We’ve all had the if onlys. If only I had waited to get married. If only I had landed that job. If only I hadn’t let people treat me that way.

It’s easy to look back on our lives with everything we know now and fall into regret or self-judgment. With years of experience behind us, our perspective sharpens, but it can also become unforgiving. Therapists call this hindsight bias: the tendency to evaluate past decisions with the clarity we didn’t have at the time. In midlife, when reflection feels almost inevitable, hindsight bias can make earlier choices seem flawed or shortsighted, even when they weren’t.

We all tend to romanticize the past. Sometimes we remember only the highlights and forget the stress, uncertainty, or limitations we were living with. Other times, we do the opposite, focusing on what went wrong while overlooking what was meaningful or necessary in that moment. Looking back, life can appear far simpler than it truly was.

But the truth is, we were always doing the best we could with what we knew at the time. And midlife offers us a powerful opportunity—not to rewrite the past, but to understand it more fully and with greater compassion. Let’s take a closer look.

Understand Your Bias

Let’s say Meghan has always regretted not completing graduate school. She perceives that she put a lot of effort into school, only to give up. However, Meghan is forgetting all of the other things that were happening at the time. While she was trying to finish school, Meghan’s mom got sick, and she had to help take care of her. She couldn’t work her part-time job, and bills started piling up. She wasn’t able to focus on her schoolwork with everything going on in her life.

The next year, when things settled down, Meghan found out she was pregnant. She needed a steady income and better healthcare. It wasn’t feasible to return to school. Once Meghan made it through those times, they didn’t seem so bad. But back then, they were overwhelming, and she had little flexibility in what she could do. Often, we do not give credit to the important choices we made. Most people do the best they can at any given time, during any situation. Why would they do otherwise?

Question Your Assumptions

So, if you are having regrets, it’s helpful to question your thoughts about them. Often, regrets are connected to cognitive distortions, or false beliefs that aren’t based in reality. Processing will help you work through these thoughts and their related feelings. It’ll also correct the record on any inaccurate beliefs you may have. Try asking yourself these five questions to help you challenge your distorted beliefs:

If you could have made a different choice, why didn’t you?

This question isn’t meant to be judgy, but thought-provoking. If you still harbor regret for a choice you made or didn’t make, think it through. Why did you make that choice at the time? Like with Meghan, there is probably quite a bit more to the story. If you are having trouble remembering the details, try journaling about what you do remember. This can help you trigger old memories and bring greater clarity and perhaps plausibility to the choices you made.

Are you judging “younger you” based on what “wiser you” knows?

Wisdom comes with life experience. There are some mistakes we simply can’t avoid. If we could, we wouldn’t learn anything new about life. We’d walk around like zombies. Life includes the hard stuff, which helps us enjoy the good times. We often make many of these mistakes when we’re younger, which is part of growing into an adult. You might be looking back at yourself and judging your choices as an older, more experienced self. Consider if that’s fair to “younger” you.

Are you blaming yourself for things that weren’t (at least not entirely) your fault?

When it comes to heavier things in life, like traumatic events, it’s common for people to blame themselves for what happened. This is particularly the case for women, who may face greater expectations and pressures. Blaming yourself may make you feel like you had more control than you really did at the time.

Your brain may be responding this way to a trauma in order to provide you with a sense of security. However, self-blame rarely makes you feel better. The truth is, you likely made the best decision you could at the time to survive a difficult situation. If you feel you made choices that put you at risk, you obviously didn’t have the experience yet to fully understand such risk at the time. If that’s the case, ask yourself question #2 again.

After a trauma, many women also wonder if they somehow wanted something bad to happen to them. This is another way to blame yourself. If you wonder about this, then consider why it would still disturb you now? The fact that you worry about it now speaks to the fact that you didn’t intend for it to happen.

Are you assuming a better outcome from a different choice?

It may feel as if we’d just made different choices, then everything would be different now. That may be true, but not necessarily in the way you think. We’re usually filling in the blanks on the “if onlys.” You might think, “If only I had left that relationship earlier, I’d be happier now.” In actuality, you don’t know what would have happened if you had made a different choice.

You could have ended up in a string of unhealthy, dead-end relationships that left you in even worse shape. Or, maybe the one who got away or the guy you thought would be your Prince Charming, later turned out to be a womanizer and a creep. The fact of the matter is, you may not have been as happy in the alternative reality as you think.

Moreover, while you may have stayed in that bad relationship longer than you had planned, you likely followed your instincts at the time. You made the right decision to leave when you found the necessary resolve and best opportunity to do so.  

Are there things you learned because of what you experienced?

It would be nice to move through life making all the right choices and avoiding hardship altogether—but that’s not how life works. Especially by midlife, most of us understand that the moments we once wished away often shaped us in meaningful ways. Difficult experiences can lead to unexpected growth, new opportunities, or at the very least, the realization that we are more resilient than we imagined and capable of turning even hard chapters into something worthwhile.

Are there things you like about yourself, or your life, that you wouldn’t have if your past had been different? Have you ever used what you’ve been through to better understand and empathize with others? Are you wiser and more enlightened now as a result of your past experiences? If so, these are the ways that past events—no matter how regrettable you may think they are—have actually shaped the positive things in your life and worked together for your good.

Find Support

Sometimes, especially in midlife, looking back isn’t about getting stuck—it’s about finally making sense of things. This season of life has a way of inviting reflection, and if you let it, that reflection can bring a sense of peace you may not have had before. Questioning the harsh assumptions you’ve carried about yourself or your decisions can be surprisingly freeing.

But if you still feel tethered to the past, it may be a sign that you don’t have to sort through it alone. A trusted friend can offer perspective without the weight of your history, and a skilled therapist can help you unpack moments that never quite got resolved.

The bottom line: be gentler with yourself. Midlife isn’t just a time of reckoning, it’s also a time of release. You are allowed to reinterpret your story, to soften your judgments, and to move forward with more compassion. Healing doesn’t erase the past, but it can change your relationship to it and make more room to enjoy the life you’re living now.

Jennie Lannette, LCSW, is a licensed therapist and professional mental health writer. She specializes in treating trauma, PTSD, and relationship struggles. Multiple sites have featured her writing, including Medium and Psychology Today.