Diary of a Career Path Death Wish
This is a work of fiction. Names, characters, places and incidents either are products of the author’s imagination or are used fictitiously. Any resemblance to actual events or locales or persons, living or dead, is entirely coincidental.
I read the harsh reviews of the company on GlassDoor, all the warnings about a psychopathic CEO who executives would hide from in the bathroom. Then as I got closer to making a move, a concerned coworker put me in touch with a former employee of the company. She strongly warned me against what she called a toxic culture. She outlined mass firings and the unhinged leader of this company.
I had interviewed with the VP of marketing, an upbeat Indian immigre with a pedigree that included 3M and Staples. I got the sense she was a careerist most comfortable on conference calls, endless email threads, building consensus among stakeholders, a skilled if slightly tedious player in the corporate world. She didn’t have strong experience managing creative service directly, and seemed somehow less sophisticated than the people I had been working with. But she seemed nice enough with her sing song accent and positive vibes. I told myself that this kind of place was ripe for someone like me to come in and make an impact.
I was able to negotiate more money, which was a priority since at the time I was underpaid. So against my better judgement, I went for it anyway...out of greed, a misguided sense of adventure, fatalism, or a death wish. And now I’m in the cage with an aggressive, irrational bear. Don’t make any sudden movements. Stay calm, yeah yeah yeah. That I volunteered for this duty calls into question not only my career decision making, but my very rationality.
Day One: You’re In the Army Now
The building I am assigned to has super modern offices, with requisite innovation company ping pong table, free snacks and sodas, lunch catered several times a month. Almost immediately I began hearing a lot of references to “Charles” and soon came to understand how the figure of Charles looms over everything. It takes on a sort of Gatsby-like aspect, the mysterious, aloof tycoon that nobody quite understands.
I learned some of the details of his impressive rags-to-riches story. Like a lot of recent American entrepreneurial heroes, he and his buddies bailed out of college and launched their business. It’s sort of a cliched thing now, but at the heart of it is the real chutzpah to say “fuck it” I can do this better! They started cleaning buildings out at the HP corporate campus. He refigured the whole process, introducing systems and processes in a business that was old school and analog. His program empowered and trained people, added transparent client reporting, metrics, and a technology platform linked to an app that managed the whole operation.
Like a lot of recent American entrepreneurial heroes, he and his buddies bailed out of college and launched their business. It’s sort of a cliched thing now, but at the heart of it is the real chutzpah to say “fuck it” I can do this better!
Day Two: An Audience
I arrived to the office and learned that Charles had summoned me. As we walked across campus, my boss coached me not to get personal, and not to ask about the jets. Presumably, he’s too busy and private a man to suffer these sorts of personal quarries. We entered the stately headquarters building of the airbase, an historic concrete art deco affair with a vaulted two story lobby. The large compass artwork on the terrazzo lobby floor bespoke the glory days of aviation. We were ushered into his lair on the second floor. He walked in and immediately mentioned my airplane wreck story, a memoir on my website about a plane wreck I was in in 1986 with my dad, also a pilot. He was fascinated, saying several times, “You guys are lucky to be alive.” It was a pretty sweet moment for me, and a great ice breaker. It also made me realize this guy does his homework, reading deep into my site, past all the professional content.
And then he talked for the rest of the meeting. He talked about reinventing janitorial market space. He used several business world analogies to talk about disruption: Starbucks, Apple and Uber. I would come to know this practice of business case studies very well, all the stories about innovation. One of his stock stories is about the computer mouse, how it is the lynch pin feature that made computers so essential, how Xerox Park showed it to Steve Jobs in the early 1980s because Xerox didn’t understand the value of what they had. And how Jobs stole it. And also the story of the swipe function on a mobile phone, the effect it creates for the user, the perception of movement, and the lawsuit between Android and Apple over the swipe as intellectual property. With these lectures about disruption, he showed himself a savvy student of recent business history. I enjoyed this heady exchange. And tried to ask a few good questions and not say the wrong thing.
I noticed his slightly unusual manner, pulling at his collar, clearing his throat...a wiry tall guy in his late 50s, sort of a shifty style, hard to pin down. He smiled often but it was an impatient slightly uncomfortable smile.
I noticed his slightly unusual manner, pulling at his collar, clearing his throat...a wiry tall guy in his late 50s, sort of a shifty style, hard to pin down. He smiled often but it was an impatient slightly uncomfortable smile. He wore a utilitarian uniform of worn jeans and an untucked button down shirt and hiking style sneakers. There are shelves filled with model airplanes behind his desk. I notice his kids’ artwork and photos and the trinkets of a good family man.
