The Jack Sparrow Guide To Making Your Career Dreams Come True

by Hashim Warren

Jack Sparrow

Recently, for the first time, I watched the entire “Pirates of The Caribbean” trilogy over a two week period (thank you, Netflix).

I was amazed by the special effects and exciting story. But what really struck me is how much you can learn about achieving you career goals in the entertainment business by studying the films’ protagonist, Captain Jack Sparrow.

Capt. Sparrow was a man of contradictions. To his crew he seemed talented but confused. And despite his bouts of flakiness, he had a drive that rivalled any other pirate, and possessed a knack for finding creative ways to getting the job done.

Sound familiar?

Talk to anyone who has ten years in this business and their career story will sound similar to any old school pirate’s. Island to island, opportunity to opportunity they both go, looking for the next big treasure.

It’s true – professionals doing mainstream work can count on knowing where their career ladder is located and how to climb it. However, creative professionals like you have to get comfortable sailing with invisible and unpredictable winds, like a pirate hunting for gold.

So, how do you live with the uncertainty of our business and still make your dreams come true? Learn from the master pirate, Jack Sparrow.

Choose Your Island

Captain Sparrow didn’t sail with a treasure map. You don’t have a map either, and that’s a good thing.

A 20-year career plan is useless for you. In less than a decade a new technology, a new law, or a new format for entertainment could make everything you know right now obsolete.

You see, Sparrow’s secret weapon was a magic compass that pointed to the holder’s deepest desire. In the same way, you need to find your own compass that aims you toward what you want the most.

It’s pretty simple. What is your dream for the short term? It’s OK if it’s about making more money, and it’s fine if it’s a passion project that you’ll do for free. The important part is to have absolute clarity on what you want in the next 6 months, year, and 3 years.

Why 6 months? It’s enough time to develop new habits that can change your career path.

Why a year? It’s enough time to make a dramatic change. It took a friend at Lifetime Television a year to visit India 3 times and decide to work there full time.

Why 3 years? It’s enough time to master a new skill and completely change your life. A designer friend of mine spent the last two years getting his MBA, even though his rockstar work was already in high demand. Now he’s qualified to be someone’s rockstar boss and I already see new doors opening for him.

Do you know exactly what you want in your career right now? It’s OK if you don’t know how to get there (remember – maps are useless), but it’s disastrous if you don’t at least know what it is.

Feed The Gatekeepers

Every treasure that Jack Sparrow wanted had to come through negotiating or teaming up with someone else. Whether it was about getting his ship back, or breaking Davey Jones’s curse, Jack had to convince others to help him make it happen.

Look back at your own life. You’ll find that your biggest breaks came through other people. Someone had to say “Yes” for you to land that gig or run that project.

So, to make your dreams come true in the next 6 months to 3 years, you need to identify your gatekeepers in advance. Then figure out what they need to make the decision of working with you as easy as possible.

For example, I know who the gatekeeper for the success of Career Green Light is. I’ve never met her, but I have a name for her. I know how she works, and I know what stresses her out during the day. I know what kind of blog photos will make her smile, and I choose those for each post, regardless of what I think about them.

Most career advice in our business will tell you how to get past gatekeepers using charm or “small” acts of deception. I prefer to actually be the homerun the gatekeeper is looking for, so I don’t have to play any networking games.

Television executive DMA shared how she presented herself as a “Systems Queen” whenever she interviewed at networks. It didn’t matter how much DMA loved story formats, or how good she was at hiring talent. For networks with a workflow problem she was the perfect hire.

When you anticipate and position yourself as your gatekeeper’s dream come true, they will happily help your dreams come true.

A Pirates Life For We

So, that’s Captain Jack Sparrow’s secret to success.

Without a map he went towards his goals. He found key people to help him along the way. And he gave them what they wanted so he could get what he wants.

It’s the only method that works for a pirate, and it’s the only strategy I’ve seen work in the entertainment industry.

This blog post is a part of a series on career development in the entertainment business. If anything you read here helps you, please share it with a colleague today.