Catch-22
I finished re-reading Catch-22 for the third or fourth time last night.1 It seems to call to me every five years or so, which I am realizing as I type this, also tends to line up nicely with each major shift in my life. The last time I read it was back in 2018. I had recently quit SpaceX (for the second time2) and was in the middle of struggling to build a remote drone data company in Alaska, which I kept afloat by doing work for space companies on the side. It hadn’t yet dawned on me that I should probably make the side-hustle that paid my bills my full-time pursuit. Oh well, it would come to me sooner or later.
At that moment, my side hustle was leading the demolition of the Rotating Service Structure for SpaceX on their then-new pad, LC-39A with a bunch of Cajuns that I met while building the barge a few years before. That’s a pretty wild story in its own right3 and is a chapter in my forever-work-in-progress book. I flew back and forth from Alaska on rotation, staying near the site a few weeks at a time during major moments in the demolition. I read a few pages of Catch-22 every night by the pool at my hotel in Cocoa Beach, which was originally opened by the Friendship 7 astronauts but had been transformed into a La Quinta during some dark chapter in its history.
There’s a different theme of the book that grabs me each time I read it. Back then, it was Snowden’s Secret4 which he spilled to Yossorian in the tail of the plane as the crew dodged flak during a mission. This time it was the absolute incompetence of the various Generals, Corporals, and other people in charge, and their manipulations of the airmen to grow their little empires. Throughout, the leaders are lost in the game and bureaucracy of war, more than they are on winning it. They’re worried about getting features in the Evening Post, sending memoranda, figuring out who is forging Washington Irving’s name to documents, and having tight bomb patterns (a concept they made up, yet which still means nothing to them).
Characters like General Peckham and General Dreedle are locked in a cold war for power. They’re ruining people’s lives — and ending them — just to try to stand out to the next person up the chain and get under each other’s skin. Worse is Lt. (later, Lt. Gen) Scheisskopf5 who couldn’t give a damn for missions and only wants to make everyone march in parade, the purest performative act he could subject the crews to. Worst of all, in my opinion, is Milo Minderbinder who is so effective at running his scammy Syndicate that he ends up supplying the Germans and quite literally bombing his own squadron.
Who Are We Building For?
As anyone who has read it knows, Catch-22 is simultaneously hilarious, horrifying, haunting, and deeply frustrating6. This time through it has left me feeling that whether we are building something in hard tech, for some other kind of startup, or are turning the crank at a day job to make more time for our writing hobby, we have to ask:
Who are we doing this for?
Now, this is different than the question of “what are we doing this for?” That’s a question that grew loud during the pandemic lockdowns. As Cal Newport points out in his book, Slow Productivity, we became expected to do everything, all at once, and right that moment. Few concessions were made for parents juggling kids or getting booked into endless zoom meetings from 0800 - 1800 each day. That sucks, and hopefully we’re coming to a point where we deal with that as a culture more wholistically. But I think, at the risk of skipping a step, that this second question just ends up begging the first: Who are we doing this for?
If we’re feeling lofty, we might say it’s for the company mission. Or we might say it’s for the team or a particularly good boss. More practically, we might say it’s for our kids, or our live-in parents, or just to make ends meet. I’ve given every single one of those answers at one point or another, sometimes more than one at a time! Well, except for the ‘company mission’ thing; I never drank the Kool-Aid at any space company I was fortunate enough to go on adventures with7. Sometimes, the answer for me has been just that: for me. Early on in my career, I made a lot of selfish choices to boost my resume and chase what I perceived as glory.
But the question of who we’re doing something for also extends outward from ourselves. Who is benefitting from your work? Whose mission are you enabling with your effort? I think about this a lot as I watch my old boss melt down on his imploding social media website on a near-daily basis. I’ve seen similar dynamics play out on much smaller scales at startups I’ve worked with around the country.
What is the story we’re telling about ourselves — individually and as a society — by who we’re championing?
And can we change it?
Low Ego, High Ability
I suppose it was an appropriate time for me to once again read Catch-22. I sold my company, and I am on a kind of self-imposed sabbatical where I’m trying to take things slow and figure out what the hell to do next. It feels oddly similar to my time at night by the pool in Cocoa Beach six years ago. I don’t know what the plan is, but the next adventure is just around the corner, I’m sure of it.
The key, I am learning, is to move in an expanding spiral instead of just going in circles through each of these cycles. Therefore, I try to do things a little bit better each time. My last cycle, which started with the barge and tower demolition then ended with Launch Co., taught me a lot about how to do the what. I got the chance to help solve amazing challenges across the space industry — and even send some stuff of our own to space — with some of my favorite people alongside. However, the work we did was pure engineering — it focused only on the how and what of a challenge. As such, to be quite frank, we enabled a lot of clients who probably shouldn’t have been enabled. It was easy to rationalize since we were bootstrapped and had kids to feed and mortgages to pay, but it didn’t always feel great.
This cycle I want to help people connect more to the why of their pursuits than the what. I have never been more disabused of the notion that some widget, gadget, company, panacea, or other deus ex machina is going to come along to save us than I am right now. Even if you disagree and think there is a silver bullet on the way, I think that we can at least all agree it sure as hell ain’t gonna come from the billionaires. Building is just as important as ever, but the who and why of the build matter much more than the what this time.
To better connect to my own why I have started surrounding myself with even more of my favorite type of people: low ego, high ability. People who have done truly amazing things but see those achievements for what they are: a mix of luck, privilege, hard work, and a dash of relentlessly practiced skill. It’s been fun to explore projects with collaborators new and old such as the Arctic Encounter Symposium, Swage Ventures, and most recently Borealis, a two-month remote work opportunity that provides everything people need to come explore Alaska8.
My hunch is that, more than anything, fixing what’s broken in our world might be more about fixing our approach: our approach to ourselves, to our world, to our work, and to one another. We have everything we need to build whatever we want. We just need to remember who we’re building for, both within and without.
It’s the copy I’ve had since high school. It’s well-worn to say the least — the cover is peeled, pages are starting to fall out from the loosening binding, and my English teacher’s name is written neatly on the inside cover. I should probably mail her a replacement copy.
For the second time. Long story, which I’ll tell sooner or later.
Pictures and a short write up are on my portfolio, here: Demolition of the Rotating Service Structure.
Snowden’s Secret is this: That man is matter. Ripeness is all.
Literally translates to “shit head.”
Damn, couldn’t come up with fourth word that starts with ‘h’. So close.
Which, I’ll argue until I die, makes one a much better employee.
Shameless plug: please sign-up and come hang out with us in Alaska for an adventure!