How to Design a Life You Won’t Regret in 10 Years

You ever catch yourself staring at a photo from a decade ago and wonder, “What the heck have I been doing with my life?” Yeah, me too. It’s wild how time slips by, and suddenly you realize that the life you’re living might not be the one you wanted. Designing a life you won’t regret in 10 years isn’t some pie-in-the-sky dream. It’s about choices, clarity, and courage rolled into one messy, beautiful experiment called life.

Here’s the thing: no one sits you down and hands you a blueprint for a regret-proof life. You have to build that with your own hands, sometimes with shaky tools, sometimes with a hammer that’s more like a feather. It’s about being brutally honest with yourself, facing the parts you don’t want to look at, and then daring to make changes that feel intimidating. But the payoff? Freedom. Peace. The kind of joy that bubbles up because your life is actually yours.

Stop Waiting for “The Right Time”

Let’s get something out of the way—waiting for the perfect moment is a trap. That mythical “right time” never appears with a fanfare and a marching band. It’s a lie we tell ourselves to avoid rocking the boat. Ten years from now, you could be looking back wishing you’d started that passion project, had that honest conversation, or taken that leap. Or you could be proud that you didn’t wait.

Start by asking yourself the hard questions. What’s gnawing at you? What would you regret not doing? It’s uncomfortable, but that discomfort is a sign you’re onto something real. The first step toward a life you won’t regret is to quit the mental gymnastics that keep you stuck.

Define What “Success” Means to You

Spoiler alert: success isn’t a universal constant. If your definition of success is climbing the corporate ladder, that’s fine. But if you want to spend your days painting, traveling, or raising tiny humans who think you’re a superhero, that’s equally valid. Too often we buy into society’s version of success without checking if it aligns with our soul.

Spend time figuring out what really lights you up. Does it involve money, yes, but what else? Freedom? Creativity? Connection? What fills you up instead of draining you? When you nail down your personal definition of success, everything else becomes clearer. Choices become easier because you have a compass pointing north.

Cut the Crap That Doesn’t Serve You

Here’s a truth bomb: your time and energy are finite. You only get so many hours on this spinning rock. So why waste them on things that don’t matter? Toxic relationships, dead-end jobs, habits that numb you out—these are the things that quietly build regret over the years.

I’m not saying you have to cut everyone out who’s ever annoyed you, but you do need to be ruthless about what you allow in your mental and emotional space. It’s like cleaning out a closet. If it doesn’t fit or make you feel good, toss it. The more space you create, the more room there is for what truly matters.

Build Habits That Anchor You

You know those people who seem to have it together? They’ve probably got habits—tiny rituals that keep their lives steady when chaos hits. Building a life you won’t regret isn’t about giant leaps every day, but about consistent steps that add up.

Maybe it’s journaling every morning, going for a walk, or setting an intention before you dive into work. Whatever it is, make it non-negotiable. These habits become the scaffolding of your life, holding you up when the winds blow hard.

Learn to Say No Without Guilt

If you’re anything like me, saying no feels like a personal failure at times. But here’s the secret: every no is a yes to something else. Saying no to commitments that drain you means saying yes to your energy, your peace, your dreams.

This isn’t about being a hermit or completely self-absorbed. It’s about boundaries. The kind of boundaries that keep you sane and protect your time like a dragon guards its treasure. Saying no is an act of self-respect.

Invest in Experiences, Not Just Things

Memory is a sneaky thing. When you look back, it’s not the stuff you owned that makes you smile; it’s the moments you lived fully. Trips, deep conversations, learning new skills, laughing until your face hurts—these are the treasures that accumulate into a life well-lived.

Don’t get me wrong, stuff isn’t the enemy. But if your choices are between buying the latest gadget or investing in a class that excites you, the class usually wins in the regret department. Experiences shape you from the inside out; things just collect dust.

Get Comfortable With Being Uncomfortable

Growth isn’t cozy. It’s awkward, painful, and often downright scary. But it’s also the only way to build a life you won’t regret. When you step out of your comfort zone, you open doors you didn’t even know existed.

Think about people you admire. Chances are, they took risks, failed, got back up, and kept going. They embraced the suck because they understood that comfort zones are beautiful prisons. Break out.

Keep Your Eyes on the Long Game, But Play in the Present

It’s easy to get caught up in future regrets and spiral into anxiety. But life is happening now, right here, right now. Designing a life you won’t regret in 10 years means making choices today that align with your vision, but also savoring the small wins.

Balance planning with presence. Celebrate the moments that feel like victory—finishing a project, having a deep chat with a friend, savoring a cup of coffee without scrolling your phone. The future you is built on these tiny bricks of now.

Surround Yourself With People Who Challenge and Support You

Your tribe matters. If your circle is full of naysayers or energy vampires, it’s going to be a heavy climb to where you want to go. But a community that challenges you to grow and supports you when you fall—that’s a game changer.

Find people who inspire you, who tell you truths even when it’s uncomfortable, and who celebrate your wins like they’re their own. These relationships become the wind beneath your wings when you doubt your flight.

Don’t Let Fear Write Your Story

Fear has a sneaky way of dictating our lives if we’re not careful. What if I fail? What if I’m not good enough? What if everything falls apart? Those “what ifs” can freeze you in place. But here’s the kicker: fear is often lying.

You don’t have to live a fearless life. You just have to live it despite fear. Every step you take while your heart is pounding is a victory. Every time you show up when the voice inside screams to run, you rewrite your story. Don’t let fear be the author of your next decade.

If you’ve ever felt stuck or like you’re drifting through life without a map, remember that designing a life you won’t regret is an ongoing process. It’s messy, imperfect, and uniquely yours. For some extra inspiration and practical guides on finding your true north, check out the insightful resources on discovering your life purpose.

So, what’s the life you want to tell your future self? Start shaping it today. Because ten years from now, you deserve to smile at the reflection in the mirror, not grimace.

Author

  • Milo Falk

    Milo Falk is a contributing editor at WhatIsYourPurpose.org. He works at the intersection of purpose, and disciplined practice. Clear prose. Verifiable sources. When Scripture is in view, he handles the text with context and cites respected scholarship. His pieces include checklists, prompts, and short studies designed to move readers from insight to action the same day.

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