The Compassionate Corporate Warrior’s Journey

Written by Jory Des Jardins

Older man sitting in subway station with sign that reads “Seeking Human Kindness”

A couple of years ago I had a neighbor who’d scored a big job at an ascendant tech company. This company had captured my admiration for its underdog mentality, constant innovation, and willingness to publicly declare when it got something wrong and then fix it. I recall commenting to my neighbor, for example, how impressed I was with the company’s policy toward enforcing gender pay equity after an internal team had discovered a compensation discrepancy between male and female executives.

I was saddened to hear when, four months into the role, my neighbor shared with me that she was no longer working at the company. The role wasn’t a fit, she said almost nonchalantly, and she was “shown the door.”

My neighbor moved on to other more fulfilling roles. But our conversation stuck with me. I knew my friend was accomplished, intelligent, and thoughtful. I recall feeling disappointed that a company with such an impressive growing legacy of doing the right thing was such a mismatch with someone I admired.

Years later I spoke with my neighbor about her experience, when I was experiencing first-hand disillusionment with a company I had, perhaps, placed on a pedestal too soon. She shared that now, looking back, there was an almost defensive inter-validation mechanism that existed in the company. And that others, by virtue of their tenure, or perhaps in defense of it, extolled their brand of corporate brutality as a necessary component of the company’s success. And employees, sensing that their career survival was dependent on acclimating with the predominant culture, played along.

At the company I was working at during this time, I found a few kindred spirits whom I suspected were genuinely nice people who had also managed well in its rigidly demanding culture. I asked one how he managed the “personalities” on the teams. His answer sounded more like a combat strategy: Basically, he said, throw others under the bus before you get thrown under. But, he added as a qualifier, only do this if absolutely necessary.

Another colleague who wasn’t so nice but had just been promoted, said, when I asked her how I could be a better manager, that she’d fired most of the team she inherited, and now everyone got along just fine.

I’m obsessed with the series, Cobra Kai, on Netflix, the modern-day continuation of the 1980s Karate Kid film series, starring Ralph Macchio as the nice-kid-turned-Bruce-Lee, Daniel, and a cast of other dudes I might have dated in high school. Despite the ridiculous bench-clearing karate grudge matches (which make this must-see watching for my kids), I want to see how the sides play out, where they merge, and when backed up against the wall, who will do the right thing.

Actor Martin Kove, playing Sensei John Kreese in Cobra Kai, strides forward while saying, “Weakness is unacceptable” in front of wallpaper that reads “Strike first, strike hard, no mercy.”

While we may be culturally appropriated to assume that the non-aggressive approach of Daniel-san (played by Ralph Macchio) and his dojo, Miyagi-do, is the “right” side to root for, the “better” philosophy is not always so obvious. Miyagi-do may seem more virtuous, but it also perpetuates a naïveté that sometimes does more harm than good. In some cases students “win” battles when they stop the bonsai-gazing and assert themselves. On the “bad” Cobra Kai side, students lose love interests, friends, and self-respect by blindly asserting just to win. The more contemplative, skilled, and compassionate of both crews end up being the natural leaders who can end the destructive rivalry.

These kids are the true Warriors, because they fight even when they are losing, even when the momentum is not in their favor. I aspire to be like them.

I think back to my neighbor’s comments often, as an operator and advisor to startups building their cultures, of how seemingly visionary companies built on doing good, self-actualization, disrupting the status quo, connecting the world, and customer obsession are revealed to have harsh, combative, undermining, or even unethical cultures. The traits that got a company somewhere, such as grit, adaptability, ingenuity, or authenticity, get weaponized. Success becomes a religion, and those who question the path are weeded out as “untrusted,” “in over their heads,” or worse, “not a fit,” which connotes unworthiness.

In work cultures we practically worship at the altar of the asshole personality, whose selfishness, lack of empathy or ethics, and disregard for the dignity of others are lionized, at least until lawsuits are filed, quarters are missed, the confessional on Medium comes out, or the IPO fails.

I’ve been one of those hard-driving managers who needed to check myself when I judged peers who didn’t put in effort in the same manner I did. I’ve also been on the other side, where I had to prove myself across a network of conflicting stakeholders who judged how I approached a problem, knowing that no matter what I did, at least one side would not be supportive.

I haven’t always wanted to do the work of seeing a colleague eye to eye, presuming they are doing their best, and building an environment that supports their best work. That would take a lot of effort, and in cultures that value product over people, revenue growth over interpersonal growth, it’s a waste of time. It could even get you fired.

