In March, Pippa and I flew to Portland, Oregon to visit Lewis & Clark College. She was in the homestretch of her college search.
When she met up with her student host for a planned overnight, I wondered what to do. I love to cycle, but the nearest bike rental shop was four miles away and I didn’t have a car. Then I stumbled on this on my walk back to the Airbnb:

I did a quick pedal to Reed College, which is only four miles from Lewis & Clark by car, but further when you include all the bike switchbacks on the way down to the Willamette River.

I was curious about Reed because that’s where Apple visionary Steve Jobs attended for a year before he dropped out.
Steve Jobs Fail
Back at the Airbnb, I did a deep dive on Jobs and Reed and found this copy of his job application from 1973, right after he withdrew, but before he left Portland:

It’s an epic fail. Position desired? Blank. Past employment? Nada. Access to transportation? “Possible, but not probobale.”
Naturally, this one-pager sold recently for $174,757.
Leonardo da Vinci Contrast
As with Steve Jobs, I dug into Leonardo da Vinci while traveling. We flew to France on vacation in summer 2016 and visited Château du Clos Lucé in Amboise, in the Loire Valley. This is where da Vinci spent the last three years of his life, dying 500 years ago last month.

Da Vinci arrived in Amboise in 1516 at age 64, having crossed the Alps from Italy on a mule, with the Mona Lisa in his saddlebag. He moved there at the behest of a patron, King François I, who wanted to make Amboise the center of the French Renaissance. Da Vinci had a rock star reputation at that point, and the jobs came easy.

Over 30 years earlier, in 1482, da Vinci was 30 years old and much less established (Mona Lisa, The Last Supper, helicopter invention, etc. were still to come). Between gigs, he crafted a job application that he sent to Ludovico Sforza, Duke of Milan. It’s so remarkable, I’m including it here in full (translated from Italian):
“Most Illustrious Lord, Having now sufficiently considered the specimens of all those who proclaim themselves skilled contrivers of instruments of war, and that the invention and operation of the said instruments are nothing different from those in common use: I shall endeavor, without prejudice to any one else, to explain myself to your Excellency, showing your Lordship my secret, and then offering them to your best pleasure and approbation to work with effect at opportune moments on all those things which, in part, shall be briefly noted below.
- I have a sort of extremely light and strong bridges, adapted to be most easily carried, and with them you may pursue, and at any time flee from the enemy; and others, secure and indestructible by fire and battle, easy and convenient to lift and place. Also methods of burning and destroying those of the enemy.
- I know how, when a place is besieged, to take the water out of the trenches, and make endless variety of bridges, and covered ways and ladders, and other machines pertaining to such expeditions.
- If, by reason of the height of the banks, or the strength of the place and its position, it is impossible, when besieging a place, to avail oneself of the plan of bombardment, I have methods for destroying every rock or other fortress, even if it were founded on a rock, etc.
- Again, I have kinds of mortars; most convenient and easy to carry; and with these I can fling small stones almost resembling a storm; and with the smoke of these cause great terror to the enemy, to his great detriment and confusion.
- And if the fight should be at sea I have kinds of many machines most efficient for offense and defense; and vessels which will resist the attack of the largest guns and powder and fumes.
- I have means by secret and tortuous mines and ways, made without noise, to reach a designated spot, even if it were needed to pass under a trench or a river.
- I will make covered chariots, safe and unattackable, which, entering among the enemy with their artillery, there is no body of men so great but they would break them. And behind these, infantry could follow quite unhurt and without any hindrance.
- In case of need I will make big guns, mortars, and light ordnance of fine and useful forms, out of the common type.
- Where the operation of bombardment might fail, I would contrive catapults, mangonels, trabocchi, and other machines of marvellous efficacy and not in common use. And in short, according to the variety of cases, I can contrive various and endless means of offense and defense.
- In times of peace I believe I can give perfect satisfaction and to the equal of any other in architecture and the composition of buildings public and private; and in guiding water from one place to another.
- I can carry out sculpture in marble, bronze, or clay, and also I can do in painting whatever may be done, as well as any other, be he who he may.
Again, the bronze horse may be taken in hand, which is to be to the immortal glory and eternal honor of the prince your father of happy memory, and of the illustrious house of Sforza.
And if any of the above-named things seem to anyone to be impossible or not feasible, I am most ready to make the experiment in your park, or in whatever place may please your Excellency – to whom I comment myself with the utmost humility, etc.”
It’s remarkable for a couple reasons:
First and foremost, it is laser-focused on the prospective employer’s needs, instead of da Vinci’s skills and past achievements. The skills and achievements are simply assumed, perhaps even if they don’t exist.
Also, it’s extremely persuasive, due to a combination of solid wordcraft, and credible exaggeration. Imagine being the Duke of Milan and receiving this bold letter from the young prodigy of Florence. What Renaissance Duke wouldn’t want “kinds of mortars; most convenient and easy to carry; [that] can fling small stones almost resembling a storm”?
On a side note, I love his little offhand mention at the end: BTW, I’m also kinda good at art and architecture. Sort of equivalent to the personal interests section at the bottom of the modern resume, where you hope your oddball experience or talent that doesn’t fit anywhere else will somehow strike a cord with the interviewer: “What?!? You play the Hungarian zither also? You’re hired!”
Two Geniuses, Two Approaches
Two geniuses, and two very different approaches to snagging a job. Yet, they were both ultimately super successful.
One conclusion: It doesn’t matter much how you apply to a job, a smart person will always be successful.
I think that’s a poor take. Da Vinci lived in a time when engineers and artists were fully dependent on their sponsors – the reigning kings and lords. He didn’t have the option to create MonaLisa, Inc. and mass sell cheap art prints to the people.
Steve Jobs, on the other hand, was born at a time when technology was just becoming miniaturized and affordable, at the same time consumers were generating more personal wealth and disposable income. It was a great time to start a technology venture – as Bill Gates (also born in 1955) would attest.
The Take Home for Regular People Like Me
Twenty-first century America is still a good time and place to start a company and seek a fortune, but most of us probably don’t have the same business smarts and tolerance for risk that Jobs and Gates did.
So if you’re like me, when you are applying to a job or internship, be like a 15th century Leonardo da Vinci: focus relentlessly on your future employer’s needs and how you can creatively fill them.
No one but you and your mom really cares about the gold star your teacher affixed to your calculus homework, or the Employee of the Month honor you earned at your last job.