When you’re working, one of the most common questions to ask new people you meet is what they do. Before the Global Financial Crisis in 2008, I happily said I worked in banking. A big part of my identity was where I worked for 60+ hours a week.
After leaving finance in 2012, I noticed I gradually lost interest in what people did for a living. Part of the reason was that I didn’t want anybody to ask me what I did for a living. I lost all my status.
During social settings, the last thing I wanted to do was think or talk about money. Therefore, I kept Financial Samurai and my old career mum. I knew others felt the same, so I never delved deeper into their professions, even if they volunteered.
The final reason why I stopped asking people what they did was that I often came away disinterested with their responses. Here in San Francisco, many people work in tech, finance, or law. If you’re not working in a well-paying profession, then you might be working at a startup that could make you rich.
There are some very fine people working in these professions. However, I just wanted to leave this type-A world behind, especially while I was in a social setting that had nothing to do with work. Unfortunately, my lack of interest in what people do cost me a deeper friendship.
It’s Worth Asking People What They Do
In November 2017, I joined a local Softball Meetup group. I wanted to diversify away from my tennis club friends and meet new people. I played softball growing up overseas (baseball wasn’t allowed at international schools) and wanted to get back into it.
One of the very first people I met at softball was a guy named Wynn. We immediately hit it off because we were both about the same age. I hadn’t played softball in 10+ years and neither had Wynn.
Despite the mix of sometimes rough personalities in meetup softball, Wynn was always the nice guy who got along with everybody. He was a team player who never complained about where he batted in the lineup or where he played on the field (unlike me sometimes).
Wynn got better and better over the years as a regular attendee. He was also someone who always had my back when someone else would put me down for a bad play.
A Temporary Scare
Then one day, Wynn stopped coming for about a month. It turned out he had gotten into an accident in his Smart car, those tiny two-seaters. During a downpour one day, he said he was driving down a highway ramp and hydroplaned.
He ended up breaking some bones, but thank goodness he was alright. I told him I had gotten rid of our Honda Fit for an SUV because we had just had a baby. I had witnessed too many accidents over the years. Further, I also noticed I was bullied more frequently when I drove a smaller car.
He decided to replace his totaled car with an SUV.
Before his car accident, we had been talking a lot about fatherhood because I was a new dad. He said he wanted to be a father, but was OK with not having children because his wife was unsure.
I was careful not to impose my feelings about being a parent on him. But I did tell him that one of my regrets was not having children sooner. Seeing how kind Wynn was to everyone, I knew he would be a great father.
The Surprise Announcement
A couple of years later, in 2020, Wynn told me some good news. His wife was pregnant! During the greatest time of uncertainty, I was elated to hear that he was going to be a father.
I shared with Wynn everything I knew about being a new father. We talked about what books to read, birthing doulas, night doulas, au pairs, tag-teaming night duty, parental leave strategies, and whether his pregnant wife should get the vaccine or not so close to birth.
We had both been going to every batting practice together during the entire pandemic. Every week, I was excited to meet up with Wynn to hear how his wife and baby were doing. I felt like an excited soon-to-be uncle!
Then on May 13, 2021, his beautiful baby daughter was born. I was thrilled to see her pictures on Facebook. I joked with him, “I guess I’ll see you next year!
However, I was secretly hoping he’d come back sooner. In a league mostly dominated by single men in their 20s and 30s, it was nice to have a fellow newbie dad to commiserate with when we messed up.
I’d also finally have someone my age who could better empathize with not diving for a ball or running at full sprint all the time. Pulling a muscle would pose challenges the next time we wanted to pick up our daughters.
The Tragic News
The last time I saw Wynn was on Saturday, August 14, 2021 at softball meetup. He went 3-for-4 with one stolen base, two RBIs, and three runs. Back when we first met in 2017, he would have gone 1-for-4 or maybe 2-for-4 with no RBIs.
Wynn never quit running hard.
Sadly, Wynn passed away that evening from an apparent heart attack. He was only 42.
We were going to spend the next decade swapping dad stories and child-raising strategies while on the field or in the dugout. We were going to keep sharing drafting strategies and taking turns trying out each others’ bats.
Softball and fatherhood. Fatherhood and softball. I had met a great friend and now he is gone.
Wynn Padula, The Film Maker
I lament never asking Wynn more about his career in filmmaking. I knew he did some type of cinematography, but I didn’t bother to inquire any further. He also didn’t brag about any of his accomplishments.
But it turns out that Wynn was a great filmmaker and cinematographer!
He was the Co-Producer and Director of Photography of Slomo, a brilliant short documentary about a neurologist who decided to give up his career and the money to live a simple life.
We have literally been talking about this topic on Financial Samurai since 2009.
From overcoming the downer of no longer making maximum money to shunning fame and attention, Wynn spoke my language and I didn’t even know it!
The documentary was shortlisted for an Academy Award and the winner of Best Short Documentary at SXSW and IDA. Please spend some time watching his documentary below. It would mean a great deal to me for you to honor his work.
Then, in 2017, Wynn released a Netflix original documentary called Resurface. Resurface is about a veteran who was on the verge of suicide before finding an outlet in the form of surfing. Wynn directed the film with his friend, Josh Izenberg.
I cannot believe it.
