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Ask It: The Question That Will Revolutionize How You Make Decisions

Compiled by Chuck Olson

Ask ItTitle: Ask It: The Question That Will Revolutionize How You Make Decisions

Author: Andy Stanley

Copyright Date: 2014

“Your greatest regret could have been avoided had you asked this particular question and then acted on your conclusion.”

Talk about setting the hook in the opening pages!

In his book, Ask It: The Question That Will Revolutionize How You Make Decisions, Andy Stanley delivers. Big time. From cover to cover, he provides a filter that is at the same time faithful to the Scriptures and readily accessible for the choices of everyday life, both big and small.


Book Description:

Should I take this job? Buy this house? Marry this person?  We ask questions every day about the choices we face. But are we asking the most important question of all?

In Ask It, Andy Stanley identifies the one question that makes it easy to determine the answer to all other questions. You’ll learn how to make decisions with confidence simply by applying the question that brings clarity to life’s most challenging decisions.

Book Quotes:

Your greatest regret could have been avoided had you asked this particular question and then acted on your conclusion. LOCATION: 70

Having watched dozens of people methodically waste their lives, potential, and money, I’ve concluded that while nobody plans to mess up his life, the problem is that few of us plan not to. That is, we don’t put the necessary safeguards in place to ensure happy endings. LOCATION: 125

At the age of twenty-five, I came across three verses in Scripture that totally changed the way I made decisions. I suddenly had a new filter through which to evaluate every opportunity, invitation, and relationship—everything I was asked to do, everything I was tempted to become a part of. I began to consider my whole life through this new grid, a grid that boiled down to asking one simple question. LOCATION: 136

Here’s what Paul wrote: Be very careful, then, how you live—not as unwise but as wise, making the most of every opportunity, because the days are evil. Therefore do not be foolish, but understand what the Lord’s will is. (Ephesians 5:15–17) …Or to turn it around, Don’t be careless how you live. In other words, following Christ is not a casual endeavor. It requires extreme caution. If we are serious about living out the values the New Testament teaches, we must watch our steps. After all, we know from experience how easy it is to stumble. LOCATION: 204

Then without so much as a pause, Paul discloses the criterion by which we are to measure and judge every one of our choices. In the six words that follow, we are given the grid through which we are to evaluate every invitation and opportunity. Here is the standard, the yardstick by which we are to assess our financial, relational, and professional decisions. Get out your highlighter. “Not as unwise but as wise.” LOCATION: 206

The question that sets us up for success where it counts, the question that enables us to consistently apply the commands of the New Testament is this: What is the wise thing to do? LOCATION: 209

Typically when making choices, we run our options and opportunities through a more generic and far less helpful grid. There are several variations, but the question we ask ourselves is this: Is there anything wrong with it? The assumption is that if there is nothing wrong with what we’re doing, it must be okay. If it is not illegal, unethical, or immoral, then it qualifies as a live option, right? Biblically speaking, if there is not a “Thou shalt not” associated with it, then it’s safe to assume it qualifies as a “Thou certainly shalt if thou please.”…Yet, if we are honest, this question drives far too many of our choices. It goes something like this: How close can I get to the line between right and wrong without actually doing something wrong? The Christian version goes like this: How close can I get to sin without actually sinning? LOCATION: 220

The moral of the story is, just because there isn’t a “Thou shalt not” attached to a situation does not necessarily mean it is a “Thou shalt.” What’s morally and culturally permissible is often not what’s best for us. LOCATION: 245

But the question he gave us is not, Is there anything wrong with it? The question is, Is it the wise thing to do? To foolproof your life, you must ask it of every invitation, every opportunity, every relationship. LOCATION: 250

Our heavenly Father never intended for us to live life at the level of what’s permissible, legal, acceptable, and not prosecutable. To do so is tantamount to organizing our lives around the question, How close can I get to sin without sinning? LOCATION: 257

Instead, we are meant to analyze every opportunity and invitation through the lens of wisdom. Every choice should be tested by asking, What is the wise thing to do? This is what Paul was getting at when he admonished us to be careful how we live. LOCATION: 259