Details of a Humble Upbringing
In a subsequent meeting, he was telling us the story of how there are certain expectations that modern consumers have, making this point to distinguish what is the ante to get in the game and what is the actual extra value you need to deliver. His analogy was about how today consumers just expect the car to start. And went into a tangent about the crappy cars they had when he was a kid that would stall out. He said, “you’d be getting dropped off at school and hoping the car wouldn’t stall out in front of the school…” And then a little aside with a wry smile,”that’s a character-building moment.” He said it like there’s a lot more to that story, and the vision of an embarrassed kid in the back seat came into focus.
I managed to hear some of the local lore floating around about Charles, the story of his poor upbringing in the south area of town. There was a story about the Huffy bike and that other kids had Schwinns and he had a Huffy and later after he was successful one of the Schwinn kids approached him for money and he said fuck you, you had the Schwinn.
I am acquainted with the scion of a family that owned shopping malls and commercial real estate. I did some design work for him over the years and our daughters are friends. He shared that Charles said to him at some function or event “my mom was your grandmother's seamstress.” Charles never forgot the feeling of being the poor kid...that that’s what has propelled him upward. That chip on his shoulder driving his business ambition. It is not lost on me that a less ambitious guy like myself can’t understand a man like this.
There seem to be many lawsuits in Charles’ world, maybe the natural product of his level of business. One in particular showed his shrewdness in the realm of real estate speculation. It’s a second or third-hand story I heard about his dealings with the Greek godfather figure in town who has endowed arts buildings and other civic things. This guy has the reputation as a shady dealer. So in the crash of 2008 land became really cheap. Charles and he were going to partner on a big tract of land. With a price tag in excess of $10M, it was a screamin' deal, a fraction of the previous value. Charles got wind that this guy was going behind his back to buy the land by himself. Charles bought the land before he could. There was a lawsuit, and Charles prevailed. The guy is a straight up gunslinger, and he’s really not afraid of anyone. There are not a lot of people you can say that about.
Qualifier: those stories are at least second hand and unverified. But I do know the showy, real estate developer crowd was all trying to out-impress each other, and there’s Charles, way richer than all of them, a self made guy in a low rent market space, who didn’t give a shit about their pecuniary theatrics...and they were all jealous of him and didn’t understand him. He seemed to like being an under-the-radar guy. He has no interest in publicity—just wants to keep growing his biz and making more money.
Hard-Ass with a Big Heart
As things progressed, I began to notice the fear his senior people had of him. I was hired into a strategic marketing manager role and was invited to meetings of his leadership team on a big opportunity—a 10-million square foot corporate headquarters campus up near Seattle (for one of the world's technology giants). There was a sense of people waiting to see what he thought before responding. Measured, chicken-hearted responses. Although, to be fair, he has many key people who have been with him for years and decades.
In that meeting I saw something impressive business-wise. The customer wanted a fee-at-risk contract in which some of the payment (our money) would be paid based upon meeting performance benchmarks. The finance guys were concerned about this deal point, that it could put the company in a tough spot financially. As the meeting progressed you could see his opinion forming. He finally said, “Hell yeah, I want that. We will win that. I’ll take that risk all day.” His confidence was impressive. It would not be the last time I would see the swagger. Our company won that contract on a bid that was lower than what was sustainable given the scope. And he immediately began laying the groundwork to renegotiate a high price based on the operational excellence we would deliver.
As the months went on, I was called in to meet with him many times to share our work. He proved to be one of the most difficult clients in my career. Ideally, design is a conversation between client and creative. But he would lecture us, far ranging disjointed lectures. His mercurial mind shifts never seemed to provide the definitive answers and direction we needed. Often on successive meetings we got contradictory direction. On more than one occasion we came out of meetings with our heads spinning, not sure what the takeaway was. He knew the business so well but struggled in conveying his vision to his creative and technical teams.
Charles has an innate distrust of marketing, and rightly so. He routinely calls bullshit on all the juiced up, phony claims and boasts that he calls “fluff.” He’s told us on many occasions, “Everyone says they are the best...don’t tell me...show me...I’m not selling blue sky.” In the business world, this is a refreshing perspective, and it is a big part of his appeal with clients. But the other side of the coin is that a presentation can’t be all demo. There have to be some words to give context. And that’s where it became a sisyphean exercise to overcome his skepticism.
Charles has an innate distrust of marketing, and rightly so. He routinely calls bullshit on all the juiced up, phony claims and boasts that he calls “fluff.” He’s told us on many occasions, “Everyone says they are the best...don’t tell me...show me...I’m not selling blue sky.”
