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Better Decisions, Fewer Regrets: 5 Questions to Help You Determine Your Next Move

Compiled by Chuck Olson

Title: Better Decisions, Fewer Regrets: 5 Questions to Help You Determine Your Next Move

Author: Andy Stanley

Copyright: 2020

In the early pages, well-known author and pastor Andy Stanley in Better Decisions, Fewer Regrets: 5 Questions to Help You Determine Your Next Move, sets the hook with these penetrating words: Decisions are your steering wheel…which means…and this is big: Your decisions determine your story. 

From there, he trots out five decision-making filters:

• The Integrity Question: Am I being honest with myself…really?
• The Legacy Question: What story do I want to tell?
• The Conscience Question: Is there a tension that deserves my attention?
• The Maturity Question: What is the wise thing to do?
• The Relationship Question: What does love require of me?

Shove this book to the top of your got-to-read list. You’ll be glad you did (and you’ll wish you would have had a copy sooner!). And here are the Book Notes to get a glimpse of the insights that lie in wait.


Book Description:

Good questions lead to better decisions. Discover five game-changing questions to ask every time you make a decision–questions that will help you in your finances, relationships, career, and more.

Your decisions determine the direction and quality of your life. Your decisions create the story of your life. And while nobody plans to complicate their life with bad decisions, far too many people have no plan to make good decisions.

This book will help you live differently.

In Better Decisions, Fewer Regrets, Andy Stanley will help you learn from experience and stop making bad decisions by integrating five questions into every decision you make, big or small.

You’ll discover how to:

  • Develop a decision-making filter that reveals which choices will likely lead to positive results in your life.
  • Avoid selling yourself on bad ideas and making quick decisions when time is short.
  • Find truth and clarity in any tricky decision.
  • Improve relationships and heal division through better decisions.
  • Discover the reasons behind your decisions so you can move forward with positive changes.
  • Consider the long-term impact of your choices so you can write a life story worth celebrating.
  • Easily identify any red flags that signal which decisions may result in future regrets.

Better Decisions, Fewer Regrets will set you up for success in every season of life, for the rest of your life.


Book Quotes: 

Good questions lead to better decisions…And better decisions lead to fewer regrets.  LOCATION: 93

Truth is, most of us resist uninvited questions when making a decision. In the moment, we feel like we’re being questioned rather than simply being asked a question. Big difference. When we confuse one for the other, our defenses go up and our learning aptitude goes down. It’s virtually impossible to welcome new information or insight when we’re convinced our judgment is being questioned. This is especially true when making personal decisions. After all, they’re personal! Translated, it’s nobody’s business.  LOCATION: 97

There’s no getting around the fact that well-placed, appropriately timed, thought-provoking questions result in better decisions and fewer regrets.  LOCATION: 104

Clay Christensen, a professor at Harvard Business School, said, “Questions are places in your mind where answers fit. If you haven’t asked the question, the answer has nowhere to go. It hits your mind and bounces right off. You have to ask the question—you have to want to know—in order to open up the space for the answer to fit.”  LOCATION: 106

Counselors understand that we hominids have a greater propensity to follow through on decisions we make rather than advice prescribed to us. So counselors painstakingly scatter breadcrumbs along our paths to lead us toward making our own good decisions. The breadcrumbs are . . . you guessed it . . . well-placed, appropriately timed, thought-provoking questions.  LOCATION: 110

I want to add five questions to your existing arsenal of questions. Five questions to ask every time you make a decision of any consequence. These questions are so simple that once you see the list, you may wonder if you even need to finish the book.  LOCATION: 129

There is no necessary correlation between knowing and doing.  LOCATION: 133

Here they are: The Integrity Question: Am I being honest with myself . . . really? The Legacy Question: What story do I want to tell? The Conscience Question: Is there a tension that deserves my attention? The Maturity Question: What is the wise thing to do? The Relationship Question: What does love require of me?  LOCATION: 138

Your decisions . . . along with your responses to other people’s decisions, which are also your decisions . . . are about the only thing you can control in life, which means your decisions are how you control your life. Decisions are your steering wheel. Your joystick. Your keypad. Which means . . . and this is big: Your decisions determine your story.  LOCATION: 150

Every decision becomes a permanent part of our stories. That being the case, we should stop at every decision-making juncture and consider the story we want to tell. Perhaps more compelling, we should consider what story we want told about us. The good news is that you get to decide. But you decide one decision at a time because you write the story of your life . . . one decision at a time.  LOCATION: 154

