How Regret Is Costing Your Health: How to Break the “Should Have” Loop
Regret is the heavy echo of decisions we wish we'd made differently. Those continuous “what ifs” and “if onlys” that loop in the mind and weigh heavy in your the chest. For women over 40, regret often accumulates like clutter: career choices or education not pursued, relationships tolerated too long, health and self-care deprioritized, dreams set aside for the sake of everyone else.
Left unchecked, regret does more than sting emotionally, it actively derails health and wellness.
Regret doesn’t have to be a life sentence. Recognizing regret, reclaiming those lessons learned, and redirecting that energy into clear boundaries, simpler choices, and small, fierce acts of self-trust transforms regret from a trap into a teacher. Each intentional choice chips away at regret and rewrites the story from “I should have” to “I will now.”
For women over 40, that transformation is the gateway to a simpler, stronger life from burnout and further regret.
Let’s talk about how we break the loop and take your health back.
The Familiar Regret Spiral
You know the spiral I’m talking about. The one where you're replaying every year you spent shrinking yourself to fit someone else's comfort, every promotion you didn't ask for because you were too busy managing everyone's feelings but your own. That regret feels like sabotage. It isn't. It's your nervous system finally sending an accurate report.
Regret doesn't mean you failed. It means you're finally awake enough to see the deal you signed without reading the fine print. The invisible social contract where you agreed to be endlessly accommodating, endlessly available, endlessly fine, in exchange for basically nothing in return. That grief you're calling "wasted time" is actually grief for the version of you who didn't know she had other options.
The wellness industry wants you to gratitude-journal your regrets into submission, slap a "that’s what women do” sticker on decades of self-erasure and call it healed. That's not healing.
Regret can sabotage your wellbeing when you let it stay unprocessed as hurt and anger. Left unchecked, regret curdles into resentment which is a form of fermented anger from things left undone and unsaid.
You don't need to forgive the past to move past it. You need to get honest about it by naming exactly what you’re resentful about and who benefitted from your silence. Once you can name it, you can finally decide to do something different rather than continue to carry the regret.
What Chronic Regret Does to Your Body
I’m not going to sugar coat this. When regret keeps you in a state of ongoing emotional distress, your adrenal glands keep releasing cortisol, and chronic exposure to stress hormones can suppress immunity over time. You may get sick more often, heal more slowly, and feel run-down even when nothing else is visibly wrong.[1]
Your immune system can be slowly reduced by the story you keep telling yourself about your past.
Research confirmed that women experiencing intense life regrets experience significantly higher volumes of cortisol, with a steeper spike first thing in the morning, and reported acute physical symptoms as a result.² Your body, brilliant and loyal as it is, cannot distinguish between a real threat and a memory you keep replaying. Every time you revisit a regret, your system floods with cortisol and adrenaline as though the threat is happening right now.[1]
Chronic emotional stress also elevates blood pressure and drives up inflammation markers in your bloodstream and these aren't just temporary spikes. When regret becomes a daily companion, your heart and blood vessels experience cumulative strain that builds quietly over time.[1]
Losing sleep? Regret-based overthinking intensifies at night when distractions are reduced and your mind has more freedom to wander which creates fragment rest and prevents the deep, restorative sleep your body needs to recover.[1]
And then there's depression. Research consistently finds that life regret is associated with lower life satisfaction and increased depressive symptoms.[3] Mount Sinai researchers found that the way the brain processes regret may be directly linked to an individual's ability to cope with stress, and that this processing is altered in psychiatric conditions like depression.⁴
Regret and depression do not politely take turns, they pile on.
Rates of depression and anxiety are notably higher in midlife, especially among women.[5] You are not imagining the feeling that life is much heavier. You're carrying a physiological burden that the wellness industry tells you to treat with green tea and a gratitude journal. No wonder you never feel better.
The Perimenopause Amplifier
If you suspect perimenopause or menopause is amplifying everything you're feeling right now, you're probably right. This article can help you learn more, Your Doctor Calls It Stress. Your Body Calls It Perimenopause.
The Two Types of Regret (And Why the Difference Matters)
Not all regret is the same beast and treating it as such is exactly why most advice about regret is useless.
