13 mistakes most women regret making in their 20s

Your 20s are supposed to be the time to figure it all out—but ask most women in their 30s or 40s, and they’ll tell you it’s also when they made mistakes they wish they could undo.

Your 20s often feel like the decade where everything is supposed to fall into place. Careers begin, relationships deepen, and independence finally feels within reach. But for women, this stage comes with added pressures. Family, society, and even workplaces tend to expect more sacrifices from women, which often leads to decisions they later regret.

The regrets that follow aren’t usually about partying too much or not eating healthier. They’re about the unique expectations women face and the choices they’re pressured into making early on. These mistakes can shape finances, relationships, and health for decades, which is why many women in their 30s and 40s often look back, wishing they had made different choices in their 20s.

Downplaying ambition to seem “likable”

Women in their 20s often soften their career goals or achievements out of fear of intimidating men or colleagues. Women sometimes downplay success in professional settings. Later, many regret how much they shrank themselves, realizing that confidence and ambition wouldn’t have pushed good people away; it would have opened more doors.

Putting relationships before career growth

Women are still more likely than men to pause or slow down their career growth for the sake of relationships. Women have reduced work hours or taken a break for family or partners, according to Science Direct. Many regret supporting someone else’s dreams before building their own, only to realize later how much time they lost catching up in their careers.

Not negotiating salaries or raises

Studies show that only 34% of women negotiate their first salary compared to 46% of men. That gap doesn’t seem huge, but over time, it compounds into hundreds of thousands of dollars in lost revenue. Women in their 20s often accept offers quickly, eager to prove themselves. Still, many regret not pushing for more once they see how men who negotiate earn significantly more doing the same work.

Letting fertility awareness slide

While not every woman wants children, many regret not learning about fertility options sooner. Female fertility begins to decline noticeably around age 30, according to the American College of Obstetricians and Gynecologists. Yet in their 20s, women often put off conversations about egg freezing or reproductive health. Later, some wish they had explored options earlier when choices were wider and costs lower.

Dating men with “potential” instead of stability

It’s common for young women to invest years in men who promise to change but never do. Many women later regret waiting around for partners to “grow up” while putting their own needs aside. This mistake is widespread among women, who are often taught to be patient and nurturing in relationships. But by their 30s, many realize those years could have been spent building a more stable future.

Overcommitting to family responsibilities

Unlike men, women are more likely to take on additional family responsibilities in their 20s—whether it’s caring for younger siblings, contributing financially to the household, or assuming caregiver roles. National estimates suggest that about 60% of unpaid caregivers are women. Many regret how much this slowed their independence, especially when those sacrifices weren’t equally expected from their brothers or male peers.

Worrying too much about body image

The pressure on young women to conform to a certain appearance is intense. By their 20s, many women regret crash dieting, unhealthy workout habits, or overspending on appearance-enhancing products. A 2017 Dove Self-Esteem Project study found that 50% of women have low body confidence. Looking back, women often wish they had adopted healthier routines and prioritized strength and confidence over chasing perfection.

Not speaking up in male-dominated spaces

Women in their 20s often regret not using their voice more in classrooms, meetings, or early jobs. Women sometimes worry about being seen as “bossy” when voicing opinions. This pressure to shrink themselves early in their careers often means missed opportunities for promotions, recognition, and leadership experience that could have set the tone for later success.

Ignoring financial independence

Some women allow their boyfriends or husbands to control their finances, especially in their early twenties. While it may seem practical at the time, many later regret not setting up personal accounts, learning about investing, or building their credit. Data shows that women invest less than men. Regret often sets in later, when achieving financial independence feels harder.

Sacrificing friendships for romance

Romantic relationships often take center stage in a woman’s 20s, but many regret letting female friendships fade. Harvard research suggests that close friendships can enhance happiness and mitigate stress, whereas isolation increases long-term health risks. Women who poured everything into relationships that eventually ended often wish they had invested more energy in friendships that could have provided lasting support and joy.

Staying in toxic jobs out of fear

Women are more likely to tolerate disrespect in workplaces to avoid being labeled “difficult.” Women experience microaggressions at work, yet many stay silent or remain in toxic jobs. In hindsight, they regret not leaving earlier for healthier opportunities, realizing the stress and lack of respect had long-term impacts on both their career growth and well-being.

Not learning self-defense

Unlike men, women often regret not preparing for safety sooner. After experiencing harassment or unsafe situations, many wish they had taken self-defense classes or learned safety strategies in their 20s. This regret is directly tied to the reality of being a woman in a world where safety isn’t guaranteed.

Delaying travel out of safety fears

Traveling solo or with friends can feel intimidating for women in their 20s due to safety concerns. While the fears are real, many women regret letting them hold them back from exploring the world when they had the most freedom. Many women want to take solo trips, but only a few actually do. Many wish they had leaped earlier.

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