How Men with Low Self-Esteem Can Break Free from Chronic Regret

Let’s face it, we all feel regret sometimes. But if you’re someone dealing with low self-esteem, that regret can turn into this persistent, almost paralyzing feeling that keeps looping in your head. Constantly dwelling on past mistakes, missed chances, or things you wish you’d done differently can trap you in a cycle of self-blame and doubt. If this sounds familiar, just know—you don’t have to stay stuck there. The good news is, you can turn things around, and it all starts with how you see yourself.

Recognize How Self-Esteem Affects Regret

Low self-esteem feeds into regret. When you see yourself as unworthy or not good enough, every mistake feels like proof that you’ll never get it right. You might obsess over a breakup you had, a career move you didn't make, or something you said—or didn’t say—a long time ago. But here’s the thing: most of that regret isn’t really about the event itself. It’s about how you’re feeling about yourself in that moment. When you start to boost your self-worth, your whole perspective on the past begins to shift.

Look at Your Past in a New Light

Regret often grows when we treat the past as the final word. But the truth is, the past is just a starting point for growth. Ask yourself: What did I learn? How did this experience shape the person I am today? Reframing doesn’t mean pretending mistakes didn’t happen—it’s about seeing them as part of a bigger story that’s still being written. And stories can be changed. When you start to see past experiences as lessons rather than life sentences, you take back your power.

Be Kind to Yourself, Not Too Hard

Many guys have been conditioned to be their own toughest critic, tying their self-worth to success or toughness. But healing from long-standing regret requires a different kind of strength—one that involves kindness. Self-compassion means accepting that you’re only human, that everyone messes up sometimes, and that you deserve forgiveness, even from yourself. Instead of asking, “What’s wrong with me?” try asking, “What do I need right now?”

Focus on What You Can Do Now

A lot of regret is tied to things you can no longer change. The only real place you have control over is the present moment. Instead of looping on what went wrong, ask yourself: What small step can I take today that moves me closer to who I want to be? Reach out to someone, apply for that job, or speak your mind. Taking action, even on small stuff, builds confidence. And that confidence helps to heal the wounds of regret.

Talk to Someone About It

Carrying regret alone makes it feel so much heavier. Talking with a self confidence therapist, a mentor, or a trusted friend can help you see things more clearly and let go of some of that weight. You don’t have to work through this on your own—connection with others is one of the most powerful ways to boost your self-esteem and move beyond chronic regret.

Final Thought

Having regret doesn’t mean you’re broken. It just means you care. But staying stuck in that feeling for too long can stop you from growing into the man you’re meant to be. If low self-esteem and regret are weighing you down, remind yourself—you’re not your past. You’re the choices you make right now. And, honestly, it’s never too late to start making different ones.

Ready to Try Therapy for Self-Esteem and Confidence in Des Plaines, IL?

If you’ve been stuck in a loop of regret, second-guessing your choices, or questioning your worth, you’re not alone—and you’re not broken. The truth is, you can start showing up for yourself differently. Therapy for self-esteem and confidence offers a space to unpack the weight of past mistakes, challenge the stories holding you back, and build a stronger, more compassionate relationship with yourself. At Shapiro Psychotherapy Associates PLLC, we’re here to help you reconnect with your confidence, one step at a time. Here’s how to begin:

• Schedule an appointment with Shapiro Psych.

• Work with a self confidence therapist who gets it—no judgment, just real support.

• Start making choices today that reflect the man you’re becoming, not the mistakes you’ve made.

Other Services Offered by Shapiro Psychotherapy Associates, PLLC in Des Plaines, Illinois

At Shapiro Psychotherapy Associates PLLC, I offer a range of therapy options for men who want to stop living in the shadow of past mistakes and start building a more confident, grounded life. Whether you're drawn to Acceptance and Commitment Therapy (ACT), Eye Movement Desensitization and Reprocessing (EMDR), Cognitive-Behavioral Therapy (CBT), Mindfulness-Based Stress Reduction (MBSR), or therapy for self-esteem and confidence, we’ll focus on what matters most to you—moving forward with purpose.

With years of experience and specialized training in evidence-based approaches, I help clients shift how they see themselves—not by ignoring the past, but by learning from it and showing up differently today. You don’t have to keep carrying regret alone. Reach out today to start building a life that reflects your growth, not your guilt.