Chasing Certainty

THE SIMPLE NEWSLETTER - ISSUE # 035

Too many business owners fall into the trap of waiting—waiting for the right time, waiting for things to calm down, waiting until the perfect moment appears. But business doesn’t work that way. There is no magical point where everything is finally settled. What separates successful leaders from those who stall is the ability to move forward while things are still uncertain.

TOM'S THOUGHTS

One of the biggest traps new business owners and accidental CEOs fall into is the illusion that things will eventually “settle.” They convince themselves that once they get through this season, land the next client, or hire the right person, then finally the chaos will calm and they can move forward with confidence. But business—and life—doesn’t work that way.

The truth is, there’s always something waiting around the corner: a new challenge, a new responsibility, or a new distraction. If you wait for things to settle, you’ll always be waiting. And worse, you’ll build your decisions around circumstances rather than your vision. That’s a dangerous place to lead from, because circumstances shift constantly.

This is why so many leaders end up frustrated, burned out, or paralyzed by indecision. They keep waiting for an ideal that doesn’t exist, instead of embracing the reality that uncertainty is part of leadership. When you accept that truth, the pressure to “get everything under control” lifts, and you can redirect that energy into making progress.

That’s exactly why Adam and I built the Intentional Focus System—to help leaders stop chasing the illusion of “settled” and instead anchor themselves to mission and vision. Because when your decisions are grounded in where you’re going, not where you are, you lead with clarity—even when everything around you feels messy.

TOM'S LESSON

Shifting your mindset away from waiting for the perfect moment takes practice, but it’s the foundation of effective leadership. Here are a few key lessons that can help you step into action with greater clarity and confidence:

1. Accept that it never settles.

Discomfort isn’t a sign you’re doing something wrong—it’s part of the entrepreneurial journey. Growth comes when you stop resisting it and start leaning in.

2. Recognize there is no perfect time.

There are more timely moments, sure, but never a perfect one. If you catch yourself waiting for the “right time,” that’s your cue to move forward now.

3. Anchor to vision, not circumstances.

Life will always throw distractions your way. What keeps you steady is a clear mission and vision that guide your choices.

4. Reframe the “I’ll do it when…” mindset.

The moment you hear yourself say, “I’ll do it when things calm down,” flip it. They won’t. Instead, remind yourself: “I’ll do it because it matters.”

CLOSING THOUGHTS

If you chase “settled,” you’ll never find it—and the pursuit will leave you frustrated, anxious, and unfulfilled. Real progress happens when you learn to lead through uncertainty, act in spite of discomfort, and stay anchored to vision over circumstance.

So stop waiting for things to calm down. The right time isn’t later—it’s now.

-Tom

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