Jocko Willink: My Messy Midlife Crisis In Human Form

Ben Freeland
Jul 24, 2018 · 8 min read

My twenty-something antiwar activist self would be appalled by my current podcast obsession.

Source: jockostore.com

The phrase “guilty pleasure” is bandied about with such abandon these days to describe any sort of pleasure that may not be the world’s best thing for you that it is quickly losing its meaning. To me, a true guilty pleasure has always been the type of pleasure that — beyond simply something like chocolate ice cream or Internet porn that may not be the best use of time or caloric allotment — causes you very real moral or ethical consternation.

Pleasures like my current obsession with Jocko Willink, former Navy SEAL commander turned motivational speaker, and author of Extreme Ownership and his self-titled podcast.

John “Jocko” Willink, for those unacquainted with the guy, is a now retired lieutenant commander in the US Navy SEALs whose 20-year military career was punctuated by deployment to Asia, Middle East, and Europe. Most notably, Jocko served as a task unit commander during Operation Iraqi Freedom, wherein he and his fellow SEALs (including controversial sniper Chris Kyle) played a decisive role in liberating the town of Ramadi from insurgent control as part of the 2006 surge.

In his post-military life, Jocko has reinvented himself as a leadership coach by way of his leadership consultancy company Echelon Front, which he co-founded with fellow ex-SEAL Leif Babin. He has also authored several books, including his cornerstone leadership manual Extreme Ownership: How U.S. Navy Seals Lead and Win, Discipline Equals Freedom: Field Manual, and a children’s book series entitled “Way of the Warrior Kid”. He is also a black belt in Brazilian jiu-jitsu, a topic which comes up frequently on his podcast (co-hosted by the always-congenial Echo Charles) together with all things to do with discipline, personal responsibility, honour, military strategy, and overcoming adversity.

The Jocko phenomenon appears to be very much of apiece with the Jordan Peterson phenomenon, and I’m sure, speaks to a broad masculinity crisis and a desire among so many young-to-middle-aged men to rediscover or salvage some sort of inner warrior strength. And I’ll be honest — I get it. I feel it acutely. When I first discovered Jocko and his podcast (thanks to his appearance on Sam Harris’ podcast) I was still freshly sober and profoundly angry with both myself and just about everybody else, and his mantras about extreme ownership (defined as taking ownership of everything in yourself and renouncing any and all excuse-making) personal accountability, as well as rebounding from disaster, seemed to be exactly what I needed to hear.

As I became increasingly obsessed with lifting weights, the Jocko podcast became my favourite gym listening. Having Jocko in my earbuds felt like I had my own private Marine Corps drill sergeant in my head admonishing me to work harder, to push further, to lift heavier — and to be better. While I quickly tired of the Peterson schtick, Jocko always seemed, well, so very reasonable and on-the-money with his assertions. Unlike so many self-help gurus, Jocko appears to be exactly what he purports to be and nothing more — a badass Navy SEAL commander who “gets after it” at 4:30 every morning (a fact he makes known through his now iconic “watch pics” on Instagram) and never quits. What’s not to like?

He’s also so frickin’ likeable too — borderline cute, in a meathead Navy SEAL sort of way.

Yeah. Just try telling that to my twenty-something self who once expended considerably time and energy protesting against the 2003 US invasion of Iraq, volunteered for Amnesty International in both Canada and Japan, devoured the likes of Noam Chomsky, Howard Zinn, and Naomi Klein, and basically never met an antiwar cause he didn’t like and embrace. To that guy, my current Jocko obsession is more than a tad embarrassing.


To be fair, I was never a pacifist per se. Nor was I ever anti-military — in fact I briefly toyed with the idea of enlisting in the Canadian Forces while in high school, until the recruiters made it clear that my asthma was a deal-breaker for them. Moreover, even my younger self would probably, had he given it the chance, found a lot to like in Jocko’s writings and podcasts, particularly with regards to martial arts. And as for the whole discipline-equals-freedom business, I wish I’d imbibed some of that earlier in life.

But in the period between 2001 and 2004 was an intense and divisive time that seemed to force everybody to “take a side” on geopolitical matters. Those toxic post-9/11 years, which saw a dim-witted US president surrounded by a cabal of chicken-hawks like Dick Cheney, Donald Rumsfeld, Paul Wolfowitz, William Kristol, and the recently rehabilitated and re-weaponized John Bolton open up a can of Texas-style whoop-ass on a country that, despite its horrible government, had nothing to do with the attacks on America of September 11, 2001, turned me into a passionate (if somewhat humourless) advocate for peace and human rights. To me, and to everyone I knew, the case for war in Iraq was absurd, obviously a naked attempt to invade an “enemy” regime, steal its resources, avenge past grievances…or something. Nobody really knew what this was about, except that it was a terrible idea and that lots of people were going to get killed.

