THE PODCAST

How Women Build Confidence Through Connection with Jillian Johnson

collaboration community empowerment entrepreneurship golf inspiration joy networking Jun 18, 2026
 

There comes a point in many women's lives when we realize we've spent years checking all the boxes.

We've built careers. Raised families. Supported everyone around us. We've become experts at showing up for other people.

But somewhere along the way, many of us stop showing up for ourselves.

We stop trying new things because we're afraid of looking foolish. We convince ourselves that everyone else has it figured out. We tell ourselves we're too busy, too old, or too inexperienced to start something new.

This week's conversation with Jillian Johnson reminded me how much confidence has less to do with certainty and everything to do with connection.

Jillian is the founder of LEGS, the Ladies Executive Golf Society, an organization helping women feel more confident and welcome on the golf course. But as we talked, it became clear that this isn't really a story about golf.

It's a story about creating opportunities.

Confidence Isn't Something You Wait For

So often, women believe confidence comes before action.

If I were more confident, I'd...
✔️ start the business.
✔️ apply for the promotion.
✔️ walk into that networking event.

But Jillian's experience tells a different story.

Confidence is built by doing. It's developed through imperfect action. Through showing up nervous. Through taking the first swing, even when you're convinced everyone is watching.

Spoiler alert: they're not. Most people are far more focused on themselves than they are on judging us.

What if we stopped waiting until we felt ready? What if that first step showed us what to do next? What if confidence was simply the result of collecting evidence that we can do hard things?

Connection Changes Everything

One of the themes that came up repeatedly throughout our conversation was connection.

Women need community.

We need spaces where collaboration matters more than competition. Spaces where we're encouraged instead of evaluated. Spaces where we can learn, grow, and belong. Spaces we create out of abundance and support for each other.

Research continues to show that meaningful relationships positively impact our emotional and physical well-being. Yet many women find themselves increasingly isolated as they move through midlife. 

Building friendships as adults isn't always easy, but it is important. 

Sometimes connection starts with simply saying yes to something new... Joining a group. Attending an event. Trying an activity you've convinced yourself you're "not good at."

Connection often lives just outside our comfort zones.

Play Is Not Frivolous

 As adults, we often treat play as something we've outgrown. We prioritize productivity over joy and responsibilities over recreation. But joy isn't a luxury... It's fuel.

Play sparks creativity. It relieves stress. It reminds us that life isn't meant to be endured. It's meant to be experienced. 

When we allow ourselves to have fun, we often rediscover parts of ourselves we've neglected for years... the curious part, the adventurous part, the woman who isn't afraid to laugh at herself while learning something new.

When we follow the fun, we become more whole. We begin to see more possibilities and opportunities. We make a greater impact for our people. 

 Following joy isn't irresponsible. It might actually be one of the wisest things we can do.

You Belong Here

 You do not need permission to take up space. You don't have to earn your seat at the table, your spot on the golf course, or your place in the conversation. You belong because you are here.

Confidence doesn't come from proving your worth. It comes from recognizing that your worth was never up for debate.

Whether it's trying golf for the first time, starting a business, making new friends, or pursuing a dream you've set aside for years, remember this:

You don't have to do it perfectly. You just have to begin. Because confidence grows through connection.

And some of the most beautiful chapters of our lives begin the moment we decide to show up exactly as we are.

~Penny

HAVE A QUESTION?

Or idea for a guest?

CONTACT ME

SUBSCRIBE FOR WEEKLY LIFE LESSONS

And the occasional cocktail recipe.

We hate SPAM. We will never sell your information, for any reason.