Amid the challenges of our marketing efforts, the complexities of the man began to emerge. He is a hard-ass businessman, but somehow has a real sympathy for the janitors, the lowest of the low in the economic pecking order. He was moving operations into southeast Asia after successfully following several multinational clients there. There was a whole issue around bringing U.S.-style labor expectations to an inefficient workforce that was practically slave labor. On several occasions he spoke from the heart about how our company’s empowered-people model would give those guys a life. And their families. Instead of working six 12-hour days, they would work five days and be more efficient. They would have that time with their families.
To illustrate the larger point about labor abuse, he’d bring up examples like Apple, who looked the other way on the slave labor at their phone plants in China. He wondered aloud how they could they do that, and he brought it up several times. I came away more confused about the seeming contradiction between an aggressive guy and this heartfelt element. He didn’t have to say all that to us lowly creatives. He meant it and in those moments, there was an unlikely sweetness and sympathy about the man.
Off With Their Heads!
It seemed like every week or two there were firings. Most notibly, the CTO, a round unfortunate guy who embarked on a lengthy plan to redo the whole band-aided together tech sub-structure of the company, instead of moving rapidly forward on the platform build-out. The platform / app would be the lynchpin to help deliver the full promise of his game-changing service delivery model. So that was Charles’ primary focus.
Technology was especially volatile, since the functionality of the app was ambitious, and IT projects like this are notoriously slower than plan. To date, it is only partially implemented. You couldn’t help noticing the weekly turnover at corporate, the revolving cast of new recruits being toured through the office. Teams came and went. He would be in a meeting and just turn to the HR henchman, Cesar, and say “Cesar, that guy is gone.” Eventually our department ended up working under the constant threat of summary dismissal.
The work culture was intense, with emails at all hours and throughout the weekend. A perpetual crisis mode with us always racing to support the sales and account teams, and also meet the arbitrary quick deadline Charles would throw at us. My boss, what she lacked as a marketing visionary, was a grinder, on conference calls and emails at all hours, trying to forge relationships across the company. When Charles said “jump,” she jumped higher and faster than anyone else in the company. In this way, she was well suited for survival. Her tactic was to keep showing Charles things, stay on top of his mind. She warned that when he stopped calling you, you were DOA. She was expert at the delicate psychology of taming the bear. And so far, she was succeeding where six of her immediate predecessors had failed in quick succession.
Even a skillful bear tamer will have close calls. Eventually his ire turned to our little marketing department. We were not pleasing him, not following his convoluted directions. Really, we were only trying to follow his directions, instead of providing our professional recommendations. This shift can occur. It’s a balance between the client’s ideas and your own expertise. His personality was so big and forceful, and I didn’t want to recommend things that might have interfered with my boss’ long-game approach. So I was not able to successfully articulate some of the things we should have been doing.
There was a Jekyll & Hyde thing going on with him. Some meetings would be great and there were jokes and genuine affection. At other times, he would threaten to fire us all and outsource the whole department. There were projects where we all believed that our jobs depended on delivering something he might like. At some point, to cope with the stress, we would just joke that it’s Doomsday all over again.
There was a Jekyll & Hyde thing going on with him. Some meetings would be great and there were jokes and genuine affection. At other times, he would threaten to fire us all and outsource the whole department. There were projects where we all believed that our jobs depended on delivering something he might like.
This week there was a particularly brutal meeting in which my boss and I were savaged. He was on a slow boil. We had brought in a content outline which is a common checkpoint before spending design hours...a good starting point. But he wanted to see design and infographic ideas, not an outline. This had not been conveyed to us. He said the outline was just his list shown back to him. He mockingly said he was the king of lists. Then he sarcastically asked my boss, the marketing VP, if he was the "List King" or the "List Tiger." She’s a dignified, accomplished woman, so it was awkward. He was so displeased by seeing a text-only outline on the screen he took out his phone and took a photo of the screen. “This is so great I’m going to take a picture.”
In frustration he threatened to break one of the two flat screens on the wall, and went into a rapid fire list of assumptions people have about him, at one point referencing his own supposed bipolar condition. And then he said,” I’m gonna jump out this window I'm so frustrated!”
He regained composure, and in a state of barely contained furiousness took us through the cutthroat mentality of his presentations to Fortune 100 heavy hitters: “I’m in front of the world’s biggest companies... you’ve got one chance to win...and I’m only there to win. They ask me, do you want to go first or last? And if I go last, I know I’ve already won.” He was trying to share with us his internal process in sales, and the importance of the graphics to him, and a message based on results, not marketing-style claims and superlatives. He has an innate sense of how to read a room and what types of things would make people want to buy. If there ever was a “closer,” it was Charles.
