When Success Looks Nothing Like You Planned

Last year, my colleague Tracy and I were driving to our Detroit “Take the Lead” conference when we paused a Tim Ferriss podcast featuring Elizabeth Gilbert. She said something that stopped us cold: she had “no cherished outcome” for their conversation—no expectations, just gratitude to be there. We looked at each other, recognizing the wisdom in those three words. What if we could let go of expectations and simply see where things take us?

Fast forward to 2025. After Detroit’s success, we launched an ambitious plan: eight Take the Lead events across the country, adding six new markets. We were ready, fire, aimmy usual approach that’s served me well in business. But this was before the federal government’s pressure against DEI, before economic uncertainty rippled through our world. What I didn’t realize was that I’d just invited the equivalent of planning eight weddings into my life.

Here’s the irony: despite that podcast moment, I absolutely had cherished outcomes. I had a vision, expectations, goals. I expanded our speaker roster, which exponentially increased our workload. By March, facing our first event with a rock-solid lineup, I knew we wouldn’t hit our attendance targets. The landscape had shifted. Previous events had seemed effortless; this was suddenly challenging, and all consuming.

Then came St. George, Utah, our final event in our spring series. Driving through that breathtaking landscape toward our event, something shifted in me. I realized I needed to release my expectations and embrace what we had created—the lives we touched, the connections we fostered. We weren’t meeting ROI, but we were getting something else: a return on joy.

Each program touched my heart. Every woman who chose to share her story on our stage was an honor. Last Thursday in Vegas, a presenter who’d spoken at three events asked me about my highlights. I told her the truth: hosting conferences where women like her chose to give their time and talents. That was a surprising outcome I never knew I’d one day cherish.

Let’s bring this to you.

As you reflect on this past year, did anything not go according to plan? Have you paused to consider what did happen—something positive, something unexpected? Sometimes things turn out better than planned, just not in the ways we anticipated. It’s hard letting go of expectations. You might even need to grieve them. But staying open means another lesson, another gift, can find its way to you.  

Questions for Reflection:

What expectation or “cherished outcome” have you been holding onto that might be keeping you from seeing unexpected gifts?

When something didn’t go according to plan this year, what positive outcome emerged that you didn’t anticipate?

What would it mean for you to approach your next challenge with “no cherished outcome”—simply showing up with gratitude and openness?

If you expanded your definition of success beyond metrics —perhaps by joy, connection, or impact —how would your recent experiences look?

What disappointment might you need to grieve before you can fully appreciate the surprising gifts it brought into your life?

With gratitude and no cherished outcome –

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