What I Learned About Success From A Drunken Pirate!

There’s lessons a’plenty to be had from watching Captain Jack Sparrow succeed, fail, succeed again, fail again and persistently follow his own inner compass through one adventure after another in the Pirates of the Caribbean movies.  You may be wondering what this has to do with running a successful business?

Well, grab a chair & a jug of rum and let me show yarrrrrrrr!

(If yer only here for the free PDF, jump to the bottom of this post. The PDF will help you create your own inner compass for exactly how to use these ideas to boost your own biz success…)

1. The journey is more fun than the destination

Sure, the Fountain of Youth was pretty interesting and being back in the real world after escaping Davy Jones’ Locker was such a relief after contemplating being stuck in the Underworld forever and it’s always rewarding to finally have the treasure you seek in the palm of your hand!

But it’s nothing compared to the experiences of getting there.

Which was more thrilling – being on the Black Pearl in the middle of the Sea in sparkling sunshine? Or the fact that you got there after goddess-infused crabs carried your beloved Pearl across the desert, into the Hades sea at which point you had to flip the boat upside down at sunset in order to be right side up at sunrise?

Without the journey, there’d be no movie. You fall in love, make friends, deepen the bonds of teamwork, find adventure and truly experience LIFE during the journey from one milestone to the next. Enjoy the journey. The destination will be easily replaced with a new goal, a new milestone, a new shiny object as soon as you’ve achieved it.

The destination is temporary. The journey is EVERYTHING!

2. Mindset will lead you to treasure over and over and over again

Ever notice how Captain Jack Sparrow’s arrogance is equal to his ability to find the most obscure treasures on the planet? He doesn’t seem to know the meaning of “failure,” “can’t” or “impossible.”

Jack’s mindset is what frees him to persevere in even the most insane situations.

Be like Jack. Act as-if it’s all part of the plan, even when it isn’t. Know that it will all work out in the end. Have confidence that you already have the unique skills and talents to succeed.

“Because I’m Captain Jack Sparrow” should be your new mantra! (Except it will probably work better if you use your own name…)  ;)

3. Magic is a crucial element to any endeavor of importance

Call it whatever you want – magic, mindset, intuition, creativity, faith, spirit, God, the Universe, human will, mother nature – magic is a necessary ingredient in massive success.  Jack would have stayed dead if it weren’t for Calypso and Elizabeth would’ve lost Will forever if it weren’t for the curse of Davy Jones.  Maybe magic won’t bring people back to life in your own world, but it can perform miracles in your biz.

Embrace it, weave it together with your dreams, make room for it in your life, feed it daily. Give it room to grow and allow it to play a part in your business. Choose a word that feels 100% authentic to you and then infuse your brand with it. Let it be the sparkle in your eye as you give presentations, the wind in your sails as you race towards your goals, the breath of life and inspiration that flows through your words & posts.

Your biz can’t thrive on strategy and action alone. There needs to be energy, passion, creativity, MAGIC!

4. Action trumps strategy

If you’ve joined the email list and watched the video training in the Real To Ideal Toolbox, you’ve heard me talk about Action and Strategy being 2 out of 3 necessary ingredients in the formula for success. In that video, I describe the pitfalls of action without strategy and vice versa.

Captain Jack Sparrow is a PRIME specimen of using strategy and action effectively during his exhilarating escapes. (His escape from the palace, right in front of King George being an ideal example!)

But in a situation where you have to choose, action is more important than strategy. It’s better to get out there and take action then to spend too much time planning what action to take. Often times, the strategy is already fully formulated inside ourselves and is waiting for an opportunity to present itself. Action allows strategy out of hiding.

For example, Jack’s escape from the British naval ship Endeavor shows his innate understanding of all the ship’s resources available and he easily uses them to his advantage.  He doesn’t need to think about how to point the cannon at the mast and use it’s energy to propel him into the air and over to the safety of his own ship, he just knows how these things work from using them every day on the Pearl. He’s in his element, the strategy lives inside him. He needs only a situation upon which to act.  If he were to stop and think about it, he’d get stuck in inaction and run out of time to escape. 


5. Rum is more important than gold (especially when marooned on an island with no commerce)

There will always be things in this life that are more precious than gold. Live for those things. Gold is fleeting, gold is just a shiny object. Live for the truly important things in life. Your freedom, your family, your tribe, your mission in life, your philanthropy, your legacy, etc.