As painful and insulting as that meeting was, I could see how he could turn on the charm in presentations. And the decks had to be just right for him. He was really explaining his key marketing problem: that company growth was limited because it relied on his own personal pitch—all the expertise, command, and charm that came from his 35 years in the business. He was trying to scale his own salesmanship by using static Powerpoint decks. As PowerPoint is the de facto corporate medium, we were going to live or die based on our ability to conjure the right bulleted lists and icon sets.
He was trying to scale his own salesmanship by using static PowerPoint decks. As Powerpoint is the de facto corporate medium, we were going to live or die based on our ability to conjure the right bulleted lists and icon sets.
In his stream of consciousness rant, he suggested that if my boss were at Amazon, Bezos would fire her with a smile on his face—the hint of firings was ominous given his track record. Later, she joked to the team that she just got fired by Jeff Bezos. She is a cold-blooded pro who seemed unfazed by the experience.
This episode tracked with the stories we heard of him telling the operations guys they weren’t qualified to work the counter at Chipotle. He must have had the self awareness to know he had a problem with his own management style, because that same week he brought in the former CEO of my old company, to coach him. We'll call him Roger. Roger had built a mid-sized regional eye care insurance company into a national player. Roger told the leadership team that he used to be a micromanager but growth at his company accelerated only after he delegated and let people do their own thing. Pretty standard business class wisdom. Charles joked that he would find out whatever his team shared in confidence with Roger.
As we were leaving that unhinged meeting, he noticed the shocked look on my face and called after me,”cheer up Justin!” I wasn’t sure if this was gallows humor or that he suddenly felt bad. I waved and kept walking. I came back to my desk and wrote my resignation letter. Not sure if we would end up getting fired...trying to sort through whether it would be better to leave on my own terms than face this no-win situation. Running through my mind was the prospect of having to come home and tell my wife who is also busting her ass to put three kids through college. I was beating myself up for not looking for a new job harder...unable to overcome the exhaustion in the evenings after a whole day in the cage with the bear.
Tenacious Versus Stupid
I drove in the next day and a line from an old ad I did came into my mind: “Heart of a Fighter.” Cheesy, I know. But I made up my mind to get up off the deck after that beating and come back for more. Was this tenacious, sadistic or just foolish? Or the beginnings of my descent into a Stockholm Syndrome obedience?
We partially redeemed ourselves with new design options for his infographics. His assistant, who had been in the nasty meeting, offered to take us out for happy hour. My boss later figured out that Charles asked her to do that. But that meeting made me realize this drama-filled stop on my career path was an unsustainable situation. Maybe the only takeaway for me was to write this story and come out of the crucible of this experience stronger and better.
So I am left to help my boss tame the bear, and to reflect on this complex and interesting dude and the unique challenges of his absolute power—no board or shareholders to answer to. Charles is a real entrepreneur, not like the textbook kind minted in assembly line business schools. He’s a modern American cowboy, a rogue individual. Real entrepreneurship isn’t as pretty as it looks in the pages of Fast Company. In this sense, Charles is like Steve Jobs and other visionaries who were often assholes. The standard line about innovation in silicon valley is “move fast and break things.” It has an aphoristic sexiness to it, as long as you don’t get caught in the path of forward progress.
Charles is a real entrepreneur, not like the textbook kind minted in assembly line business schools. He’s a modern American cowboy, a rogue individual. Real entrepreneurship isn’t as pretty as it looks in the pages of Fast Company.
A guy like Charles has a persona that a garden variety cubicle guy like me can’t quite wrap my head around. That day, a Dickensian fantasy kept running through my mind where Charles has a Scrooge-like epiphany, and dashes across campus greeting people magnanimously, under the joyous realization that life is short and there are essential things to reconcile. Yeah, right.
Later in the day I was sitting though yet another tedious meeting—mid level people and a few VPs. All the typical archetypes were represented: the guy who scores cheap points by saying “let’s take a step back,” the consensus builder, the heads-down note taker, the true believer, the ass kisser, the pseudo visionary, the reiterater, the contrarian, all the creatures of the corporate menagerie. They were speaking in the hackneyed shorthand of meetings: run it up the flagpole, find synergies, move the needle, low hanging fruit, things actionable, on and on. At one point, we were discussing our standard line for the Audit process: “The closer you look the better we look.” It’s one of Charles’ favorites. Someone jokingly suggested "Come at me!” as an alternative to express the idea that we welcome client scrutiny. That’s it! My new mantra.
More to follow in this melodrama...maybe. Until then, I’ll be steeling myself with the inner noise of death metal...channelling an apocalyptic sensibility...Slayer, Venom, Possessed, Cannibal Corpse, Spirit Crusher. I am a hollow-eyed corporate zombie with a death wish. Either I’m in survival mode or I’m somehow developing a masochistic affection for this place….crank it up, asshole! What are you lookin at!?! COME AT ME, BRO!!!
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