Becoming an Iconoclast Means Breaking Your False Gods With Kristina DiPalo
- Brainz Magazine
- 1 day ago
- 6 min read
Tricia Brouk helps high-performing professionals transform into industry thought leaders through the power of authentic storytelling. With her experience as an award-winning director, producer, sought-after speaker, and mentor to countless thought-leaders, Tricia has put thousands of speakers onto big stages globally.
Being able to support speakers in using their voices for impact is a privilege, and I had the pleasure of sitting down with Founder Kristina DiPalo where we talked about her watershed moments, their connection to resilience, and why the world needs more iconoclasts.

Kristina, you speak about how we have to break icons before we can become an iconoclast. What do you mean by breaking icons?
Let’s start with icons themselves. An icon is a representation, an image, a likeness. On a personal level, we all represent certain characteristics and aspects that make up how we see ourselves and how others see us. In a sense, we are all unique icons.
When that iconic definition of ourselves becomes misaligned with how we are really behaving in the world, we experience a lot of tension. It’s like feeling you are walking around in someone else’s shoes. They keep you moving ahead, but boy, do they hurt your feet.
When you realize you are wearing someone else’s shoes, you’re being called to assess where you are in your life and re-align what you are in the world with who you truly are. You’re being asked to break the icons you are living.
Taking on the mantle of breaking those icons makes you an iconoclast. Literally, a breaker of icons and the one who challenges and breaks free from what no longer works.
And why is this important for leadership, business, and impact?
It matters across every corner of human endeavor, this willingness to challenge our assumptions and methods when things are out of alignment.
For leaders, especially those responsible for delivering value to customers and various stakeholders, losing sight of the essence of what makes your company or institution valuable can blind you. You make decisions that are biased toward reactivity instead of proactivity. For example, in the late 2000s, internal messaging tools, like Yammer and Jive, were the rage at large companies. These tools were meant to increase connectivity within internal networks and move work along at more efficient rates. They were introduced as add-ons, and quite honestly, employees didn’t see how to integrate them into their workflow routines. So companies launched leader chats and open question sessions, hoping that people would see their value. It took a while and successive versions before employees adopted them. If leaders more concretely connected their company’s essence, like being the swiftest R&D shop in the industry, for example, with how the new tool made this happen better, the impact would have been greater sooner.
There was an opportunity to leverage technology to “break” the way people were working to deepen internal organizational networks and keep pace with changing market expectations. To align the what with the who.
Tell me more about the concept of a watershed moment, that I have heard you speak about.
A watershed moment is that experience of great tension. The moment you come to terms with the fact that you are not living in a way that recognizes and respects your deepest self.
Watershed moments happen everywhere. They happen to individuals. They happen with businesses when a company is struggling to figure out what they bring to the marketplace and what their current and potential customers expect of them. Recognizing and navigating through a watershed moment is a hallmark of resilience. It’s a time to choose how you want to respond to the present and redefine the future.
Watershed moments happen collectively, too. I can’t tell you how many people have told me in recent months that they no longer recognize the country or the world they are living in. They are afraid that new technologies and tone-deaf leaders will strip away our greatest power, our humanity. They are aching for someone or something to open a path to a less scary, more human-centered future.
What was your watershed moment, and how do we know if we are in one?
I’ve had many watershed moments in my life, but it took a long time to see them in that light. The last one I went through, the biggest one, happened about 8 years ago. It was a confluence of events ranging from the ending of my marriage to questions about my career direction to, ultimately, the passing of my mother. All these events were happening around me, but the real internal watershed moment was taking off the mantles I had been wearing for so long (wife, communications strategist, daughter) that no longer fit. I had to morph into a new version of myself that still held fast to the elements I knew to be true.
The people I’ve coached and the friends who have gone through similar watershed moments have something in common. They know that the discomfort of holding on to what isn’t working is far worse than the anxiety of taking the risk to change.
What does becoming an iconoclast mean when it comes to business growth?
There comes a moment in every organization’s life when what had been working no longer does. When the connection between core purpose and defining characteristics is lost. When it keeps going through a cycle of reinvention with little improvement in outcome. The systems, stories, and symbols that built your legacy start to feel heavy. The icons that once inspired your people begin to limit them.
Wise leaders embrace the necessity of challenging and, when needed, breaking the methods and strategies that no longer work. Perhaps the company has tried too hard to follow the pack or has ventured into products and services that don’t align with its core strengths. Becoming an iconoclast in these circumstances is not destruction. Its creation. Creation leads to growth and sustainability.
That leads me to this Kristina, you have led some incredibly lucrative initiatives in the multi-billion dollar M&A space. How has this kind of experience reinforced you owning being an iconoclast?
Either working within a company or as a consultant, I’ve been a communications leader during multiple monumental transactions. It was exciting to be at the forefront of such changes. The ones that were successful were those where a new entity emerged from the best of the prior organizations.
This is not an easy thing to do. You’re effectively taking prior entities, living organisms in a lot of ways, that functioned with their own ways of working, priorities, and mores to create a new living organism that hopefully lives up to expectations. As I worked with companies going through this process, it was clear that leaders need wisdom to capture the best of the old and courage to discard or break what should not carry forward. The first part was relatively easy. The second part, the courage to discard or break, was not. The second part required being an iconoclast for the sake of future success.
If someone reading this is on the verge of breaking their own icons and becoming an iconoclast, what are the questions they need to ask themselves to know they are ready?
The questions are ones you might be asking yourself already:
Am I happy with who I am at work?
Am I happy with who I am at home?
Am I happy with where I am heading?
What remains true in me of who I once knew myself to be, and what needs to break?
This is just a start. You can dive a little deeper through a quiz I created. It will help you discover how close you are today to the person you once imagined you would become, where you got out of alignment, and whether you are ready to become an iconoclast.
There is also a version available that looks at iconoclasm in business. You can reach out to me here to get a copy.
What would you tell someone who feels they are already an iconoclast? And what are their blind spots?
I’d say “Congratulations!” You are self-aware, willing to question patterns and ways of being when they feel out of date, and are courageous enough to do what it takes to ensure what you are in the world is aligned with who you are within.
The blind spots come from success. Becoming an iconoclast is momentous. It takes a great deal of courage and faith to honestly ask yourself these questions and make the decision to break what is no longer working. So it’s easy to think, “Wow, I’m glad I only have to do this once in life.” The truth is, everything around you keeps changing and evolving. Which means that you may not always be present to the subtle ways you become misaligned again. You forget that being an iconoclast is not about having a title. It’s about the never-ending quest for alignment.
Tricia Brouk, Founder of The Big Talk Academy
Tricia Brouk helps high-performing professionals transform into industry thought leaders through the power of authentic storytelling. With her experience as an award-winning director, producer, sought after speaker, and mentor to countless thought-leaders, Tricia has put thousands of speakers onto big stages globally. She produced TEDxLincolnSquare in New York City and is the founder of The Big Talk Academy. Tricia’s book, The Influential Voice: Saying What You Mean for Lasting Legacy, was a 1 New Release on Amazon in December 2020. Big Stages, the documentary featuring her work with speakers premiered at the Chelsea Film Festival in October of 2023 and her most recent love is the new publishing house she founded, The Big Talk Press.



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