The Best Question Ever: Can It Fool-Proof Your Life?

The Best Question Ever summary…preceded by the worst conceivable introduction!

I was walking down the aisle at Amazon one day…well, there is no aisle per se, I suppose I was ‘online browsing’ – but let’s get real, Amazon browsing is digital aisle walking. 

Anyway, I noticed a book titled, “The Best Question Ever,” written by Andy Stanley.

I didn’t know if this guy really found the most profound inquiry or whether he simply enrolled in rhetoric at Trump University.

Nonetheless, I was captivated and compelled to purchase it. I just had to know what the damn question was. 

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Additionally, I was well versed in Charles Stanley’s work – Andy’s father – a well-known Baptist preacher and prolific writer, whom I always enjoyed. This produced an assurance that even if the question tanked the book probably had something genuine and profitable to offer.

When the book finally arrived I feverishly read until I arrived at the question – which much to my dismay, was actually a little more than a quarter into the book.

Sure, I know you’re thinking, “Tim, why not just jump ahead directly to the question?”

Because that would literally soil my soul – my brain registers shortcuts as anathema and dries my literary veins (and I have a pinch of serious OCD).

So What’s The Greatest Question Ever!

*Drum roll please*

“What Is The Wise Thing To Do?”

Really??? That’s the greatest question ever?

C’mon, Stanley quit horsing around.

Let’s hear the real question.

But Andy is adamant, that in terms of decision-making, this is the best question ever.

To be honest, I was intrigued. Moreover, as he explained, I found myself in total agreement. 

So let’s examine it further. 

The Greatest Question Ever Has A Broad & Narrow Road 

Wisdom’s road is narrow.

It doesn’t leave much wiggle room.

For instance, when you want to start cutting corners, taking shortcuts, and climbing over people’s backs, wisdom has preventive measures in place.

It simply won’t permit the moral deviation. 

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On the other hand, the “it’s ok” road is a bit broader.

When you’re hit with a moral dilemma and begin to rationalize with the “it’s ok, it’s not too bad, not that big of a deal,” all predictability and safety provided by wisdom fly out the window. 

This is what is tricky, it’s quintessential self-deception; folly wearing the mask of wisdom. 

And yet, isn’t this always how it is? 

Every action always comes with a cost-benefit analysis, no matter how cursory.

One can arrive at the conclusion that the emotional elevation produced by heroin outweighs the consequences that follow. Of course, a non-addict would be repulsed at such a thought. Only, this is never how the conclusion is arrived at. 

It first started with a thought such as “one time won’t be that bad,” or “it’s just a pill, it’s not like I’m doing heroin.” Nobody just starts with “I may end up dead, but heroin has a far superior payout than that!”

No. Self-deception begins with the most subtle of lies. If it didn’t, it would never sell you! 

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So this book primarily is a weapon against the insidious foe of self-deception (simply albeit powerful – think the pebble in David’s slingshot vs. Goliath’s face). 

With this in mind, Andy Stanley proposes 3 ways to implement the greatest question ever.

1.) In light of your past experience, what is the wise thing to do?

This greatest question has a strong subjective undercurrent. The wise thing, in this sense, may apply to you but not to everyone else. For example, consider the choice to drink.

Let’s meander back to 15-year-old Tim. When alcohol was first presented to me, I eagerly took it. But in light of my past experience was this the wise thing to do? 

Sure, I had DARE (Drug Awareness Resistance Education) with officer Steve in grade school. I was aware of all the terrible things which could occur. Yet I looked around me with suspicion because it appeared most folks drank with immunity. Not only that, but they appeared to be having the time of their lives.

Nonetheless, I recall vividly my mother giving me the exhausting don’t drink lecture (probably with a wine glass in her hand!). 

“Honey, you’re Irish with a long history of alcoholism in your family.”

As if this was convincing. Persuasion wasn’t her strong suit. 

Yes, my family was rife with addiction but surely I was the exception. What kid doesn’t think this? Bearing in mind my families history, certainly drinking would not be the wise thing to do. If only I applied that line of reasoning. Rarely does any youth so blindly listen. 

Nonetheless, addiction is lived forwards but understood backwards. It’s not about simply saying no to the beverage. It’s about saying no to specific behaviors which enable the unwise decision to drink in the first place.

For instance, If I’m experiencing a desire to get high, to steal, or to do something equally stupid, in light of my past experience what is the wise thing to do?

If in the past I’ve isolated, then the wise thing would be to socially connect. If I’ve failed to speak up, then I must now get vocal. If I simply ignored it, then I must now engage it full throttle. 

You’re picking up what I’m putting down.  Simple but not easy. It’s so obvious you just might miss it. Thus, is the nature of wisdom; the most evident of all courses.

*The greatest question has a hidden assumption: that you want to change your life and start making the best possible decisions. Undoubtedly, this will not resonate with everyone but to those it does ring some bells, blessings will surely follow.*

2.) In light of my current circumstances, what is the wise thing to do?

This point is fairly obvious and per my understanding implies self-awareness. Indeed, if we are to have sound emotional health we need to know with absolute clarity our restrictions and limitations.

I see this all the time in church circles, as well as AA/NA service commitments. We fail to take into consideration our current circumstances, namely our current emotional state and of those around us.

Allow me to illustrate…

Let’s say I’m attending a social function, let’s call it an AA meeting. 

Now, I’ve been exhausted all week. My blood pressure is so high that when I exhale my ears whistle. 

