Meet Paul Epstein

We caught up with the brilliant and insightful Paul Epstein a few weeks ago and have shared our conversation below.

Paul, so good to have you with us today. We’ve always been impressed with folks who have a very clear sense of purpose and so maybe we can jump right in and talk about how you found your purpose?
My transformative moment came during a leadership retreat when I was the Chief Revenue Officer for the San Francisco 49ers. This retreat completely changed my life. Before the retreat, I had my ‘why’ and values as these abstract ideas, but this experience propelled me to think about how they actually applied to my everyday life, starting on Monday morning. I focused on how I could make decisions, take actions, and show up in a way that was driven by purpose. That focus fueled my passion for ‘Monday Momentum’, and the rest, as they say, is history. As soon as I got back to the office, I couldn’t stop talking about it, and my enthusiasm was infectious. Soon, people on my team, the coaches, players, and even HR were asking about the ‘why’ mindset. This led to me becoming known as the “why coach” at the 49ers. Leaving the sports world behind and diving into coaching others about purpose was the most significant graduation of my life, from career to calling.  I’m now on a mission to pay this gift of purpose forward and help others discover their own purpose, then put it in action.

Thanks, so before we move on maybe you can share a bit more about yourself?
I’m a keynote speaker, bestselling author, and the founder of the Win Monday community. My whole mission is about impact and purpose. It all started when I found my own ‘why’ while working in the NFL and NBA. From that point on, I decided my career wouldn’t be confined to sports; I was ready to make an impact by helping people and organizations thrive. Now, I travel the world speaking, I’ve written two bestselling books, “The Power of Playing Offense” and “Better Decisions Faster”, and I’m building the Win Monday community. You can sign up at WINMonday.win. My goal is to help people become that unstoppable force through daily growth, momentum, and ultimately, living with purpose.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
Confidence:

To me, confidence comes from knowing your values and consistently acting on them. I have a simple journal exercise to help people with this (you can find it by joining the Win Monday community at WINMonday.win). The idea is to fill in the blank: “I will live my value of ______ by ______(action tied to that value)___”. Every action driven by your core values builds unshakeable confidence, because it marries ‘who you are’ to ‘what you stand for’ to ‘how you show up’.  The compounding effect of this alignment is you as your most confident self.

Decision Making:

I have a framework I call the “head, heart, hands” equation that’s the focus of my book, “Better Decisions Faster”. By aligning your mindset (head), authenticity (heart), and actions (hands), you can make the best decisions quickly. It’s about filling your life with “green lights” for go, knowing your “red lights” to avoid, and navigating those tricky, in-between “yellow lights.”  I call this the messy middle, and conquering the messy middle of yellow has been the biggest transformation for everybody that’s applied the head, heart, hands equation to their daily lives.

Leadership:

We often associate leadership with titles and authority, but that’s just the surface. True leaders inspire, care, challenge, and show unwavering consistency. The best leaders are those we admire because of their actions and character. Before we can lead anyone else, we need to lead ourselves. If you embody the qualities of the leaders you admire most, you’re already a great leader.  No title required.

To close, maybe we can chat about your parents and what they did that was particularly impactful for you?
My parents inspired me to be a person who makes an impact and to always lead with courage. The most defining experience of my life was losing my father when I was just 19. He was my hero, a continuation school teacher who worked with kids who’d been given up on. Years after his passing, his former students would tell me that he was the person who finally believed in them. It was then I truly understood what impact really means. I made a promise to myself to live a life dedicated to making a difference and leaving people and places better than I found them. My father’s passing was the worst day of my life, but it led me to my purpose.  The only standard I now live by is: did I make my hero proud?

My mom is the embodiment of strength and resilience. After losing my dad, I watched her pick herself up each day, heal, and live courageously. Her example breathed life into me during that dark time, inspiring me to do the same. I truly believe that pain, once healed, can transform into a powerful purpose that drives us forward.  This is the gap between drifting by default, or living with purpose, ON PURPOSE.  We always get to decide.

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