What I Wish I Knew in My 20s

The Truth About Your 20s: A Defining Yet Difficult Decade

Contrary to cultural idealizations, Dr. Jay emphasizes that the 20s are neither carefree nor the happiest years for most people. Instead, this period is marked by overwhelming uncertainty across every life domain: jobs, relationships, finances, and self-identity. Every 20-something faces multiple "firsts and worsts"—first jobs and worst jobs, first relationships and worst breakups—making these years emotionally intense and often confusing. Older adults may underestimate this struggle because young people often lack traditional markers of adulthood like owning a home or having children, but what Dr. Jay highlights is that the absence of these milestones creates its own type of anxiety rooted in unpredictability.

A central message Dr. Jay shares is that feeling stuck, overwhelmed, or paralyzed by uncertainty in your 20s is not a failure but a normal sign of growth. She encourages young adults to move beyond mere reassurance—which often only provides temporary relief—and instead to engage actively with their challenges. Starting early to figure out career goals, relationship values, and life plans sets a critical foundation that affects not only the 20s but the decades to follow.

Career and Identity Capital: Building Foundations for the Future

Dr. Jay identifies the first decade of work as pivotal, with long-term earning potential and career trajectory largely shaped by experiences gained in your 20s. However, this is also a period when many encounter underemployment or unemployment; at any given time, about half of 20-somethings are either unemployed or working jobs that don't fully utilize their education or talents. While the marketplace is challenging and disrupted—with unpaid internships becoming the norm rather than an exception—building what Dr. Jay calls "identity capital" is key to long-term success.

Identity capital consists of experiences, skills, relationships, or credentials that add value to your professional and personal identity. It could be a formal degree, a certification, meaningful internships, or even skills gained from seemingly unrelated jobs, provided those experiences contribute to growth and leverage future opportunities. Dr. Jay stresses the importance of being intentional and proactive: taking incremental steps toward a career that fits one's skills and passions, trying different roles without fearing "failure," and approaching jobs as one- or two-year commitments that build toward something bigger. She also highlights the importance of developing life skills like having difficult conversations and networking, which are rarely taught formally but crucial for career advancement.

The Complex Reality of Dating and Relationships in Your 20s

Relationships in your 20s carry immense weight, as the partner you choose often becomes, in effect, your new family. Dr. Jay points out that romantic relationships are probably the biggest contributors to happiness—or unhappiness—in life. However, many young adults postpone dating or avoid commitment because it feels daunting amidst all the other uncertainties of this decade.

She cautions against sliding passively into relationships without intentional decisions, a phenomenon she calls "sliding not deciding," where couples drift into cohabitation, engagement, or marriage without conscious commitment or conversations. Such sliding often leads to dissatisfaction or even divorce later on. Being intentional about relationships means having "29 conversations" — a framework Dr. Jay developed to encourage partners to discuss key issues such as money, kids, religion, parenting styles, and sexual expectations early on, as well as maintaining ongoing dialogue about the health and trajectory of the relationship.

Dr. Jay challenges the popular notion that being single in your 20s is ideal, noting research that shows a large majority of young adults who remain single and avoid commitment feel dissatisfied or lonely. Men, in particular, often experience dips in self-esteem when single into their late 20s. She explains that dating is a skill and a learning process, much like career development, where trial and error help identify what works and what doesn't. This underscores the importance of engaging in dating intentionally rather than passively waiting for "the right person" or fearing rejection.

Perceived Desirability, Social Anxiety, and Building Social Confidence

Another important theme Dr. Jay addresses is the impact of "perceived desirability" on young adults' self-esteem and social confidence. This concept refers to how much a person feels wanted or desired by others, which often shapes how they navigate relationships and social situations. Many young adults base their perceived desirability on past experiences, particularly painful ones from high school or early dating, which can trap them in negative thought patterns and distortions, such as black-and-white or catastrophic thinking.

Social anxiety and social uncertainty are extremely common among people in their 20s, especially as they navigate new social landscapes without the stable networks they had in childhood or adolescence. Dr. Jay distinguishes between normal developmental social uncertainty—which is transient and tied to situational discomfort—and clinical social anxiety, which is more severe and disabling. She advocates for exposure and engagement as the best medicine for social anxiety: by pushing through discomfort and practicing difficult conversations and social interactions, young adults gradually build the skills and confidence needed to thrive socially. Importantly, she stresses the need for ongoing skill development, regardless of whether one uses medication, pointing out that medications alone do not teach coping skills or problem-solving abilities.

Family Planning and Reproduction: Facing Biological Realities with Courage

Dr. Jay candidly discusses the realities of reproduction and family planning in the context of your 20s and early 30s, emphasizing that while societal trends point to delayed parenthood, biological factors, particularly for women, cannot be ignored. Her own experience of a serious conversation with her dissertation advisor at 34 highlights that intelligence and ambition in career do not exempt one from making intentional decisions about family.

She stresses the importance of early education and honest reflection about what one wants from life—whether that includes children or not—and encourages young adults, especially women, to think about having children as a beginning rather than an end. Parenthood often ignites a new level of purpose and ambition. Dr. Jay encourages people not to wait until "the last minute" to start family planning, recognizing that having children is a lifelong commitment that requires you to be present and healthy well beyond the initial birth years.

Hope and Forward Momentum: The Promise Beyond the 20s

Despite the overwhelming challenges of the 20s, Dr. Jay closes on a hopeful note, supported by longevity research and mental health data that consistently show life improves across the 30s, 40s, and beyond. She acknowledges that this decade represents a low point for many in emotional well-being, but it's also where the greatest opportunity for growth exists. She encourages listeners to have the courage to imagine their lives going well as the necessary first step toward meaningful change.

Dr. Jay reminds us that adult development doesn't stop after your 20s—anyone feeling stuck in later decades can still course correct. The intention, courage, and small consistent efforts made in any stage of adulthood can lead to fulfillment and happiness. Her parting advice is a timeless proverb: take care of the minutes, and the years will take care of themselves. By living intentionally today, young adults and those beyond can build a life they love.