When I was working in banking before the 2008 Global Financial Crisis, I was proud to tell people about my job. It was a big part of my identity, considering I spent over 60 hours a week there. But after I left the finance world in 2012, I found myself less interested in what others did for a living. I didn’t want to talk about my job, and I didn’t want to ask others about theirs. I didn’t want to think about money in social settings, so I kept quiet about my past career and my Financial Samurai project.
I also found that I wasn’t really interested in the responses I got when I did ask people about their jobs. In San Francisco, it seemed like everyone worked in tech, finance, or law, or was trying to strike it rich with a startup. I wanted to escape that high-pressure world, especially in social settings. But my lack of interest in people’s jobs cost me some deeper friendships.
In 2017, I joined a local softball group to meet new people outside of my tennis club friends. I met a guy named Wynn, and we hit it off right away. We were both the same age and hadn’t played softball in over a decade. Wynn was a great guy, always friendly and a team player. He was always there for me, even when others criticized me.
Then Wynn stopped coming to softball for a month because he had been in a car accident. He was okay, but he had broken some bones. After the accident, we talked a lot about fatherhood, as I was a new dad and he was considering becoming one. I told him I wished I had become a parent sooner, and I knew he would be a great dad.
In 2020, Wynn told me his wife was pregnant. I was thrilled for him and shared everything I knew about being a new father. We went to batting practice together every week during the pandemic, and I was always excited to hear updates about his wife and baby. When his daughter was born in May 2021, I was overjoyed.
But then, in August 2021, Wynn passed away suddenly from a heart attack. He was only 42. I had lost a great friend.
I regret not asking Wynn more about his career. I knew he worked in cinematography, but I never asked for more details. It turns out, Wynn was an accomplished filmmaker. He had co-produced and directed a short documentary called Slomo, which was shortlisted for an Academy Award and won Best Short Documentary at SXSW and IDA. He also directed a Netflix original documentary called Resurface.
I was amazed to learn about Wynn’s success. He was incredibly humble and never bragged about his accomplishments. As a fellow creator, I understand the desire to have your work seen and appreciated.
I’ve learned that it’s important to ask people about their work. It’s a sign of respect and shows that you care. Creators take risks by putting their work out there, and they deserve recognition. I wish I had asked Wynn more about his work. He was a talented filmmaker and a kind person. I miss him dearly.
Life can be cruel to good people. It’s hard to cope with grief, and it’s important to appreciate others and criticize less. If you haven’t sorted out your life insurance, please do. You never know what might happen.
I’m donating all revenue from this page to Wynn’s family and plan to host a yearly Wynn Padula Memorial Softball Tournament. Thank you for reading and supporting.
