Are You Making Life-Changing Decisions Alone? 5 Questions to Ask for Better Outcomes

Want to Live with Fewer Regrets? How to Use a Simple Framework to Guide Your Next Big Move.

Learn a proven framework to make better decisions and reduce regrets in your career, relationships, and finances. Discover five powerful questions that create self-honesty, long-term vision, and wisdom, helping you build a life story you’ll be proud to tell. Facing a tough decision? Continue reading to apply the five essential questions to your current challenge, learn how to separate emotion from wisdom, and start building a life with intention and fewer regrets.

Genres

Communication Skills, Motivation, Inspiration, Personal Development, Career Success

Transform how you make decisions with five key questions.

Better Decisions, Fewer Regrets (2020) presents a systematic approach to making choices that align with your values and goals. It introduces five essential questions designed to serve as a compass for your decisions, helping you avoid common pitfalls that lead to disappointment and lead a positive life.

Sarah stares at the job offer on her desk: double her current salary, a prestigious title at a Fortune 500 company, and the career breakthrough she’s dreamed of for years. There’s just one catch – it requires moving 2,000 miles away from her aging parents who, increasingly, need her support.

Meanwhile, across town, Marcus sits with his laptop open to two browser tabs: one showing his student loan balance, the other displaying house listings. His grandmother’s unexpected inheritance either could wipe out his debt or finally get him into homeownership, but not both.

What should they do? All of us face decisions that have the power to reshape our lives, yet we often lack a reliable process for making the right choice. Too often, we rely on incomplete information, emotional impulses, or outdated assumptions, leading to regret or missed opportunities.

In this summary, we’ll see that making better decisions starts with asking the right questions. We’ll explore five powerful prompts designed to transform unconscious decision-making habits into a deliberate, thoughtful framework – so you can make choices you’ll feel proud of years down the line.

One choice after another

Picture your life right now – your relationships, career, finances, health, daily routines. For the most part, your current circumstances aren’t the product of luck, timing, or what others have done to you. Your life trajectory has been shaped by the choices you’ve made along the way. This might sting a little, but it can also be incredibly empowering. If your past choices brought you here, your future choices can take you somewhere better.

Unfortunately, knowing this doesn’t automatically make you better at choosing which life choices to take. Ever notice how you can spot exactly what your friend should do about their toxic relationship, but you can’t figure out your own love life? That’s because emotions hijack our judgment when we’re personally invested in the outcome.

And yet most of our biggest regrets aren’t spontaneous mistakes. They’re carefully planned disasters. That incompatible marriage? You probably spent months planning the wedding. That failed business venture? You wrote a business plan, filed paperwork, and invested your savings. That crushing credit card debt? It accumulated through hundreds of individual purchases that seemed reasonable at the time. As the author puts it, we literally “plan our regrets” through a series of smaller decisions that, collectively, create bad outcomes. So how can you tell when you’re on the wrong track? One red flag is the need to over-justify. If you catch yourself thinking, “But this makes sense because…” or weaving elaborate explanations for why something will work out, chances are your rational mind is working overtime to silence your intuition.

The challenge, then, is moving from simply knowing better to consistently choosing better. That shift requires a different approach: making decisions that are less emotional and reactive, and more thoughtful and intentional. Which brings us to the first of five essential questions.

Stop believing your own spin

It’s 2 AM. You’re wide awake, scrolling through social media even though tomorrow’s important work presentation looms large. Or you’re in a bar, and you tell yourself “just one more drink,” despite knowing full well that you’ll need to wake up in only a few hours. These small decisions might seem trivial, but they point to a deeper reality: often, the biggest obstacle between you and the life you want is your own ability to deceive yourself.

That’s why the cornerstone of good decision-making isn’t intelligence, experience, or even good intentions – it’s brutal self-honesty. If you can’t lead yourself with clarity, you’ll struggle to lead others.

The most dangerous lies aren’t the ones you tell others – they’re the elaborate stories you tell yourself. When you make a poor decision, your mind immediately begins crafting justifications to maintain psychological comfort. These aren’t outright fabrications; they’re sophisticated mixtures of truth, half-truth, and convenient omissions that eventually become your accepted reality. You start believing your own spin.

