Climb The Career Ladder Using The Frank Sinatra Principle

In many industries, even the most talented must “pay dues” before they can play. And while there’s value in mastering the basics of knot tying before one captains a sailboat, it’s a shame that arbitrary time requirements can clog the talent engine of an organisation or stall the career of a creative person.

Image adapted from BokehStock, Gts and Inga Nielsen (Shutterstock)

The conventional paths to the best jobs are fraught with bureaucracy — most companies have a conventional waiting period before one can move up the ladder. Promotions happen once a year. A Partner has to retire or die in order for you to make Partner yourself — even if you’re skilled enough to do it. From management to government to arts and sciences, “years of experience” is one of the first things asked for in a job application; time spent gets equated to merit. Yet — some of the most successful people in the world (and in history) are the youngest or fastest-moving — they get further faster by circumventing this antiquated requirement.

One of the ways they do it is through what I call The Frank Sinatra Principle. Frank explains it himself in New York, New York:

My little town blues

They are melting away

I’m gonna make a brand new start of it

In old New York

If I can make it there

I’ll make it anywhere

It’s up to you

New York, New York

Frank’s articulating a timeless idea when he sings, “If I can make it there, I’ll make it anywhere.” He’s talking about associating brand equity wherein New York becomes a yardstick, a proxy for credibility. New York’s reputation for “only the strong survive” meant that if Frank succeeded there, he’d be seen as success material (internally and by others) no matter where he went.

We can apply this principle to climbing our own career ladder: to meet a minimum standard of cred for a given task, you can either show years of experience, or you can show that you’ve “made it” somewhere comparable. You might be the worst investment banker in NYC, but when you move to Kentucky, people will say, “She was a banker in New York. She must be good…”

In other words, you need a good brand to borrow from, and to use that brand to “prove” you can make it elsewhere. A hacker will use this idea to work her way from small brand to slightly bigger brand, and repeat. Rather than climbing the ladder, she’ll switch between ladders whenever she gets stuck but feels she has the skill to perform one level higher.

This works because people are generally willing to give an up-and-comer a chance if she’s reaching up from one rung lower on the ladder. But not five. A business will hire a director from another company and make her a VP, but it’s rare to promote an intern to VP. Because even important and busy people are willing to take small chances, you can use the “Sinatra” credibility of something slightly smaller than the place you’re aiming for to move up instead of time spent.

I’ll illustrate with a personal example:

When I first moved to New York City to study journalism, my goal was to pop out of grad school as a writer for my favourite magazine, WIRED. I soon learned, after pitching a story to WIRED during my first semester, that magazines use “dues” to filter the barrage of pitches random writers send each week. Editors are so busy they won’t even look at a pitch unless it’s from an established writer or someone who already writes for them.

“Sorry for that dose of cold water!” a WIRED editor wrote, after kindly letting me down. I soon learned that the conventional career path for an aspiring magazine journalist often goes something like the following in the world of old publishing:

1. Get a crappy job as an intern or poopsmith at the magazine you hope to one day write for.
2. Work hard enough to get noticed and eventually upgraded to the slightly less crappy role of Fact Checker.
3. Pound away the months in your lonely back crevice of the office until some kind editor lets you write a tiny story that no one else has time to bang out.
4. Keep writing the perfunctory stories until you get promoted to Reporter.
5. Work for years  — often on stories you’re not interested in — until one of the feature writers or columnists dies of liver failure.
6. Congratulations! Your high-profile dreams have come true! Unless, of course, there’s another, more senior writer (or better butt kisser) in line for the position before you, in which case, go back to Step 5.

What I realised, however, is that my WIRED editor wasn’t actually looking for a magic number of years of experience; he was looking for a quick way to determine whether I had what it took to meet WIRED’s tough editorial standards. A career climbing the magazine ladder inside of Conde Nast was one way to prove it. But when I looked at the career paths of some of the youngest feature writers for WIRED and other big publications, I realised that it wasn’t the only way.

What I really needed to do was to find what I call the Minimum Required Credibility (MRC for short) to put the editor at ease.

