The external transitions we face are often the perfect opportunity for God to do some of His deepest internal work in us. — Michael Whittle
Michael Whittle is a pastor, entrepreneur, and founder of Pulpit AI, a tool designed to help pastors and church teams transform sermon content into discipleship resources. From planting churches in Los Angeles to navigating the tensions of ministry and business, Michael brings unique insights into calling, identity, and creating tools to serve the local church.
In this conversation, Michael shares:
👉 How pastoring during 2020 shaped his perspective on discipleship and digital formation.
👉 Why pastors often wrestle with the tension between ministry and entrepreneurship—and how to navigate it.
👉 The surprising response to launching Pulpit AI and why he believes pastors are some of the most undervalued creators today.
👉 How transitions refine identity and purpose—and why it’s crucial to untangle what’s beneath our desires.
Whether you’re a pastor, entrepreneur, or someone navigating a season of transition, this conversation is packed with wisdom, encouragement, and practical advice.
The Birth of Pulpit AI: A Tool Born from Real Ministry Needs
Pastors are some of the most underappreciated content creators. They deliver fresh, meaningful content every week—but it’s often underutilized.
Michael’s journey to founding Pulpit AI began during his time pastoring in Los Angeles, particularly in the challenging season of 2020. Leading a congregation of predominantly young adults, Michael saw firsthand how digital spaces were forming people far more than church spaces. This realization led him to ask a critical question:
How do we take what we’re already doing—our sermons—and use it to better disciple our people throughout the week?
What started as a tinkering experiment—using AI to repurpose sermon content into email newsletters—quickly snowballed into something much bigger. After tweeting about the idea and launching a basic landing page, Michael woke up to 600 signups in the first weekend.
I knew the problem was real because I’d lived it, but the response blew me away. That moment validated not just the need for Pulpit AI but also the hunger for tools that empower the local church.
Navigating the Tension Between Ministry and Entrepreneurship
For Michael, the journey hasn’t just been about building a tool—it’s been about navigating the deeper tension of balancing ministry and entrepreneurship.
I grew up in a church culture where ministry was idolized. For a long time, I thought that pursuing anything outside of full-time ministry meant I wasn’t following God’s calling. But over time, I’ve realized calling is much more expansive than a single role or title.
Michael speaks candidly about the doubts and internal wrestlings that come with stepping into new spaces:
- On the tension of identity: I used to think if I wasn’t a full-time pastor, I wasn’t living out my calling. But calling isn’t confined to a title. It’s about following Jesus, being faithful, and stewarding what God puts in front of you.
- On pastors and entrepreneurship: Pastors often leave opportunities on the table—opportunities to use their gifts in new ways, to provide for their families, and to expand their impact. Entrepreneurship doesn’t compete with calling; it can complement it.
Lessons from Building Pulpit AI
1️⃣ Clarity Comes After You Start
Michael shares that the vision for Pulpit AI didn’t arrive fully formed—it evolved through action.
I didn’t sit around waiting for a perfect plan. I started small, tested the idea, and let it grow organically. The clarity came after I took the first step.
2️⃣ People Want to Help
I’ve been blown away by the generosity of others. From pastors testing the tool to friends cheering me on, people want to see others succeed. You just have to be willing to ask.
3️⃣ Doubt Is Part of the Journey
Even with early success, Michael faced doubts—not about the problem he was solving, but about his own ability to execute.
Entrepreneurship is a roller coaster. Some days, you feel like you’re building the next big thing; other days, you wonder if it’s all going to fall apart. But doubt keeps you sharp and reliant on God.
4️⃣ Transitions Reveal What’s Beneath the Surface
Every external transition has brought up internal questions about identity, control, and trust. These moments of change aren’t just about what’s next—they’re about who you’re becoming.
Advice for Navigating Transitions and New Ventures
- Ask the Hard Questions:
Why am I being drawn to this? What’s beneath the surface? Untangling the ‘why’ is crucial before making big decisions. - Start Small:
If you’re curious about something, take small steps to explore it. You don’t have to leap into the deep end—test the waters first. - Don’t Go It Alone:
The wisdom of many counselors has been a lifeline for me. Whether it’s mentors, coaches, or trusted friends, surround yourself with people who can give you perspective and challenge your blind spots. - Be Patient with the Process:
Transitions are messy and often slower than we’d like. Give yourself time to reflect, untangle, and let the dust settle before making major moves.
Redefining Calling and Flourishing
Michael challenges traditional views of calling, encouraging leaders to embrace a more expansive and holistic perspective:
Calling isn’t a puzzle to solve—it’s a posture of faithfulness. It’s about being who God’s called you to be in every season, whether that’s as a pastor, entrepreneur, parent, or friend.
For Michael, flourishing isn’t just about success—it’s about relationships, peace, and leaving a legacy.
At the end of the day, flourishing means my wife and kids still want to be around me, my friends can hold me accountable, and I’m using my gifts in ways that bring joy and impact.
Lessons on Transition and Curiosity
Curiosity has always been the connective tissue in my life.
Michael credits his curiosity as the key to navigating life’s transitions. Whether stepping into new ventures or processing significant changes, his willingness to ask questions and explore the unknown has led to meaningful growth.
Key Practices for Embracing Curiosity:
- Ask Why: Michael reflects on the importance of asking, “Why am I drawn to this?” Understanding the deeper reasons behind your desires can lead to clarity.
- Follow the Rabbit Hole: Small, low-risk steps—like experimenting with an idea or having exploratory conversations—can open new doors.
- Make Time for Discovery: “Give yourself permission to read, explore, and think deeply about what excites you.”
Michael’s journey with Pulpit AI began as a small experiment, repurposing sermons into newsletters. That curiosity eventually became a full-fledged business that’s helping churches disciple their people more effectively.
Key Takeaways on Transition:
- Transitions feel high stakes because they often involve identity. “Who am I now? What’s next for me?”
- Beware of quick decisions during transition: Let the dust settle before making major life changes.
- Invite wise counselors into your life to offer perspective and accountability.
Michael’s reflections challenge us to see transition not as a disruption, but as an opportunity for refinement and realignment.
Practical Advice for Leaders in Transition
Michael offers this advice to leaders navigating the tension between where they are and what’s next:
- Do the Internal Work: Spend time with God, mentors, or even a coach to untangle your motivations and fears. “Bringing your thoughts to speech is one of the most healing things you can do.”
- Build a Trusted Community: Surround yourself with people who can offer clarity and wisdom.
- Start Small: Test ideas with small, low-stakes experiments before committing to major changes.
- Don’t Rush: Give yourself time to process and let God reveal the next step.
Key Takeaways from This Conversation
Signs You Might Be Wrestling with Calling:
- You feel torn between multiple passions.
- There’s tension between what you’re doing and what you feel drawn to.
- You’ve begun questioning long-held assumptions about purpose and identity.
How to Navigate the In-Between:
- Be willing to explore new ideas—even if they seem unconventional.
- Surround yourself with wise counselors who can offer outside perspective.
- Release the idol of calling and focus on faithfulness in each season.
Where to Connect with Michael Whittle
- Twitter/X: @MichaelWhittle
- Pulpit AI: pulpitai.com
Michael’s story is a reminder that calling is dynamic, transitions are refining, and the things God puts in our hands—whether ministry or business—are tools to serve His purpose.
Whether you’re launching something new or navigating a season of change, remember: clarity comes after you start, and God’s grace is with you every step of the way.
Everything just changed, now what?
In a season of transition, it’s hard knowing what to do next. Finding Your Way to Flourishing is your free guide to crafting your Next Step Statement so you can move forward with clarity and confidence.