Life has a habit of sneaking up on you. One day, you’re 25 with a bright, exciting future ahead of you, and the next, bam, you’re 50, staring down the barrel of middle age, wondering where all that time went. And let’s get real—hindsight is brutal. When you hit the big Five-O, the regrets start to wrack up. Some might surprise you, and some will sting but don’t worry; there’s still time to get your act together. Let’s talk about the things you start regretting when you hit this milestone and what to do about them.
1. Not Telling People to Get Lost
As you get older, you take less BS and may begin regretting all the times you didn’t stand up for yourself and the time and energy you wasted on the wrong people. Whether it was that one toxic boss, manipulative friend, or a family member who always rubbed you the wrong way, not cutting ties sooner because you were afraid of hurting someone’s feelings or making a scene can haunt you. The wiser, more confident 50-year-old may wish you’d been more honest with yourself and others and more careful of who you let into your inner circle. Start speaking your truth now—it might be uncomfortable, but time is precious, and you deserve to be around people who uplift you.
2. Not Quitting the Job You Hated
By 50, you’ve probably had many jobs you loved and definitely one or two that you hated. Or if you spent your entire career in a job you loathed, you will regret playing it safe for too long. You might also beat yourself up that you didn’t take that big promotion you didn’t take, start that side hustle, or move to the other side of the world when you had a chance. The good news? It’s not too late to shake things up. Pivot, take that risk or reignite that passion project you shelved. Life doesn’t stop at 50, so neither should your ambition.
3. Not Taking a Solo Trip
Now that you’re comfortable in your own skin and prefer your own company, you could kick yourself for not taking more solo trips. It might have felt scary and lonely at the time, but travel enriches your life, and you grow by pushing yourself out of your comfort zone. There’s something transformative about traveling alone—the freedom, the self-discovery, the adventure on your own terms. Plan that solo trip now, even if it’s just a weekend away. It’s never too late to fall in love with alone time or a new country.
4. Not Pursuing That “Crazy” Dream
By the time you hit 50, you’ll regret not going after that “crazy” dream—the novel you never wrote, the band you didn’t start, the screenplay you thought was too unrealistic. Sure, at 20-something, it did seem crazy, and life sort of just…got in the way. But at 50, you realize the only crazy thing was thinking you didn’t have time or couldn’t make your dream a reality. It’s not too late to make it happen. Dust off that old dream, give it life and remember that passion is ageless.
5. Not Investing in the People That Matter
When you turn 50, it becomes crystal clear who your real friends are. You’re at an age where you can’t hold up the facade anymore, and you may regret not putting more effort into the friendships that mattered and wasting time on the ones that didn’t. Don’t let people guess how you feel—say it. Tell your partner, friends, and family how much they mean to you. Expressing love is never a waste and will come back to you in spades.
6. Not Learning to Love Your Body Earlier
You realize your body is a temple that has carried you faithfully throughout your life as you get older. At 50, you will wonder what on earth you were thinking, hating on your body and obsessing over your flaws. Especially when your joints start to ache, and you no longer have the energy you used to. With age comes wisdom, and you realize life is for living, and wasting time worrying about your appearance is futile. You can’t change the past, but you can show your body all the love it needs now. Get fit, eat well, and thank it for its five decades of service.
7. Not Setting Stronger Boundaries
Once you learn to set boundaries, you’ll wish you did it earlier. If you spent your life people-pleasing or letting others take advantage of your compassion and kindness, it can eat you up. Start saying no and prioritizing yourself. Whether it’s declining extra work, cutting off toxic relationships, or even just carving out more “you time,” boundaries are essential, as you’ve learned the hard way. It’s never too late to draw a line in the sand. Teach people how to treat you by respecting your own limits first and letting them know what’s non-negotiable.
8. Not Apologizing When You Should Have
We all mess up, and during the messy business of life, it can hurt others, strain friendships, and even fall out with people. Your egos can get in the way when you’re young. When you turn 50, you tend to turn inward and look backward and may regret not extending an olive branch or apologizing to someone you cared about. It’s not too late to reach out, apologize, and heal any rifts or wounds. Make the choice to release those old grudges now; they are only robbing you of energy and a relationship that may have been meaningful. People change, so have you, and now you’re starting to see everything in a new light.
9. Not Spending More Time Alone
When you’re younger, you live for your friends and socializing, and you often run yourself ragged trying to do everything and be there for everyone. In your 50s, you’ll realize that solitude is a gift, and you need to honor your need for downtime. You may regret not carving out more alone time for self-reflection, self-care, and refuel. If you’re constantly surrounded by noise and people or tend to overgive at the risk of your sanity, you miss the chance to tune into your own needs and listen to your body. Schedule more solo dates—go to dinner, see a movie, or even take that solo holiday. Or just relax and enjoy being by yourself.
10. Not Being More Adventurous in the Bedroom
Yes, we’re going there. By 50, you really get in touch with your body and your sexuality and may regret not being more adventurous with your partner or having more partners, especially if you married early. Perhaps you regret letting shame, insecurity, or monotony hold you back from exploring intimacy. Sexuality doesn’t have an expiration date, so get out of your comfort zone now—start with self-pleasure, and you might be pleasantly surprised.
11. Not Taking Better Care of Your Mental Health
Mental health might have been a taboo subject when you were younger, or maybe you were too focused on surviving to check in on it. When you turn 50, the effects of stress, anxiety, or untreated depression you’ve been numbing can rear their ugly heads, and you could even feel a mid-life crisis of sorts. This could be the manifestation of years of pent-up stress or repressed trauma you never worked through. Now that mental health is out of the closet, you can come out, too. See a therapist, do some soul exploration through meditation and mindfulness, and take up yoga. Your mental health is as important as your physical health and is an investment in your future happiness.
12. Not Investing in Your Skin
It’s not just your mindset that changes when you’re 50; your fresh, radiant, plumped skin will now be showing signs of fine lines, wrinkles, and sagging. Youth is wasted on the youth, and if you didn’t prioritize your skincare routine or wear sunscreen every day, you probably regret it now. Aging is part of life, but there are ways to rejuvenate your complexion and give you a healthy glow. Invest in antioxidant-rich skincare products, look to hydrating firming ingredients like peptides, hyaluronic acid, vitamin C, and niacinamide, exfoliate 2-3 times a week, and indulge your complexion in professional facial treatments and even age-dying procedures like botox—everyone’s doing it.
13. Staying Married for the Kids
If you stayed married for your children, even when you and your partner were miserable, you know firsthand that sacrifice took a major toll on your mental health and your happiness. Now that you’re 50, you could deeply regret this decision, especially if you didn’t feel like you were living life authentically or ruined the chance to meet your true soulmate. Don’t sabotage your happiness now by regretting the decisions you made in the past. Divorce happens every day, and the second act can be amazing.
14. Not Dressing the Way You Wanted
Life’s too short to conform. Growing up, we tend to wear what everyone else is to fit in. We don’t want to stand out in the crowd, which often means throwing our personal style under the bus. If you fell into this trap, it’s time to overhaul your wardrobe. Whether it’s a funky hat, a great vest, or a whole new fashion aesthetic, your 50s and beyond are about being free to be fabulous.