Ours is a culture that encourages us in the most provocative ways to do everything in our power to try to satisfy appetites that can never be fully and finally satisfied. LOCATION: 273

Most Americans are overweight and overleveraged. We eat too much and spend too much. By far, the biggest online moneymaker is pornography. Consider this: American men spend billions of dollars every year to look at pictures of women on their computer screens. Billions of dollars. LOCATION: 280

But lifestyle changes don’t happen until an individual faces the facts. It is not until a person acknowledges the truth and quits lying to himself that something positive takes place. And once someone has turned the corner mentally, it’s amazing how quickly that person is able to break unhealthy habits and begin new routines. LOCATION: 320

Bankruptcy can have the same effect. So can an unwanted pregnancy, a letter from your spouse’s attorney, a DUI charge, or a trip to detox with one of your kids. And perhaps that’s what it will take. There is something out there somewhere that will get your attention. Unfortunately, that something may scar you as well as scare you. You may be left with limited options and reduced opportunities. So why let things go that far? Why not face up now to what you know in your heart your heavenly Father wants you to do? LOCATION: 325

Your personal history is unique to you. And the sum of your past experiences predisposes you toward specific weaknesses and strengths in your relationships, finances, career, etc. For example, your personal history makes you more prone to temptation in some areas than in others. Consequently, what’s safe for some folks may not be safe for you. There are activities that others find it easy to walk away from while you are prone to overindulge. So every decision, invitation, and opportunity that comes your way needs to be filtered through this question: In light of my past experience, what’s the wise thing to do? LOCATION: 363

Your past experience must be a grid through which you evaluate every decision. Chances are, there are places you have no business visiting because of your history—places that would have no impact on the average person, but the average person doesn’t share your experience with those environments. Perhaps there are certain types of people you have no business spending time with. Being around them triggers something unhealthy in you. LOCATION: 377

Does the way you were raised predispose you to an area of temptation to which most people seem immune? If so, admit it. Own up to it. Don’t be content with merely doing the right thing. Do the wise thing. LOCATION: 391

Here’s the second form of the question. In light of my current circumstances, what is the wise thing to do? LOCATION: 395

So in light of what’s going on in your life right now, what is the wise thing for you to do? As you consider your frame of mind, your emotional state, and even your physical health, what is the wise thing to do? As you consider your current responsibilities and commitments, things that a year from now may not be a factor, what is the wise thing to do? LOCATION: 433

In light of my future hopes and dreams, what is the wise thing to do? LOCATION: 442

As a parent, I constantly urged my kids to make today’s decisions in light of tomorrow’s hopes and dreams. The future is what brings today’s choices into proper focus. Making choices with the end in mind goes a long way toward ensuring a happy ending. LOCATION: 458

Asking our question with the future in mind casts a trenchant light on the validity of our options. The deceptive shades of gray dissipate. The nature of the journey on which we are about to embark becomes painfully clear. So clear that we are tempted to look away, to retreat to the often-rehearsed excuses that have buttressed our misguided decisions for years: I’m not doing anything wrong. People do it all the time. I’m not hurting anyone. I can handle it. There’s no law against it. Nobody’s going to find out. Nothing’s going to happen. LOCATION: 479

As you evaluate where you are financially, relationally, morally, professionally, and spiritually, what would you do differently in each of these areas if you were to embrace our question? In light of your past experience, current circumstances, and future hopes and dreams, what is the wise thing to do financially? Relationally? Morally? Professionally? Spiritually? LOCATION: 529

The tragedy of being a fool is that eventually you’ll inflict harm upon someone else. There’s always collateral damage. And while the fool may protest all day long, “Well, that wasn’t my intention,” the reality is, No, but you’ve still hurt that person. LOCATION: 599

So you see, that’s why we ask the question: In light of my past experience, in light of my current circumstances, in light of my future hopes and dreams—regardless of where that leads—if I was wise, what would I do? LOCATION: 647

