If it's not working - try the opposite
And how top gun and tank tops make for great career trajectories
Growing up I loved jets. Planes. Anything with wings (I also loved Teenage Mutant Ninja Turtles, Ghostbusters, and Legos but those are all topics for another Neatworking).
I spent hours building models of fighter jets.
F-18s, F-14s, F-4s, if it had an “F” in front of it, I likely built a model of it.
I learned a lot of great lessons building models (again, gotta save some material for other Neatworkings), and I would spend hours delicately positioning these models all over my bedroom - at one point even using fishing wire and push pins (and in the process creating more holes in walls than my parents likely approved of) to mock up in-air dogfights around my ceiling fan.
I would go to airshows with my father (who was equally enamored with things that flew), and likely saw the movie Top Gun just a few too many times (but is there really a TOO MANY when you’re talking about Top Gun?)
In fact, I almost dropped out of law school for planes.
I mean, I at least seriously debated it - after spending a year generally disenfranchised by the entire legal industry, law school, classes, reading, the whole thing (you try sitting through a year of CIVIL PROCEDURE classes and tell me you aren’t also thinking about dropping out) - and was one crisp signature away from dumping it all to join the Navy in hopes to cram my way into a flight window rapidly closing with age (believe they don’t let you into flight school if you’re over 28, which seems a bit ageist, doesn’t it? Here I am, 38 years old and never been healthier. C’mon Uncle Sam, let me into the cockpit!).
Of course - reason (and the already sunk cost of one year of law school) won over, and here I sit, not really a “Tom Cruise in Top Gun” kind of guy, but instead a “Tom Cruise in The Firm” kind of guy (I mean, I’m not really wearing as many suits, don’t get a mercedes lease, and certainly not discovering the dirty underbelly of my firm’s legal practices through the legendary Gene Hackman - but I’m closer to that than I am to Top Gun, or - say - a “Cocktail” Tom Cruise kind of guy)
One day, I’ll be a fighter pilot. Maybe it won’t be of an F-14, but you can be damn sure it’s going to be some ridiculous looking bubble cockpit private plane, painted up to be just as loud as the car I’ll pull up to it in. I’ll walk around it slowly, tracing every edge with my hand, before dramatically putting on ray ban sunglasses, cranking up the engine, and flying into the California sunset (queue “You’ve Lost That Lovin’ Feeling”)
In reality we all can’t be fighter pilots (or insert whatever childhood dream you had).
But that doesn’t mean our dreams are out of reach.
It just means our dreams may materialize differently than we initially imagined.
It just means we find ways to be pilots in our own right.
And when you’re given that chance, whatever it may look like, whether it puts you in a cockpit or not, you recognize it. And you take it.
My chance came just a year later, in my final year of lawschool - nabbing a job working for the National Aeronautics and Space Administration in their Chief Counsel’s office (another great story for another Neatworking) - feeling like all those clips of Top Gun, Apollo 13, The Right Stuff, and other movies my Dad made me watch begrudgingly growing up (all of which coincidentally turned into some of my favorite movies, and I plan on doing the same to my son btw) were finally coming true in their own special way for me. It remains one of my proudest career moments.
I remember my first day, driving through the security gate in Cape Canaveral, pulling up to the parking lot at NASA headquarters, and just taking it all in. This is where it all happens. And I’m here. I’m part of it. I was (in microscopically small fractions based on my contribution) launching rockets. I was flying. I was a pilot.
Now you may be wondering - how this ties into our title, and how we’re going to break out of this wistful walk down Evan Ferl memory lane…
Well, let’s do just that: enter our Neatworking connection for this week: Jon Navarro (Digital Health Product Leader)
Jon and I met through a mutual friend, Arthur Wang (check out his Neatworking article here), and during our time together hit it off famously - as you’ll see why shortly.
Jon grew up in a town called Cicero, just outside of Chicago - famous for being the operating headquarters of Al Capone, a man who reportedly killed over 200 people, yet upon arrest was only convicted of tax fraud (man, the US Government really showing you where their head is at on this one, huh) - and Jon remarks that his main dream growing up was to “just get out of that town.”
Well, I won’t spoil the ending but Jon did (he lives in Manhattan Beach now, which sounds like a place in New York City, but its like if New York City moved to California and instead of a ridiculous sky scraper wasteland that somehow hasn’t figured out how to optimize it’s trash collection services - turned into a beautiful west coast beach town…so basically nothing like NYC) - and along the way, without knowing it, we shared similar experiences - a love of planes and aviation, an embrace of the nontraditional career path, and most importantly, a similar entrepreneurial origin story: Jon, spending the early part of his professional career designing and printing aviation themed t-shirts, and me, spending the early part of my professional career designing and printing ridiculous 80’s themed tanktops (man, its a wonder anyone even takes me seriously these days…they do…right?). Its one of my favorite parts of these Neatworking connections, the shared stories - and more importantly - the shared emotions, of a career spent not just dreaming, but achieving - finding our own ways to become pilots.
Permission to buzz the tower?
The pattern is NOT full, lets go!
Growing up Jon spent his summers at ~40,000 ft – usually somewhere in-between Illinois and Mexico, on his annual trips to see his grandparents in Guadalajara - a past time which made him fall in love with flying, and more broadly, the aerospace industry itself. And in a much more direct fashion than I (who used his dream as an “i’m out of this place (law school)” rip cord that I was never quite able to pull) - pursued his dream directly in college, studying aerospace - and in the process - finding out just how hard of an industry it was to break into.
Jon remembers his time approaching graduation (less than) fondly, recounting the ~500 applications he sent out into the aerospace ether (shoot, what is a better flying term for this….)
Ah.
He sent out into the jetstream (nice.)
With no traction. No response.
First application to Boeing - pass.
