This is an excerpt from my diary. Click here for more information on this series.
October 12th, 2022
“Life became so busy with ambition.”
That’s Andrew Sullivan, famed British-American writer and contributor to almost every major magazine at one time or another, paraphrasing a line from Cyrus Habib, a blind go-getter whom many regarded as a rising figure in the Democratic Party.
Frank Bruni, himself a famed American columnist for The New York Times, touches on Cyrus’ story in his new book The Beauty of Dusk: On Vision Lost And Found which chronicles his own experience losing his vision and how it led him on a journey of self-reflection and reappraisal.
Cyrus had seemingly everything going for him. He was a Rhode Scholar at Yale Law School, and roommate of Ronan Farrow (that is to say he was well-connected). He was the youngest person ever to serve as Lieutenant Governor of Washington, and was so well-liked that he was the presumed future governor of the state. And he was such an ace at fundraising for the Dems that he was a presumed pick for a cabinet position in the Biden Administration.
But in 2020 he decided to chuck all that out the window to up and become a Jesuit Catholic priest.
As he relayed to Frank, he made that decision because he felt he’d reached his boiling point with the Tyranny of Ambition, the Tyranny of Worrying About What Other People Thought of Him, the Tyranny of Making Every Decision in Accordance With His Conditioned Impulse to Prove To Others Just How Capable He Was. He’d had enough. Had he done anything in his life that wasn’t in service of these ill-fated pathologies?
As Frank articulates, Cyrus was “just such an interesting portrait of someone who decides to—and learned how to—tune out all that noise that governs life for so many of us.” He listened to his “truest, purest, humblest inner voice.”
Andrew, a gay man, confronted these sorts of questions himself when he was 30 years old. The AIDS epidemic was in full swing, and many of his friends were succumbing to the disease. He feared he might be next. It reoriented the way he thought about his life. He realized how illogical this notion of ‘destiny’ was. “Why am I basing my life on things that may well never happen?” he asked himself.
Success, acclaim, name-recognition. What’s it all worth? And why obsess over ego-driven things like these which are elusive, and, not to mention, subjective, meaning hollow?
Maybe ambition isn’t a virtue after all.
“The illusion of control is what I lost,” Andrew claims. He became more present once it dawned on him that there may not be a tomorrow. He became more “efficient” with the people in his life who he determined really mattered. He no longer had any time for those “friends” he deemed “not really friends.” The barometer in his life was: “Am I doing something meaningful today?”
But he lamented to Frank that once the crisis had subsided and it was clear that he’d get out the other side unscathed, he began to lose sight of these revelations. The jungle grew back. It always grows back when you stop actively cutting, pruning, weed whacking. That’s a metaphor international relations scholar Robert Kagan uses to describe the Machiavellian world that rears its ugly head in those moments when America decides to shirk it’s superpower responsibilities. But I think it applies here too.
Very quickly, Andrew Sullivan became a zombie again. He didn’t feel good enough just being. The accolades he’d already brought home weren’t enough.
The trophies aren’t any good if they stop stacking up, even for just a little bit. The overachiever only feels good when he’s in the thick of it. To not be in the thick of it makes the overachiever feel like an underachiever, even if the last trophy came but one month earlier.
Andrew suggests that he has, on countless occasions throughout his life, succumbed to this irrational pull. Was he publishing gripping commentary on the idiosyncrasies of the day? Was he growing his subscriber base on his new Substack®?
I’VE OCCUPIED A SIMILAR HEADSPACE as Andrew Sullivan, Frank Bruni, and Cyrus Habib as of late – the headspace that says “ENOUGH!” to the self-flogging.
For the first time in my life, I’ve begun to confront my own mortality, and have, over and over, asked myself the proverbial question:
“What’s it all worth, anyway?”
Morbid? By definition. Healthy? I think so.
One of the power-hungry characters in House of Dragon, the new spinoff of Game of Thrones, provided an answer in the form of the same question when he said:
“What is this brief mortal life, if not the pursuit of legacy?”
Legacy is everything, and yet it is nothing. For the dog-headed pursuit of burnishing it risks ignoring the present moment—the only thing guaranteed. It risks ignoring those in your life whom you love.
You can have goals, but if you fetishize those goals—if you hold them up on a golden platter as the goodie that, once attained, will finally make you happy and keep you satiated—you’re living an unconscious life. And you’re fooling yourself. How can you be conscious, living in the here and now, if so much of your mental bandwidth is spent dreaming, or, more often, fretting about the future? And the future doesn’t have to be 10 years from now. The future includes that board meeting you have tomorrow, or that phone call you’re gearing up for with a family member where you’ve gamed out how you’d respond to every line of questioning you could think of.