Notice how this pattern plays out in three areas where people accumulate their biggest regrets: purchases, relationships, and habits. That expensive gadget you convinced yourself was an “investment,” the romantic partner you pursued despite obvious red flags, or the “harmless” habit you assured yourself you could control? Each began with an internal sales pitch. Your heart generated a desire, then instructed your brain to construct seemingly rational reasons for getting what you wanted.

Breaking free from this cycle begins with facing an uncomfortable truth: self-deception isn’t a temporary weakness you’ll outgrow, it’s hardwired into human psychology. The only antidote is constant vigilance. Accepting this fact gives you a healthy skepticism about your own motives, making it harder for rationalizations to take root.

The practice itself is simple, but not easy. Start by asking yourself one critical question: Am I being honest with myself? Use your own name when you ask it, and if you can, ask it in front of a mirror. Stay curious about the feelings that surface, especially the uncomfortable ones – they’re often signposts that you’re finally brushing up against the truth.

Think like a biographer of your own life

You’re at your high school reunion, and someone asks what you’ve been up to for the past decade. What story will you tell? Is it what you want it to be?

There’s no escaping it. Every major choice you make becomes a permanent chapter in your personal narrative. Whether it’s taking a job, ending a relationship, or responding to a crisis, these decisions accumulate over time to form the complete story of your life.

So before making any significant decision, remember to ask yourself this simple but profound question: what kind of story do you want this choice to become part of?

Shifting your thinking in this way moves you beyond immediate consequences to consider the eventual narrative that will emerge. It helps you recognize that even private decisions inevitably become public parts of your story over time.

One of the biggest obstacles to story-conscious decision-making is the fog and distortions that emotions create. When you’re in the grip of strong emotions – whether excitement, anger, or desire – your judgment becomes clouded by immediate pressures and feelings. You lose sight of long-term consequences and focus only on what feels compelling right now. The antidote is to pause: when it’s apparent that a decision carries strong emotional weight, step back and ask how it fits into the larger story you want to live.

Commit to choices that create stories you’ll be proud to tell. Avoid decisions that would leave you hiding details or bending the truth. With each crossroad, ask yourself: How does this alter my story? Does it align with the life I want to narrate? Don’t just consider what you might gain – reflect on the lasting narrative you’re constructing, and how it would sound if told to the people you respect most.

Because in the end, the immediate rewards of a choice fade. What endures is the story of how you got there. So choose the path that leaves you with a story worth telling – and retelling.

Listen to your discomfort

Ever notice how your stomach drops the moment someone asks if you’re “absolutely sure” about a major decision? That’s because that sinking feeling isn’t coincidence. It’s your internal warning system trying to get your attention.

When you’re wrestling with an important choice, one of the most valuable questions you can ask yourself is this: is there an underlying tension or discomfort that I need to examine? This isn’t about second-guessing every minor decision, but rather developing sensitivity to those moments when something feels off, even if you can’t immediately articulate why.

Your brain processes information at multiple levels simultaneously. While your conscious mind analyzes pros and cons, your subconscious often picks up on patterns, inconsistencies, or potential problems that haven’t yet surfaced to rational awareness. This creates internal tension – a sense of hesitation or unease that serves as an early warning system for decisions that might lead to regret.

The challenge is learning to recognize and respect these internal signals rather than dismissing them as irrational fears or overthinking. Sometimes this tension manifests as physical discomfort, a nagging feeling that won’t go away, or an inexplicable reluctance to move forward despite what logic says. Other times it appears as external feedback from trusted friends or family members who express concerns about your direction.

Don’t make the mistake of rationalizing away this discomfort. Instead, explore what it might be telling you. Just because you can construct a logical argument for your decision, that doesn’t mean your emotional resistance is invalid. Emotions often contain valuable information that logic has not yet processed.

The key is patience with uncertainty. When hesitation arises, resist the urge to barrel through it. Sit with the discomfort a little longer. Ask yourself: What is this tension trying to tell me? Sometimes it fades as you gather more information or clarify your priorities. Other times, it nudges you toward a different path – one that may not have looked as attractive at first but turns out to align more closely with your authentic self.

