The Courage to Be Seen: How Authenticity Builds Real Connection in Midlife

Hi, I’m Cheryl Dillon, a life coach, writer, and founder of Funderful Experiences – home of The Uplift newsletter and the Connected Hearts membership community.

I believe midlife should be a time of possibility and reinvention, not resignation. It’s about shaking things up and stepping boldly into this chapter in a way that feels true, fulfilling, and fully yours. I created Funderful Experiences to help women shape a joyful, vibrant, and inspired midlife – one defined by growth, curiosity, and genuine connection to themselves and others.

And in this post, I want to talk about one of the most powerful – and surprisingly vulnerable – parts of that process:

Showing up as your full, real self… even when it feels risky.

Behind the Confident Smile

Recently, I found myself staring in the mirror, barely recognizing the woman looking back. I was getting dressed for a Woman’s Club celebration – a vintage-themed event where we all wore 1920s attire.

There I was: flapper dress, feathered headband… heart racing.

From the outside, I probably looked poised and confident. But here’s my confession: despite appearing bubbly and outgoing, I battle social anxiety more often than I let on. The irony isn’t lost on me – a life coach who helps women build confidence, wishing she could sneak out the side door.

I’ve spent fifteen years helping clients step into their potential, yet when faced with a room full of strangers, my own self-doubt still kicks in. I can talk about personal growth all day long, but give me a crowd, and suddenly I’m scanning for the nearest exit.

The Shift

That night, something shifted.

As I took a few tentative steps into the room, I felt that old impulse to shrink – to soften my edges and become a watered-down version of myself I thought would “fit in.”

Then I caught myself.

Stop editing yourself, Cheryl.

I stopped trying to silence my natural directness or worry about how I might be perceived. Instead, I introduced myself to a woman standing nearby with a simple, honest statement: “I’m new. And a little nervous.”

Her reaction was immediate and wonderful. She laughed in relief and said, “Thank goodness. I thought I was the only one who still gets overwhelmed at these things.”

Just like that – the ice melted.

The Magnetic Power of Authenticity

That moment reminded me of something I already knew but sometimes forget: The fastest way to connect isn’t by pretending to have it all together – it’s by being real.

I didn’t say anything profound or perfectly timed. I simply told the truth. And it turned out to be exactly what someone else needed to hear.

When we hide the parts of ourselves that make us human – the nerves, the quirks, the “too much” or “not-enough” – we’re not protecting ourselves; we’re blocking connection.

We build walls and then wonder why no one can get close.

Authenticity isn’t about being loud or fearless. It’s about being honest. It’s that quiet courage to show up as you, even when it feels risky.

No, I didn’t close the place down that night; I still snuck out early (baby steps!). But I drove home proud – not because I faked confidence, but because I chose to show up as myself instead of a filtered version I thought would be easier to love.

This is the truth I work with my coaching clients on every day: the courage to be yourself is the foundation for all meaningful change.

Authenticity gets a lot of airtime these days, but in real life, it’s a practice – not a personality trait. It’s the quiet decision to stop apologizing for ourselves and to drop the mask we’ve been holding up so long we forgot it wasn’t our face.

The Invitation of Midlife

Midlife, to me, is the ultimate invitation to show up again – fully, imperfectly, and unapologetically.

It’s the season where we get to redefine who we are without asking permission. We’ve spent decades showing up for everyone else – our partners, our careers, our families, our responsibilities. Now it’s our turn.

To show up for ourselves.

To be brave enough to walk into new spaces.

To be open enough to connect for real.

Because showing up as your whole self is where everything real begins.

Where in your life might you be hiding behind a “confident smile” when what you really crave is genuine connection?

Try This: A Simple Tool for Showing Up

To help you ground yourself before your next social event or large gathering, try this simple micro-practice. It’s an effective way to calm your nervous system and shift your mindset from performance to authenticity.

The Three-Breath Reset:

• First breath: Inhale deeply. Affirm: “I am enough just as I am.” Exhale completely.
• Second breath: Inhale. Affirm: “I am comfortable being myself around others.” Exhale.
• Third breath: Inhale. Affirm: “I love and approve of myself.” Exhale completely.

This simple, grounding ritual centers you on the truth: you are ready to show up – as you.

“Authenticity is the daily practice of letting go of who we think we’re supposed to be and embracing who we are.” — Brené Brown