Ask People What They Do, They Might Surprise You

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

Wynn Padula and baby Diana, father, husband, award-winning cinematographer - ask people what they do

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.

Related posts:

The Importance Of Having A Death File

Maybe Quitting Is The Best Decision After All

Dear Older Parents, Having Children Later May Be Better After All

44 thoughts on “Ask People What They Do, They Might Surprise You”

  1. 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.

  2. 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.

    1. 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?


    A beautiful story.
    A true friend.
    A short life.
    A poem on film.
    Like life precious and too short.
    Do what you want.

  4. Karima Khalil

    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.

  5. Aloha Sam,

    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.

  6. Hi Sam,

    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.


  7. 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.

    Thanks Sam.

    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.

    1. Hi Steve!

      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!


  8. Roy David Farhi

    Saw this film years ago and thought it was brilliant then and even more so now as wealth accumulates and societal values move further out of hand. I personally have moved closer and closer to Minimalist lifestyle; realizing never wore that Rolex, a bigger house wont make me happier and 12 suits not being worn probably better to just have one good suit. Your friend did Yeoman work on this and I am so sorry for the loss Sam. Make it always a personal mantra to read your writings and reflect on the message and mission.

    thank you always

  9. Sorry to hear about your friend. And thank you for sharing his video. I found it very interesting. My favorite line was when he stated the people cheering when he glides by are cheering for the one who got away. Nice.

  10. Beautifully written. In my experience a good friend is worth so much. During this life it’s easier to make $1m than to find a friend like you had

  11. Thanks to all those who spent time watching Slomo in the post and Resurface on Netflix. Wynn would have really appreciated your time. I watched Slomo two more times and really resonated with his mantra of “do what you want.”

    For those who inquired about fundraising, the softball community did host a couple of memorial game fundraisers this past weekend to support his family. We will do one yearly from now on.

    Thanks for your words of support. My main concern is for the well-being of Wynn’s family. He had a good support network in the Bay Area and was loved by many.

  12. Thank you for sharing Sam. Beautiful story, I’m so sorry for the loss of your friend. I pray for his wife and daughter, I hope they are ok and have the strength and courage to get through this tragic loss.

  13. Thank you for this.

    As a result of reading this I immediately watched Resurface on Netflix – what a moving & beautiful film. Your friend was clearly hugely talented and a beautiful human.

  14. Sam,

    I am so, so sorry. There are never any words for grief such as this. He sounds like a great man, father, and friend that anyone would’ve been blessed to know. If we can help in any way, please don’t hesitate to ask. You all are not alone in your grief – I’d wager that you have a whole community standing alongside you.

    1. John Johnston

      Such a beautiful short film. As Slomo says, “Do What You Want Too.” Wynn produced and left a legacy of his work for people like myself to view. May he rest in peace. Sorry for the loss.

  15. sorry for your loss of a friend . they are so rare.
    is your house in lake tahoe ok? with the fires and all.
    regards eema

  16. Dear Sam, I’m so sorry for your loss. Wynn sounds like a wonderful person. Will join you to honor him and explore his films. Take care.

  17. Sam
    So sorry for your loss. Wynn sounded like a great guy. While very difficult to lose those we love always remember how fortunate we are to have experienced those wonderful people and the love they brought into our lives.

  18. Grief and loss is so challenging. Like you Sam, most people think about what we should/could have done differently when confronted with loss. Hindsight is 20/20, but it’s also misleading, as no one has the power to change the past. I would encourage you to shift your mindset, and simply cherish your memories of Wynn. Everything happened the way that it did for a reason, but we may never truly understand why. Sam, I’m so sorry for your loss. Sending you peace, kindness, and love.

  19. Big Geek Daddy

    I was saddeneded to read this as I had originally watched SLOMO back in 2014. I enjoyed it so much I posted it to my site and shared it with my subscribers. I’ll get it shared again soon as it’s a wonderful short film.

  20. Hey Sam,
    So sorry for the immense, devastating loss. Extremely well-written and this post has done a phenomenal job in celebrating Wynn’s amazing accomplished life.

