Thrive in 2025: Change Challenge - Revisit Some of the Most Pivotal Moments of Change in your Life

This year I’m kicking off 2025 by issuing a Change Challenge - an exercise where you revisit some of the most pivotal moments of change in your life. The new year is a great time to reflect on where you’ve been and how you’ve come to arrive exactly in this moment, today. This is also an important fact-finding mission! If you want to decipher what the next great chapter of change might be in your life, you will need to analyze the major events of the past, what new learnings you might find there, and what clues they provide for the future you are still working to build. 

I’ve created a tool to help you document your process through change this year - Feel free to download and follow along in this guide! 

ChangeChallenge_Guide.pdf

Download PDF • 900KB

Ask yourself these questions to generate a list of changes you can use for this exercise. We’re going to deep dive into one of these significant moments of change.

• What’s the most recent pivotal change you’ve faced?

• Which one felt the hardest, but ended up being the most transformative?

• Which change left the biggest mark on your life – the one you’ll never forget?

• What failure taught you the most?

• Which success made you feel on top of the world, but revealed a whole new side of yourself?

• Which change fills you with pride today?

Using the guide, you will determine which of these has the most unprocessed learning for you to work with, and when you have time, I recommend you dedicate the effort to thinking through each one.  Let’s jump right in with the item from the list you feel has the most teach you right now – whether that’s the change that has been the most challenging, most impactful, a quick success, your most powerful learning through failure, the one that’s provided long-lasting pride or even your most recent significant change. Choose the change story you feel most interested in revisiting first today. (And by all means, if a change is too raw or powerful for this type of deep dive, especially navigating this exercise alone, simply do NOT do it! Skip that one and focus on another change archetype for now).

As you’re working through these change questions, it’s important to “go from your gut” and not overthink the answers too much. We are trying to come at some of these old stories with a new lens, so pay attention to what is coming up that’s new or different than how you’ve thought or talked about it before. 

I suggest a couple of quick scaling questions on dimensions that will apply to all changes you will continue to face in the future: how positively or negatively you felt about this change at the time it occurred, as well as how much control you felt you had over it. This can be a really helpful frame of reference to be mindful of as you use the learnings from this exercise to navigate future changes. 

We’ll next try to recall the narrative we’ve historically held around this change. How did we talk about it? What specific words and phrases were used? I’ll then challenge you to rewrite this script. At first simply shifting the language, as this can give yourself permission to think about it in new, non-fixed ways. Then taking some aspect of this story that you take for granted, and explaining it as though to a stranger. Finally, you will seek to document at least 1 new perspective on this event through fresh eyes. 

Then I invite you to expand upon that learning by identifying 2 positive traits about yourself evidenced in this change story. I recognize some people really struggle to see themselves clearly in a positive light, so imagine it’s a friend or family member making the observations. Or even imagine a dear friend shared a similar tale. What positive characteristics would you take away from their action and decisions during this event?

Did you learn something you can synthesize into a new tool, approach or perspective that you will carry forward to help you in your next change?

You’ve made it through the exercise – you did great and hard work!

I hope you’ll take some time to recognize and reward yourself. As you have the time and energy, work through this exercise with other pivotal moments of change that you feel still have lessons to be learned. 

Tomorrow, I will publish an example of what this exercise looks like for one of my key pivotal change stories. Did you have any similar insights? If so, please share your thoughts in the comments below. I can't wait to hear from you!