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20 Brutally Honest Lessons I’d Give Any Millennial About to Hit 40

Homepage,Self Love
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April 17, 2025
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Jordan OMalley

So you’re staring down the big 4-0. You’ve survived dial-up, downloaded music one track at a time, and watched social media turn from novelty to necessity. But here’s what no one tells you: life at 40 hits differently. Before you get there, these honest truths could save you time, money, and a few gray hairs.

Your Body Isn’t on Auto-Pilot Anymore

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That bounce-back energy from your 20s is not coming to your rescue anymore. Aches show up uninvited, and skipping sleep hits harder than a hangover ever did. Regular movement, basic strength training, and real sleep are now non-negotiable if you want to feel decent by Thursday.

Stop Waiting for the ‘Right Time’

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There’s no magic window where life gets easier or less chaotic. If you’re holding off on taking that trip, starting a business, or learning something new, start now. Perfect timing doesn’t exist—and by 40, procrastination disguises itself as caution. Just take the leap and figure things out on the way down.

Friendships Require Maintenance

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You will soon realize that friendships don’t survive on group chats alone. People get busy, tired, or just distracted. If you want to keep your people, you have to show up—physically, emotionally, or even with a dumb meme. Good friends become harder to make, and the old ones won’t stick around without effort.

You Can’t Ignore Money Anymore

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If you’ve been avoiding your retirement fund, drowning in lifestyle creep, or relying on “future you” to save the day—it’s time to stop. Compound interest is still your friend, but it’s not as forgiving. Get serious about budgeting, saving, and investing before your margin for error gets razor-thin.

Mental Health Deserves a Seat at the Table

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You don’t have to be falling apart to need support. Stress, burnout, and emotional fatigue are real, especially in a world that expects you to do it all. Therapy, journaling, or even just naming your feelings can go further than toughing it out.

Careers Aren’t Straight Lines

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That five-year plan you made in your 20s? It’s okay if it got shredded. Many people shift careers—or rethink what success even looks like at different points in their lives. Don’t let fear of starting over keep you stuck. Growth may look like a failure right before it starts to make sense.

Time Feels Like It’s Speeding Up

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A week used to feel like a week. Now, it blurs between work, family, and a calendar full of “shoulds.” Use it wisely and make room for things that are meaningful. You won’t recall the laundry, but you’ll remember the Sunday coffee with someone who made you laugh.

You Outgrow People—and That’s Okay

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Not every friendship is built to last decades. You’ll change, they’ll change, and sometimes the connection doesn’t survive. That doesn’t make it a failure. Letting go of expired relationships frees up space for new ones that reflect who you are now.

You Are Not What You Own

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Remember that nothing is going to fix your insecurities. Not the bigger house, the flashier car, or the upgraded gadgets. If you’re chasing purchases to impress people who don’t even know your middle name, stop. True confidence is knowing your worth without a price tag.

You Can’t Multitask Your Way to Happiness

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Being busy is a distraction instead of a badge of honor. If every day feels like a sprint to bedtime, you need to rebrand your life. Doing fewer things with more presence leads to better outcomes—and a lot less regret.

Parenting Is Both Beautiful and Brutal

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If you’re raising kids, you’ve likely discovered this already. It’s equal parts magic and mayhem. Don’t let Instagram fool you—everyone’s winging it. Ask for help. Prioritize connection over perfection. And take care of yourself, too, because burnt-out parents aren’t doing anyone any favors, least of all themselves.

Health Screenings Are Your New Sidekick

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Colonoscopy, skin checks, blood pressure readings, all of these are boring. But they are important for your well-being. Preventative health care is smarter (and often cheaper) than waiting for things to go wrong. If you're afraid of doctors, understand that catching something early can mean the difference between a quick fix and a life overhaul.

Regret Loves the Risks You Didn’t Take

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It’s rarely the mistakes that haunt people in their 40s—it’s the silence. The thing you didn’t say, the job you didn’t take, the person you let walk away will all come back to you. Be smart, yes, but don’t let fear steal your chances. Safe isn’t always satisfying, and comfort zones rarely lead to good stories.

You Don’t Need Everyone to Like You

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At this point, people-pleasing starts to cost too much. Not everyone will understand you, agree with you, or root for you. That’s okay. Respect and kindness matter. But other people’s approval is optional. Focus on being someone you like and admire—then let the rest shake out however it does.

Comparison Is a Never-Ending Trap

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There will always be someone doing better—at least from the outside. Social media is a highlight reel, which means you cannot treat it like your life story. If scrolling leaves you anxious or discouraged, take a step back. Your timeline is your own. And your progress isn’t late just because someone else seems ahead.

Peace Outweighs Ambition Sometimes

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You were told to hustle, climb, and chase goals. But what if rest is also a goal? What if the real prize isn’t a title but peace of mind? It’s okay to scale back, pivot, or walk away from “success” that costs too much of your soul.

Apologies Don’t Fix Everything, But They Help

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You’re going to mess up. We all do. Saying “I’m sorry” won’t undo everything, but it shows growth. Keep in mind that avoiding accountability is a fast track to bitter endings. Repair what you can, even if it’s awkward.

Learn to Enjoy Your Own Company

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If silence makes you squirm, it's worth exploring why. Life gets loud—work, kids, relationships, obligations. Learning how to be content alone is a gift. It lets you make better choices, not desperate ones.

Your Parents Are Aging Faster Than You Realize

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If you're lucky enough to still have your parents around, call them, visit them, and listen. The dynamic shifts, and they may need you more than they let on. This chapter is hard to prepare for, but being present matters more than knowing what to say.

No One’s Coming to Rescue You

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You are responsible for your happiness, your peace, and your choices. Waiting for someone else to fix your life is a setup for disappointment. Take the wheel. You don’t need to have all the answers—you just need to start driving.

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