The Princess Bride Guide to Beating All Odds

If you’re like me (and probably a few million others), The Princess Bride was a movie that captured your imagination as a child or young adult.

There are so many reasons that The Princess Bride is awesome, but as I rewatched it the other day (just cuz), I realized the thing that grabbed me most in this story is the ability to stay focused and fully committed to a purpose, even against overwhelming odds.

As I watched, point-for-point, how Westley won back his true love, I became intensely inspired to examine for the League just what principles he followed to arrive at his ultimate victory: beating the forces of ill to win true love.


So, come with me to sail the high seas, brave the fire-swamp, come back from the (mostly) dead, and ultimately overcome all obstacles to win your destiny.

First a quick video to get you in the hero’ing mood:

1. As you wish…

The first lesson the young farm boy imparts on us is this: believe in something bigger than yourself.

The young Westley believes in true love. How do we know he does not simply lust after Buttercup as many a young man would?

Because he is content to simply serve her and make her life sweeter through his service- whether she knows it or not.

When we believe in something bigger than just our immediate personal needs and desires, our whole life takes on a unified purpose. ‘As you wish’, was Westley’s way of saying yes, again and again, to that in which he believed. For him it was true love.

The first step for you is exploring what it is you could truly commit your whole self to; something that inspires and compels you to grow beyond your current size and serve with your whole heart.

Truly, all great lives through history were motivated their great why, their great purpose.

So, what’s yours?

2. This is true love. You think this happens every day?

princess-bride-true-loveThe second lesson we receive from Westley is a natural development from the first: find a simple focus for your big purpose.

It’s all well and good to believe in true love, but as humans occupying physical bodies we work best when we have a simple and tangible focus anchoring our lofty purpose. For Westley, the embodiment of his big purpose was obviously Buttercup.

As another example, I believe in empowerment: that we are each so powerful and capable to consciously create a life and world that is deeply fulfilling and abundant. This belief inspires and compels me, but it finds practical expression through this website, through the League of Awesomeness, and through my programs.

I have seen many people get stuck after finding their big purpose because they don’t know how to channel it into a clear and manageable focus.

So, epic adventurer, this is your next exploration: what is the simple focus that will anchor and guide your destiny?

3. No one would surrender to the Dread Pirate Westley.

westley-action-figureAfter a seemingly cruel twist of fate at the start of the movie, Westley returns to regain his true love Buttercup. But, he is not the same Westley as before.

He has taken on a new identity: the Dread Pirate Robberts.

Not only that, but during his time away, he leveled up every attribute of himself: sailing, sword fighting, charisma and leadership, poison immunity…even his lip-stache!

In this way, Westley gives us the third lesson in attaining our destiny: Let your purpose transform you.

There is an old saying: as we build the road, so the road builds us. As we commit ourselves to a purpose, inevitably we are changed in the process. This is another way of appreciating the ‘Observer Effect’ in physics, which says that ‘the act of observation will affect the phenomenon being observed’. It’s just the other way around: by observing some phenomenon, we are changed.

Simply put, don’t be attached to the current version of yourself. Be ready to change as your walk your path. Each challenge, each victory, each defeat will transform and refine you. Often this means letting go of your old stories to make room for new ones. And when you are coming from a place of higher purpose and clear goals, this transformation is a very good thing.

Ultimately, you will become the sharped blade necessary to pierce through to your destiny, just as Westley had to become the Dread Pirate Roberts to overcome the obstacles between him and his true love.

So, given your destiny and focused purpose, how are you transforming to become what you must be?

4. …So I think no man in a century will suffer as greatly as you will.

We can’t get around it: the more we step into our destiny, the more life will challenge us.

As I mentioned in a previous post, this is akin to the whet stone for our sharpening knife.

Ultimately, it is a very necessary process; but that doesn’t mean it can be challenging as hell sometimes (not to mention overwhelming).

Enter: the Cliffs of Insanity, the Fire Swamp and the Pit of Despair.

The Cliffs, Swamp and the Pit are symbols of ultimate challenge and suffering respectively in the movie; and they teach us a great lesson about commitment to high purpose: you must be willing to endure great hardship to achieve your destiny.

It doesn’t mean that the universe is sadistic, as is Count Rugen. Rather our commitment to something bigger than ourselves necessitates that we become bigger than ourselves along the way; and one of the most powerful ways to do that is to have our perceived limitations tested, again and again (and again).

We must prove our skill, our strength and our wit–even when it involves Sicilians.

We must face our personally tailored flamespurts, lightening sands, and ROUS’s (though personally I don’t think they exist).

Such challenges will shake us to our very core; they will strip us down and build us back up. This is why believing in something bigger than yourself is so important: it creates the inner strength necessary to face overwhelming challenges, again and again.

So, how will you face the hardships that stand between you and your destiny?

5. Your brains, Fezzik’s strength, my steel

fezzik-brute-squadOne of the best answers to the question above is to league up with other awesome adventurers.

Westley would not have come close to succeeding if not for Inigo and Fezzik. And remember, he only had their help because he chose not to kill them when he had the chance. Why? Because he respected their moral and good natured characters.

Success studies, as well as the biographies of the truly fulfilled, reveal a trend: successful people do not lock themselves away in ivory towers, but rather intentionally surrounded themselves with noble companions that hold complementary values and purposes.

Collaborators, masterminds, work-out buddies: these relationships help you to see more clearly, act more boldly, and stay on course when things get rough.

So, who are the people in your life that you can begin to create more empowering relationships with? And if you don’t currently have any, how and where can you begin to find such worthy companions?

…This one left them all behind.


Remember, when you decide to do something, to really see it through fully, you embark on an adventure that you will return from fundamentally changed.

You will be tested in many ways, and made ready to receive the fruit of your efforts. And, your story will feel like the greatest ever told, as you are its protagonist.

So, let’s review once more the life lessons the great Westley displayed on his quest to win true love:

1. Believe in something bigger than yourself.

2. Find a simple focus for your big purpose.

3. Let your purpose transform you.

4. Be willing to endure great hardship.

5. League up with other awesome adventurers.

Though we can glean much wisdom from this movie, it is also important to remember that your quest is not a once-and-done Hollywood affair; it happens again and again, in large and small ways, ever evolving and you do. So get ready to begin once again your neverending story (ha!).

If you feel inspired, please share below with the League your answers to any of the 5 points above.

In unmasked awesomeness,
Eka, aka SuperSpark

Featured Image Credit

Enjoyed the article?

Join the League to deepen your adventures in awesomeness and to receive the Stress and Negativity Transformation Guide free!


Comments are closed.