The Huffington Post -- Death of a Mentor: What I Learned about the Meaning of Impact

Check out my latest article on The Huffington Post.  I’ve also pasted it below.


A year ago today, I experienced the first death of a friend.

It was one of those crisp days between Christmas and New Year’s Eve when the financial district is quiet because people are off for the holidays. I packed up at the office and headed downtown to do some last minute gift shopping and walked into Old Navy.

That’s when I got the text. Mayor Wasserman passed away, my dad said.

I stood in the store clutching a plaid shirt and didn’t know what to do. Outside, parents were tugging their kids along, cars were driving by, and a street performer was still playing his drums for a small crowd. A great man was gone. But the world hadn’t stopped moving, hadn’t stopped spinning, hadn’t stopped anything.

I remember the first time I met Mayor Wasserman 10 years ago when I was a freshman in high school. I wanted to create a program to donate backpacks and school supplies for underprivileged children in the Bay Area and soon realized that I knew nothing of what it would take to actually execute. He reached out to offer support when most people – including myself at times – thought I was crazy. I eventually grew the program over the next 5 years and it shaped my personality, goals, perspective.

But before there was leadership, there was a lot of fear.

I was 16 and had never planned anything bigger than a birthday party. So when I approached store managers at Wal-Mart and asked them to donate merchandise, they were naturally skeptical. People hung up and the rejection was worse in person. By the time fall came, no one had donated anything, but my aunt had already promised backpacks to a local shelter. I used my personal savings to purchase the backpacks and was ready to give up.

Somehow Mayor Wasserman, who was a City Council member at the time, heard about my project and thought the idea had potential. He invited me to speak at the local Rotary Club. So I went to the next meeting, got behind a dark wooden podium, and tried not to glance down at my index cards too many times. At the end of the presentation, several members took out their checkbooks to donate. I was surprised, humbled, and encouraged.

Later that week, Mayor Wasserman and I had lunch. We talked about the speech and he provided feedback. At the end, I admitted that it made me nervous to speak with strangers, especially a big group of them.

He said, “I’m better in small settings too. I like one-on-one situations.” Wait. How could a former police chief and an elected official possibly feel uncomfortable in the spotlight? Yet he was a self-proclaimed introvert. He probably didn’t remember telling me that, but I’ve never forgotten it.

I had tried hard all summer to be strong because my task demanded it. I called people when I hated talking on the phone, took rejection like it didn’t hurt, and introduced myself with a handshake that was intentionally too firm. I learned how to be assertive and presentable.

But despite the progress, I still felt scared every time I got on a stage to speak. When Mayor Wasserman told me that we had that in common, it was as if my guilt lifted. It was okay to feel scared. And more importantly, it was possible to succeed despite it.

In the future years of running Packs of Love, I eventually secured donations from retailers, including Wal-Mart, Target, JanSport, Pentel. I learned through trial and error and got smarter, more resilient, tougher. I learned that there are parts of my personality that are changeable and parts that aren’t. I learned that there are different modes of leadership and I have to find what is authentic to me.

Since then, I’ve had several new challenges, new roles, new projects. I’m concerned with making an impact, like most people in the Silicon Valley are. But in between those moments of working on big ideas, I try to remember that sometimes it’s the small interactions with people around you that make a difference.

The last time I saw Mayor Wasserman was about six months before he died. We got lunch. He arrived at the sandwich shop carrying a respiratory machine with two tubes that connected to his nose. His hair was whispery white and he looked old. I never got to send him a follow up email. I should have. Maybe he didn’t know how much an honest conversation or encouraging word meant to a kid – but it set in motion a string of positive actions that helped me become the person I am today – and I hope to honor his legacy by passing it forward.