When Routine Feels Safe – but Stale

When’s the last time you tried something new?

I’m not talking about a new restaurant or nail color. I mean something that made your heart race a little – because it was unfamiliar, a little scary, but quietly exciting.

There’s a subtle ache that can sneak up in midlife – the sense that your world has gotten smaller without you meaning for it to.

Same places.

Same routines.

Same conversations.

Comforting, yes. But also… a little flat.

Sometimes what we’re really missing isn’t more time or energy – it’s something new. A fresh challenge. A small risk. A spark that reminds us we’re still evolving, still becoming, still allowed to want more.

Midlife is prime time for exploration.

Because if we’re lucky, we’ve got decades ahead of us. Why not fill them with more than routine?

If your spirit’s been nudging at you to try, explore, or create something new – listen. You don’t need a perfect plan. Just a little courage… and a willingness to follow your heart.

When Change Feels Awkward (and a Little Terrifying)

Here’s something I’ve learned this past year: “Trying something new” sounds simple – but it rarely feels that way. New means unknown. It means being awkward. It means giving up the comfort of autopilot and saying, Okay, I’m willing to be a beginner again.

And that’s not easy – especially in midlife, when we’ve worked hard to figure some things out. Who wants to go back to square one? (Certainly not me – I just figured out how to use my air fryer.)

But I couldn’t ignore the pull. I kept thinking, If I keep doing what I’m doing, I’ll keep getting what I’m getting. And that wasn’t what I wanted.

So I started making changes – not because I felt bold, but because I felt stuck.

And… I may have overcorrected. (After all, I’m from Jersey. We go big or go home.)

I enrolled in an event planning program. I joined a new organization where I didn’t know a soul. I started volunteering.

Then I launched Funderful Experiences – a business rooted in everything I care about, but had never fully put into the world. Starting something from scratch in your 50s and saying, “This matters to me” takes guts. It’s vulnerable, it’s energizing… and yes, it’s terrifying.

Apparently I was on a roll, because I even signed up for voice lessons – reigniting a passion I’ve carried for years. And tried stand-up paddleboarding – something I’d talked about forever but always found a reason to avoid. (Turns out, the paddleboard doesn’t care that I used to be a good swimmer. It wants balance. Which I do not always have.)

Was I scared before every single one of these things? Absolutely.

But I stopped letting fear be the reason I stayed stuck.

I started talking to myself the way I would a close friend: You’ve got this. Just try.

I didn’t wait to feel brave – I used the fear as fuel. Because the possibility of what could come next felt more powerful than the fear of falling flat on my face. (Or into the lagoon.)

The Power of Saying Yes (Even When You’re Scared)

It wasn’t always graceful. Most days I felt – and still feel – like I have no idea what I’m doing.

But every single new thing stretched me. Every single one reminded me: I’m not done growing yet.

And neither are you.

Midlife isn’t a time to shrink. It’s a time to shake things up – even if it’s just one small step at a time. It’s not the end of the road. It’s the part where the scenery changes – and you realize you’re the one holding the map.

We’ve never been wiser, more self-aware, or better equipped to try something new than we are right now.

And when you surround yourself with people who are also saying yes to possibility, something magical happens – courage multiplies.

When’s the last time you felt both nervous and excited about something? What might happen if you said yes to that feeling again?

Midlife woman balancing on a stand-up paddleboard, smiling with confidence and joy as she tries something new.

Try This: The “New Thing, Small Step” Challenge

Pick one new thing this week – an experience, habit, or idea – and say yes to it. It doesn’t have to be dramatic. Let it be small, meaningful, or even a little silly.

Maybe it’s taking a different route on your walk, looking into a class you’ve always wondered about, or finally writing down that idea that keeps tugging at you. The point isn’t perfection; it’s motion. Because curiosity is enough to start. Confidence comes later.

And if you’re not sure what your “new” is yet? That counts too.

Your small step might simply be making time to ask yourself: What am I curious about? What would feel energizing, meaningful, or just plain fun?

Remember:

  • Reinvention isn’t selfish. It’s survival.
  • Curiosity is a sign of life – not immaturity.
  • There is no “too late” for doing what lights you up.

Start small. Begin where you are.

Because you’re not out of time – you’re right on time.

“You are never too old to set another goal or to dream a new dream.” — C.S. Lewis

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The Uplift is where real talk meets real growth – filled with fresh perspective and actionable tools for women ready to make midlife feel lighter, brighter, and a lot more Funderful.

About the Author – Making Midlife Funderful

Cheryl Dillon

Cheryl Dillon, CPC – Certified Life Coach, Writer, & Founder of Funderful Experiences

Cheryl Dillon is a life coach, writer, and founder of Funderful Experiences, home of the Connected Hearts membership – a community helping women shape a midlife chapter that feels joyful, vibrant, and fulfilling. She’s also the creator of The Uplift, a nationally read newsletter that blends storytelling, coaching, and humor to help women reconnect with themselves and each other – bringing more laughter, purpose, and heart to everyday life.

Cheryl’s work centers on the belief that genuine connection, meaningful experiences, and joy have the power to redefine this life stage. With a background in psychology and coaching, she brings a refreshing mix of real talk, warmth, and wisdom to conversations about friendship, identity, and how to truly thrive in midlife.

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