Cloaks, Masks, and Daggers

A special thanks to our sponsors for making this newsletter free for our readers:

It’s tough out there. CMO Huddles helps B2B CMOs gain the confidence, colleagues, and coverage they need to succeed. Ask Drew Neisser for a guest pass.

Need to hire a CMO or VP of Marketing? Want the ‘make money’ variety, not the ‘make it pretty’ variety? I recommend Erica Seidel of The Connective Good. Join her newsletter.

May is Mental Health Awareness Month; today is my most important article. 

I am here to share my demons authentically and reach readers who may not have the conviction or platform to do so. Or maybe to help those with their own struggles that don’t witness how others navigate to survive. You are not alone.

Yes, even executives—in all their glory, cloaked in leadership and successful prestige—yes, even you—are not alone. Even you face tremendous hardships.

Such is the reality of a life we all have in common—if we could only afford to take the time to genuinely listen and learn from one another without judgment. 

In this, we all share an identity. A human identity. 

Unfortunately, we default to hide the real agony we face. Maybe we sense that sharing our personal afflictions makes us weak. Maybe nobody would admire you—if they really knew you.

Ironically, we tell others that we’re an open book.

We often use the word transparency like we know what it means. It’s a badge of honor to be an authentic and transparent leader. But in reality, this is usually more corporate guile. Empty words spoken that fall on our ears—our ears that we all train as bullshit detectors.

Seldom do we have the courage to build authentic relationships. 

Our proclivity for deception frequently impacts our spouses and closest friends. Do they really know the real you? Do you know the real you?

If you can’t open up to those with whom you share a home, how should anyone be authentic at work? How can you be authentic when you are responsible for hundreds of subordinates that need to do what you say? Your career is on the line, after all. They must believe in the cloak and mask you parade to the world. Your survival depends on it.

What about being authentic when networking for professional reasons? Fat chance. 

Sometimes those duplicitous masks are more elaborately grown. I’d be so bold to say that many are so comfortable behind the comfort of their fictional facade that they can no longer ascertain what is authentic and what is only show.

Can we even separate fact from fiction anymore? Does it matter?

I’ve learned that we all keep secrets. 

Some are more compelling than others, such as substance abuse, sexual indiscretion, family trauma, and childhood PTSD. I’ve learned a thing or two while confidentially consulting powerhouse executives behind closed doors. 

Many have achieved success by outworking their hurt. I know I’m guilty of burying my head in some insignificant yet time-consuming work project to avoid my personal dealings with lurking demons. Or it’s daddy issues, the casual armchair psychologist may declare.

Whatever it is that brings you shame, you are not alone. 

It may just be that taking your conversations to the next level of intimacy could unlock new heights in your career—and life. I’ll elaborate, as I am fortunate to have deep experience discussing deep experiences with successful business folk like you.

What I learn behind closed doors is astonishing. 

I won’t out anyone in particular—rather, this is an open kimono piece on why I’m drawn to no-judgment and no-fluff executive coaching. Listening and learning from others as a trusted confidant is life-changing.

I discovered that I’m not such a tortured anomaly. Others have entrenched pains that we’ve never even seen in movies—and they lead a seemingly successful executive presence.  However, getting the juicy conversations out of a professionally guarded executive shit-slinger is nearly impossible. And I’m paid handsomely to do it. 

I am not alone.

You are not alone.

I’ve found meaningful discourse can thrive when (and only when) you strip away all of your societal cloaks. And there is much to discover when you learn about the often troubled inner workings of others. So here goes.

…And after a while, you can work on points for style

Like the club tie and the firm handshake

A certain look in the eye and an easy smile

You have to be trusted by the people that you lie to

The above lines are from Dogs on the 1977 release of Pink Floyd, Animals—an adaptation of George Orwell’s Animal Farm. It accurately criticizes how we “mask up” and lie to those around us. I suspect it’s usually not malicious. 

As a rebellious teenager, nothing moved me more than directing my youthful wrath at “the man” and late-stage capitalism. I found myself in hot water more than a few times by chanting Rage Against The Machine, Killing in the Name. After all, our dystopian society is very real, depending on where your family scratches roost in the pecking order.  

Although, in hindsight, my disdain should be pointed toward Prozac, Vicodin, and Sky Vodka—or the multiple incarcerations of my step-father for losing the battle to his aggressive torments. 

One of the reasons I understand how to negotiate well—is that from a young age—I needed to negotiate to survive. Before I knew what it meant. Sometimes that meant masking up. 

A chameleon knows when to disappear. 

It’s possible that being a product of the system and the hypocrisy of knowingly being shepherded to obey society, I myself need to obsess on why I, too, am guilty of masking up when I work so hard to be transparent. God knows I humbly brag often enough about being candid and direct.  

Now I’m speaking to you, friend. 

You will not always feel like the hero in your story. You may feel like a letdown. As if the pressure of providing is too much to shoulder and you’re not up to the challenge. 

Hell, even when absolutely killing it, we’re never truly good enough, and we will never rank as high as others, so we keep chasing an elusive, what exactly?

You are always responsible for an increased workload and the beacon of earning potential for your family. It’s all on you—so mask any challenges and sure up your certain look in the eye and an easy smile.  

Do you need to mask your reality?

Add unemployment and tying your self-worth to your career—which many readers feel today— and you have a recipe for a challenging road to plow. 

I suspect this is why so many executives struggle with substance abuse. Substances can mask our feelings without sorting out our heads to address them in earnest. Or perhaps overbearing parents could be to blame instead. Okay, boomers, you screwed it up for us.

Having felt this off and on for over a decade, I’ll go deeper.