On that night on March 20, 2003, as I watched the first bombs drop on Baghdad from my university dorm TV room, I sat in stunned silence, genuinely hoping that I had been completely wrong about the wrongness of this war. And I’m sure everybody else in the room was thinking the same thing.

Over 15 years have passed since that day and the Iraq War still leaves me scratching my head. If anything, the consequences of that war have proven to be worse than anything I could have foreseen at the time. Iraq remains a basket case, even with the ISIS menace more or less dealt with, and statistics still reveal a country decidedly worse off in terms of life expectancy, health indicators, status of women etc. than it was under the odious Baathist regime of Saddam Hussein. The end of the war, as overseen by Barack Obama, appears to have pleased nobody, creating a power vacuum that the Islamic State was all to eager to fill — marking an end to a military campaign that was far too long for everyone involved but also wholly inadequate for the job of nurturing a stable and democratic Iraq to maturity.

For all these reasons and more, I get decidedly queasy when the conversations in Jocko’s podcast turn to American action in Ramadi or elsewhere in Iraq — especially when his guests are themselves former SEALs, marines, and other US military personnel who served in this awful war. If Jocko could just stick to martial arts, military history and strategy, and inspirational stuff about discipline and life planning, I could listen all day. But when it comes to the Iraq stuff, I can’t get behind it.


But shouldn’t veterans of the Iraq War — like veterans of any war — be able to talk frankly, even proudly, of their service, even if the war itself was a gargantuan mistake? This truth dawned on me while watching Ken Burns’ wonderful PBS documentary series entitled The Vietnam War — to this date the most exhaustive examination of America’s tragic entanglement in Southeast Asia, featuring interviews with former combatants from all sides as well as civilian bystanders. A recurring theme throughout the series from the standpoint of the American servicemen interviewed is that many were so ashamed of the war they had participated in, and felt so much unspoken (as well as overt) hostility towards what they had done, that for decades they didn’t talk about it at all, further exacerbating whatever post-traumatic stress they were already saddled with.

The pain of holding all that in can only be imagined. Clearly we don’t want to make the same mistake when it comes to the veterans of the Iraq War, a war with many obvious parallels to the Vietnam conflict.

Jocko Willink — much to his credit — never celebrates warfare (much less that particular war, although not surprisingly he eschews commentary on the politics that led to it), and frequently emphasizes the horrors of it. That said, he doesn’t shy away from acknowledging how he and his fellow servicemen were fired up to see action in the war, and in many cases even dreaded the end of it — an uncomfortable fact about warfare that until recently was strictly the domain of challenging movies like Apocalypse Now and Full Metal Jacket.

The fact that certain people, like Jocko — as he readily admits, were born with a bee up their butts to be warriors and to fight and even kill for their country is a fact that most of us, myself included, have a hard time wrapping our heads around. Moreover, the fact that we’re all probably better off for the fact that some among us are wired that way is a hard truth to swallow.

I am still at heart a meditation-practicing, Kumbaya-singing Buddha-headed peacenik, and I’m sure I always will be. Were the United States or some other country to start beating the drums of war in some serious way (unless it was against a Hitler-type figure who obviously needed to be stopped that way) I would still be the first one out there on the streets to protest it, and given the capricious character of the Russian puppet who currently occupies the White House, I wouldn’t be surprised to see it happen given the right geopolitical concatenations.

But I’m also more nuanced in my views than I used to be. Nuanced enough to understand that our world is a messy, complicated place full of contradictions, and that one can’t simply draw a line in the sand and put the peaceniks on one side and the evil, nasty chicken-hawks on the other. Nuanced enough to understand that war is a job — even a raison d’être — for many, and that with nationalism and far-right populism on the rise virtually everywhere, war is a global reality we’re still far from doing away with altogether. And also acquiescent to the fact that, at age 41, my days as a potential member of the “warrior class” are long over — with or without my legacy of childhood asthma. That combat rubber raiding craft has sailed.

To put it another way, Jocko Willink is the living embodiment of my messy midlife crisis, of my quest for a new focus, meaning, and masculine identity in a very strange world. He is a living reminder of everything I could be, as well as everything I’m not, could never be, and in all fairness would never truly want to be. The martial arts and fitness stuff will forever fire me up, just as the stuff about Iraq will (probably) always make me feel somewhat sick to my stomach, and for all the right reasons I’m inclined to say. He is my reminder that our world is complicated, paradoxical, and often blatantly unfair, and that the only way to not get bowled over by depression is to regroup, refocus, and plow through it all.

To which Jocko would invariably reply: “Good.”

Ben Freeland

Written by

Writer. Teacher. Grammar cop. Distance runner. Historian in the wilderness.

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