The Courage to Look Foolish: Why Fear of Looking Stupid Keeps Us from Living Boldly

"Sometimes the thing feels foolish, but you do it anyway."

— Bob Burg and John David Mann, The Go-Giver

There's a moment before every significant leap in life when everything inside you screams that you're not ready. You don't know enough. You’re not prepared. It will make you look stupid.

And yet, sometimes the very thing that feels foolish is exactly what you need to do. Those feelings of inadequacy are often the Divine impulse whispering you’re on the right track.

I learned this lesson the hard way when I stepped into church planting. I had no manual for building a congregation from scratch, no advanced degree in organizational leadership, and certainly no foolproof strategy for creating a meaningful community in a skeptical world.

What I had was a calling, a handful of people willing to take the journey with me, a few bucks, lots of faith, and the uncomfortable realization that I was going to have to figure it out as I went.

The imposter syndrome was relentless. Who was I to start a church? What did I really know about shepherding souls or managing the complex dynamics of a growing community? Every decision felt like it was being made by someone who was still pretending to know what they were doing.

One day, we gathered in our living room for a Bible study. And a man asked: How do we know you can preach? Why should we trust you to start this church? It was an honest question because a group of people were taking a leap of faith to follow a dude who they barely knew.

Yeah, what if I sucked at speaking? Sure, what if I embodied poor leadership, and the church tanked before it got off the ground? All possibilities.

But here's what I discovered: we're all pretending. We all have moments of uncertainty and imposter syndrome. Everything is faith because nobody knows the future.

The difference between those who move forward and those who remain paralyzed is the willingness to embrace the foolishness and do it, anyway.

The Prison of Other People's Opinions

Fear of judgment creates an invisible prison. We rehearse conversations that haven't happened yet, imagining critics who may never materialize, and editing our dreams down to what feels "reasonable" or "safe."

We abandon callings because they might raise eyebrows. We shrink our ambitions to fit what others expect from us. Let’s be honest, we often play it safe because of our families, partners, or community’s opinions matter more than our own, or God’s.

The opinions of others become a tyrannical force, dictating not just what we do, but who we become. The loud voices of Opinion, drown out the voice of God calling you into your purpose.

Often losing our True Self in the process.

But here's a paradox. The very thing that feels foolish to us often appears courageous to others. What we experience as inadequacy, others may see as humility. What feels like stumbling around in the dark may look like pioneering to those watching from the sidelines.

When I started planting churches, I was convinced that everyone could see through my inexperience. Instead, I found people were drawn to authenticity more than expertise. They didn't need me to have all the answers; they needed me to be honest about the questions.

My passion for building faith communities, despite all of my inexperience and stumbling around, became a testimony of faith. It rubbed off on the people I was called to serve.

The Biblical Case for Holy Foolishness

We are in good company. People have wrestled with the idea of foolishness and the opinions of others driving their lives for thousands of years.

Scripture has a lot to say about the wisdom of appearing foolish in the world's eyes:

"But God chose the foolish things of the world to shame the wise; God chose the weak things of the world to shame the strong." (1 Corinthians 1:27)

This isn't a call to be actually foolish or unprepared, but rather a recognition that God often works through unlikely people in unexpected ways. The shepherd boy facing the giant. The fishermen becoming apostles. The stuttering prophet leading a nation out of bondage.

The pastor becoming an accidental entrepreneur.

"If any of you thinks you are wise by the standards of this age, you should become 'fools' so that you may become wise." (1 Corinthians 3:18)

There's a kind of foolishness that is actually profound wisdom—the willingness to look naïve in the service of something greater than ourselves. It's the courage to plant seeds we may never see grow, to build bridges we may never cross, to start conversations we may not live to finish.

We spend unhealthy amounts of time worrying about the perception of others. Often people we will never meet, or people who will never buy what were selling. The world is good at calling wisdom foolishness. Not everyone has to understand what you’re up to.

"For the message of the cross is foolishness to those who are perishing, but to us who are being saved it is the power of God." (1 Corinthians 1:18)

The most transformative acts in history have often looked foolish to contemporary observers. Love over logic. Service over self-promotion. Sacrifice over safety.

Nobody could’ve dreamed up the cross. The path of redeeming the world through death, the death of Jesus of Nazareth sounds bonkers. But on the other side of the cross is resurrection. The other side of the coin nobody saw coming. Death overcome, sin overcome, and hope given to mortals and a fractured world.

We see only death when we have unspiritual eyes. From God’s perspective, he sees goodness, and life. People see what we’re doing and say that’s foolish. God sees it as wise, good, and right.

Practical Steps for Doing Foolish Things

1. Start Before You're Ready

Readiness is often perfectionism in disguise. If you wait until you feel completely prepared, you'll wait forever. The skills you need often develop in the doing, not in the planning. Take the first step, knowing that clarity comes through action, not contemplation.

2. Reframe "Failure" as Data

Every mistake is information. Every awkward moment is education. Every time something doesn't work as planned, you're gathering intelligence for the next attempt. When I stumbled through my first sermons or fumbled through difficult pastoral conversations, I wasn't failing—I was learning on the job.

3. Find Your "Foolish" Community

Surround yourself with people who understand that growth requires risk. Seek mentors who remember what it felt like to be beginners. Connect with peers who are also willing to look foolish in pursuit of something meaningful.

There are other people who see what you’re doing and want to cheer you on. They don’t see foolishness, they see God at work.

4. Practice the Art of "Good Enough"

Perfectionism is fear dressed up as high standards. Learn to distinguish between excellence and perfection. Excellence serves others; perfection serves anxiety. Ship the blog post. Launch the project. Have the conversation. You can always improve version 2.0.

5. Develop Your "Why" Muscle

When your motivation is clear and compelling, the opinions of others carry less weight. Why are you doing this thing that feels foolish? Who will benefit? What problem will be solved? A strong sense of purpose makes you less susceptible to the fear of judgment.

6. Celebrate Small Acts of Courage

Notice and acknowledge every moment when you choose courage over comfort. Called someone even though you were nervous? That's courage. Did you share an idea, although it wasn’t fully formed? That's courage. Volunteered for something even though you felt under qualified?

That's courage.

7. Remember That Everyone's Making It Up

The dirty secret of adulthood is that everyone is improvising more than they let on. The people who seem to have it all figured out are often just better at managing their uncertainty. Give yourself permission to be human—learning, growing, and occasionally looking foolish in the process.

The Foolish Path Forward

Looking back on my church planting journey, and later entrepreneurial adventures, I realize that my willingness to look foolish wasn't a bug in the system—it was a feature. It kept me humble, made me relatable, and created space for others to join me in the messy, beautiful work of building something meaningful together.

The thing that feels foolish might just be the thing the world needs you to do. What makes you effective might be precisely your inexperience. Your uncertainty might create the space for others to contribute their gifts. Your willingness to stumble forward might inspire someone else to take their first courageous step.

The choice is simple: you can spend your life managing how you appear to others, or you can spend it actually living. You can edit yourself down to what feels safe, or you can embrace the glorious foolishness of becoming who you're meant to be.

Sometimes that thing feels foolish, but you do it anyway. And sometimes, that's exactly how transformation begins.

-Ryan