Trailhead Thoughts

“We do not learn from experience. We learn from reflecting on experience.”

- John Dewey

Trail Map - Learn. Think. Act. ™

You Can’t Reflect On What You Are Going To Do

📚Learn

It is impossible to reflect on what you haven’t done.

That road trip you planned, but didn’t take? No Memory.

That speech you rehearsed, but never gave? No lessons learned.

To reflect, you must first take action.

Reflection isn’t about planning - it’s about learning from what already happened. To make reflection a powerful habit, use this 3-step process:

  1. Set a Trigger - end of a sprint, a walk, a photo, an icon.

  2. Ask 3 key questions -

    1. What’s working?

    2. What’s not working?

    3. Where am I stuck?

  3. Document It - whiteboard it, journal it, take a picture.

🤔Think

Pause and consider:

  • Are you actually making progress toward your goals or just staying busy?

  • When was the last time you stopped to reflect on your work or life?

  • What pattern would you see if you looked back at the last 30 days?

💪 Act

Start today:

  • Pick one daily or weekly trigger to pause and reflect.

  • Answer the 3 questions.

  • Capture it in a way that works for you (photo, note, voice memo) then adjust. Improve. Keep going.

  • Remember, DO first. REFLECT second. REPEAT.

Beyond the Trailhead

You Can’t Chart The Next Turn Without Looking Back

There’s an old saying in trail climbing: You can’t chart your next turn if you don’t look back at the path you’ve taken. The same goes for leadership and business performance. Reflection isn’t a break in motion - it fuels motion.

Most of us are great at moving. Doing. Checking boxes. But stopping to reflect? Not so much. It’s usually the thing that gets skipped when we get busy.

The way we see it reflection isn’t wasted time, it’s how motion gets turned into progress.

It’s the difference between running in circles and walking the trail with purpose.

When’s the last time you stopped to look at what’s working in your business? Or what’s not working? Most teams don’t pause until the wheels start to wobble. But reflection when done consistently keeps the wheels aligned before they start to wobble.

If you need more than intuition to buy in, here’s the data. Teams that reflect regularly perform up to 20-25% better. Not because they work harder, but because they learn faster.

So, how do you build reflection into your routine without it feeling like another meeting that could have just been an email?

Try this:

  • Pick your moment. End of the month, end of a project, or even Friday mornings over coffee.

  • Ask 3 questions:

    • What’s working?

    • What’s not?

    • What’s next?

  • Write it down. Journal, whiteboard, or voice memo - it doesn’t matter. Pick what works for you.

  • Share it. Bring your team into it. Reflection done together builds trust and accountability.

Clarity doesn’t come from thinking harder. It comes from creating space to notice what’s actually happening.

November is when we think of giving thanks - but as leaders, we shouldn’t limit our practices of reflection and gratitude to one month a year. A monthly ritual of reflection builds culture, clarifies priorities, and creates a forward moving rhythm. Take a moment. Look back. Learn. Then lead with more purpose.

As we have said, reflection is powerful, but it can be even more impactful when you have a guide and a framework to help you make sense of what you see. That’s where Mike comes in. Through his use of Strategic Whiteboard Sessions, he helps teams slow down enough to ask better questions, spot blind spots, and create clear next steps that lead to progress.

If your team could use a pause to refocus, realign, and reset your direction, this is your moment.

Voices from the Trail

Hitting the Trail

Planning your 2026 offsite, SKO, or leadership retreat? Bring in a speaker who doesn’t just inspire - he equips. Mike helps teams turn ideas into execution through clarity, communication, and actionable frameworks that stick long after the event ends. Whether your goal is to reset strategy or to build momentum for the year ahead, Mike’s sessions are designed to spark alignment and drive results.

Click here for more information.

Announcements

Is your 2026 event already on your mind?

Before you book the speaker or build the agenda, grab this quick guide:

The Real Magic of Kickoffs: Why Margins Matter More Than Meetings

It’s packed with 5 practical shifts to help you design SKOs, retreats, and offsets that actually connect and stick.

Perfect for People teams, Sales Enablement leaders, or anyone who’s ever been handed “the event.”

coachsimmons.com

That’s it for this week.

Reflection turns motion into progress and progress is a whole lot easier when you’re not hiking alone.

If this week’s issue helped you think, plan, or see things a little clearer, a little differently, share it with a teammate or a friend.

Because better leadership, communication, and execution?

They spread faster when we walk the trail together.

Forward this email or send them here to subscribe: findmycatalyst.com

The Find My Catalyst Team

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