Honoring internal tension doesn’t mean being paralyzed by doubt. It doesn’t mean ignoring logic either. It means treating your emotions as legitimate signals, data points to weigh alongside reason. Because when you do, your decisions become not just smarter, but truer.

A wisdom-first approach

You’re standing at a crossroads, with several clear paths in front of you. Which one will you choose? This is where wisdom becomes your most valuable compass.

Many people approach decisions by asking only whether something is wrong or technically permissible. They live like drivers who push the speedometer right up to the limit, students who submit work at the last possible second, or spenders who max out their credit cards without going over. This edge-dwelling mindset treats life as a game of “how much can I get away with?” But wisdom calls for a different lens.

Instead of asking what’s merely acceptable, ask: What’s the wise choice? What decision will best serve my long-term flourishing? That shift moves you from minimum standards to optimal outcomes. After all, a choice can be legal, moral, and socially acceptable – and still be profoundly unwise for your situation.

This is where personal honesty matters. What seems harmless to your friends may be dangerous for you, depending on your history with certain temptations, relationships, or patterns. Wisdom requires acknowledging those vulnerabilities and choosing accordingly, rather than pretending they don’t exist.

Circumstances matter too. During times of stress, grief, financial strain, or major transitions, your decision-making capacity narrows. Wise people recognize this and often defer major decisions until the storm passes, knowing that temporary conditions can create permanent consequences.

Perhaps most importantly, wisdom is about direction. Every choice either moves you closer to – or further from – your aspirations. Your daily decisions should align with your long-term goals, yet people constantly make choices that undermine what they say they want most.

The difficulty is that modern culture works against this wisdom-first approach. We’re constantly nudged toward instant gratification, boundary-pushing, and quick fixes. Destructive options are more accessible than ever. Swimming against these currents requires deliberate effort – but the reward is ending up where you intentionally steer, rather than drifting wherever the current takes you.

Let love take you higher

When it comes to relationships, we’re often taught to use the Golden Rule: treat others as you would have them treat you. Yet there’s an even higher standard available to us; one that goes beyond reciprocity to something more transformative. This rule can elevate our relationships from mere fairness to something that can genuinely heal and restore connection. The rule is this: love others as we’ve been loved ourselves, in our best moments.

You’re standing outside your teenage daughter’s room, just as she’s slammed the door in your face. Your mind is racing with comeback arguments and angry feelings. But beneath the hurt, a quieter voice asks a different question entirely – one that could change everything about how this moment unfolds. The question is: what would loving this person well look like, right now?

It’s a question that can help you guide every decision you make about others, whether you’re dating, parenting, managing a team, or simply being a neighbor.

When you embrace the question of how to love well, love transforms into virtues and concrete actions. Patience becomes moving at someone else’s pace rather than demanding they match yours. Kindness means responding to weakness by offering your strength instead of highlighting someone’s shortcomings. Love means celebrating others, keeping envy from poisoning your joy in their success. Selflessness means prioritizing others’ needs, while forgiveness means refusing to keep score and choosing to see the best in people.

And it’s an approach which eliminates the loopholes and technicalities we sometimes create for ourselves to justify bad behavior. You can no longer tell yourself “Well, they never specifically asked me not to share that embarrassing story” or justify cutting remarks by saying “I was just being honest – no one said I had to sugarcoat it.” When love becomes your guide, these clever justifications dissolve.

You can no longer justify questionable behavior by asking what you’re allowed to do, because the question becomes, “What would love do?”. Making this choice may require immediate action: apologizing for past wrongs, rebuilding damaged relationships, or initiating difficult conversations. There’s no guarantee others will respond positively, but if you have the courage to follow through on what love demands, your life – and the whole world – will be better for it.

Conclusion

The main takeaway of this summary to Better Decisions, Fewer Regrets by Andy Stanley is that making decisions you’ll be proud of requires asking yourself five essential questions.

First, are you being completely honest with yourself? Second, what kind of story will this choice create? Third, is there some tension here you should explore? Fourth, what choice is the wise one? And finally, what would loving others well look like?

Remember, life’s path is the result of the countless choices you make along the way. Ask the right questions, choose wisely, and you can build a life you’ll be happy looking back on.