You see, what we do with our time is more important than simply knowing what time it is, how old we are, or even how much time we have left. The fact that time is life and can’t be recovered is why we must place this priceless commodity under the scrutiny of our much bigger question: In light of my past experience, my current responsibilities, and my future hopes and dreams, what is the wisest way to invest my time? LOCATION: 685

When random urgent activities constantly interfere with strategic deposits of time, it is like throwing away our most precious commodity. It is worse than wasting time. We waste our lives. LOCATION: 763

The important areas of life require small deposits all along the way. And if you miss those opportunities, they are lost forever. LOCATION: 786

But if you are willing to harness your time and appropriate it strategically, things can be different. You will be healthier physically, relationally, spiritually, and possibly, financially. You will look back at this next season of life with few, if any, regrets. Not because of a single day or a single burst of activity, but because of a single decision: the decision to get full value out of your time by making small, incremental investments of time in the things that matter most. LOCATION: 818

Nothing has stolen more dreams, dashed more hopes, broken up more families, and messed up more people psychologically than our propensity to disregard God’s commands regarding sexual purity. Most of the major social ills in America are caused by, or fueled by, the misuse of our sexuality. If issues related to sexual impurity—adultery, the shrapnel associated with adultery, addiction to pornography, AIDS and other sexually transmitted diseases, abortion, the psychological effects associated with abortion, sexual abuse, incest, rape, and all sexual addictions—were to suddenly disappear from society, imagine the resources we would have available to apply to the handful of issues that would remain. LOCATION: 865

I started this book by saying that we have all done things we regret. We regret some decisions because they are embarrassing. Other regrets stem from decisions that ate up our time or wasted our resources. But no regret runs deeper than the regret associated with unwise moral decisions. In time you may find you are able to laugh about wasted money and poor time management. But when it comes to moral failure, time doesn’t help. Nobody ever laughs about an affair, a divorce, a sexual addiction, or abuse. In the arena of moral failure, the regret runs deep and the pain can traverse generations. Chances are, your greatest regrets in life fall somewhere within this category. LOCATION: 873

While the outcomes of sexual sin are predictable, the decisions that set us up to sin sexually are equally predictable. And—and this is a big and—our question will enable you to see those decisions for what they really are. If you’re willing to face up to the fact that your temptation, circumstances, and feelings are not unique to you, this question will empower you to make choices that will set you up for success rather than failure in this crucial arena of life. LOCATION: 913

Our greatest moral regrets are always preceded by a series of unwise choices. Not wrong choices, not impermissible, not illegal, but unwise. We choose ourselves to the brink of disaster because none of the choices we make along the way are “wrong.” So we don’t hesitate. LOCATION: 933

How did we get ourselves into such messes? We made a series of unwise choices—unwise choices that sent us beyond the point of no return. The names and faces change, but the sequences and outcomes are tragically similar. We may think our situations are different and, therefore, what is wise for most isn’t wise for us. LOCATION: 939

Every poor moral decision is prefaced by a series of unwise choices. LOCATION: 996

Wake up! You never intended to get yourself into any of the situations you now regret. Right? Your financial, moral, professional, and relational regrets all came about unintentionally. Nobody intends to blow up a marriage. Nobody intends to become buried in debt. Nobody intends to destroy a career. Nobody intends to be alienated from his or her children. Nobody intends to become addicted to anything. Your own experience substantiates the fact that intentions are pretty much a worthless defense against temptation and regret. It takes more than good intentions to cross the finish line in any area of life. LOCATION: 1047

There is a certain emotion associated with fleeing. Fear. We flee when we know we are in danger. Fear prompts us to flee. The reason we don’t flee sexual immorality is that we don’t fear it; we naively believe we can handle it. So instead of fleeing, we flirt with it. We snuggle up next to it. We dance around the edges. After all, we aren’t doing anything wrong. LOCATION: 1151

The truth is, when painful emotions are running high, we don’t really care about making wise decisions, and so we pretty much do what we feel like doing. We are drawn toward activities that distract us from our pain, and therein lies the problem. It is next to impossible to discern the voice of wisdom when our emotions are raging. LOCATION: 1230