So then, which is better? Miyagi-do or Cobra Kai? Does playing the hard game make you win? Do “nice” people do better? Do they build great companies? Can compassion and excellence co-exist?

Though my position on this is entirely self-serving. I was never very good at figuring out who to screw over to prevent getting screwed over, much like I’m not very good at chess — my kids have now surpassed me there. I’m an ENFJ riffing on this. And what do hunches have over mixed proof that asshole cultures actually win?

Fortunately there are people who actually put some rigorous thinking into it. At my current company, Simon Sinek’s book, Leaders Eat Last is recommended reading. Our founders insist on a “people-first” model, meaning that team well-being comes first. If a ball gets dropped, someone responds with, “How can I help?”

Is this model failure-proof? No. And compassionate management doesn’t preclude difficult conversations and doing the work. But it certainly makes these things more pleasant. It makes success more meaningful.

If we can agree that compassion is the better path, we should consider moving the goalposts to success up closer. Investing in people by presuming their worth upfront may mean giving them time to grow, investing in their ideas with no immediate proof they will work, and actually meaning it when saying they can take mental health days. Double-digit-percentage revenue growth is possible, and likely over time, but maintaining that growth as the primary objective is when culture starts to slide into madness.

Man bursts up yelling something excitedly, then a group of people sitting at tables throw paper and cheer.
Man bursts up yelling something excitedly, then a group of people sitting at tables throw paper and cheer.

Are we entering the age of Digital Cults? If so, I’ll be on the Digital Playa…

I was incredibly grateful to Angus Nelson, who a few weeks back gave me my first tutorial on the mobile-audio-social platform Clubhouse (I’d link to it, but all you’ll see on the site is FOMO-inducing messaging saying you can’t get in unless you’ve been invited). I’ve been a lurker for months, which may come as a surprise to those who know me and my, well, loquaciousness. The truth is, I’ve had both a deep desire and deep fear of engaging, despite my history of building social communities and digital influence networks.

As Angus was sharing best practices for managing trolls on the platform I was one part planning my first talk and one larger part wondering if I needed yet another digital obsession keeping me from from my kids ( who have their own digital obsessions to be pried away from) and another platform popularity contest to win. For 3s on the Enneagram, Clubhouse is like a bump of crack cocaine dipped in dark chocolate and dusted with Ecstasy. I get the shakes just thinking about it.

Oh, but Jory … who said anything about a popularity contest? Clubhouse is meant to enable communities to engage each other in ideas!

Yes, thank you, self-justifying subconscious, for that bit of reassurance. But did you not read Sam Lessin’s column on Clubhouse and the evolution away from the community model of social platforms? Apparently we’ve grown out of it. Social media has become ubiquitous to the point of needing to re-establish lines of hierarchy and enable pulpits in order to stand out. Lessin dispassionately makes the case for why social has transitioned to a more hierarchical structure before using his outside voice calling Clubhouse a Digital Cult.”

He writes:

“The weakening of digital communities and rise of digital cults that we are seeing is inevitable. A similar pattern played out millennia ago in the physical world, as large cults and autocracies came to dominate small local communities. It is reasonable that the same cycle would repeat at warp speed in the digital space.”

He describes the Distinction Between Traditional Digital Communities and Modern Digital Cults:

“Communities are places where people value the viewpoints and stories of other group members and care about their standing in the minds of those others.

Cults, on the other hand, are places where people want to hear from a powerful leader and care about their standing in the eyes of the leader but not necessarily other cult members.”

Apparently them’s fighting words, judging by the discussion in the comments that ensued.

But Lessin’s analysis might have forced me to cough up those worries I’ve been harboring of getting sucked in, spit out, kicked around by hucksters who promise I’ll make money if I listen to them, or worse, that I’ll be turned away and shamed by folks with more cred in the space, whose elbows are sharp and who love lawless bully pulpits.

Pale boy with braces grimaces and cries out as camera zooms in, then smiles.
Pale boy with braces grimaces and cries out as camera zooms in, then smiles.

It’s quite possible that Clubhouse will be a lead-or-follow kind of place, one where we either speak or listen, but cannot do both unless we choose to hang in the lounges, where agendas don’t exist but chance encounters with like-minded souls might. These might be the cavernous, ambient-lit warehouse spaces of this new social internet. And since it’s audio I won’t need to bring my glowstick…


Steam rises from various flasks and volumetric tools attached together with metal clamps and filled with different-colored liquid.
Steam rises from various flasks and volumetric tools attached together with metal clamps and filled with different-colored liquid.

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Check out the benefits of our Early Access Program. Peace out.

Originally published at

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