Or, if you’re like me, live for the freedom AND the rum! (And the whisky! And my most beloved First Mate – who came up with the title for this post…)

Gold will only get you so far. LIFE and the people you surround yourself with will take you infinitely farther.

Plus, when you do things for the money, people can feel it.  If you do things because you’re committed to helping people, teaching, your own personal development, making the world a better place, improving lives or even just because it’s FUN, clients will flock to that and the money will follow.  But do the same things for money alone and you will always struggle to earn any at all.

If you have trouble getting past the money part, think about why you want the money.  Imagine you have a cardboard sign that says “Will Work For…”  What would your sign say?  Will Work For Freedom To Live The Life Of My Dreams?  Will Work So My Sweetheart Can Quit?  So My Kids Can Go To College?  So I Can Take Better Care Of Myself?  Think about the real reasons you want to succeed and not the gold that’s merely a middle man.


6. Competition is less fun than camaraderie

Captain Jack Sparrow and Barbossa had every reason to compete.  They were, after all, fighting for command of the same ship.  But, despite this competition, they often found themselves working together for a bigger cause.  And in the end, their partnerships were much more fun and yielded bigger rewards than anything they did solo.

So stop thinking of everyone as competition and start asking how you might both be more successful if you combined forces.

Another prime example – all those who competed for Elizabeth’s heart.  But would we be satisfied if anyone other than Will were to win?  It’s clear that Will was Elizabeth’s “ideal client.”  Despite Jack’s charm and Norrington’s wealth + good standing, no one resonated with Elizabeth the way Will did.  It wasn’t really a competition.  When you resonate with your ideal client, there is no competition.

So look at your “competition” as a potential allies instead and see what’s possible.

7. Perspective is everything

One man’s trash is another man’s treasure. Sunrise here is sunset somewhere else. The ultimate expression of freedom is a ship or a business, depending on who you ask.  (“That’s what a ship is ya know, it’s not just a keel and a hull and a deck and sails, that’s what a ship needs.  But what a ship is… What the Black Pearl really is… Is freedom.“)

It doesn’t matter what other people want, or what other people have. Strive for what’s important to you. For Jack, it was always the Pearl. For Elizabeth it was always what’s right & just. For William, it was always Elizabeth.

#FindYourIdeal and always keep it in your sights. Always be working towards what you love most in life, whatever is the highest expression of freedom for you.

A compass that points specifically to your most valued desires is the most important thing in the universe.

This is such a wonderful analogy for business!! Who cares about a compass that points true north? That will only lead you to things already known! Strive for the unknown, the unmistakable, the INCREDIBLE!!

Dream big, figure out what your highest ideal is and then chart a course for that! Create the map as you go, be not afraid of uncharted waters, let the winds of inspiration guide you!


Create the map as you go, keep your ideal ever in your sights & let the winds of inspiration guide you! [Tweet that!]


8. Love transcends all resistance

If you’re an entrepreneur, you’re overtly familiar with resistance. Resistance is as common to success as electricity is to internet access.

You’ve probably felt resistance from friends and family, resistance from people who read your posts, resistance from your bank account, resistance from deep inside your heart, resistance from your own confidence and mindset. Resistance is everywhere when you’re building something epic.

And nothing squashes resistance more completely than love.

Next time you feel friction in your biz, from any aspect, pour love into it.  Ask yourself, how can I turn this into an act of love? How can I cancel this out with love?
MANY times, you will find it’s SELF LOVE that’s needed in these situations! The need to forgive yourself, go easy on yourself, take care of yourself.

So you made a decision that didn’t pan out, or you wasted money on snake oil, or you poured all your time and energy into something that failed and you feel like you have nothing to show for it. So what? You’re still here and you’ll survive to work another day. Show yourself some gentility and love and know that nothing is ever wasted. Every experience teaches you important lessons and makes you who you are.

Let love overcome resistance.

There’s no escaping that all the Pirates of the Caribbean movies are love stories.  Will’s love for Elizabeth, Davy Jones’ love for Calypso, Jack’s love of himself (“I’ve always wanted to do that” after kissing Angelica disguised as himself!), Angelica’s love for her father Blackbeard and so on… 

Think you can’t use this to overcome resistance in your bank account?  Reread #5 (and download the freebie at the end of this post for more!)