Moral of the story: regardless of how things are going or have gone, you are responsible for you. You get to write the story.  LOCATION: 163

Our decisions are heavily influenced by our emotions and our appetites. Research suggests we aren’t able to make decisions apart from our emotions. Experience confirms our appetites often overrule our intelligence. Otherwise nobody would have to remind us to exercise and eat right.  LOCATION: 187

As soon as you start selling you on anything, you should hit pause. Here’s why. We rarely have to sell ourselves on a good idea.  LOCATION: 231

The challenging thing about surprise decisions is the time frame. It’s usually short. Because the time frame is compressed, we rarely have time to get the information we need to make a good decision. But the decision must be made!  LOCATION: 248

Your legacy, your mark, your fingerprints on the future are determined by the decisions you make. As we will discover with question #2, thinking in terms of legacy brings extraordinary clarity and context to the decision-making process. LOCATION: 264

The point is this: We never know what or who hangs in the balance of the decisions we make. But what we do know is this: Private decisions have public outcomes. Your private decisions probably won’t stay private. Your personal decisions will impact some other persons.  LOCATION: 287

The Integrity Question: Am I Being Honest with Myself . . . Really?  LOCATION: 294

The easiest person to deceive is the person in the mirror.  LOCATION: 295

What’s up is that when it comes to good decision-making, we face our greatest challenge every morning in the mirror. Self-leadership is the greatest leadership challenge any of us face. But self-leadership is a critical component to our success in every arena of life. You’ll never be a leader worth following if you don’t lead yourself well. And while that’s apparent if you have an official organizational leadership role, it should be equally apparent if you’re a parent.  LOCATION: 307

Exceptional self-leadership, not authority, is the key to sustained influence. We rarely open ourselves up to the influence of people we don’t respect, even if they have authority over us. So, whether we’re talking about your professional life or your personal life, exceptional self-leadership is important. Your influence won’t last if you don’t lead yourself well first. Great leaders last because they lead themselves first.  LOCATION: 316

You can’t lead yourself if you’re lying to yourself.  LOCATION: 320

Nothing changes until we are brutally honest with the person in the mirror.  LOCATION: 354

Tell yourself the truth even if it makes you feel bad about yourself. And what do “Plastic Truth” and false narratives have to do with decision-making? A false premise will result in a faulty decision. You can’t make the best decision for you until you are honest with you.  LOCATION: 356

You may not owe it to anyone else. But you owe it to yourself to be honest about why you choose what you choose, why you’re deciding what you’re deciding. There’s no win in selling yourself. There’s no win in justifying options.  LOCATION: 373

You rarely have to sell yourself on the right thing to do, the healthy thing to do, the responsible thing to do. You just know. Good ideas rarely need any defense. When you start selling yourself, you need to hit the pause button and ask, “Am I being completely honest with myself . . . really? If so, why am I selling myself so hard?” The wise thing to do is usually so compelling it doesn’t need selling.  LOCATION: 495

The moral of the story is . . . and you’re going to hate me for this . . . most of us want to be proven right more than we want to know what’s true. We aren’t on truth quests. We’re on confirmation quests.  LOCATION: 538

The heart, as in every heart. Your heart. My heart. The heart is deceitful. Jeremiah chose his adjective carefully. As you know, there’s a difference between dishonest and deceitful. Dishonest is easier to spot than deceitful, isn’t it? Dishonest is just straight up not honest. But deceitful? Deceitful implies an agenda. Deceitful usually includes a mix of truth, half-truth, and untruth. If our hearts straight up lied to us all the time, that would be easy to catch. But deceitful? Deceitful is more difficult to detect.  LOCATION: 629

Jeremiah’s words explain why smart people make not-so-smart decisions.  LOCATION: 656

Curiosity will keep you focused on the frontiers of your ignorance. That’s where we learn. That’s where we gain insight. It’s where we catch sight of our prejudice and our narrow-mindedness. When it’s uncomfortable . . . and it will get uncomfortable.  LOCATION: 686

And while being honest with ourselves can be a bit terrifying, being honest with ourselves, telling ourselves the truth, can be . . . liberating. In fact, it’s almost always liberating.  LOCATION: 705

Jesus said, “You will know the truth, and the truth will set you free.”  LOCATION: 709

Am I being honest with myself . . . really? Am I telling myself the truth or selling myself a regret?  LOCATION: 714