Second application to Northrup - pass.
[insert the other 498 aerospace companies] - pass.
A situation we have all found ourselves (or will find ourselves in) at some point in our careers.
I remember applying for my first general counsel gig while working as a (senior) associate counsel at VMware (convinced that the “senior” qualifier in front of my title and a fresh new MBA diploma would make me a shoe-in for so many GC roles that I’d have to beat recruiters off with a stick).
Then I remember applying for my second general counsel gig.
Then I remember applying for my third.
ANYWAYS fast forward six months later – there I was - still applying (again sorry to ruin the story but I finally landed one).
There’s a quote people throw around fairly regularly, attributed to Albert Einstein, “Insanity is doing the same thing over and over and expecting different results.” (well, shove it, Einstein, I finally got different results)
But Jon recalls a much different quote resonating with him during his days of cover letter hell: “If it’s not working, try the opposite”
A quote his uncle used to tell him growing up, and one that I may just need to remember in my next “Einstein Insanity” moment.
Well, Jon did just that. The opposite.
While the rest of his recently graduated colleagues kept shooting resumes out into the aerospace ether, Jon took a different course. He figured if the companies that built aircrafts weren’t interested in him, the companies that BOUGHT those aircrafts just might be.
“Instead of applying to the Company, I’d apply to the Customer”
Dang, genius!
501(ish) applications later, Jon submitted his resume to Delta and sure enough - became their newest Jet Propulsion Engineer (a job title that sounds ALMOST as cool as fighter pilot, tbh)
While all his peers were grinding away at wing design, Jon was working directly with the customer - and the customer’s customer - gathering data - learning about product development - and as a result – ended up being recruited away from Delta by - you guessed it – Boeing.
(btw…I wonder if they had one of his old rejected resumes lying around? Funny enough, in the not so distant past a company I tried for MONTHS to get to talk to me…sent them linkedin connection requests, emails, edible arrangements, you name it, and never gave me the time of day…unprompted a few months later (where nothing about my current role had changed) pinged me about an “exciting role with their team” - to which I responded “yea you should have about 50 of my applications already just give those a look” (not exactly but it was something close to that response)).
And Jon attributes landing (get it? LANDING?!) his job at Boeing TO doing the opposite. Applying to the customer, not the company. Starting his career in an opposite direction as his peers, and now, entering the aerospace giant with something none of his peers had: direct knowledge of the customer. Huge.
(And something he never would have gained if he hadn’t done the opposite)
Its always funny how things tend to work out when you spend your time finding the (open) windows instead of staring at the (closed) doors. Doing the opposite. Walking the road less traveled. A lesson I tell graduating law students any chance I get (advice I’m sure they rapidly dismiss upon hearing of a big law job being posted, but that I hope at some point they take to heart) - creative paths don’t lead you away from your goal - more often than not - they lead you to it.
For Jon, his creative paths led him across disparate industries – from beginning his career in aerospace, to a pivot into e-commerce, and eventually to where he sits today: Healthcare Tech.
Healthcare has always been an interesting, if not uncomfortable, industry for me – even the business side of the house - mainly due to one simple gating issue: I hate hospitals.
Well, I don’t HATE them – I just am deeply afraid of them.
Turns out, so was Jon.
I remember when my son was born, having to spend days in the hospital. Surrounded by taupe walls, plastic tubes, and beeping machines. Nurses and doctors buzzing around without explanation. And in the corner, me – nervous as hell despite not even being the reason we were in the hospital in the first place.
But experiences like that can do a funny thing to fear. It can change it. It changed it for Jon (I’m still working on accepting that change in myself). And after hospital visits for both of his son’s births, that fear changed into something much more powerful, it evolved - into appreciation.
Appreciation for what the doctors and nurses in that building do, and for what the people in that building go through.
And appreciation can do a lot more for us than fear ever could.
Its why when Jon got a call six months later from Cedars Sinai (btw, never knew there was an S on the end of CedarS until this Neatworking article) about a job opportunity that would take him out of his comfort zone, bridging his product work with his recent hospital experience, he didn’t let those since-conquered fears come back and get the best of him – he did the opposite, he said “yes”.
Jon joined Cedars to lead their front-end product development team, helping optimize patient experience, making their website and patient resources engaging, easy to use, and driving humanity and passion, while reducing fear – all in his own way, through product.
Jon was a pilot again.
But instead of flying planes, he was guiding patients.
From being sacred to - making a difference - all in the same industry.
And at the end of the day, isn’t that what being our own pilots is really all about?
Figuring out that special way we can make a difference – how we can feel like Maverick - whether its saving the world from the cockpit of a fighter jet, or making the medical industry more approachable for patients from an office chair in front of a computer – we can all be heroes in our own right. We can all be pilots.
And Jon continues on his flight path, now not just working as a product manager, but also as a coach to a healthcare tech accelerator aimed at making software and services for children in the hospital system, and as an advisory board member to one of his friend’s companies (and now his second mention in this Neatworking article alone!) Albert Wang @
Quite a journey - nowhere near ready for landing - and one that started by watching others’ flight paths and doing one key thing differently: the opposite.
So for all your pre-flight cadets out there, still finding your own way to the cockpit, remember - you may not end up exactly where you planned, but that doesn’t mean you haven’t arrived exactly where you should be. We are all our own pilots, and we can all make a difference - just sometimes that difference starts with asking something different of ourselves - breaking ourselves free of standards and traditions - and doing the opposite.
I don’t have a fighter jet. No cool callsign. Can’t walk into a bar in Navy dress whites and sing Righetous Brothers while the crowd looks on and cheers.
But that doesn’t make me any less of a pilot.
And doesn’t make you and less of one, either.
Now get out there and fly.
Awesome perspective Evan!