Regret: A Powerful Path to a More Aligned Life

We all mess up. But you don’t have to get stuck in a pit of regret. Here’s how to transform this challenging and confusing emotion into your greatest ally for finding clarity and alignment in 2024.

Photo by Kyle Kesterson

Being human means fucking up from time to time. Sometimes, we really fuck things up. Other times, it’s a minor fuck-up. Either way, it’s not what we want, but the reality is that it’s gonna happen at some point. 

Everyone makes mistakes. We miss opportunities. We do or say the wrong thing. We make bad decisions. We take a path that leads us somewhere we don’t really want to go. 

Enter regret, the painful and nagging feeling of wishing you had done things differently. Regret can be an emotional minefield that disrupts our equilibrium for months or even years. The higher the stakes, the more intense the regret. Maybe you made a bad investment or bought the wrong house. Maybe you never made the effort to heal your relationship with your father before he died. Maybe you had an affair. Maybe you said something hurtful that you can never take back. 

You get the idea. Regret is a natural and healthy response to these kinds of situations, but left unchecked, it can fester inside of us and cause real harm. When unmanaged and unanalyzed, regret can even affect your hormones and immune system.

I want to offer a new perspective that can help you shift your relationship with this emotion. What if I told you that regret isn’t a problem, but instead it’s a powerful messenger and ally guiding you towards a more aligned life?

The Emotional Fallout of Our Mistakes 

If you’ve ever found yourself ruminating over past decisions, wishing you could turn back time and make a different choice, you're not alone. This is a universal human experience. It would be great if we could all just forgive ourselves for our mistakes, learn the lesson, and move on. But that’s not always the case. Instead, we sink into a pit of regret and obsessive regret is implicated in anxiety and depression. This dark, lurking emotion can haunt us for years after ‘the event’—that singular unfortunate thing we did (or didn’t do). 

I invite you to consider: What if underneath your regretful ruminations were unfelt and unprocessed emotions with important—and potentially life-changing—messages to share? In my experience, that is exactly what’s going on. 

These emotions contain valuable information that can help you live in a way that is more deeply aligned with who you really are. In fact, they may be the key to true fulfillment. I have witnessed with clients how the messages contained in these unfelt emotions help them get back on track with how they actually want to live—and not only back to where they were before, but actually better off and more fully aligned with their values, precisely because of what they’ve learned from their missteps.

So how do you make contact with these emotions? Start by planting your feet firmly on the ground and turning towards what you’re feeling. In a moment of ruminating on a bad choice, ask yourself a simple question: "What am I feeling right now?" This might sound overly simplistic, but it's a crucial first step. Then, stay with it. It might take more than a few minutes to get at what’s really going on. Meditate on this question, journal with it, and take it on a long, contemplative walk. Eventually, your intention and attention will guide you to the emotions underneath your thoughts. 

When you feel the regret rising up, really go into it. Encourage the emotion to grow inside you. It’s a counterintuitive move, but it works. What other emotions do you feel circling around this feeling? Regret doesn’t usually come alone. Are you ashamed? Is there sadness over a loss that resulted from your decision? Are you angry at yourself or someone else? Are you frustrated that you got off-track? Sit with the feelings. 

Then ask yourself, "Where do I feel this in my body?" Emotions tend to manifest physically as sensations or tension in specific areas. Pay attention to these bodily signals, bringing your awareness to the places where you’ve found that the emotion resides. These physical sensations are like road signs guiding you through your emotional landscape. As you feel them, you may find that more feelings arise, ones that you may not have even known were there. We want to go into those spaces, connect with the emotions, and invite them to soften.

Let It Be: Acceptance & Compassion  

The next step is to bring acceptance and compassion to the places where we’re hurting. 

This can be challenging, especially when you’re dealing with deep, dark emotions like regret, shame, and guilt. Remember that these emotions are part of the human experience, and it's okay to feel them. Try saying to yourself, "I feel regret and that’s okay." This simple acknowledgment can be remarkably liberating. It's an act of self-compassion that can release the grip of ‘negative’ emotions.

You likely won’t be able to process or release your emotions until you can muster at least some acceptance of them. You may have a lot of resistance here. You may find yourself getting hung up on thoughts like: How can I accept this when I’m clearly such an idiot? or I really fucked up—why do I deserve any compassion? This is often where we get stuck in the process. We don’t allow ourselves to be ‘excused from the table.’ We must pay for our mistakes. We must punish ourselves. We must continue to feel bad. 

This is where self-compassion comes in. I want you to acknowledge that you’re just a flawed human doing your best, just like everyone else. There’s a great lovingkindness meditation from Buddhist psychologist Kristin Neff that uses the mantra: “May I be kind to myself.” Speak to yourself the way you’d speak to a close friend who’s going through the same situation. 

With compassion, it becomes easier to shift the lens and see yourself not as a failure, but as the kind of person who learns from their mistakes. You’re someone who gathers learnings from situations that didn’t go well—what’s so bad about that? Accept that the situation went in a direction you did not want or hope for. Accept the emotions that arose as a result. This acceptance and compassion is what can carry us to the other side.

Mining for Wisdom

Now comes the interesting part. As you sit with these emotions and offer them acceptance, you will begin to notice something remarkable—images, phrases, wisdom, guidance, or a message hidden within the emotional turmoil emerges. These insights are beacons guiding you toward a more aligned life.

Regret, at its core, is a signal that something in your past actions or choices was not in alignment with your true self or your values. It didn’t lead you in the direction of the life you want to be living. Maybe a not-so-great move to a new city helped you realize that community is actually the most important thing in where you choose to plant roots. Or your regret over missing an exciting business opportunity might show you that you’ve over-prioritized safety at the expense of growth. 

This is how regret becomes a compass pointing you toward a more authentic and aligned future. Sometimes we have to learn things the hard way—there is no way around it. Ideally, we strike a balance where we learn from regret without letting it weigh us down. When we venture off-course, we are going to feel pain. And thank god for that. Our emotions are a built-in system running in the background, sending us signals that something is wrong. At first, they send signals in the form of whispers but venture too far off-course, and those signals will become sledgehammers straight to the skull.

Let’s be grateful for this system. Let’s hear the message. “I got too caught up in material possessions.” “I prioritized the flashy crowd instead of the friends that are good for my soul.” “I took on way too much.” Let’s feel the pain of getting it wrong. And let’s trust that when we come to another fork in the road, next time we will choose more wisely. 

Taking Aligned Action 

The final step is taking action to get yourself in alignment. This could involve making amends with someone you've hurt, changing your course of action, or simply taking note of how you’ll do it differently next time. When you do this, regret becomes a catalyst for positive change.

This is the complete process of regret. This is what it looks like to close the loop.

To recap: regret isn't an enemy to be avoided. It's a teacher, a messenger, and an opportunity for growth. It invites you to reflect, learn, and evolve. I don’t want to see any of my readers tattoo NO REGRETS going forward. The next time you feel the sting of regret, welcome the opportunity to course-correct to a better life.

As you navigate the journey of transforming regret, keep in mind that it's okay to seek support from a skilled therapist, counselor, or coach if needed. For particularly challenging situations, having a compassionate guide can make all the difference.