5 Life-Changing Questions

Simple, Effective, and Infuriating.

Written by Daniel J. Cuesta | Insight 46 | May 21, 2025

In a modern world, it's helpful to have contemporary metaphors and analogies.

We are humans, and yet, day by day, we act more and more robotically; through this phenomenon, we have suffered a loss of function and are in need of a reboot, update, or downright reprogramming.

We have lost the ability to connect our head box with our heart box, and that has cost us our peace of mind and clarity of thought.

When we don’t align what we say, what we do, and who we are with the genuine emotion and reasoning behind our decisions, we drive through life with pyramids for wheels instead of firm, well-rounded tires.

Connecting our head boxes with our heart boxes starts with asking one question many times. 

The “5 Whys” is a problem-solving method centered on finding root causes and causal connections by backing a subject into a corner and not letting it go until it sweats through five rounds of the simple question “Why?”

It might sound simple, but it’s a heavy-hitting experience. Don’t believe me? You should try it sometime.

My mother introduced this technique to me around the beginning of my high school career. It led to deep frustration that later turned to gratitude and greater appreciation after I stopped accepting my decisions at “face value” and began digging deeper and coming to terms with what I wanted to hide.

The most memorable of these moments occurred on the car ride back from campus on a breezy Florida afternoon. 

“How was your day, hijo?” My mother asked tenderly.

I responded with a brief yet polite “It was okay. How was yours?” in a tone indicating it was “not fine” and that I was most likely not up for talking about it… 

Which, of course,  meant we ended up talking about it. (Gracias, Mama, I am so thankful we did.)

She asked what was going on, and I shared that I was frustrated with an instructor that day for calling me out in class with a question I was not prepared for.

I felt disrespected. 

She asked, “Why?”

I followed with, “Because I'm normally so good in that class, and she’s never done that before, I felt ashamed.”

Again, she simply asked, “Why?” and I rattled off, “Because she said it in front of all my friends, and there was nothing I could do.” 

Calmly driving, with her eyes on the road, she went in for round three, “You normally don’t mind what others think of you … Why this time?” (At this point, I was getting a bit vexed)

With irritation  in my voice, I remarked, “Because ‘she’ was there, and I hate messing up in front of her.” (Yes, I had a slight “crush” at the time…)

And my mother, so wise and tender, finished me off with a straight and delicately crafted verbal punch to the soul: “Why?” 

My gaze dropped, and my weight shifted towards the window, “Because I fear she won't reciprocate, and the feelings won’t go both ways. What if it's not mutual? I don’t know how to cope with failing like that.”

There we had it—the real reason I was off—an accurate diagnosis: I had an aching heart. The feeling of disrespect was a mask I grabbed onto to avoid feeling what I needed to.

I wasn't flustered about getting a question wrong or being challenged on my preparation. No, I typically welcomed new thoughts and was eager to pursue an increase in knowledge. Behind that veil of an excuse lay a fragile and sentimental realization that my head and heart were having trouble reconciling with one another. 

I wasn't allowing myself to be vulnerable, so I quickly built up a wall of protection, something we all do. It’s so easy and can be done at a moment's notice.

The problem is that many times, the lies we tell others, we end up believing ourselves, and at the end of the day, that may hurt them, but it will most definitely hurt you.

Don’t psych yourself out: The greatest lies ARE the ones we tell ourselves. 

They lead to us pursuing OTHER people's dreams. 

They entangle us in situations we never wanted to be in by confusing our senses into thinking we seem more remarkable, somehow superior, or better off because of the masks we wear and not for the people we are.

From then on, I realized the value in being sincere in my feelings. This required a constant fight to the ground. I lost a few times, but looking back, I don’t regret the bruises that taught me how to think, feel, and act in accordance with the truth.

Smoothing out the edges and connecting my head box with my heart box has brought profound clarity. While the road may not always be smooth, I know the tires I'm rolling on are well-fitted and can handle the rocky terrain because there is no misalignment between what I think and do and how I perceive the feelings surrounding it.

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Typically, our first excuse or thought of something comes at face value and is not our heart's true intent or that object's real motive. Underneath these masks, we all have underlying currents and movements that contribute to orchestrating the grand scheme of the play in which we live.

To best sort through the noise, brush away the fog, and distinguish fact from fiction, asking “Why” five times will prove enlightening beyond belief.

This week, tackle every vital decision, emotion, or conversation with this strategy. 

Implement it while going to sleep, waiting in line, or teach it to a friend and ask them to challenge something in your own life by asking, “Why?”

See how far you can go, what you discover, and realize there is more to what meets the eye. Some trees' roots spread deeper than we would have ever thought.

Wrestle and sweat if you have to, but come face to face with what is happening while dropping the masks you have been hiding behind along the way.

Fight the good fight. Go all the way. Don’t stop till the bell rings. Why?

Because whatever you do now will be worth it… later. (Hebrews 12:11)

- Making The Most Of Being Curious

Daniel J. Cuesta

Sources:

The 5 Why’s: https://tulip.co/glossary/five-whys/#:~:text=Five%20whys%20(5%20whys)%20is,the%20question%20%E2%80%9CWhy%3F%E2%80%9D.