This past year one of my Vanderbilt students asked me to write him a letter of recommendation for law school. Matthew knew it was a long shot to be accepted to a top-notch law school right out of undergrad, but he was willing to put in the work. He studied all summer to get a top score on the LSAT. And got the score he needed. First step complete. Next steps – application and letters of recommendation.

Then Matthew asked to meet with me to ask for a recommendation. Pay attention here students and anyone else asking for a recommendation – ask to meet in person to demonstrate how much this “ask” means to you.

After our first meeting, I asked Matthew to define his personal mission and vision for his future. He came up with an initial draft, but it didn’t get deep enough for me. “Why law school?” I asked. “But why corporate law?” I asked again, pushing him deeper into himself. I was ready to push him a few more times (remember the value of 5 whys of root cause analysis?) but gave him a break and asked him to send me an email after taking more time to think.

Matthew has spent many hours crafting his multi-tiered plan to accomplish his mission.  In addition to entering corporate law, he plans to start a non-profit organization that provides transportation, surfboards, wetsuits, education, and dinner to inner-city youth on a weekly basis.

Then I asked Matthew, “why kids?”

This was his response. “I won the lottery growing up. I was raised in a two-parent household where my father had a good job, and my mother was able to stay at home and raise my brother and me. My parents encouraged us to explore our passions and paid for us to do so. My story is not the same story for tens of millions of children around the United States.”

I discovered that Matthew has a heart for those in the minority as he comes from a bi-racial family with lived experience. In high school, Matthew had the opportunity to volunteer for a homeless shelter in Santa Ana, CA and this experience has made all the difference in his life – it sparked the desire in Matthew to give back to local communities. At the shelter he interacted with teenagers who looked like him but never had the same opportunities he was blessed to have. He remembers telling a few of these teens that he had gone surfing earlier that morning and noticed their faces light up. This initial spark has grown into a flame 🔥where Matthew is determined to serve others who have not had his privileges.

With a little pushing, Matthew discovered his real why. Have you discovered yours?

Need help finding your why? Drop me a line and let’s put a plan together.

Fly high,


By the way, Matthew, got into UCLA law school. Next time I see him I’m going to ask him to go surfing!

Want to know more of my story and my why? Check out my book: Flight Lessons: Navigating Through Life’s Turbulence and Learning to Fly High.

#mentor, #mentorship, # leadership, #why

Photo by Jeremy Bishop on Unsplash