All these years, I had no idea Wynn was such an acclaimed filmmaker. Perhaps 0.1% of filmmakers ever win an award, let alone seven. Maybe even less get to produce their own Netflix original documentary.
How many highly-accomplished people do you know would refrain from telling hundreds of people over the years about their success? Wynn was so humble. He was the best type of person.
As a fellow creator, all we want is for our work to be seen, read, or heard. We put everything into our craft so that someone, somewhere might appreciate our work.
People Might Surprise You
We might choose not to ask what people do because we don’t want to seem nosy or competitive. But the reality is a lot of people will gladly tell you what they do if you just ask.
We spend so much of our lives working on something that’s hopefully meaningful to many. Yet, we don’t want to sound like we’re bragging about our accomplishments. Therefore, we seldom ever volunteer information and stories about what we do.
However, once you get to know someone over several encounters, please ask them what they do. Give them an opportunity to share their background. I now see asking people what they do as a sign of respect. It shows that you care.
Creators are always taking risks by putting their work out there. Every little criticism stings, but they continue to create because that is what they love to do. If you meet a creator, please dive in.
I’m sorry Wynn for never asking more about what you do. You were so talented outside of softball, but you were also so humble.
Thank you Wynn for your kindness to me and to everyone around you. Your films have expertly captured the plight of the human condition – how we all need purpose to keep on going and how sometimes, we might change our minds and that’s OK.
I will miss you so much my dear friend.
Readers, how can life be so cruel to good people? How do you cope with grief? What is a polite way to ask someone what they do? Is it possible for us to appreciate more and criticize less, especially if we aren’t willing to take a chance ourselves? If you have not gotten your life insurance sorted out, please do. You just never know.
Note: I am donating all revenue generated from this page to Wynn’s family. So far, I have given $1,638 and plan to host a yearly Wynn Padula Memorial Softball Tournament. Thank you for reading, watching, and supporting.
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Mike Lewis says
Thanks for sharing, Sam. You lost a good friend, a talented filmmaker, and father. Slowmo was inspiring- Wynn made a difference in this world. We can all take a lesson from him.
This is a moving piece Sam. Thanks for sharing. One reason I don’t ask new acquaintances what they do is because I’m not sure they want to talk about what they do, especially if they’re not doing anything ‘fancy’.
I’ve also been pondering around getting an SUV – moving from my Honda Fit.
Why someone needs to do something “fancy” in order to talk about it. Why people that brag about leaving their jobs always go out of their way to point out it was on “financial/tech/medical” as if only those are worth leaving and brag about?
DAN CARROLL says
A beautiful story.
A true friend.
A short life.
A poem on film.
Like life precious and too short.
Do what you want.
Karima Khalil says
Thank you for sharing Wynn’s story and his film. Your message is a reminder to us all. Your friend’s warmth and kindness clearly show in his smile.
Thanks for the post and for sharing this video by your good friend. I’m sorry for your loss and for his family – it truly is a reminder how precious life is and how our time is a gift – as cliche as that may sound.
Sorry to hear about Wynn.
I watch the Slomo movie. It was amazing, eye-opening, and inspirational!
I’m really glad you shared it.
Thanks for all your great articles.
Sam thank you for sharing this today, and I’m sorry for your loss. Your friend sounds like an amazing guy and I’m grinning from ear to ear right now.
I graduated from college in 2006, and moved out to San Diego with my brother to began life in the “real world.”
We rented an apartment right on the beach in Pacific Beach, and we lived right next door to this really eccentric guy named Slomo.
I’d see him in the morning when I’d be leaving for my crappy sales job, and he’d have the biggest smile on his face
On weekends, I would walk down the boardwalk, trying to figure out what the heck I wanted to do with my life, and I’d HEAR Slowmo coming before I saw him. He had this little boombox he’d wear on his hip, and eventually he’d come zipping through the crowd, skating by on one leg, still smiling.
I’d think to myself “that’s a guy who’s got it figured out.”
It was walking down that boardwalk in Pacific Beach, 23 years old, certainly inspired by Slomo, where I started planning an escape from the rat race – I knew I couldn’t work in my corporate sales job for 40+ years!
I came up with a plan to start living more adventurously, changed careers, moved cross the country, and eventually started my own business! Comically, my whole goal with the business was to just give myself some freedom and happiness and live life on my own terms.
And it worked!
12 years later, I now have 30+ employees/team members, and this pandemic has given me a chance to step back and reevaluate once again. Lots of reading, journaling, and long walks.
I’ve been forcing myself to ask the right questions: how do I actually want to spend my time? What is really important? What do I really need to be happy?
Thank you for this reminder of the shortness of life, and for sharing Wynn’s documentary. It’s amazing how small and connected life can be, and I’m smiling ear to ear realizing that Slomo is still influencing my life, 17 years (and a lifetime of experiences) later.
PS: I found the book “Not Fade Away: A Short Life Well Lived” to be a great book to remind us ho precious life really is. It’s incredibly thought-provoking, sad, and ego-shattering.
Financial Samurai says
Thanks for reading. And amazing you got to see Slomo in action for so long. There world really is small isn’t it? You’ve been building a great business for so long, I’m impressed! Enjoy your well-deserved success.
And maybe you can kick my butt to get in better shape if ever we meet up!