong social ties. Since humans are born underdeveloped, they are especially dependent on the care and protection of others and are open to being educated and socialized to a far greater extent than any other animal.

Even though I wasn’t in any real danger at school, not fitting in felt like an existential threat. Similarly, even if being passed over for a promotion is not a life-or-death situation, it can feel like not only a threat to our livelihood but also a fundamental rejection of who we are.

WHY WE DEFAULT TO SUPPRESSING SELF-COMPASSION

Rejecting self-compassion as a human and as a leader comes naturally for most of us. Practicing self-compassion is incredibly difficult and requires concerted effort and strength. The false stories I believed about myself started in childhood and followed me into adulthood: I’m not good enough. I’m stupid. I’m weak. I have to prove myself. I’m a fraud. By now, you may be getting an idea about the false narratives you have replayed over and over in your own head. And as if mercilessly judging ourselves wasn’t enough, we have tried to “fix” our supposed defects with perfectionism, self-criticism, or punishments.

Don’t be surprised if this process feels awkward and scary at first. Challenging these old stories with self-compassion can feel counterintuitive, but it’s the essential foundation for reaching our leadership potential. Although it’s difficult, even painful, to dig into these hard truths about ourselves, it’s also hard to continue on with our two jobs, listen to our WIMPs instead of our highest self, and always feel the need to hide and cover. Performing and pretending is hard. Being fully human as a self-compassionate leader is hard too. Often we don’t have a choice between hard and easy. We only get to choose between two hard options. So pick your hard.

The next chapter will dig into my definition of self-compassionate leadership: its three integral aspects, what it is and isn’t, and how to spot the traits of self-compassionate leadership in yourself and others.