Captain Jack Sparrow Philosophy

Perhaps a strange source to find inspiration from but among the most powerful reasons to see Jack Sparrow the unlikely hero from the Pirates of the Caribbean series as someone we can learn from can be seen in the opening scene with the character as he rides a sinking ship into Port Royal during the start of the first film. Jack acts as the king of all that he surveys and though we can sense Inklings of the delusional and the deranged in him we believe in him.

We believe in him because he believes in himself and so in this post we’ll be going over Jack Sparrow philosophy from the Pirates of the Caribbean series and the ways we can apply his principles into our own conduct.

1. The problem is not the problem, the problem is your attitude about the problem.

The most prevailing inspirational quality of Jack Sparrow is his playful attitude. The playfulness with which he approaches all the scenarios that he encounters himself in the Pirates of the Caribbean series.


Jack Sparrow is someone who is betrayed, abandoned in life-threatening situations and yet what attitude does he maintain through all of it? Almost sort of a delusional grandeur and ease a creativity, a flow and almost a party like quality to him that makes him incredibly attractive. Not only attractive but incredibly potent in the way he carries himself.

There’s a quote from the Hindu sages that goes something like this – flexibility is life rigidity is death which is to say the closer you are to being flexible about, things ease. What Bruce Lee called being water my friend then the more powerful you are.

If you’re too trapped in one line of thinking being super attached to one result, one way of doing things, the more rigid you are, the more close to death you are.

Consider people who you’ve encountered in your life with the opposite mindset of playfulness. They’re extremely rigid, they’re trapped to one result and they’re completely grumpy and annoying to be around.
If something doesn’t work out in their line of thinking and their protocol of working having such a severe degree of rigidity about the way things should play out, it makes one weak, it makes one less effective.

One thing that Jack does incredibly well no matter the problem, no matter the circumstance, he’s flexible, he’s playful and he maintains a great attitude.

2. Take criticism in a positive way and have self-branding

In an exchange between Commodore Norrington and Jack Sparrow, Norrington says this – “you are without a doubt the worst pirate I’ve ever heard of” to which Jack Sparrow responds “but you have heard of me“.

Now I like this principle especially as someone who is an actor, as a creative and as an entrepreneur and many of us can relate to this. We are afraid to put ourselves out there, we’re often so attached to the artistry of our result that we would prefer actually not being heard of, not being seen than being seen in a negative way.

Many times actors, musicians, people who have that creative desire within them they’re super trapped by their own psyche, their own thinking and they think if I’m gonna put this out there I don’t know if I can do this.

I absolutely love the fact that Jack Sparrow is thrilled at the fact that Norrington has heard of him, you have heard of me at least. you’ve got that. He sees that as such a positive thing and it is a positive thing we are in some ways living in very strange times. This is the digital era having a digital presence and having a sort of portfolio of work that represents you in your professional capacity or whatever capacity that you feel is an expression of yourself.
It’s not only important and useful for anyone, it’s incredibly necessary. Often times the people who are the most amazing at self-promotion are also incredibly obnoxious and so we think to ourselves – “Well I don’t want to be like that” and we look down on such people I’m talking about genius marketers who some of us might instinctively think as less than they’re of a different terrain a more obnoxious terrain.

Yet if people don’t know you whether you’re an actor, a musician, then you might as well not exist in that line of work. It’s just a fact of modern times you’ve got to be willing to promote your work and even if some people might label you as the worst pirate that they’ve ever heard of, you should be cultivating that sense of being heard of in the first place.. So while this is a very small line within the parts of the Caribbean series I think it’s well worth reflecting on what can you do to promote yourself, what can you do to brand yourself and market yourself because if people don’t know what you do then the skills you have, the talents you have, they really have no leverage, it’s the knowing that gives you power.

3. Chase your purpose and freedom

“Wherever we want to go, we go. That’s what a ship is. It’s not just a keel and haul and deck and sails that’s what a ship needs but what a ship is.. what the Black Pearl really is is freedom.”- Jack Sparrow

What Jack loves most isn’t money, isn’t women although he does love chasing and participating in those things, his greatest love is a ship that’s his purpose and the ship the black pearl represents freedom.

This notion of chasing what’s truth, what’s your purpose, what’s your freedom is really an important thing to remind yourself of on a daily basis.

Once we hit our goal objectives it’s insane how quickly the mind is willing to become dissatisfied with those results and yet we get trapped into this result that isn’t actually real. The money is only a representation of something what you’re actually chasing above all else is your purpose and your freedom.

Jack Sparrow recognizes this the ship represents something above all else, it represents his purpose. When he’s holding that wheel and he’s setting sight on a new ambition on a new Isle that he could go to a new treasure that he could chase it’s not about the money it’s about being in alignment with what you’re meant to do and about having the freedom to chase what gives you excitement.

4. Why fight when you can negotiate

Jack Sparrow is someone who has a profound understanding that having a lot of friction, having a lot of hard work, gritting your teeth through a certain thing, it’s not always the right way to go.

In fact, Jack Sparrow looks for any opportunity to make things easier to take the easy path. Sometimes, it does this to an extent that makes him a bit of a scoundrel, a loveable scoundrel but also he has a real understanding of when to apply grit, virtuoso, figure, action and times where he can just find ways to weasel around scenarios. That’s more easy, that’s more free-flowing and isn’t so training.

I think there’s a real movement right now towards hustle culture. One of the most popular speakers on YouTube seems to be David Goggins and what is he famous for – running a hundred miles on his own and breaking all the bones in his feet. I personally find that a little ludicrous. I do have a deep admiration for hard work hustle pushing through pain and boring mundane activities to get the results that you want but life isn’t just about being the warrior, life also has an element of being playful and at times chasing things with ease.

There’s a book called “Power Versus Force” in which the author basically talks about the two types of activities that you can take on to get work done.
Power which has an elegance a grace and an ease that goes into doing things and so you’re not always just gritting your teeth and just chasing down objectives with the maniacal vision but rather being elegant in the pursuit of things.
Then there’s force which is just that hustle mentality of trying to get things done right now.

One thing that Jack Sparrow does beautifully knowingly or unknowingly, always finds ways to do things with ease, when he can.

One of scenes early on in the first movie, when he and Will Turner are trying to get to a ship to basically steal it, they use this boat and they use an air bubble through that rowboat to get to the ship.
So Will Turner says “this is either genius or madness” and
Jack Sparrow says  – you know you’ll be surprised how often those two things mix together”. That sort of thinking, that sort of creative thinking is an indication of what happens when you operate from ease rather than force, you don’t always have to use force sometimes you can just use negotiation.

5. The seas may be rough but I am the captain no matter how difficult I will always prevail

I really love this attitude that prevails in all the swashbuckler stories. The idea that sometimes they’re down on luck, sometimes you get scratched in the face and yet you can still come back from it, you can still face the storm.


It’s one of the reasons why I love Jack Sparrow because regardless of how tumultuous the storm is, regardless of how strange, weird and downright terrifying circumstances can get for him, he’s always willing to make it a good time.


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An Ambivert, music lover, enthusiast, artist, designer, coder, gamer, content writer. He is Professional Software Developer with hands-on experience in Spark, Kafka, Scala, Python, Hadoop, Hive, Sqoop, Pig, php, html,css. Know more about him at

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