Group One: The Regrets You Cannot Change
The relationship that ended before you were ready. The parent you lost before you made peace. The years you spent managing everyone else's feelings while yours turned to sediment at the bottom of our dreams.
You survived the best you could with what you knew at that time.
Psychoanalyst Erik Erikson’s final stage of human development is, simply put, about looking back on life and deciding if you feel it was well lived, which is referred to as ego integrity, or full of regrets, which leads to despair. [6] When we see our lives as unproductive, feel guilt about our past, or feel that we did not accomplish our life goals, despair often leads to depression and hopelessness.[7]
But Erikson's theory understood what the self-help industry does not: the goal is not to eliminate regret entirely. We can experience both ego integrity and despair and learn from them without living in eternal bitterness.⁸
You might imagine that reducing regret would create a serene, floaty peace with your past. If only that were possible. What you are aiming for is the weight to lift and this is accomplished by learning to accept your past and understanding that you were doing the best you could as the person you were back then.
In plain language: the path through your regrets is to change how you hold their story.
Group Two: The Regrets That Still Have a Door Open
Some of what keeps you in the regret cycle is not grief, it’s recognition. The career pivot you never took. The creative work you set down in your thirties because someone needed dinner made and forms filled out and logistics coordinated. The places you always meant to go. The degree you haven’t finished. The version of yourself filed away under "maybe someday when the kids are grown".
Someday has an expiration date of right effing now.
If you're ready to figure out what actually matters to you at this stage of your life, The Essential is the category where that work begins. You can learn more here: Essentialism: The Art of Focussing On What Really Matters.
You do not have to fix your entire life by midnight. Resolution starts with a single, sharp boundary. Look at your Group Two list—the regrets where a door is still open. Pick one thing. A class to register for, a boundary to set, a difficult text to send. Do it today. Show your nervous system that the version of you who shrinks is no longer the one running the show.
The Woman on the Other Side of Regret
If you’re in midlife, this is the time the “should-haves” have lost their power because you stopped using them to prosecute yourself. It’s a time to pause, regroup, and think about how you can better meet your own needs in the future.[13]
The woman on the other side of regret isn't living a perfect life,she's just stopped letting the ghost of her past choices run her current nervous system. She has traded the loop for the present.
If this article spoke to you or answered questions, leave me a comment below, I respond to every comment. You might inspire other women who are struggling with their identity.
Melissa
Sources
Reachlink. (2026). What regret does to mental health and how to heal. Reachlink.
Wrosch, C., Miller, G. E., Lupien, S., & Pruessner, J. C. (2007). Regret intensity, diurnal cortisol secretion, and physical health in older individuals. Health Psychology, 26(4), 418–425.
Linden, M., Maercker, A., & Müller-Werdan, U. (2024). The relationship between life regrets and well-being: a systematic review. Frontiers in Psychology, 15, 1515373.
Sweis, B., Durand-de Cuttoli, R., & Russo, S. J. (2022). Brain's sensitivity to different types of regret may impact mood disorders like depression. Science Advances. Mount Sinai Health System.
Wiener, J., Alessi, N., & Stone, D. (2026). Understanding midlife crisis symptoms: Signs and solutions. Fast Psychiatry.
Erikson, E. H. (1982). The life cycle completed. Norton.
McLeod, S. (2025). Erikson's stages of development. Simply Psychology.
Psychology Town. (2025). Embracing integrity vs. despair in later adulthood. Psychology Town.
Tranter, L. J., & Koutstaal, W. (2008). Achieving ego integrity: Personality development in late midlife. Journal of Research in Personality, 42(4), 1004–1019.
Wrosch, C., Bauer, I., & Scheier, M. F. (2005). Regret and quality of life across the adult life span: The influence of disengagement and available future goals. Psychology and Aging, 20(4), 657–670.
Vanden Berghe, W., Vansteenkiste, M., Soenens, B., et al. (2021). The role of ego integrity and despair in older adults' well-being during the COVID-19 crisis. PMC, 7914386.
Social Work Exams. (2024). Erikson's integrity vs despair stage: A complete analysis. Social Work Exams.
Kentucky Counseling Center. (2025). Regrets after midlife crisis: How to make peace with your past. Kentucky Counseling Center.
