I’ve always loved a good plan. I’m the guy who wants a strategy for the strategy. And why not? Whether you’re scaling a business, leading a team, or managing your life, planning feels like a badge of wisdom.

What’s more, if something in the plan isn’t working—you fix it. As an entrepreneur, that’s the job, right? Spot the broken things, step in with the solution, make it better, keep moving.

It’s why I used to bring a metaphorical toolbox to every meeting. Broken process? I’d duct tape a workaround. Sluggish sales? I’d hammer down on accountability. Conflict on the team? I’d wield my emotional intelligence like a Swiss Army knife, convinced I could smooth over the cracks.

But somewhere along the way, my love of planning (and fixing anything that disrupted the plan) turned into a problem. My so-called “wisdom” started looking a lot like control. That’s when I began paying more attention to what Proverbs says about planning:

“Many are the plans in a person’s heart, but it is the Lord’s purpose that prevails.” — Proverbs 19:21

There’s a tension here—one you’ve probably felt, too. On one hand, Proverbs is full of encouragement to plan carefully and act wisely. On the other, it reminds us that we don’t control the final outcome. It’s not anti-planning—it’s just anti-grip-tight control. And that distinction has reshaped how I think about leadership, work, and what it really means to lead with humility.

Planning (and leading) like Jesus

As purpose-driven entrepreneurs, we often carry a double burden. We’re not just building for success—we want to steward well, make a difference, do work that matters. That’s a beautiful thing. But there’s a subtle danger: when our drive to do good gets tangled up with the need to make our plans succeed exactly the way we imagined, we start to clench a little tighter. We become control freaks. We stop leading with people and start leading at them. And sometimes we miss what’s actually unfolding in the moment.

If you look at the way Jesus led, it’s striking how present and responsive he was. He wasn’t rushing from task to task with a color-coded planner. He had a clear purpose, yes—but he also made space for interruptions, for people, for the unexpected.

On his way to save Jairus’s daughter, he stopped to acknowledge the woman who touched his cloak in faith. When a blind man cried out to him from the side of the road, he paused. He welcomed children others saw as distractions. At a wedding in Cana, he hesitated—but still turned water into wine.

Jesus didn’t bulldoze his way through a to-do list. He walked with purpose, but also with attentiveness and trust.

Don’t ignore the yellow Jeeps

A mentor once told me to keep an eye out for a yellow Jeep—and sure enough, I noticed a dozen that day. It was a simple lesson: what you look for, you start to see. If you’re looking for frustrations, you’ll find them. If you’re looking for grace, you’ll find that, too.

When I was locked in on my own plans, I was blind to the “yellow Jeeps” right in front of me—opportunities, insights, people who didn’t fit my script but were part of the bigger picture. Planning without perspective makes us miss what’s actually being offered to us along the way.

Jesus and the wisdom of Proverbs remind us that planning well isn’t about having a flawless roadmap—it’s about paying attention. Wisdom is responsive, not rigid. It makes space for grace.

Planning insights from Proverbs

Here are three ways Proverbs continues to shape how I think about planning today:

• Start with wisdom, not hustle.
  “The plans of the diligent lead to profit as surely as haste leads to poverty.” (Proverbs 21:5)
  Planning is a discipline, not a race. Diligence means slowing down long enough to think well and seek insight before acting. I’ve learned to check myself: Am I moving fast because I’m focused—or because I’m anxious?

• Don’t plan in isolation.
  “Plans fail for lack of counsel, but with many advisers they succeed.” (Proverbs 15:22)
  We weren’t meant to figure everything out alone. Wise planning includes trusted voices—people who can offer challenge, encouragement, and clarity.

• Trust the bigger picture.
  “In their hearts humans plan their course, but the Lord establishes their steps.” (Proverbs 16:9)
  Even with the best strategies, there’s still mystery. Some detours are the destination. Some interruptions carry the most meaning. It’s okay if things don’t go exactly as planned—sometimes that’s where the best growth happens.

Planning the Proverbs Way

Faith-rooted planning isn’t about controlling every outcome. It’s about showing up with diligence, seeking wisdom, inviting others in, and holding your plans with open hands. That kind of planning frees you to lead with courage and flexibility.

So as you plan for your next quarter—or your next big step—consider asking:

• Am I making space for wisdom, not just efficiency?
• Am I inviting voices that sharpen my thinking?
• Am I holding my plans with enough humility to allow for the unexpected?

Planning with Proverbs isn’t just good theology—it’s good leadership. And it leaves room for the surprising ways things might unfold.