Honestly, I look as bad as a feel – like a heaping pile of “please save me from myself!” 

Anywho, I show up at the meeting for some much-needed camaraderie and social catharsis. I just need to sit and listen – take the sidelines approach and be one of the many rather than the main attraction. 

I know this, I’m becoming more self-aware.

Then, seemingly out of left field and in a sheer panic someone asks me to share my story, to “preach the hope,” they say. They also close the inquiry with “remember you can’t say no to a service request.” As if the request was sectioned from the mouth of God himself.

I cringe and say “yes, anything for the newcomer.” 

Yet, intuitively I know today is the day I need to listen; the day I need to sit; the day I need to bench my ego, but I say yes anyway.

In this scenario, my emotional state has everything to do with immaturity, but I’m calling it “spiritual maturity.” It has everything to do with peer validation, fear, and self-interest, but I’m calling it “faith without works is dead.”


Because I do it all. I’m Mr. AA.

If you need help?

I’ll drop whatever I’m doing and I’ll be there. Doesn’t matter if it’s my kid’s ballet recital or date night with my wife, I’ll jettison it all to navigate to you. 

I’m a few years sober, my ego is so big it could kill a lesser man, and I’m literally withering away mentally and emotional; spiritually dying but thinking its spirituality. “I’m just being of service like someone was for me,” is my anthem. 

Can’t you see it?!

Far from being spiritual this is unhealthy and should be appropriately tagged emotional immaturity merely hiding underneath the concept of God and selflessness. 

Everyone has their limitations. Inability to recognize this is a recipe for burnout and ineffectiveness. Saying “no” is sometimes the wisest course to take. 

Sure, I may feel guilty for saying no. I may feel obligated and less than. But in light of my current circumstances and current condition, the wisest course of action would be to take a seat and realize I’m just apart of the group. 

Certainly, sometimes a speaking commitment would be the precise thing I need to do – for instance, if I was isolating, detaching from passion, and keeping things to myself – but that’s why the greatest question ever is always reduced to the individual and cannot be the same across the board.

3.) In light of my future hopes and dreams, what is the wise thing to do?

Addiction and other mental health disorders all have one commonality: short-sightedness. There exists this willingness to sacrifice long-term reward for short-term gain. Or, perhaps better said, the inability to see the long-term consequences of pursuing every short-term reward.

This pertains to every human being, after all, the book was written for people in general, not a specific demographic. This blog, however, emphasizes life recovery and thus tries to maintain that theme in every article. 

The inability to see long-term consequences of pursuing every short-term reward goes by many names: sin, dukkha, irrational core belief, cognitive distortions, Maya, the disease, pāpam, ego, flesh, and the list goes on. All of humanity is affected; this is important to note. 

Nonetheless, in terms of wise decision making this element must factor into the equation. And it cannot wait until the last minute when the proverbial shit hits the fan. It must be practiced with the most minute of details. 

For example, every night prior to bed I can either make the choice to delay gratification – which is going to sleep – and iron my clothes in preparation for the next day. Or, I can fall asleep and scramble in the morning to get everything done (I should mention that I officially enter sloth mode upon awakening, I literally am useless for the first hour). 

In terms of my immediate future, it would be wise to handle it the night before. It might annoy me that night but I’ll be happy in the morning, and my clothes won’t look like I just pulled them out of a dumpster (more like one of those nifty donation clothing bins, not necessarily referring to the dumpsters at McDonald’s – not all dumpsters are created equal!).

Now let’s enlarge the scope here. 

Let’s look at meditation. It’s proven, the results are in and the data is measurable and demonstrable; it does the following:

  • Changes the physiological structure of your brain
  • Reduces anxiety
  • As powerful as an antidepressant
  • Improves attention 
  • Statistically, it’s monumentally in overcoming addiction 
  • Powerful agent in overcoming social anxiety and developing social skills

So, that’s it. Meditate once and the results are yours for the taking. Not!

No one seriously thinks the results are anything but incremental. You don’t step into the gym, bench press 60 pounds and then the next day kick it up to 250 pounds. It’s a process. It’s incremental, the value is cumulative. 

Stanley remarks, “There is a cumulative value to investing small amounts of time in certain activities over a long period.”

To name a few:

  • Exercise
  • Therapy
  • Meditation
  • Prayer
  • Spiritual formation
  • Spending time with loved ones
  • Church, AA/NA, or attendance with whatever community you are involved with.

The payout is in the long-term. Odd, the most rewarding and healthy activities – in terms of emotional, physical, and spiritual well-being – are built up over time. Brick by brick; slowly but surely. 

Intellectually we know this, but the visceral pull of the present instant payout is so appealing we deceive ourselves into living unwisely. And since we intellectually understand this, we must sell ourselves a line of unadulterated used car salesman B.S. 

Unfortunately, once we take that car off the lot it becomes questionable whether we are even in a fit condition to ask ourselves the greatest question ever. We can’t even trust our judgment!

Enter stage left: the second greatest question ever…

*Drum roll please*

“‘What do you think is the wisest thing for me to do?”

Lost time cannot be recovered, so find a mentor, a teacher, someone you recognize as an authority, someone who embodies wisdom, and begin by asking this simple question. Practice doing this until it becomes a habit.

I’ll close with a wonderful description of precisely what it takes to become wise:

It’s being willing to do what you do not want to do; usually, this is listening to what you do not want to hear. Eventually, this becomes what you want to do, then you have the privilege to tell others who do not want to hear about it.

best question ever

Timmy G (2019)