Decision #1: The Integrity Decision. I will not lie to myself even when the truth makes me feel bad about myself.  LOCATION: 743

You’ll never get to where you need to be until you acknowledge where you actually are to begin with. So be honest.  LOCATION: 748

The Legacy Question: What Story Do I Want to Tell?  LOCATION: 768

Every decision you make becomes a permanent part of your story. The story of your life. What story do you want to tell? What story do you want told about you? The good news is, you get to decide. But you decide one decision at a time, because you write the story of your life . . . one decision at a time.  LOCATION: 769

Every decision you make, every decision becomes a permanent part of your story. The story of your life. Every decision you make has an outcome, a consequence, a result. It may be good or bad. Desirable, undesirable. Expected, unexpected. Whatever the case, that outcome becomes a permanent part of the story of your life.  LOCATION: 838

The primary reason we don’t think in terms of story when making decisions is that story is later. Decisions are now. We think about later, later. As in later when it’s too late to do anything about it. We don’t think in terms of story because we’re distracted by the pressure and emotions we feel in the moment.  LOCATION: 884

When confronted with anything or anybody that has strong emotional appeal, press pause, not play. Strong emotional appeal should trigger a red flag, not a green light. When something is emotionally appealing, instead of leaning in, we should step back. Not because he’s not the one. He may be. Not because it’s not a good investment. It may be. Not because it’s not the perfect job. It may be. We should step back because anything with strong emotional appeal . . . even the right thing . . . clouds our judgment. So pause. Get your bearings. Go home and think about it. Call a friend. Consider your story.  LOCATION: 919

What do you do when you’ve got the power and your decisions determine your enemy’s destiny? What do you decide in a moment like that? It depends on the story you want to tell. Joseph’s response to his brothers is a reminder that unpleasant circumstances create unprecedented, eye-popping, attention-getting, decision-making opportunities. When you decide what everybody expects you to decide . . . what they would decide if they were you . . . nobody notices. But when you decide against the norm, the tide, human nature, your story stands out.  LOCATION: 1165

Every decision you make becomes part of the story of your life. Every relational, financial, and professional decision and the outcomes of those decisions become permanent parts of your story. We’ve all lived long enough to have a few chapters we wish we could erase. No doubt you have a few stories you wish you could rewrite. We all do. We call it regret. But chances are, the decisions that led to your greatest regrets could have been avoided if you had paused to ask yourself, “What story do I want to tell?”  LOCATION: 1223

The Conscience Question: Is There a Tension That Deserves My Attention?  LOCATION: 1262

Inebriated people can’t pay attention to the cues around them or the internal tension within them. But we sober people are often guilty of choosing to ignore the cues around us and the internal tension within us. Intoxicated people can’t pay attention to social, cultural, and relational cues. But we’ve all seen sober people refuse to pay attention to those same cues. The inebriated aren’t even conscious of their consciences. But we’ve all seen what happens when sober people choose to ignore their consciences—that internal tension that always deserves our attention.  LOCATION: 1297

Experts sometimes refer to this phenomenon as a red flag moment, an internal sense of “I’m not sure why, but something about this doesn’t feel right.” When that happens, you owe it to yourself to pause and pay attention to the tension.  LOCATION: 1311

To be clear, I’m not suggesting you prioritize emotion over reason in the decision-making process. But I am suggesting you pay attention to what initially may appear to be an unreasonable emotion. Emotions play an important role in good decision-making.  LOCATION: 1328

As you consider your options, as you consider moving down a particular path, as you consider what to do next, if there’s any hesitation around a particular alternative, pause and allow . . . and I don’t know any other way to say this . . . allow that emotion, that tension, to rise up and get as big as it can possibly get before you decide. Don’t start selling yourself. As we’ve discussed, we have the ability to sell ourselves right past that pesky tension that deserves our attention.  LOCATION: 1406

Face that tension until either it goes away or you decide to go a different way. Pay attention to the tension. What begins as an uneasy feeling is often supported later with reason. Information. Insight. But if you don’t pause, you won’t see it.  LOCATION: 1411

Disappointment is always connected to an unexpected outcome. When you make a decision assuming an outcome and the outcome doesn’t materialize, what do you experience? Disappointment. Ignoring that tension in your gut sets you up for disappointment. Paying attention to that tension is how you avoid unnecessary disappointment.  LOCATION: 1498

