Facing Your Choices in Your 40s and 50s

THE RECKONING

Your 40s and 50s have a way of holding a mirror up to the life you’ve lived so far. The choices you made (or didn’t make) in your teens, 20s, and 30s now show up in sharp relief—quite literally in your butt, your bank account, and your face.

It’s not subtle, either.

It’s that unmistakable moment when 

you look at yourself and wonder:

• Did I exercise regularly, or did I treat my body like a rental car with extra insurance

• Did I eat well, or have I been in a decades-long committed relationship with processed foods?

• Did I slather on sunscreen or let the sun tattoo its history onto my skin?

• Did I moisturize my face and neck, or am I now living with regret every time I glance in the mirror?

• Did I save money, or did I blow it all thinking there’d always be time to “get serious” later?

• Did I ever take the time to learn what compound interest means, or am I learning it the hard way now?

And then the kicker:

Was I the ant or the grasshopper?

The ant and the grasshopper fable feels uncomfortably relevant here. If you’re unfamiliar, we’ve got you covered: The Ant and the Grasshopper: Life Lessons on Work and Play.

For some, this reckoning is a moment of pride. You stayed disciplined, made smart choices, and are now reaping the rewards of your hard work and forethought. Congratulations—please tell us your secrets.

For others (read: most of us), it’s a sobering experience. Choices that seemed inconsequential back then—skipping the gym, ignoring that retirement account, forgetting SPF—now feel glaringly obvious. The face you’re aging into, the body you move through the world in, and the financial safety net (or lack thereof) you’ve built are constant reminders of what you prioritized.

And here’s the real existential rub:

Is it too late to fix it?

Let’s be honest: Some things might be harder to reverse. No moisturizer will completely erase sun damage, and no crash savings plan will make up for decades of financial neglect. But that doesn’t mean all is lost. It just means it’s time to get pragmatic.

What Would You Tell Your Younger Self?

If you could go back, what would you say to the version of you who thought life was endless and consequences were for other people? Would you shout, “Put down the tanning oil!” or “Get a Roth IRA!” Or maybe just whisper, “Be kind to yourself—you’ll need your own support one day.”

That self-reflection can be painful, but it’s also an opportunity. The reality is, you’re still here. Maybe not where you thought you’d be, but you’ve got time to assess, course correct, and set yourself up for a better future. And let’s be honest, you’re probably smarter now than you were then.

Midlife Reflection: What Really Matters?

Here’s where things get tricky. Are these metrics—your waistline, your wrinkles, your retirement account balance—really the ones that matter? Or are they just the easiest things to measure?

This is a chance to take stock of the whole picture:

• Physical Health: Can you move well? Sleep soundly? Feel good in your body most days?

• Financial Health: Are you making progress toward financial independence? Do you have a plan for the future?

• Mental and Emotional Health: Are you happy? Do you feel fulfilled? How’s your stress level?

• Relationships: Are they supportive and reciprocal? Do they enrich your life?

When you step back and look at the whole, it’s less about perfection and more about balance. Maybe you’ve nailed some areas and need work in others. That’s okay.

Where Do You Stand?

Now’s the moment for radical honesty. Ask yourself:

• How happy am I with where I am?

• What areas feel good?

• What areas need serious attention?

• What’s one thing I can start doing today to feel better about my trajectory?

This isn’t about beating yourself up. 

It’s about accountability and taking control of what’s within your power.

Preparing for the New Year

As we edge toward the end of the year, it’s the perfect time to reflect. Not just on what went wrong, but on what you want to change. The start of a new year feels like an open door, a reset button waiting to be pressed.

We’ll be launching a  Midlife Reflection Challenge to help you take stock of your life and make actionable plans for the year ahead. Over the course of two weeks, we’ll walk you through:

1. Assessing where you are now (physically, financially, emotionally, spiritually).

2. Identifying areas for improvement.

3. Setting goals that are realistic and meaningful.

4. Creating a plan to act on those goals throughout the year.

The challenge isn’t about perfection. It’s about progress. It’s about making the second half of your life something you’re proud to live.

What Would Your 80-Year-Old Self Like to Tell You Now?

Imagine sitting down with your 80-year-old self—a version of you who has seen it all, survived it all, and hopefully thrived through it all. What wisdom would they offer you today? Perhaps they’d urge you to stop sweating the small stuff and focus on what really matters: nurturing relationships, taking care of your health, and finding joy in the everyday.

They might remind you that the life you’re building now will shape their comfort, happiness, and peace of mind. Will they thank you for prioritizing health and saving for the future? Or will they wish you’d lived a little more freely, laughed a little louder, and spent more time with loved ones instead of worrying about things that, in hindsight, seem trivial?

Your 80-year-old self likely doesn’t want you to aim for perfection; they just want you to make choices that align with what truly matters. The message is clear: Think about the legacy you’re leaving for yourself, and live in a way that allows you to look back with pride, not regret.

Final Thoughts

The choices you made earlier in life may be staring you down now, but here’s the thing: Every choice you make today shapes the life you’ll look back on in another 10, 20, or 30 years. The mirror is yours to define.

Let’s tackle it together.

What do you think? 

Ready to brainstorm the reflection challenge and course content?

Join the Radiant Creative Living community for free and connect with like-minded individuals on the journey to getting centered, living authentically, and becoming as Radiant as you’re meant to be.