There have been dark times, particularly in my early twenties. I struggled to feel good enough and accepted by others. I held onto friendships where I was only around to be the butt of the jokes. To be mocked for lacking money or for being white trash. 

I didn’t value my time. Or myself. Just waited for the ding on the phone to hope someone was thinking about me and wanted something from me. That dopamine hit felt like validation misconstrued as being valued. 

I wasn’t valued, I was easy and eager to please.

Perhaps this is why I hammered on accelerating my career so much—and took a strong sense of ego, pride, and identity into my job title. I could control the outcomes, and the game is devoid of emotion and aligned to dollars and cents. Nothing too real to dive into there.

I let my ego drive me to homelessness, spending a summer sleeping in the skatepark at Maidu Park in Roseville, California. Then got out of it, leased a convertible BMW, and rode the bipolar high of executive ego again.

Thrilling masks cloaked rotten insides. You are not alone.

I have contemplated and attempted suicide. Sometimes the darkness and the demons press so hard on your soul that the only control you have left is to end it all.

Fuck, that’s pretty hard to write. But I reckon I haven’t written truer words.  

Maybe forcing myself to put this into the world is helping me come to terms with why so many choose to bottle it all up. To mask up.

I may not know the right way, but corking it all inside isn’t it.

Maybe you have a few skeletons for which society would ostracize you—maybe hard truths will help you. Maybe a dose of naked reality is therapeutic.

 I, Jacob Warwick, am the product of rape. I have never met my biological father.

I am often used as a leading argument for the pro-choice movement. I once doom-scrolled a post on Reddit about the dilemma of keeping a rape baby. 

The overarching sentiment is that nothing good can come from a rape baby. Some children of rape are bold enough to say they wish they had been aborted instead of living with the torment and reality of being the seed of a violent devil.

Some of the more sane replies also tell, “It’s ultimately your choice, but if I were in your shoes, I would put myself first and terminate the pregnancy as soon as possible.”

Reading from thousands with an opinion but little knowledge of being in the shoes of the by-product would have you think no woman can live with the reality of bearing the fruit of their abuser. I won’t pretend to understand how these women feel. 

But I can share how I feel.

Mother’s Day is Sunday.

Blessed is a word that doesn’t do my emotions justice. I’m grateful my mother didn’t have access to Reddit in 1989. She chose to keep me against the wise counsel of others, and the ripple effects of that decision continue to cascade to your inbox every Thursday. 

Lucky me; lucky you.

Sunday also marks my wife Mary’s first Mother’s Day. Our son Noah is 3 months old today. 

Believe it or not, Mary had a significantly more traumatic childhood than I did. She is my muse. She inspires me to be an authentic, stronger, and more Godly man. I digress.

My faults continue to laugh in my face. And life continues to throw lemons our way, even though we continually pray that the worst is behind us.

I happen to carry a bastard (pun intended) cystic fibrosis gene from my mother’s rapist, Donny. And together, Mary and I shared the mutation in our beautiful boy. Sigh.

What an ass-kicker. My acceptance of that news is documented in the article linked above—but dammit if I’m not irritated at the cards being dealt.

Alright—I am going to pause here. I assure you that I am genuinely at peace and doing well. 

Writing about difficult experiences without sounding like you’re reaching for a pat on the back or tossing invitations to the pity party is difficult. 

That’s not my intent. 

Rather, I intend to provide a glimpse that not everything you see is as it appears. And that you are not alone. This article isn’t so much about me—as it is about us.

 Just last night, Mary, Noah, and I were rocking on the wooden loveseat on our porch. The Montana spring breeze hits differently after a long cold winter. I took a deep breath and thought, “Life doesn’t get any better than this. Right now, this moment, this is heaven.”

I choose to share my story with my clients occasionally—and when I have the courage to be as open as I have in today’s article, real conversations ensue. Maybe it will inspire you to do the same with someone you trust.

I have found that removing my cloak invites others to unburden themselves. 

I’ve learned of executives navigating traumatic loss. Family deaths, a stage 4 prognosis, miscarriages, prison sentences, suicides, substance abuse, adultery, homelessness, and more. All the awkward ick that gucks up the idealistic painting that life is supposed to be. The stuff we’re all afraid to talk about.

Whatever it is that gucks up your life, you are not alone. 

Together we can support one another without judgment. It takes courage, bravery, and active listening out the whazoo—but we owe it to those around us. And we all know that someone owes it to you.

Although the glitz of executive life is often hotly celebrated as the pinnacle of success in the American Dream—remember—not everything is as it seems.

Today may be the day we need to call someone out of the blue with a simple, hey, I’ve been thinking about you. I love you.

Drop your cloak, remove your mask—and if you find a dagger in your back for being yourself—keep at it until you find your tribe. 

Your best days are yet to come.

When you're ready, there are 4 ways I can help you.

Elevate Your Executive Game Join my exclusive coaching program and strategize with the top 1% of leaders. Outmaneuver competitors, secure coveted roles, and shatter compensation benchmarks.

Boost Your Brand to 10,000+ Executives Sponsor Execs and the City for unrivaled exposure to 10,000+ engaged executives and 32,000+ LinkedIn followers. Amplify your message and grow your influence today.

Captivate Your Audience Book me for keynotes and workshops that motivate. From influence and persuasion to negotiation and sales, I’ll deliver lasting impact. Inspire your team now.

Win High-Stakes Negotiations Founders, CEOs, celebrities, and athletes: gain a master negotiator’s edge in turnarounds, M&As, and major contracts. Secure optimal outcomes in any challenge.

Gain a competitive edge.
Join 10,000+ global readers receiving an original take on career strategy every week.


Share this Article