9. Charisma is more important than predictability

If you tried to sum up Captain Jack Sparrow in one word, Charisma would be an effective choice.  The man ooooooozes charisma!

“Me, I’m dishonest, and you can always trust a dishonest man to be dishonest. Honestly, it’s the honest ones you have to watch out for.” – Jack

You don’t need to swagger like Keith Richards to charm your audience, but you can build an equally irresistible brand for your biz.  Be real, be authentic, chase genuine engagement and connection instead of dollars.  Follow your heart, don’t hold back, dream big and be confident that you deserve those dreams!!

Charm your ideal clients by being the best version of yourself you can be.  

Be the fierce leader they need you to be.  No one could ever accuse Captain Jack of playing small.  Same goes for Davy Jones – even with a broken heart, he stood tall and owned his curse while being the kind of leader his men looked up to.  Everyone loves Will Turner because he stood up for what he believed in, stayed true to his word at all costs and fought til his dying breath to remain honorable and trustworthy.

You’re capable of all this and more too!

10. Abundance comes to those who seek

You don’t stumble onto hidden treasure and you’re unlikely to stumble onto massive, sustainable success.  You go after it.

You check your compass, you aim your ship, you follow the winds, you keep your tribe happy, your pursue leads and adjust accordingly.

You try, you fail, you try again. You persevere no matter what.
Keep seeking, keep listening, keep adjusting and keep going after your dreams!

11. Those who succeed once will succeed again and again and again no matter how many times misfortune befalls them

Ever notice how some people will make a fortune, then lose it all, only to build it right back up again in no time? Success is something you can harness and once you do, no misfortune can keep you down for long.

Jack lost the Black Pearl over and over again but he always got it back in the end. (“He’s either the worst damn pirate that ever lived or the best…”)

He found fortunes, only to give them up to someone else, knowing there would always be another fortune to pursue.
Become a successful person and don’t worry about the size of your current fortune. Focus on BEING a successful person who will always rise to the top.

12. Having skills is more valuable than having money

One thing Jack and all the other pirates (including Will and Elizabeth) proved time and time again, is that skills/wit/cleverness are more valuable than money.
All of Elizabeth’s father’s money wasn’t going to help her get out of dangerous situations, but her cleverness often did.
Jack lost treasure as often as he found it, so his ability to find it again and again was more valuable than possessing it once.  The British Navy had far more money, ships, guns and resources than all the pirates put together, yet Jack and Will easily tricked them out of the fastest ship in the Caribbean, Jack easily escaped right out from under King George’s nose, escaped the noose, escaped death, escaped Calypso’s wrath and so on and so on.

Skills will lead you to more money faster and more easily than money will lead you to more money.

13. Leadership is a balance of commanding your ship and earning the loyalty of your crew

Blackbeard knew how to command a ship, but no one on his crew was willing to die for him. Barbossa led a successful mutiny, not because the men preferred him but because they preferred the treasure he promised.  The pirates didn’t follow Elizabeth ten feet in the 1st movie when she wanted to go back for Jack in the cave of Cortez’ gold, but by the 3rd movie she’d been appointed Pirate King and roused the crew to war with her Hoist The Colours speech.  She’d earned their faith through her own dedication and loyalty.

But the only captain any crew followed faithfully, that they lined up to work for, that they’d risk their own lives for time and time again, was Captain Jack Sparrow. What did Jack have that the others didn’t? It wasn’t the promise of treasure, it wasn’t a ship (for plenty of times he had none), it wasn’t his title or his wealth.  It was a combination of charm, action, reputation, wits, experience and leadership skills.  He knew how to effectively guide both the ship and its crew with absolute confidence.

So what does this mean for you?  How can you harness these ideas in your own business?  How can you RUN THINGS like a Pirate Queen???

Get The Free PDF Of HOW To Turn All This Info Into Inspired Action To Boost Your Biz

This has been FUN and all, but let’s talk action!  Ready to apply all of this to your own biz?  To swagger like Keith Richards?  To live life like success is the ONLY option?  To attract treasure as easily as you attract rum?

EXCELLENT!  Then download the PDF and get to work!  It’s FILLED with practical exercises, mindset shifts and words of wisdom to show you EXACTLY how to apply these lessons to your own biz.

Sail over yonder to get it ~

(If you’re already on the email list, you’ll find the PDF in the treasure chest of resources along with enough booty to sail any biz to success!  If yer not on the list yet, ye best be joining the crew…)