Befriend The Devil's Advocate:
- Daniel Cuesta
- Apr 18
- 4 min read
(The Power Of Asking "Why Not?")
Formal education widely follows a set of curriculums that encourage growth in the maths, sciences, and arts but lack an explicit passing of knowledge and the cultivation of most things relating to the heart, soul, and mind.
In recent decades, the implementation of psychology, as well as a seemingly culture-wide analysis of faith into these standards of study, has helped ease into understanding why it is that we operate the way we do, our connection to one another, as well as our relation to the more excellent divine.
But still, so many of us exit our institutional educations and support ourselves on too rigid scaffolding made of “inside-the-box” thinking and conventional approaches to problem-solving.
We are so often preconditioned to ask “Why?” that we forget to wrestle with “Why not?”
While this is not a critique of the system itself (as it has its flaws and benefits), there is a certain beauty and comprehension of a matter that can only be achieved by deconstructing an antithesis or befriending the devil's advocate.
Sincere questions and unbridled inquisitiveness are guides along the road to authenticity and a life with no regrets.
We have lost the art of optimistic skepticism.

The birth of the phrase “The Devil's Advocate” is a curious thing and finds its roots within the Catholic Church.
It's a term originating from the former office within the church known as the Promoter of the Faith or Promotor Fidei in Latin. Those assigned this responsibility were tasked with examining the life of any soul up for beatification or canonization.
These individuals committed themselves to cross-analyzing, retracing, and ensuring that miracles attributed to these potential reputation bearers were a matter of fact and verifiably true. The presentation following the preliminary research often included various unfavorable facts in hopes of targeting flaws in character or other potentially misaligned representations of their saint-like behavior.
In other words, they focused solely on challenging the “Why” and asking the “Why not’s.”
While the Promotor Fidei’s roles have been minimized in recent years since Pope John Paul II revised the canonization process in his 1983 work Divinus Perfectionis Magister there is nevertheless a sentiment here worth exploring and committing to practice:
Applying ruthless and unbiased scrutiny to our most important decisions ensures clear-headed actions and just reasoning.
Furthermore, it assists us in making delayed gratification-oriented plays that, more times than not, are the best thing we could have done for ourselves.
Now, some things have stood the test time for a reason, and while challenging them will help grow you in your convictions, going against them may prove damaging. This is not an argument to “be different” for the sake of “being different,” but a wake-up call to not settle for the stamp and repeat answers rattled off of command by those who say, “This is the only way.”
Employing the devil's advocate is a strategic move that interrogates a subject, strips it to its skin, and leaves it vulnerable to being fully known. It aims to get to the heart of a matter and truly understand its motivations and underlying currents.
It starts with an openmindedness to alternatives and ends with a firm conviction in belief.
When you know what you know and why you know it, no glitter can distract you from your path or substitutionary mirage that can tempt you enough to veer.
Once you get into the habit of challenging presumptions with “Why” and “Why not?” you will find a thin veil of well-crafted excuses behind many decisions we make.
It’s the “Well, everyone does it,” “They said I ‘had’ to,” and “If I don't, then it’s the end of my career,” whispers we tell ourselves in self-soothing swaying.
We craft justifiable reasons to present to the world as a valid excuse for a particular action that ten years down the line leads to:
“Of course, I didn't even start that creative project… everyone told me artists starved.”
“No, I never asked them if they were free that night… I was told they would never consider me.”
“I never took that step of faith because I feared losing it all, and I didn't want them to be right … so I risked nothing and have nothing to show for it.”
What kind of story do you want to tell, and what thin excuses do you need to tear down by challenging with “Whys” and “Why not’s?”
The devil's advocate (Promotor Fidei) might just be your friend.
—
In my life, this has taken on a series of forms, mostly in my unconventional preference to shoot shots without an explicit guarantee of success.
But this has also led to great internal peace, which comes at no price and is one of the greatest treasures if achieved.
The Devil doesn't bargain, and we should never buy into any deal he may try to make, but his advocate (in the metaphorical, not literal sense) does pose thoughts worth considering and dilemmas that should be addressed.
Seeing the other side doesn’t hurt, and it may just provide alternatives or a deeper conviction that, down the road, will prove more valuable than the blind “accept it because you were told” routine.
Hear both sides. Take full inventory. Then proceed.
Clarity, peace, and a life of no regrets exist when you “Make The Most Of Being Curious.”
- Making The Most Of Being Curious
Daniel J. Cuesta
Sources:
History of the Devils Advocate, Britannica: https://www.britannica.com/topic/devils-advocate
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