That internal hesitation, that red flag, is often God’s way of turning us in another direction. People yielded to God don’t attempt to play God. They don’t predict outcomes. Instead, they surrender. They obey. They follow. As much as they want anything, they want to be able to lie in bed at night knowing that things are good between them and their heavenly Father. And rightly so. As my dad is fond of saying: “God takes full responsibility for the life wholly yielded to him.”  LOCATION: 1545

So pay attention to the tension. If you don’t, you may wake up on the other side of a decision you wish you could go back and unmake.  LOCATION: 1549

The Maturity Question: What Is the Wise Thing to Do?  LOCATION: 1623

So what is this unexamined assumption that makes us comfortable living, dating, spending, eating, drinking, driving, and flirting so close to the edge of embarrassment or worse? For the sake of clarity and emphasis, I’ll state this unexamined and oh-so-flawed assumption four ways:

If it’s not wrong, it’s alright. If it’s not illegal, it’s permissible. If it’s not immoral, it’s acceptable. If it’s not over the line, it’s fine.  LOCATION: 1662

Before long we’re asking, How far over the line can I go without getting caught or experiencing consequences? How unethical, immoral, or insensitive can I be without creating unmanageable outcomes? How long can I neglect my family, my finances, or my health without feeling the effects? How much can I indulge an addictive behavior without actually becoming addicted? It’s a slippery, sinister slope. And it all begins by asking the wrong question: Is there anything wrong with this?  LOCATION: 1672

An option can be both not wrong and unwise at the same time.  LOCATION: 1704

So if you will allow me to be so bold, I would like to suggest you establish three reference points that relate to our fourth question. These will be easy to remember because each of the three is simply an extension of the question. Here they are all rolled into one memorable phrase: In light of my past experience, my current circumstances, and my future hopes and dreams, what is the wise thing for me to do?  LOCATION: 1833

The purpose of our fourth question isn’t to stop you from doing something wrong. It’s to keep you from doing something unwise.  LOCATION: 1956

But if you never stop long enough to decide ahead of time where you want to be, you will live your life unaware of the sacrifices necessary to get there.  LOCATION: 1997

Everybody ends up somewhere in life. I recommend you end up somewhere on purpose.  LOCATION: 1998

Don’t settle for good, legal, permissible, acceptable, tolerable, not prosecutable, or normal. If you do, you will eventually find yourself living dangerously close to regret. You’re better than that. You deserve better than that. Your family deserves better than that.  LOCATION: 2005

The Relationship Question: What Does Love Require of Me? LOCATION: 2026

What you refuse to acknowledge will follow you into your future. It will shape the story of your life.  LOCATION: 2040

Jesus’s love for the men in the room, rather than his authority over the men in the room, is what he leveraged to instruct and inspire the men in the room. The men in that room would not see him seated on a Jewish throne. They would see him hanging from a Roman cross. It was his gory and gritty sacrifice, not a keep-your-hands-clean holiness, that compelled his disciples to eventually take up their own crosses and follow him. If you are a Christian, that should stop you in your tracks.  LOCATION: 2155

Jesus’s new, all-encompassing command was far less complicated than the prevailing system. But it was far more demanding. There are no loopholes, no work-arounds in this brand of love. LOCATION: 2177

This clarifying, but terrifying question should stand guard over our consciences. It should serve as guide, signpost, and compass as we navigate the unavoidable complexities inherent in every relationship. It should inform how we date, parent, boss, manage, and coach. It should form a perimeter around what we say and do in our roles as spouses, coworkers, and neighbors. LOCATION: 2225

This question gives voice to God’s will for us on issues where the Bible, as well as all other religious literature, is silent. It fills the gaps with disquieting precision. It succeeds where concordances fail. It quashes the insipid justification, “But the Bible doesn’t say there’s anything wrong with ______.” It closes loopholes. It exposes hypocrisy. It stands as judge and jury. It’s so simple. But it’s so inescapably demanding.  LOCATION: 2228

When unsure of what to say or do, ask what love requires of you.  LOCATION: 2235

Our five questions are more than a decision-making filter. These questions will steer you in the direction of God’s general will for your life. And . . . and this is big . . . they will position you to discern or recognize his personal will for your life as well.  LOCATION: 2436

Good questions lead to better decisions. Your decisions determine the direction and quality of your life. Your decisions serve as the framework for the story of your life. So write a good one. While there’s nothing you can do about the decisions you’d choose to go back and unmake, remember this: Your regrets are only part of your story. They don’t have to be the story. LOCATION: 2476


Note: should you wish to find any quote in its original context, the Kindle “location” is provided after each entry.


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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