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A Leap of Faith

Updated: May 27

I was heading up sales and business development for the San Francisco 49ers, loving my coworkers, loving my team, and loving life—in and out of Levi’s Stadium. With a vision to prepare myself for the C-suite, I knew I had some holes, some of which could come back to haunt me. To date, all of my functional experience was in sales and marketing. With aspirations to lead a sports organization, I needed to gain the knowledge of how business unit heads across all verticals think, operate, and make decisions. So, I made a bold decision of my own—one that was not the norm in my industry. My decision led me to an environment I never anticipated returning to. After a thirteen-year gap, I was going back to school.


With a concentration in leadership development, I entered the Executive MBA program at the University of Michigan. I joined the cohort based in Los Angeles, where we would spend about 80 percent of our time over the twenty one-month journey; the other 20 percent was back at the mothership in Ann Arbor, strategically timed in the non-winter months. We Angelinos aren’t a very pleasant people when it dips below a brisk fifty degrees!


This was my opportunity to level up as a leader and surround myself with some of the best and brightest across industries and roles so I could return with an elevated career trajectory and a broadened perspective.


In the sports business, I always had mentors. Within my MBA program, for the first time in a business setting, I had an executive coach. Little did I know that our first coaching call would open my previously fixed mindset. That mindset was set to continue the climb within my dream industry—an industry you don’t leave on your terms when things are going well


I still remember my former boss in the NFL League Office saying the easiest thing to do is stay on the treadmill you’re on. My executive coach challenged that notion. By the time we hung up the call, I started to believe there could be other treadmills to run on.


You want the details?


Let’s do it.


My coach got a feel for my role, then asked a series of questions: “What do you love about it?


What do you hate about it? What’s in between?”


After I answered, she asked me to go deeper on what I loved about my job.


I said, “I love the people side. I love being a coach, just like you. I love molding, growing, and developing talent. I love motivating with the hope of inspiring. I love when people max out on their potential because of the belief I poured into them. When they break through, it literally lights me up.”


She excitedly responded, “That’s fantastic! Now, on a good day, what percentage of your time are you doing that?”


Ugh. I started to slouch down in my seat, knowing the reality was far from ideal. Purely to save face in the moment, I padded the truth and said 20 percent.


She then probed, “If I were to wave a wand and you became your boss tomorrow, would that number, 20 percent, go up, down, or sideways?”


In my head, I thought, More strategy, less people.


So I said, “Down.” Then came the question that changed everything. It turns out, it would go on to alter my entire career and life plan.


My coach asked, “So, what are you after?”


It was a simple yet profound question that I had never thought of, but was ready to hear. I had been fixated on this linear path. This treadmill where A led to B then to C. It was predictable. I could see each step. I knew others that had already taken the path. I too was capable of continuing on the treadmill. It was just a matter of time until the next opportunity tapped me on the shoulder. I felt fully in control of my destiny.


Processing my thoughts around “what I was after” left me with a feeling I had not sensed in over a decade. One of freedom. One of possibility. One of opportunity. One of “What if . . .?”


I was excited to not know all the answers. Excited about the blank canvas. And excited for the ability to pave my path and author my story.


But how could I?


I had invested nearly a decade and a half of sweat equity in the sports business.


I loved the industry more than words could describe, and I loved the 49ers organization to no end. They were first class through and through—treating my family like gold. I loved our leadership. I believed in our culture. I adored my team. My career was on a fast track. I was running away from absolutely nothing.


And yet, prompted by my coach’s question, there was an undeniable tug in my mind. I was now thinking about what I was running toward versus what I could be leaving behind.


This unanticipated feeling was building momentum. It was not optional; I was going to get off the treadmill.


But when? To do what?


The Power of Playing Offense will fill in the holes of my story—and I hope encourage you to write yours with renewed passion and purpose.


For more information on The Power of Playing Offense, visit www.powerofplayingoffense.com

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