Wise people know when they don’t know, and they’re not afraid to go to those who do know. When wise people bump up against their limitations, they stop and ask for help. LOCATION: 1259

To complicate things, we are especially resistant to advice in the three areas where we are most vulnerable—the three areas that typically prove to be the sources of our greatest regret: how we allocate our time, spend our money, and handle our relationships. LOCATION: 1314

Let’s face it, most of us are hesitant to pursue counsel in the areas where we need it most, and we resist counsel when it is offered. LOCATION: 1318

So since your personal decisions will be seen by, judged by, and experienced by others, why not involve others to begin with? Why not benefit from the insight you will be judged by? While it is true that what you choose to do may not be anybody’s business, it is equally true that much of what you do will become other people’s business. They’re going to know, they’re going to judge, and they might even be significantly affected. So why not invite a few choice people into the decision-making process with you? It certainly won’t hurt anything. In fact, it could make all the difference in the world. LOCATION: 1348

You will never be all you’re capable of being unless you tap the wisdom of the wise people around you. Sure, you may get by. You may even do better than most other people. But you will never reach your full potential without help and advice from the outside. This is true professionally, spiritually, financially, and even relationally. I say even relationally because it can feel so unnatural to seek relational advice, especially at the outset of a relationship. LOCATION: 1362

Why not pause long enough to listen to the people who have faced what we’re facing, people who have already been through what we’re about to go through and are wiser for their experience? Experience is a good teacher, especially if it is other people’s experience. There’s no point in learning something the hard way if someone else has already paid that price. LOCATION: 1386

Wise people know when they don’t know. The fool is the person who convinces himself that he knows more than he really knows and doesn’t need to ask anybody anything. At the end of the day, the wise man breathes a sigh of relief; the fool, a sigh of regret. LOCATION: 1434

In every field it is both the knowing and the doing that make for success. You must first know how things work and then submit yourself to those principles, laws, and techniques. It is what you know and what you do with what you know that make the difference. LOCATION: 1519

Let me take it one excruciating step further. How do you expect to make a masterpiece of your life if you are unwilling to surrender to the Author of life—the One who knows which textures and colors are best blended for the outcome you desire? How do you expect to make wise decisions regarding your family, marriage/love life, and career if you are not willing to submit to the promptings of the One who knows more about those things than you or I ever will? LOCATION: 1536

Wisdom begins with the recognition of who God is. This does not mean simply recognizing his power and knowledge. This is recognizing that you are dealing with the one and only Creator of all things. God with a capital G. Wisdom begins when we rightly recognize God’s position as God! LOCATION: 1547

Lest we lose sight of the highly relational side of our heavenly Father, Solomon restated his point in different terms. Here’s how the entire verse reads: The fear of the LORD is the beginning of wisdom, and knowledge of the Holy One is understanding. (Proverbs 9:10) Allow me to paraphrase this amazing verse for you this way: Wisdom begins when we recognize that God is God and then we respond accordingly. The proper response, of course, is surrender. Once we have surrendered, God is more than happy to reveal more and more of himself. And as we discover more and more of the character and nature of the Father, we gain greater understanding of the world he has created. Our expanded understanding results in an improved ability to choose wisely. Thus, true wisdom begins with a proper recognition of who God is coupled with a proper response—surrender. LOCATION: 1553

A wise physician does not ignore the way God created the body. A wise accountant does not ignore the principles of mathematics. The beginning of wisdom is recognition of and submission to the One who designed things to work the way things work. LOCATION: 1573

In the end, here’s what it all comes down to. Our willingness to ask and respond to this question depends upon our willingness to make an important decision—the decision to fully submit our lives to our heavenly Father. This is where wisdom begins. LOCATION: 1593


Chuck Olson

As founder and president of Lead With Your Life, Dr. Chuck Olson is passionate about inspiring, resourcing and equipping Kingdom leaders to lead from the inside out.  To lead, not with the external shell of positions, achievements or titles, but from an internal commitment to a deep, abiding and transparent relationship with Jesus. Serving as a pastor and leadership coach for over forty years, Chuck has a track record of building these truths deep into the lives of both ministry and marketplace leaders.

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