It’s a contradictory aspect of being an adult: the point where most millennials believed they had life all mapped out becomes the point where they’re understanding how much wrong turns they have taken throughout the process. And now, with the oldest among this generation entering their 40s, the introspection is flooding in and it’s clear, familiar, and filled with hard-won insight.
From frozen careers to missed travels, these regrets aren’t simply cautionary tales they’re profiles of a generation shaped by the Great Recession, rising cost of living, and hustle culture that valued hustle over wellness. The bright spot? Every regret carries a lesson, and those approaching midlife can still make positive changes. Take a peek at most surprising and most common regrets that older millennials share, and the lessons that will prevent any individual from falling into them.
1. Worrying Excessively About What Others Might Say
Few millennials will admit to remaining in 20s gigs due to complacency, even after development had leveled off. A Reddit user confided that leaving a comfy job ended up netting them close to a 50% increase. Career coaches agree and note that delaying a switch costs years of incremental income and frozen professional growth. So: comfort comes at a cost and in an increasingly fluid job market.
2. Neglecting Health during Childhood
From loss of hearing to recurring back pain, bodily regrets emerged frequently. A number admitted to brushing aside early alerts, thinking that youth was protection. Said one therapist to CNBC Make It, “Health provides a kind of freedom and joy that few appreciate until it’s gone.” Take away: invest in your body today, since the payback accrues in its entirety.
3. Not Prioritizing Self-Worth
Self-acceptance arrived late for others often in the 40s. Opting out of social media and worrying less about how others thought helped others accept themselves at last. Professionals such as Tess Brigham emphasize that worrying less about others’ opinions allows energy to flow toward truly living. A sad result? Allowing that many years go by before discovering that self-worth isn’t selfish self-worth is foundational.
4. Losing Time with Family and Friends
Accounts of missed moments with parents or grandparents were also the most poignant. A millennial described missing out on valuable time with a terminally ill father in favor of job responsibilities an act that still haunts them. Psychology professionals make it clear that connections, and not career sheets, are the foundations of long-term fulfillment. The tip: create space with those closest to you before it’s too late.
5. Not Having Saved Early Enough
Financial mistakes headed the list, and most members wished they had begun retirement savings in the teens or early 20s. Compound interest is a mighty tool, but it only works if you allow it enough time to do its thing. In a Harris Poll, almost 60% of grownups identify failing to save as their largest money blunder. Small, steady savings create security that lasts far beyond short-term spending.
6. Allowing Fear to Halt Great Ambitions
From writing to business ventures, hundreds of dreams were deferred by fear or self-doubt. In author Ossiana Tepfenhart’s words, “Most dreams don’t need a full-time commitment in order to get started.” Regret often stems not from failure, but from never having tried. Solution? Take baby steps, but take them today momentum builds confidence.
7. Ignoring Red Flags in Relationships
Others maintained unhealthy relationships much longer than they should have, ignoring telltale markers of manipulation or abuse. Companionableness kept them bound, even if security or joy was on the line. Relationship coaches recommend that you listen to your friends’ worries and look for patterns early intervention can prevent years of suffering.
8. Missing Out on Life Experiences
Whether it was missing out on road trips with a grandparent or missing out on nights out in their 20s, many regret not seizing moments of adventure. In the mind of one millennial, “Work to live, don’t live to work.” With leisure time at all-time lows among those in the 35–44 age bracket, according to the American Time Use Survey, making time for joy is more important than ever.
9. Delaying Homeownership
some regretted missing out on affordable housing in the early days, only to encounter today’s high rates. Though property ownership isn’t important to all, professionals such as Jung Hyun Choi caution that years of renting translate into more unpredictability in retirement. Creative financing and timing make the difference between regret and endurance possible for those who intend to buy.
Millennials approaching 40 are discovering that regret isn’t just about missed opportunities it’s about missed priorities. The common thread in these stories is a call to act sooner: to value health, relationships, and personal goals before they’re sidelined by fear or busyness. For those still climbing toward midlife, these lessons are more than hindsight they’re a roadmap to a future with fewer “should haves” and more “glad I dids.”
