Great Thinkers: How to Live Without Regrets

Introduction

Regret is a frustrating, sometimes even heartbreaking feeling. It’s the sense that you could have made a different choice—taken a risk, spoken up, or walked away—and ended up in a better place than you are now. Regrets can pile up over your lifetime, leaving you weighed down by “what ifs” that make it hard to fully appreciate the life you’re living.

But regret doesn’t have to define your life. You can avoid or minimize the choices that lead to regret, and you can turn the regrets you do have into something more productive—life lessons. Ahead, we’ll explore eight Great Thinkers’ advice for living without regrets.

Volf, Croasmun, and McAnnally-Linz: Chart Your Life Philosophy

One way to live with fewer regrets is to clarify the kind of life you want to live. In Life Worth Living, three Yale professors—Miroslav Volf, Matthew Croasmun, and Ryan McAnnally-Linz—explain how to do this. They say you need a life philosophy, or a set of personal guidelines that encompasses all your beliefs about what it means to live well. This framework should address every major dimension of life, including:

• Your existential welfare (the purpose and significance of your life on Earth)
• Your emotional welfare (your emotions and how you value them)
• Your material welfare (your physical needs, resources, and living conditions)
• Your moral welfare (the sense that you’re generally a virtuous person)

Volf, Croasmun, and McAnnally-Linz argue that having a life philosophy helps you live more intentionally. Without one, you might act on your instincts or assume that you should strive for the things everyone else is striving for, when really you’d be happier going against the crowd. But once you have a vision of what it means to live well, you can make thoughtful choices about how to behave and what to pursue. As a result, your life will reflect your values, and you’ll be less likely to look back wishing you’d lived differently.

To define your life philosophy, the authors recommend spending time in contemplation. The world is full of different ideas about what it means to live well, and it’s worth sifting through them to see which resonate with you. You can draw inspiration from anywhere, including the diverse sources Volf, Croasmun, and McAnnally-Linz explore, like Confucius, Plato, and Oscar Wilde.

Think carefully about how these perspectives can improve each aspect of your welfare—the existential, the emotional, the material, and the moral—and stay open to new wisdom. The authors recommend setting time aside for this every day. This helps you keep your life philosophy top of mind, apply it to your daily decisions, and catch drift early—so you can course-correct before small compromises become big regrets.

Gilbert and Stanley: Be Honest With Yourself

Knowing what you value in life is different than pursuing it—so while defining your life philosophy is a good first step toward preventing regret, you can’t stop there. You must also make choices that align with those values. This isn’t easy, though. In Stumbling on Happiness, psychologist Daniel Gilbert says you’re prone to making mistakes that don’t align with your values because you’re not being honest with yourself.

Gilbert argues that your brain is primed to mislead you. You assume that your memories give you a clear sense of what you like and dislike, but your recollections are biased and incomplete. Likewise, when imagining the future, you tend to focus on the most obvious details and overlook how quickly you adapt to changes—leading you to overestimate how good or bad certain outcomes will feel. Because you’re working with flawed information, you often misjudge what will make you happy. As a result, even your most well-intentioned choices can steer you away from the life you truly want, setting the stage for regret.

Gilbert argues that there’s no correcting this—despite your best intentions, you simply can’t overcome your brain’s biases, which means you can’t make choices that are guaranteed to make you happy. So, he argues, you can only find happiness and avoid regret by accident.

Other thinkers, like evangelical pastor Andy Stanley, have a different point of view. As he explains in Better Decisions, Fewer Regrets, Stanley agrees with Gilbert that most regrets result from self-deception: Either your brain’s shortcomings prevent you from seeing the right path forward, or you tell yourself stories to justify poor choices that will lead to regret. But unlike Gilbert, Stanley believes you can get around these obstacles—and start making choices that will make you happy—by asking yourself five questions:

1. Am I telling myself the truth? This prompts you to stop ignoring information you don’t like, which helps you make better decisions. For example, you might tell yourself pizza won’t give you heartburn—but if you’re honest, you know it will and you’d regret eating it.
2. How does this fit into my story? This prompts you to consider whether you’ll feel proud of the decision you make. For example, if you want the story of your life to feature love more than money, you’ll spend more time nurturing relationships than on work.
3. What am I ignoring? This prompts you to listen to your gut, which can remind you of your values. For example, your gut might know you’re incompatible with someone you’re dating before you consciously come to the same conclusion.
4. How can I act wisely? This prompts you to consider the best course of action rather than the easiest one. For example, acting wisely might mean going out of your way to be a good friend, rather than letting a friendship wither because it’s hard to find time for it.
5. How can I act with love? This prompts you to consider how your actions affect others—because you’d almost certainly regret hurting someone else. For example, acting with love might mean choosing to forgive over seeking revenge.

