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The Only Conversation That Matters



A few times a year, people email me asking for tips about interviewing at the company where I work. I respond with a form email and the first sentences look something like this:


"Study your own resume and go through all the projects. You should be able to speak about yourself with confidence."


Somehow, this seemingly obvious piece of advice feels necessary. At least that’s what I’ve come to think after conducting nearly 100 interviews myself. I’d like to believe people aren’t aware that knowing their own story is crucial, but that’s a stretch. It’s an interview. Certainly they'll be speaking about their background and motivation. Instead, even with the explosion of self-help content, meditation, and work-life balance, most people still don’t sit down and scrutinize the only thing that matters: themselves.


The ultra-productive, super-motivated among us have been shepherded into existence thanks to many amazing souls. Tim Ferriss, Jocko Willink, Joe Rogan, Jordan Peterson - the list goes on. We gobble up their interviews with Wim Hof and Peter Attia, hoping to living to 150, then finish an Ironman, then read ancient Greek letters about temperance. Yet somehow, despite their best efforts, I’m still convinced that most people in this camp never spend time alone and contemplate.


Ryan Holiday, one of the self-improvement stars of the last decade, quotes Marcus Aurelius in every other post he writes. His books are bought by millions and Aurelius is consistently a major figure, in large part thanks to his magnum opus, his personal journal: Meditations. The Roman Emperor constantly wrote to himself; reminders of the values he sought to espouse and man he strived to become, despite the trivialities that gnawed at his mind. He ruled over perhaps the world’s greatest empire, with armies at his beck and call, yet still regularly worked through his thoughts.


Holiday calls journalling “the most important thing you can do each morning”, yet few do. Maybe we should blame Anne Frank for the notion that keeping a diary is “girly”. Given her circumstances, if regular writing is girly, call me Cindy Brady.


After I began writing for others, starting with my newsletter in 2017, something funny happened when talking to readers: I took on the personality of a “writer”. Not to me, to them. If I talked about the process, the hours sat in reflection, they showed admiration but rarely empathy. And my writing wasn’t practical advice lists about weight lifting or cold showers. Only my observations on the world, sometimes edging on sappy. I know because while writing, I’d regularly get choked up at the beauty all around us. I was trying to hit a chord. Readers appreciated it, and they enjoyed hearing me describe the internal struggle. Yet they rarely did it themselves. Sat down, put pen to paper, and worked through an idea.


Our generation isn’t as unique as we wish to believe.


"The person who reads too much and uses his brain too little will fall into lazy habits of thinking." - Albert Einstein


Yes, things have certainly changed. This was from a 1930 interview, just 3 years after the invention of television. Reading was leisure, and being a book worm took away from creative, productive, hard pursuits. TikTok, YouTube, and Netflix have replaced books in destroying the will to work. We consume rather than build. Caught in daydreams.


The super-productive, 21st century men out there are probably saying “Not me!”. But let’s be real for a minute. If Einstein’s quote is really pushing us to avoid the easy way, to have our mind go to work, aren’t we avoiding that with our intense focus on diet, exercise, and longevity - habits we yank straight from the latest episode of whoever’s podcast? Sure, we work hard, much harder than anyone thought we could, but how often are we challenging our minds? It’s like reproducing a master painting. We can work for years to repaint the Mona Lisa, but we’ll still be as unoriginal as that Harvard loser Matt Damon eviscerates at the bar.


It’s time to work, and work where it matters most, on ourselves. With ourselves. The start of the year likely comes with goal setting: six pack abs, daily meditation, clean eating. But why? There’s a good chance those goals won’t be fulfilling if we’ve never asked what personal fulfillment entails. Goal setting is not about about the list, it’s a process of discovery. Questioning why we want a sexy bod and whether it’s aligned with other aspirations. We plan to attend a career-making happy hour every week, build out a strong network, when maybe the relationships at home are the ones that deserve attention.


I’m not saying one goal is better than another. It might be, probably is the case, that meditating each day will be best for you. But why? Because Sam Harris said so? My goals are complex. They have timelines and costs. Best-case-scenarios and trade-offs that make it impossible to do everything at once. Most important, far more than all other aspects, they’re mine. Built through introspection and tough conversations.


It’s fine, hell it’s great, to read and consume from these modern, self-help savants and put their recommendations to use. But they’re only recommendations. Suggestions. Something like practice. But it’s game time and we’re out there with someone else’s game plan. Do yourself a favor: sit down and work. Word, Google Docs, use the back of an envelope if necessary. And set yourself up for success. Schedule time and space. Hours not minutes. Find a guide (like this one). Brew some coffee, throw on some music, and get the conversation started.


The Greeks told us to “know thyself”. They didn’t say it’d be easy.


"I have no leisure for them at all; and the reason, my friend, is this: I am not yet able, as the Delphic inscription has it, to know myself; so it seems to me ridiculous, when I do not yet know that, to investigate irrelevant things." - Plato

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