Episode 99: Are Your Boundaries Selfish?

I don’t think you’re lazy. I just think you might be scared. In this episode of Showing Up Scared, Jess sits down with author Jon Acuff to talk about procrastination, fear, and what’s really happening when we feel completely stuck. Jon’s work reframes procrastination as a learned coping mechanism rather than a character flaw - which means beating yourself up might not be the thing that finally gets you moving. Together, Jess and Jon unpack the fears hiding underneath procrastination, the difference between rest and avoidance, and how small actions can help us move again without waiting to feel completely confident or ready. If you’ve been staring at the same dream, decision, project, or next step for months, wondering what is wrong with you, this conversation offers a different question: What if you’re not lazy? What if you’re scared?

We talk all the time about being afraid to fail. But what if you’re also afraid it might actually work? In this episode of Showing Up Scared, Jess talks with entrepreneur and former Go + Tell Gals team member Caroline Lunne about ambition, calling, and having the courage to actually go for it. Together, they explore both sides of the fear: the fear of failing that convinces us not to try and the fear of succeeding that makes us wonder what will happen if our lives actually expand. What will people think? Can I handle the responsibility? Who will I become? This isn’t a conversation about hustling harder or building something impressive. It’s about refusing to play small when God has given you something to steward—and learning to move toward faithfulness even when failure and success both feel scary.

Have you ever felt like theology was for other people? In this episode of Showing Up Scared, Jess sits down with Bible teacher, author, and theologian Lisa Harper to talk about why theology isn’t meant to intimidate us - it’s meant to draw us closer to Jesus. Together they explore what happens when women stop believing they’re unqualified to think deeply about God. Jess shares part of her own journey from experiencing theological spaces marked by pride and exclusion to pursuing a master’s degree in biblical studies herself—a journey Lisa personally helped inspire. This conversation is an invitation to discover theology that produces humility instead of pride, confidence instead of intimidation, and ultimately a deeper love for Jesus.

What if getting dressed could actually help you show up with more courage? In this episode of Showing Up Scared, Jess talks with House of Color CEO Ally Van Iten about her journey into color and style, eventually becoming CEO. Jess also shares how having her colors done three years ago became far more significant than a wardrobe decision. During a season of deep grief and family crisis, exploring color and personal style helped her feel equipped to show up as herself again. Together, Jess and Ally talk about why enjoying beauty isn’t frivolous, how creativity reflects the heart of a creative God, and why “not worrying about what we wear” doesn’t mean we have to stop caring about beauty and style. If you’ve ever felt afraid to be seen, this conversation is an invitation to step into the fullness of who God made you to be.

What if the reason you struggle to rest isn’t that you don’t know how, but because you’re actually scared to? In the first episode of Showing Up Scared, Jess Connolly is kicking off the season by talking about a fear many of us don’t realize we’re carrying: the fear of rest. What does rest say about us? What might we have to face when things get quiet? And what happens when we stop striving long enough to trust that God can keep holding everything together without us? Jess walks through some of the fears underneath our resistance to rest. From the fear of what other people think to the fear of ourselves, losing control, and even trusting God, she unpacks why naming our fears is such an important first step toward courage. Rest is trust. And sometimes, choosing to rest is one of the bravest things we can do.