The Art of Loving Yourself (and Laughing Along the Way)

Discovering joy and self-compassion in life’s second (or third, or fourth) act

Let’s face it—starting over late in life can feel like showing up to a party where you’re not sure if you’re on the guest list. There’s anxiety, doubt, and a nagging suspicion that everyone else somehow has it all figured out. (Spoiler alert: they don’t.) But here’s the secret sauce to a successful reboot: loving yourself. No, not the fluffy, greeting-card version of self-love—this is about embracing your quirks, your wisdom, and your wonderfully imperfect self with gusto. So grab your favorite mug of coffee or a glass of wine—and let’s dive into this journey of reinvention, one hilarious and heartfelt step at a time.

Let Go of the ‘Shoulds’

If you’re starting over, you’ve probably heard a lot of “shoulds” buzzing in your ear. You *should* have done this 20 years ago. You *should* be more successful, thinner, or be the perfect wife or mother. But here’s the thing: “should” is like wearing someone else’s shoes—they pinch, they hurt, and they’re definitely not your style.

Starting over late in life means you get to chuck the societal playbook into the nearest metaphorical trash can. You’re in charge now, and the only “should” that matters is this: you *should* love the person you are today. If a thought doesn’t spark joy, toss it.

Celebrate Your Inner Phoenix

You know what’s cooler than someone who never failed? Someone who dusts themselves off, learns a thing or two, and rises like a fabulous phoenix from the ashes. You’re that phoenix. And guess what? Those ashes? They’re proof you lived, you tried, and you grew.

Embrace your story—warts and all. Those bad relationship that fizzled, the first, second or third marriages or just that bad haircut in 1997? They’re all threads in the rich tapestry of you. Love yourself not despite these moments but *because of them*. They’ve built your resilience, humor, and wisdom. Plus, they make for great conversation starters at dinner parties.

Laugh at Yourself

If you’re taking yourself too seriously, you’re missing the point. Life is a comedy, and you’re the star of the show. So, yes, you might start over and trip a few times. You may even embarrass yourself to the point of laughing at your own self and peeing your pants as I have while dancing in the middle of a floor thinking that I was great and then seeing myself on video and I really look like a robot. Or you join a book club and realize halfway through the meeting that you read the wrong book. Laugh at it. Every misstep is an opportunity to grow—and to gather hilarious anecdotes for your memoir.

Loving yourself means embracing your imperfections and letting go of the ridiculous notion that you need to be flawless. Spoiler: flawless people are boring anyway. And I am far from a boring person, nor do I want to be.

Redefine Success

When you’re starting over late in life, it’s tempting to compare yourself to people who seem light-years ahead. But here’s a radical idea: redefine success on your own terms. Maybe success for you is finally learning how to cook that perfcet meal that you love to order when your in your favorite restaurant. Or perhaps it’s spending more time with loved ones, traveling to that tiny village in Italy you’ve always dreamed of, or simply waking up every morning feeling grateful for another chance.

Success doesn’t have to be loud or flashy. It can be quiet, personal, and deeply meaningful. Love yourself enough to know that your version of success is valid—and worth celebrating.

Surround Yourself with Cheerleaders

Starting over late in life can be lonely, but it doesn’t have to be that way. Seek out people who uplift you, speak kindness into your soul, and laugh with you until your stomach hurts. Whether it’s reconnecting with old friends, finding a supportive online community, or waving at that friendly neighbor who always smiles at you, surround yourself with positivity. My new support system became some of my oldest friends. But now, we no longer rearrange our schedules for everyone else. We make time for each other to uplift one another, listen to each other’s good, bad, and ugly, and have those ‘oh my goodness’ laughs that leave us in stitches; it’s a great therapy. That’s the kind of cheerleader you need.  

And while you’re at it, be your own cheerleader. Give yourself pep talks in the mirror, write affirmations on sticky notes, and high-five yourself for trying something new. You’re doing great, even if it doesn’t feel like it yet.

Find Joy in the Process

When starting over, it’s easy to focus on the destination: landing the dream job, meeting the right person, or accomplishing that big goal. But don’t forget to savor the journey. Finding joy in the process—whether it’s stumbling through a yoga class or grinning at your first awkward attempt at karaoke—is the real reward.

Loving yourself means recognizing that life doesn’t have to be perfect to be beautiful. There’s magic in the mess, humor in the hiccups, and grace in the growth.

Never Stop Being Curious

Starting over late in life is like opening a blank notebook—the possibilities are endless. What will you fill it with? Curiosity is your best friend here. Learn new skills, explore new hobbies, or dive into subjects you’ve always been fascinated by. Taking small, curious steps can lead to big, exciting changes.

Curiosity also invites self-discovery. As you venture into new territory, you might uncover parts of yourself you never knew existed. And isn’t that something worth loving?

You’ve Got This

Starting over late in life isn’t about erasing your past—it’s about building on its foundation with love, courage, and a splash of humor. It’s about looking in the mirror and saying, “I’m proud of you,” even when the road feels bumpy. Most importantly, it’s about realizing that you’re never too old to grow, to laugh, or to surprise yourself.

So go ahead—love yourself fiercely, embrace the messiness, and give yourself permission to shine. Life’s encore is waiting for, and it’s bound to be spectacular. After all, the best stories often come from the chapters we least expect.