We were lucky to catch up with Kristina DiPalo recently and have shared our conversation below.
Alright, Kristina thanks for taking the time to share your stories and insights with us today. So let’s jump to your mission – what’s the backstory behind how you developed the mission that drives your brand?
My mission is to awaken people to what is within, what is still possible and how to become an iconoclast.
Realizing that the life you are living is not the life you envisioned is a hard realization. I’ve lived that situation both professionally and personally. Especially at what I call “watershed moments” when a difficult transition point arises – a major professional crossroad, a challenging organizational transition, the beginning of a new period of life, or wondering how you became almost unrecognizable to yourself – the ability to define or redefine oneself is an incredible act of courage and freedom.
In those moments there is a choice; to stay on the familiar but uncomfortable path you are on or intentionally break what no longer works to begin a new, fruitful and impactful stage.
I had to make such choices myself throughout my life with the largest one coming in my early 50’s. It was at this time that I began to connect the concept of icons to my own experience. About what it means to be living false ones. About breaking them in service of living resiliently. About becoming an iconoclast.
And in this moment, I realized that if I was facing such a dilemma, countless other people were as well.
I began the slow, steady process of moving toward this current work of helping people identify with what is true within themselves about who and what they are, naming what they still have left to do and experience and learning how to break the icon or the image they are living to open up the new. Breaking the icon, or image, is the heart of being an iconoclast.
This mission is meaningful for me because it is purposeful, a form of service. It is the culmination of a long career using language and meaning to frame and engage important ideas. And it speaks to renewal and growth in work and life.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
As a young girl, I was drawn to images, to icons I referred to who spoke to me. Women like Debbie Harry, Shirley Chisholm, Billie Jean King and Millicent Fenwick appeared to me as cool, complex, courageous and classy. I saw in them the kind of qualities I wished to embody when my own life turned from childhood to independent life.
I spent hours in the quiet of my room thinking of these icons, imagining who I wanted to become—a woman who is intelligent, ambitious, hungry for knowledge and experience. Who walks through the world with her own style. Who is full of love. But mostly, I imagined a woman who is her own icon.
Before becoming a keynote speaker and leadership coach, I enjoyed a varied and successful career in corporate communications that led to a varied and successful career as a consultant. I worked in financial services and bio-pharma for two decades before going out on my own over a decade ago.
Over time, I evolved my focus from strategic communications to keynote speaking and leadership coaching. An extraordinary opportunity to participate in a multi-month intensive program to become a leadership coach connected me to new work and, more importantly, to a deeper, more intuitive way of serving others. I work with professionals who want to evolve, who want to challenge themselves and their career trajectories. I’ve helped scores of people discover how to manage change with confidence and grace.
And then, the final piece – keynote speaking.
My speaking platform focuses on the challenge of staying engaged in the world regardless of age, gender, or experience. I’m deeply fascinated by the power of icons to communicate meaning and self-definition, even communicate connection. Yet as fascinated as I am by icons, I’m even more fascinated by iconoclasts—literally, breakers of icons, of old thought patterns and old ways of doing things. Being one’s own iconoclast, in service of breaking what no longer works, can open up new, fruitful and impactful ways of working, of living, of Life.
If I had to highlight what I am most proud of about my business it would be its evolutionary nature. When I first left corporate to strike out on my own, I leveraged my corporate experience in strategic communications to work with clients across my prior industry. Then the industries expanded, the work itself expanded and my focus expanded. The move toward leadership coaching, and then speaking, were nascent desires that found form only because the new relationships and engagements I had fostered in the communications field brought me opportunities I could not have conjured on my own. It was by keeping an open mind and curious spirit that I came upon what brought me my fullest professional expression.

We’d love to hear a story of resilience from your journey.
Early in my career, I was doing work that I did not like in an environment that did not suit me. While the work of my organization was interesting in a broad sense, it was clearly not the right fit for me professionally. But I had no concrete idea what I wanted my career to be and no idea how to get there.
Through the prompting of a loved one, I found a graduate program in Corporate Communications, a field I knew little about but was aligned with my love of language, engagement and narrative. While excited at the prospect, the program did not readily link up to what I was doing and I started to figure out how I could work part-time, support myself and pay for grad school. Amazingly, my employer offered to pay for the program if I moved to head up a marketing communications team in another part of the organization. I was both stunned at their generous offer and overwhelmed at the prospect of leading a team in a totally new discipline.
Rather than be overly demure or completely frightened, I jumped into the opportunity. I learned as much as I could about the work of the team and remained present to all the leaders we supported. I came to love the work and the role of leading a team. After a few years, I was ready to advance my career further and move to an entirely different part of the company. But the lessons of remaining open to change, being curious to learn as much as possible, and having faith in the unexpected remain with me to this day.

How about pivoting – can you share the story of a time you’ve had to pivot?
One of the best corporate roles I had was leading merger integration communications during the joining of two large pharmaceutical giants. It satisfied so many of my professional strengths at the time and it was a fun experience.
A while after the merger closed, and the integration team members returned to their operational roles, the company underwent a restructuring. I had gone through a similar episode with a former employer and knew it was not an enjoyable place to be. As part of the restructuring, there was an opportunity to ask for a severance package. I debated whether or not to bow out with a package or see if I could move to a different part of the organization. The idea of striking out on my own had been an alternate option for me for a few years yet I was not ready to leave this company I had grown to love. I was conflicted. I decided to go for broke.
I spoke with my boss and the head of the function to lay out a proposition: develop me further by moving me to a new part of the function or let me take the severance package. Taking the package would help the function with their headcount reduction targets so I figured it would be helpful for both parties. The proposition’s result could go either way.
What I was not prepared for was an option presented to me to stay with the function but move to a role I wasn’t interested in. There would have been many benefits from this move. I could remain employed at the company, learn about a new business line and wait until I felt more ready to start my own business.
Yet something within me was unsettled. While there were clear benefits to staying, and I didn’t feel 100% ready to become an entrepreneur, I knew the opportunity of leaving with a generous severance package would not come around again soon. So I did one of the most powerful things anyone can do. I said “no” to the new option.
Two months later I started my first assignment as a consultant and never once regretted making the pivot. I made a decision based on facts and based on faith in the unknown. It turned out to be one of the smartest decisions I ever made and a blueprint for balancing the alchemy of decision-making going forward.
Contact Info:
- Website: https://kristinadipalo.com
- Instagram: @kristinadipalo
- Linkedin: https://linkedin.com/in/kristinadipalo
- Youtube: https://www.youtube.com/channel/UCdhu0HT1r6lvK8XaeWpZJeQ



Image Credits
Micah Joel