Just spit balling here. But these are the sort of conversations I’m having with myself right now; the sort of ideas I’ve been rolling over in my mind, day in and day out.
Why now? Maybe it’s because I’m solidly in my upper twenties, a couple years into my brain being fully formed after almost 3 decades of apparent training wheels.
Or maybe it’s because I’m now almost one full year sober of the rat race, finally becoming acquainted with the real me. The creative, introspective Jack who I always was, free from the censorious grip of ‘structure’ and a career-track that discouraged out-the-box thinking. A sparkle no longer dulled by choices I made under the influence of childhood conditioning. Structure. Order. Not feeling good enough—ever. Success addition. Fiscal responsibility. FEAR!
Writing has helped me along in this process. It magnifies deliberation. I often come to AHA moments when crafting sentences. There’s something about putting things on paper that helps you think more clearly. You’re also able to identify connections between things that you otherwise wouldn’t had you not put aside some time to really ponder and sort through the inner narrative.
In a very real sense, writing has helped me understand the world and myself; to see it as it is. To see it (more) soberly, without the highly biased emotional-state-dependent foggy goggles I’ve viewed it through most of my life. Of course, general life experiences can bring some clarity too. But how much clarity? Because if the foggy goggles are still on while you’re experiencing these things—i.e. LIFE—don’t you run the risk of misinterpreting, misdiagnosing, mischaracterizing your struggles? Like – you still have the goggles on, no?
THE CHALLENGE I HAVE NOW IS PRIORITIZING what to write about. I have so many ideas, so many narratives to tell, so much commentary I want to impart. But there really are too few hours in the day and I don’t want to get lost in the writing and ignore the present moment; ignore the miracle of today; ignore the one who matters most to me in this life: Sarah.
The other challenge I have is scoping. All the pieces I’ve worked on up until this point, including many of my entries in here, have turned out longer than envisioned. I have a tendency to get lost in the minutia; to explain something into submission.
I can go down long winding rabbit holes. Sometimes gopher holes too, which are surprisingly more intricate and windy. Whereas the rabbit is stuck playing checkers, the gopher is playing 3D chess. They’re far more willing to get their paws dirty too. The Gopher is sorta like a coal miner; the Rabbit, well, the Rabbit is like that lowly pipe-layer that jumps contract to contract with dilapidated municipalities, making three dollars more than minimum wage. ← SEE WHAT I MEAN?
I think this longwindedness comes from me being worried about coming off as reductive. Minutia—DETAIL—was the name of the game in the Intelligence Community.
Or it’s just a backlog of words unsaid being said.
God knows I pushed the upward limits of that job. Made my boss nuts at first; but we soon settled into a good understanding. He wanted 8 lines. I’d give him 13 zingers that he couldn’t unsee. He’d whittle it down to 11. I’d make the case that it had to be 11.5. I’d sell him on the value add. “This is unique analysis. CIA isn’t thinking like this, nor is DIA proper. The operators down range NEED to see this.” We’d settle. Both happy. Then it was his to own with the OPS Division – our version of QC. They were the last line of defense before our intel products made their way into the briefing books for the 4-star and the head honchos at the Pentagon. Luckily, it worked out great most times. My boss carried a big stick. Lotta sway at The Command, that one. Together we pushed the best-written intel products in the building across the finish line. Syntax was on fleek. And there was artistry—yes artistry—in those bureaucratic dispatches. ← SEE WHAT I MEAN?
That is all to say, again, that maybe, just maybe, my longwindedness at the current moment is just 3+ years of bottled-up words coming out like vomit. 13 lines that are then whittled down to 11.5? That’s fucking prison for a stream of conscious. Man needs his release at some point, or he will internally combust. Didn’t matter what words were said, I just needed to meet my quota to stabilize. Like, it’s your blog – go crazy! Ain’t no space constraints. Ain’t no format Nazis up in your zone!
What am I saying? If I’m being honest, which is the point of writing in here, that’s probably only 1/4th of what’s going on. Too often my longwindedness is about that dreaded ego: my wanting to showcase how much I know about something.
And readers can see through that, my guy. No one likes a try-too-hard. It’s like the dorky dad in the New Balance® whites, and the tube socks, and the khaki shorts that hang below the knee who starts dropping slang words—or what he thinks are slang words—because he wants to come off as more relatable to his rap-music-obsessed son.
Who you foolin’, son?