So, I established myself as an experienced outsider not based on time spent, but by attaching progressively bigger and better brand names to my portfolio, leveraging The Sinatra Principle like so (well, first learn to be a good writer; I’m still working on this):

1. Find an “anti-platform”: something like a rising new blog that seems desperate for content and will let almost anyone in. Pitch it some good story ideas  —  for free — going out of your way to do tons of pre-reporting and research or even pre-writing the stories, so a blog editor could basically just click “buy it now”. (I pitched several blogs until someone gave me a shot. That person was Zee from The Next Web, then a brand new site trying to compete among a growing number of social media blogs).
2. After writing numerous stories and establishing yourself as a “regular contributor,” pitch the next tier up, and tout your experience at the previous blog. (I approached Gizmodo and said, “Hi, I’m a tech journalist who’s written for The Next Web. I have a great story for you.”)
3. Repeat Step 2 until you get where you want to be.

(My path went: The Next Web > Gizmodo > Mashable > Fast Company > WIRED. The pitch to the second WIRED editor went something like, “Hi, I’m a tech journalist who’s written for Fast Company, Mashable, Gizmodo, and others. I have a great story for you.”)

Just six months after my initial email, WIRED published my first feature-length story. Not to brag, but I now get emails every month from WIRED asking me to pitch them more. All of this happened in the time it would normally take to get to Step 2 of the traditional ladder, which I’m pretty sure is one rung above Poopsmith.

Obviously, if my actual stories at those places had been bad, WIRED would have said “come back later”. But sufficiently good writing and the brand names of other publications were all it took to establish my credibility.

Once up the WIRED ladder, it was easy to climb sideways to other publications. I continued writing for the places I loved, and soon expanded my portfolio to New Scientist, The Washington Post, and HBR. Later, when I pitched The New Yorker, all it took to get the editor’s attention was, “I write for WIRED and Fast Company.” If I could make it there, I could make it anywhere.

Any career path can be hacked this way.

The Sinatra Principle says that you can skip arbitrary waiting periods by borrowing credibility from somewhere else and using it to grab onto a sideways ladder — a different company, league, publication, what have you.

This is how, for example, the youngest Fortune 500 CEO got her job. Marissa Mayer rode into Yahoo! using her credibility as a young executive at Google (after she hit a ceiling there). It’s how award-winning actress Zoe Saldana skipped years of low-level auditions and jumped into a film career by leveraging her credibility as an accomplished ballerina to land the role of a ballerina in her first film. It’s why workers who switch jobs every two years make significantly more money than their colleagues who stay for ten (the average pay raise for a new job at a new company ranges from 10-20%, versus 3% annually for staying in one spot). It’s why we hired Eisenhower as president, though he had never been elected to a political office. After he led the Allied troops to victory in World War II, America said, “If he can make it there, he can make it anywhere.”

To recap how to use The Sinatra Principle to shorten the time to the big leagues, start by ignoring anyone who says, “you need X years of experience,” and then:

1. Find an anti-platform — somewhere that will let in anyone.
2. Do amazing work until you reach the minimum required credibility to climb one ladder rung higher.
3. Grab the next rung up, using the “Frank Sinatra” credibility from the previous gig.
4. Go back to Step 2.

In Smartcuts, I write about how computer programmer David Heinemeier Hansson (a.k.a. DHH) used this tactic to hack the ladder in competitive race car driving. While his peers hung out in each lower league for the standard one to two years, he drove the minimum amount required to advance:

“After just doing six races, I jumped into the next highest class, I did about six races again in that. I won one race, I got a third, then I moved up to this other class. I did three races in that, and then I jumped straight into basically the top level.”

He explained, “Normally, the way people do it is they go for a whole year, they try to win the championship. Maybe they do it another year because now they’re one year more and they’re more experienced.”

But DHH didn’t care about conquering small ponds; he only cared about gaining the credibility to move up to big ones. He just got enough points to qualify to become the worst driver in a better league. Then he raced until he got just good enough to be the worst driver in an even better league. And soon he was competing with the best in the world, and learning to be a better racer from them than he would if he’d kept hanging out in the sucky lower levels. (“I always wanna be the small fish in the big pond,” he said.)

Now DHH races at the 24 Hours of Le Mans and other world-class events, with a top-ranked team.

“I learned 95 per cent by spending half or less of the time [as my peers],” he said. When he graduated from the minor leagues and entered the pros, he said, “It was like holy shit, where did that guy come from?”

Consider how you can think like Sinatra in your own career and make it anywhere.

This post is adapted from the new book Smartcuts: How Hackers, Innovators, and Icons Accelerate Success, in which entrepreneur and journalist Shane Snow (Wired, Fast Company, The New Yorker, and co-founder of Contently) analyses the lives of people and companies that do incredible things in implausibly short time.