Lessons Learned from Captain Jack Sparrow
Here I present the 20 lessons he demonstrates…lessons that are available to all who set sail with a brave and adventurous heart. But read this at your own risk, as these lessons have the power to transform lives, if you listen closely enough.
1. Freedom is paramount.
As Captain Jack says to Elizabeth, “what the Black Pearl really is…is freedom.” His quest to regain the Black Pearl is one of finding his own personal freedom, to travel without encumbrance to the horizon.
2. You determine what you are, not your circumstances.
Even though Jack is without a ship for the majority of the story, he exclusively introduces himself as Captain Jack Sparrow. Why? Because he knows in his heart that a captain is who he is, regardless of his current situation. When Commander Norrington challenges him with, “Well, I don’t see your ship…’Captain,’” Jack merely narrows his eyes and responds coolly, “I’m in the market, as it were.”
3. If people forget who you are, you must remind them.
It’s not enough to know who you are – you also need to remind other people. Don’t let them play you down. Insist on the respect you deserve. Even on the gallows, Jack corrects the reference to his name. “It’s Captain. Captain Jack Sparrow.”
And when Gillette laughs at Jack’s assertion that he is taking command of the Dauntless, Jack reminds him, with the help of a pistol, “Son, I’m Captain Jack Sparrow, savvy?” Similarly, at Barbossa’s stunned reaction to finding Jack alive and well, Jack says, “When you marooned me on that godforsaken spit of land, you forgot one very important thing, mate…I’m Captain Jack Sparrow.”
4. Aim high.
Jack’s goal is singular: to regain command of the Black Pearl. This is no modest goal – his former ship is now inhabited by a bloodthirsty, crazed group of pirates who cannot be killed. The average person wouldn’t even attempt this.
But small goals don’t appear to be what motivates Jack. When he tells Elizabeth that he’s going to teach the pirate song to his whole crew (when he gets his ship back) she flatters him with, “And you’ll be positively the most fearsome pirate in the Spanish Main.” Even this is not big enough for Jack, as he counters with, “Not just the Spanish Main, love, the entire ocean, the entire world.”
5. Cultivate your own legend.
When it comes to personal marketing, Jack is an expert. He knows that if you want to become legendary, you need to put some effort into it. Mr. Gibbs tells Will of Jack’s fantastic escape from the island. Elizabeth has read of his tales of escape and conquest. And when talking with Mullroy and Murtogg (after being challenged aboard the Interceptor) he begins spinning yet another yarn with, “…and then they made me their chief.”
What is perhaps most interesting is that despite the initial suspicion with which Captain Jack is viewed, his stories elicit rapt attention, whether told by himself or an advocate. People love legends…even when they’re not sure they believe them.
6. Remember that infamy is as good as fame.
Jack seems to feel that it’s better to be known and disrespected than never to be known at all. Norrington claims, “You are, without doubt, the worst pirate I’ve ever heard of.” To which Jack responds cockily, “But you have heard of me.”
7. Keep a sharp eye.
As unsteady and oblivious as Captain Jack appears to others, he is startlingly present and aware, soaking up the details to see what may be of use to him. He recognizes Will as the son of his friend, and hearing Will discuss “the right leverage” and the “proper application of strength” leads him to develop a cunning strategy. Jack appears to know that gold isn’t just found in pirate caves and ship holds, but also in the details of everyday interactions.
8. Master strategy, but be prepared to fly by the seat of your pants, as well.
Jack is a clever, if unconventional, strategist. Nevertheless, he is prepared to take swift action without knowing how it will all work out. His escape from the Royal Navy (after rescuing Elizabeth) showed that thinking only two steps ahead of everyone else was enough to manage an escape.
9. Wait for the opportune moment…and be poised for action when it arrives.
Timing can be everything; sometimes it’s a waiting game. Will cannot see the wisdom of this. He moves ahead when the time is not yet right and later (with Elizabeth) misses his opportunity altogether. But Jack knows that success is about allowing the best circumstances to ripen, then moving into swift action…even with a pistol shot that you have been waiting to use for ten long years.
10. Develop your own sense of personal style.
Style is essential, and life is too short to waste masquerading as a copy of someone else. From the beads in his hair and beard to the kohl smudged under his eyes, Jack is style personified. Who cares if it falls in line with established fashion? One look at Jack and you know he’s an individual.
11. Don’t go anywhere without your effects.
Jack goes no where without his effects and if he has to set them aside, he cautions others to watch over them. And for good reason – his sword and pistol are the tools of his trade, and his hat? His hat is pure Captain Jack. What captain would go out into the world without his weapons and his hat?
12. Never apologize for who you are or offer explanations.
Throughout the story, people are misinterpreting Jack and his motives, left and right. He could spend time explaining himself, or apologizing for his unconventional ways, but he doesn’t waste the time. Jack knows that people will decide what they think of you regardless of what you say; what matters is what you do.
13. If playing by the rules could get you annihilated, don’t do it.
Staying alive is more important to Jack than honoring someone else’s code. When Jack reminds Will that he previously beat him in a fight, Will protests. “You didn’t beat me,” Will insists, “You ignored the rules of engagement. In a fair fight, I’d kill you.” Jack looks at him pointedly, “And that’s not much incentive for me to fight fair, is it?”
14. Make it your business to know what motivates each person you deal with, and be ready to use that to your advantage.
Jack rightly calculated that Will is motivated by love for Elizabeth, Barbossa by power and status, Norrington by his sense of righteousness, and the Governor by his desire to protect his daughter and sense of propriety. At various points in the story, he makes a proposal to each of these people and in every case he presents in it such away that he addresses their motivating need. And even when they still don’t trust him, the proposal is usually too good to resist…just as Jack intended.
15. Know that people don’t have to understand you or respect you in order for you to get what you want.
If Jack waited for validation from others, he’d get little done. And so he doesn’t wait. He moves through life being exactly who he is, reminding people of who he is (“Captain Jack Sparrow”) but not slowing down to make sure they “get” it.
16. Allow madness and brilliance to coincide.
Will can’t decide if the underwater path to the Dauntless is an idea born of madness or brilliance, and Jack points out that it’s remarkable how often those two traits coincide. And he should know – he’s a master of the brilliant, crazy plan. When Elizabeth and Will engage in “out of the box” thinking of their own, Mr. Gibbs grins admiringly and says, “Aye, daft like Jack!”
17. Remember that the only rules that really matter are these: what a man can do and what a man can’t do.
Jack doesn’t waste his time with possibilities and arguments. It’s all about what he can do, what he can’t do, and what action to take as a result. He leaves the internal struggle of conscience to people like Will.
18. Even in dire straits, keep your sense of humor.
Jack lends new meaning to gallows humor when he engages in a reminiscing chuckle as an official reads his crimes before his hanging. You can almost hear Jack’s thoughts, “Impersonating a cleric…good times, good times.”
19. Pretty, shiny things are meant to be collected – hoarded, even!
Sometimes you just need a bejeweled gold crown, and how could anyone have enough strings of pearls? Enough said.
20. Never give up.
Persistence is all the more impressive when the odds are clearly against a person. From the time of the mutiny aboard the Black Pearl to the time Jack regained the ship, ten years passed. An entire decade. And yet not once did Jack give up his goal. Sure, he may have taken some detours, drank more than his share of rum, and shared a bit of fun with the harlots in Tortuga – but he always returned to his goal of getting his ship back. With patience and a bit of assistance, Jack succeeded, too. And through this, he shares his most important message: never give up on what matters most to you.