Edmondson and Pink: Make the Most of Your Mistakes

While “no regrets” is a noble ethos to live by, some mistakes are inevitable. How should you handle it when you do make a choice you regret? Leadership expert Amy Edmondson provides a starting point in Right Kind of Wrong. She recommends developing a “fail-safe” mindset—that is, embracing the fact that it’s OK to be an imperfect person. Everyone messes up sometimes; what really matters is that you don’t get stuck in your failure. To move forward, Edmondson argues, you must cultivate three key skills:

• Resilience: This is the ability to keep trying after experiencing a setback. Instead of wallowing in embarrassment and frustration, you keep working toward your goals.
• Accountability: This means recognizing and admitting your role in a failure. Taking accountability eases your feelings of guilt, which minimizes the painfulness of regret.
• Reflection: This requires examining your failures so you can learn from them and do better in the future. Reflecting helps you see your failures as opportunities to improve, and it prevents your regrets from stacking up.

Like Edmondson, writer Daniel H. Pink argues that regret is both inevitable and valuable. In The Power of Regret, he explains that reflecting on your regrets helps you grow as a person—which means you’ll make fewer poor decisions, reducing the number of regrets you’ll end up with. He offers a five-step process for reflection:

1. Reveal your regret: Writing or talking about the mistakes you’ve made can help you release the negative feelings you have about them. It also helps you integrate those negative experiences into a larger positive narrative about your life.
2. Forgive yourself: Viewing your mistakes with empathy rather than judgment empowers you to cope with them constructively rather than avoid ever dealing with them.
3. Find something positive: Every cloud has a silver lining; finding yours can make the regret you feel more bearable. You might have missed out on something valuable if you’d made a different decision, so be grateful for what the experience gave you.
4. Find the lesson: Analyzing your regret can teach you more about your priorities in life. So, ask yourself what you’d do differently if faced with the same decision.
5. Commit to action: You may be able to remedy the mistake you made in the past—and if you can, you should. If not, you can use what you learned to guide your future actions.

Ware: Embrace Your Mortality

By processing your regret in the ways Edmondson and Pink recommend, you can avoid dying with regrets that feel too big or too numerous to cope with. People often feel saddled with huge regret in their last days, according to palliative care nurse Bronnie Ware. In Top Five Regrets of the Dying, Ware explains that these regrets usually fall into five categories:

1. Not living authentically: Letting others’ expectations dictate how you live instead of honoring your own dreams and desires.
2. Neglecting happiness: Failing to do the things that will make you happy because you believe that happiness will arrive someday in the future or that you don’t deserve it.
3. Putting work before relationships: Getting caught up in chasing material success, which causes you to overwork and lose valuable time with loved ones.
4. Not sharing honest feelings: Letting fear stop you from being vulnerable, which prevents you from building strong relationships and feeling understood.
5. Losing touch with friends: Prioritizing work and family over friendships, which leads you to miss out on the feeling that you belong and are cared for.

Ware argues that one of the best ways to avoid dying with these regrets is to embrace your mortality. Death is a normal, unavoidable part of life, and acknowledging that can give you the courage to pursue true happiness. It reminds you to be intentional with your decisions, discern what truly matters, and live each moment in the most fulfilling way possible. As a result, when the end of your life arrives, you’re less likely to look back wishing you’d done things differently.

Great Thinkers’ Advice for Living Without Regrets

• Miroslav Volf, Matthew Croasmun, and Ryan McAnnally-Linz (Life Worth Living): To avoid regret, you must live intentionally. Developing a solid life philosophy through daily contemplation can help you make more intentional decisions.
• Daniel Gilbert (Stumbling on Happiness) and Andy Stanley (Better Decisions, Fewer Regrets): When you make decisions you’ll end up regretting, it’s because you’re not being honest with yourself. Pause to consider the truth—you’ll make better choices.
• Amy Edmondson (Right Kind of Wrong): Everyone makes mistakes, but regret doesn’t have to define your life. When you mess up, take accountability, move forward with resilience, and reflect on your failure.
• Daniel H. Pink (The Power of Regret): Reflecting on your mistakes can help you grow. To reflect, reveal your mistake, forgive yourself for it, find something positive that resulted from it, learn from it, and commit to doing the right thing next time.
• Bronnie Ware (The Top Five Regrets of the Dying): Many people die with regrets —but you’ll have fewer if you embrace your mortality, which can give you the courage to live well.

What Do You Think?

What’s something you regret? Why do you regret it, and what would you do differently if you could do it over again? What, if anything, should you be doing differently now so you don’t have more regrets in the future?