Why Wins & Wrestles?

Why Wins & Wrestles?



min read

As a high achiever for over three decades, I've found that there are two key areas where I’ve been notoriously weak.

Weakness #1: Not stopping to celebrate the wins

After climbing one mountain of achievement, I was already preoccupied with how to climb the next one.

I remember the night I was crowned the winner of a “Shark Tank” backed by one of Australia’s top companies. I couldn’t truly enjoy the bubbly in my hand.

My mind was already racing with thoughts of customer testing, product-market fit, pitching, funding, etc., driven by a fear of failing the expectations of the organization and leaders who backed me.

For decades, I've had this background track in my mind saying, "James, you are behind, and time is running out."

This mindset made it hard to stop and celebrate the wins.

Weakness #2: Inability to navigate the tensions and wrestles in my life in a healthy way

Looking back, in the blur of my fast-paced achievement, I can see how I shelved important nagging questions like:

  • “Where is my life really heading?”

  • “Who am I actually becoming over the long term?”

  • “How do my loved ones really experience me?”

  • “Why do I keep turning to these vices?”

  • “Why do I feel I need to be different around this person?”

  • “Why am I spending energy trying to impress others?”

One reason I didn’t entertain these important questions is because I frankly didn’t have time to ponder. I was already in the race, competing at a high pace for the prizes I thought defined success. Time was literally money.

But perhaps the bigger issue, apart from a lack of time, was that I didn’t have the specific support and competent guidance to help me.

While I’m thankful for the mentors and advisers offered to me at different points in my life, I can see that many were often headstrong, reputation-protecting leaders who seemed to have only one way of approaching life and business.

The mantra and mode?

“Set a goal and execute it at all costs!”

But what if it’s not as simple as that? 

I’ve found (as I suspect you also have) that life and relationships are significantly more complex, messy, and nuanced than that.

So here was my gap: I wasn’t able to draw on the lived experience of those who are dedicated to working through tension in a healthy way.

Why Wins & Wrestles?

The Wins & Wrestles email drop is a way (apart from my in-depth private coaching) that I want to help others start to bridge the gaps and weaknesses I had.

I hope it encourages you to pause to celebrate the wins in your life and intentionally lean into the wrestles we high-achievers often face.

I’ll be drawing on the lives of real individuals who I have worked with or am working with, as well as my own life and other resources.

So, look out for the next Wins & Wrestles email drop.

Over To You

  1. As you look back at your life have, have you found it harder to celebrate your wins or work through your wrestles? Which of the two do you want to get better at in your current stage of life? 

  2. What was your Win & Wrestle for the past week? If you'd like to share it, I'd love to hear it. Send me a note here

  3. Know someone who would benefit from the Wins & Wrestles email drops? Invite them to subscribe here

in the midst of the wins and wrestles of your life, may you know you are seen, you are valuable and that your choices matter.

Glad to be with you on your journey,


#winsandwrestles #coaching #life #leadership #holisticsuccess

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