You risk alienating the reader. They’ll think you’ve begun to question their intelligence, or that you undervalue the time and attention they’ve given to reading your piece.
It’s also a sure way to burn yourself out, guaranteeing you’re less prolific than you would like to be; guaranteeing less of your ideas or observations get out into the world.
SO STOP IT! :)
Prioritization and scoping will work itself out if you stay here—right here. Learn to flip the bird to the ego-trip, and soon you’ll be well on your way to imparting fresh, thought-provoking ideas.
Not in order to buttress your legacy per se, but to complement your own journey, and, in the process, hopefully also provide some value-adds to others too.
Getting tired. Hand hurting. Let’s end this with a quote of unknown origin that can wrap this sucker up in a feel-good bow:
“Find death before death finds you.”
March 12th, 2023
IS ANDREW SULLIVAN HAPPY? Has he ever experienced lasting happiness past the dopamine hit he gets after publishing a piece that drives the public conversation? Or after he owns BOTH the Libs and the Trumpists during an appearance on Bill Maher’s show?
I’d venture to say that mostly the answer is no. It’s a question Sullivan himself pondered during a podcast in October, which I myself then pondered in the first entry of this periodical. Sullivan has essentially been writing about—and reacting to—news events and cultural developments in real time for like the past 30 years. He has seldom taken any breaks. He’s too often been stuck in that rat race, often seeking, as he suggests, acclaim and recognition. Life for him became “so busy with ambition.”
But Sullivan readily admits that that streak of conscious thought is usually fleeting. He only feels safe or like he’s on the right track when he’s producing piece after piece like a damn printing press. Plus – the news cycle is just too intoxicating. He is a “reactionary” after all…
I feel as if, right in this moment, it would do me well to see that trap, and consider whether I realllllllllly want to get sucked back into it. You left the churn and burn of the Intelligence Community for a reason, no?
Is Andrew Sullivan actually happy? Judging by that Bill Maher appearance it seems no. I agree with much of what he says about the excesses and contradictions of the “woke Left”—and indeed his contentions are very important to the cultural conversation—but he seems to be stuck in a sort of doom loop. Most public intellectuals are. Plus – most of what he writes isn’t lasting. His pieces, in some cases, only have a shelf life of like one week. Journalistic stories and analysis pieces are relevant for even less time than that. It really is a hamster wheel.
And even though I’m not in that world (just yet maybe), I see it. I see it on Twitter, where I follow like two thousand journalists and media-types. Everyone’s running on adrenaline, delivering news “scoops”, or promoting pieces in which they react to those scoops. In that world your professional reputation resets every Monday. It’s fucking survival. Not dissimilar from working in the Intelligence Community. You’re only as good as your last scoop. You’re only good as your last intelligence paper or briefing.
I see this in my own mind state and writing. In October, I started contributing to this churn and burn with the “This Week, Today” series on my Substack®. I’d react to two to four political, cultural, or international developments and provide some analysis. Re-reading some of those pieces months later, I’m impressed with much of my prose and the arguments I make (there’s something about having a firm deadline that strengthens the clarity and flow of your writing; no time to overthink). But make no mistake, these pieces aren’t lasting. No one’s going to go back and re-read them (well, except me).
When I started that product line, I was motivated by what you might call “feel-think.” Money was getting tight; my one-year anniversary of quitting my job was fast-approaching; and my parents were like “uhhhhhh what the fuck, dude?”, perhaps ignorant to the fact that I was asking myself the same thing just 6,000 decibels louder – a stubborn symptom of the expectations placed on me and so many of my private school-attending contemporaries, as well as my own unique cocktail of emotional conditioning.
So I did what I knew best – I started a weekly, one not dissimilar from one I produced on the inside for the government. And I told myself it would “bolster” my resume. But I quickly knew that I had, in a way, taken a couple steps back. This was something I mused about in these pages last November.
“I’m back in the rat race,” I said. “This isn’t setting yourself up for lasting happiness. Trajectory UNCHANGED, other than the fact that you’re no longer picking up a government salary that allows you to live in Hawaii.”
I’M NOW AT A BIT OF A CROSSROADS. I want to write more lasting stuff. I want to set myself up for a life that doesn’t require me to be in a rat race of any kind. I want to produce work that really affects people; work that captures the human spirit and is self-enlightening—even fun—to write; work that compliments my own journey; work that doesn’t stagnate me.
Immediately after quitting my job in November ’21, my mindset was one of uninhibited (the rat-race-participant might say ‘fanciful’) imagination. Learning about—and trying my hand at—fiction writing was the muse. I want to re-tap into that mindset in the coming months, and perhaps re-try my hand at short story writing.
