Your Guilt Isn’t a Personal Failure. It’s a System Problem.
Why women are trained to feel “never enough”—and tools to replace self-criticism with healthier motivation and care.
The Big Idea: Women are taught to feel guilty—not because they’re doing something wrong, but because they’re trying to meet impossible expectations. This constant guilt isn’t a personal flaw or a motivation problem; it’s a learned response to cultural rules that demand caretaking, perfection, and balance without limits.
Why it matters: Chronic guilt quietly erodes confidence, joy, and agency. It turns self-care into selfishness, boundaries into failures, and rest into something we have to earn. When guilt becomes the background noise of daily life, women end up overfunctioning, under-valuing themselves, and blaming their own character for pressures that were never reasonable to begin with.
Try this today: Interrupt the guilt equation. The next time guilt shows up, pause and ask two questions: What expectation am I reacting to? and Is it actually fair or realistic? Treat the guilty thought as a rough draft—not a verdict. Even naming an expectation as unreasonable creates space for self-compassion and a healthier kind of motivation.
These ideas come from the new book Guilt Free: Reclaiming Your Life from Unreasonable Expectations by psychiatrist Jennifer Reid, MD. Below, she shares five insights on how women can lower guilt—for themselves and for the generations that follow.
1. Guilt: the good, the bad, and the ugly.
Guilt, in certain circumstances, can be a helpful emotion. For centuries, humans have used guilt to help them connect, collaborate, and build community because the ability to feel guilty when we’ve harmed someone expresses to them that we care enough to feel badly about what has happened. It also motivates us to try to make a repair.
Guilt begins to lose its benefit, though, when we are victims of manipulative guilt, whether from our families, our social networks, or in our cultural experiences. “Gosh, I wish you were able to visit us more often, but I guess you’re really busy with your big, important job.” Manipulative guilt can feel pretty terrible.
The most toxic guilt, however, is the type of guilt so many women feel almost constantly. This generalized, self-critical guilt leads to thoughts like, “Why can’t I do anything right?” and “Why don’t I ever feel like I’m doing enough?” Rather than responding to a particular harm we’ve committed, we’re feeling guilty for falling short on several sky-high, unreasonable expectations. Importantly, this is not because we are getting something wrong. This is something women have been socialized to experience, often from a very young age, by the people who care for us and the culture during our lives. We are taught to feel guilty, and we are excellent students.
2. The Four Furies of expectations.
Our guilt triggers are incredibly diverse, involving our roles as friends, sisters, daughters, mothers, romantic partners, and employees. But the foundation of all this guilt is based on just two key factors: our expectations and our perceived reality. This is the Guilt Equation, which tells us that our guilt increases when what we believe we should be doing (our expectation) doesn’t match what we’re able to accomplish (our reality). If, for example, we believe a good mother would never forget to pack a bagged lunch on a field trip day, and it slips our mind, here comes the intense guilt.
The often unreasonably high expectations women face tend to fall into four main categories, which I call the Four Furies:
We are expected to be constant caretakers, making sure everyone in our lives has everything they need, even if this means (and it often does) that we put ourselves last.
We must be hyper-accountable, especially for other people’s thoughts and feelings, even though we don’t have any actual control over these: “Mom seems sad. If I were a good daughter, I would be able to say the right thing to cheer her up.”
We are expected to strive for perfection in all things, but especially in our bodies, our minds, and our self-control.
We should be able to have it all, balancing each of our responsibilities effortlessly, even when we feel totally overwhelmed.
This week, Book of the Day is brought to you by Marked by Time: How Social Change Has Transformed Crime and the Life Trajectories of Young Americans, by Robert J. Sampson. The era into which a child is born shapes their future as profoundly as race, upbringing, or neighborhood. To rethink progress, inequality, and policy, we must first acknowledge how time itself leaves a transformative mark on individual lives. Pick up your copy today.
3. Guilty can be sneaky.
Before beginning the process of lowering this guilt, it’s important to recognize another fundamental truth: guilt may be serving us in a variety of ways. We may believe we need this guilt because it provides us with something we really want—motivation. After all, if we don’t feel guilty for skipping a day at the gym or berating ourselves for choosing to sleep in a little instead of getting up with our alarm, then doesn’t this mean we will simply give up on ourselves?
Guilt can also become a protective stand-in for emotions we don’t feel safe feeling, much less expressing, such as anger or frustration. We tell ourselves, “I shouldn’t be so upset that my partner didn’t do what I asked. He’s been really stressed at work, and I should be more understanding.”
These “benefits” of guilt, however, are costly because they force us to believe we are getting something wrong, relying on harmful self-criticism to push us toward a goal. Or we repeatedly shift these difficult thoughts and feelings inward where they continue to make us miserable, with no relief in sight. Instead of guilt, we can learn to tap into healthier and more beneficial strategies, such as using self-compassion to enhance motivation and allowing ourselves to experience the full range of natural human emotions. We can also focus our all-important attention on the ways we are already showing up, and the many things we are doing well.
“Guilt can also become a protective stand-in for emotions we don’t feel safe feeling, much less expressing, such as anger or frustration.”
In addition, although we can’t control the thoughts and feelings of people in our lives, we can shape our interactions with them through crucial communication strategies, including learning to accept disappointment in ourselves and others, being clear and consistent with our boundaries, and practicing the powerful art of delegation, even when we’re met with an eye roll or other clear expressions of frustration.
4. We can SPEAK up for less guilt.
To learn concrete steps for lowering guilt, I’d like to introduce SPEAK:
Showing Up
Paying Attention
Examining the Evidence
Taking Action
Keep Going
By showing up, you are telling yourself that you are important enough to warrant time, attention and care, which is no small thing. Paying attention involves becoming a curious, non-judgmental observer of your thoughts and feelings throughout the day, which later allows you to examine the evidence for helpful clues about your own unique guilt triggers.
As you gain these crucial insights, you can begin to take action. This is not a one-size-fits-all approach but instead, it allows you to use the strategies you find most helpful. You could challenge unreasonable expectations by learning to limit unhealthy comparisons, especially with strangers on social media. You can rewrite unfair childhood scripts such as being labeled “the girl who took care of everybody,” by learning about cognitive restructuring, which involves treating your initial guilty or self-critical thoughts as rough drafts, rather than the final product. You can strengthen your sense of self-efficacy by adopting a growth mindset and using tools from positive psychology to reject the idea that you must be perfect to be loved. Finally, and most importantly, you can vow to just keep at it, every single day.
This edition of Book of the Day is sponsored by Shopify. Launch your business for just $1/month. Start selling today at shopify.com/nbi.
5. Lowering guilt for ourselves and future generations.
We have been socialized to feel guilty, repeatedly reminded that we should be striving for unreachable levels of caretaking, accountability, perfection, and life balance. This has not occurred on an individual level, however, but rather as a delayed shift of the expectations women continue to face, even as we’ve fought for and achieved more opportunities to create the families, careers, and lives we most desire.
“This can be our legacy: living our best lives with far less guilt.”
But this also represents an opportunity for massive change. Much has been written about intergenerational transmission of trauma, a powerful influence on future populations down to the level of their gene expression. What this suggests is the considerable potential for women of this time—through our refusal to continue living with constant guilt, unfair expectations, and overlooked contributions—to create a cascade of agency and empowerment that affects generations of women to come. This can be our legacy: living our best lives with far less guilt.
 | A guest post by
|