The past year and some change has been quite the journey. I’ve had my ups. I’ve had my downs, which they say are just more informative ups. I’ve had moments of clarity. I’ve had moments (many) of confused, jumbled thought. But it’s all gravy, baby!
As J.R.R. Tolkien, imagination incarnate, said:
“Not all who wonder, or wander, are lost.”
And I feel my mind and my consciousness and my understanding of things expanding rapidly—faster than it all would have had I stayed locked into my career in the IC. I’m growing markedly stronger and smarter by the day. My writing is improving leaps and bounds. I’m becoming more perceptive, and better at identifying what makes a good story—and better at structuring and telling that story.
I feel as if having a “mission statement” that could act as a North Star for the type of stuff I ought to focus my energies on in the coming months would be really helpful. Looking back at the various iterations of my Substack® “About” blurb is telling as to my shifting mental state.
It was:
“On the quirks, nuances, and contradictions manifest in our body politic and the human condition. Also – some satire and other playful musings.” ← That’s some gobbledygook if I’ve ever seen it.
Then it was:
“Challenging reductive narratives by shedding a light on the complexities inherent in many of the political and social debates of our time. Also – some satire and other playful musings.” ← Oooof. Even more goobbledygook-ish.
Then it was:
“Candid analysis and commentary on our complex world brought to you by a former U.S. Intelligence Analyst.” ← This sounds like the most boring newsletter ever. NEXT!
Then it was:
“Good-faith analysis of—and spirited commentary on—our complex world. Allergic to echo chambers and reductive thought.” ← Two things. One – em dashes in a mission statement? Really? Two – is this a Twitter® bio or???
Then, I finally landed on the pithier:
“Good-faith analysis of our complex world. Spirited commentary on its quirks.” ← I refuse to critique this last one because I don’t think I have it in me to blow it up and start from scratch.
You can see that I’m sort of straddling both worlds. The world of precision and logic (government analyst, balanced, objective) and the world of satire, imagination, playfulness (or “Mr. Fanciful” to the rat-race-participant).
Unlike the “About” blurb, the one-sentence bio on my Substack® has remained consistent throughout. It reads:
“Jack is a freelance journalist, fiction writer, and expansive thinker who’s dedicated to teasing out the nuances inherent in many of the political and social debates of our time and to shining a light on overlooked stories, characters, and perspectives.”
Perhaps I need to focus my efforts on the latter half of that blurb—“shining a light on overlooked stories, characters, and perspectives”—and less on the political (and geopolitical) piece…
The journey continues. It’s interesting how both this periodical and the one that preceded it each cover an almost-precise 6-month span. Something tells me that subsequent periodicals will cover a shorter period. Yes, I’ve got the diary bug, finally, it’s safe to say.
I feel that I’ll be writing in here more consistently—hopefully every day. Because why not? Why not document this incredible gift of life?
It really is a gift.
I’m such a lucky person.
March 12th, 2023. Entry # 2.
WENT ON A LOVELY WALK WITH SARAH after finishing that last entry. It was 19 degrees out, but lovely nonetheless. Any time I have alone with Sarah is lovely. Her family lives in a nice neighborhood. Big brick houses. Everyone has well-manicured landscaping that somehow looks impeccable even in the dead of winter. Resilient plants they have here. They can brown out and freeze to a crisp, then awaken 5 months later like nothing happened. One of the neighbors has a weeping willow. It’s so interesting how it keeps its wonderfully droopy shape, even without its leaves. You never think of a willow being made of branches like its contemporaries, but it is – branches that freeze in their extreme slouch. This one almost looked yellow. Can’t wait to see it in its livelier slouch, maybe in the coming summer. The neighborhood is something to behold in the summer, and, I must imagine, the spring too. I don’t think I’ve ever been to Omaha in the spring.
The day, it seems, just keeps getting lovelier. Sarah pulled down a red wine from my in-law’s hearty rack. After we enjoyed a couple glasses with the spareribs that we inhaled, she looked up the bottle.
We’re bursting out laughing, and feeling, perhaps, a little guilty. It’s an _____’s “_____” 2018. Guess how much the bottle goes for.
We feel so damn guilty! But as Sarah keeps telling me, “it was 2 rungs down from the top shelf!” How were we supposed to know?
In all actuality, my in-laws won’t care. Still, there is guilt. A heap of it.
Oh well. What’s done is done. So. Uhm. Cheers?!
ہ ← Can confirm that this is a wine stain. Swab and submit to Labcorp® for identification – I dare you.