    Kind Regards,

  21. FS, appreciate your sharing this personal story of friendship, based on common interest, and fatherhood. One thing you could have been sure about with Wynn, is that he wasn’t a lawyer because they tell everybody within five minutes of meeting!:-)

    My thought is that it is a tricky subject to approach, especially when meeting people. One of the smoothest people I have ever met, a family law attorney, explained that he meets all kinds of people in all kinds of circumstances. Some are unemployed. Some have service jobs (bartenders, Uber drivers, etc) and find it embarrassing. Retail. Sales. They don’t have accomplishments, like Wynn, or status like a GS investment banker. The question can come off as “where are you on the status ladder, and how do I compare?”

    Anyway, his approach has worked very well for me, “what line of work are you in?” Doesn’t put anybody on the spot, and it is quite easy to pivot when the answer doesn’t interest you. I’ve also been acquainted with some high-profile and wealthy people who prefer not to reveal that they are a radio personality (“I’m in sales”) or a writer/director/producer (“I’m a content provider”) or simply inherited great wealth (“I’m between assignments, and not looking”).

    One thing I do, is try to get to asking “what else do you like to do for fun?” People really become interesting when they talk about something (anything!) that they have enthusiasm for. Great post, thanks for sharing.

  22. I am so sorry about your loss!
    I admit I’m one of those people who doesn’t ask others what they do. I feel like people asking or replying to this suggestion kind of expect a short answer and people are way too complex for that. I’m a polymath and since that may put people off, I usually give a short answer depending on the circumstances. I don’t delve into every area of interest because I may lose people and they are usually interested in what they’re currently experiencing anyway. I even wrote a visual poem some time ago on this question – called “So what do you do?” – since most people asking it do that as a more polite way of asking how much you earn and judging whether you are worth their time and interest.
    As regards grief, the only thing I found that makes it easier is to create some artwork that retells the story of what happened. Art saves people from despair, literally.

  23. HouseSpouse

    Hey Sam – with your large readership, maybe you could pose the question of how people found out their friends were FIRE? I bet there are a lot of clues that we don’t recognize, about people who are comfortable non-workers. I called myself funemployed (happily unemployed) to a friend who realized I could work for small $ and connected me with a neat job working with kids a few hours/week.

    Thanks for sharing. Great video. I am really curious about the physiology he mentions – could that be helpful for people who are feeling down? It’s at 8:45 for anyone who wants to try to find their own meditation like this!

  24. Wow. So touched. I was bawling my eyes out by the end of this article. I don’t know your friend but feel so sad about this loss through your words. Life can really test our strength when painful events, and unexpected tragedies come out of nowhere. My heart goes out to you and his family.

    I need a box of tissues now and hugs from my family. We must treasure every minute we have even the hard ones and count our blessings every day. This is a real reminder that we just don’t know what tomorrow will bring.

    Peace and love. Hang in there.

    1. I reckon this comment pretty much captures it. This post is heading for the bookmarks, Sam.

      Sorry to hear of this loss and I’m grateful for you introducing many of us to Slomo. I vividly remember my first viewing of Resurface and where I was at the time so will no doubt be watching both in short order.

  25. Funny how asking someone what they do is such an American concept. In many other countries the topic would never come up. Yet in others, the next question is how much do you earn.

    1. Very true. Many Européens find it odd and intrusive and a reflection of dominant commercialism to ask that, and probably in part for anticipating the next question.

      Maybe one could ask “what do you do that is interesting (to you)?”. That may or may not relate to how someone earns a living.

    2. I find not asking what one does is actually rather odd. Many folks spend a majority of their waking hours at their employment. Not to ask about this topic would almost be rude. It’s the elephant in the room. For most, one’s occupation is their choice, and hopefully they enjoy it (if most are merely tolerating their work that is pretty sad). So so much happens as work, as a conversation starter, it opens a wide variety of topics to discuss.

  26. Sam – thanks for sharing. Coming from a type A town I do not ask people what they do (I feel like I already know the answer).

    Saw Slowmo before but watched it again. I would love to see a blog post about your reflections about Slowmo’s life choices. He had it all financially but lost so much of his life otherwise. I wish the financial blogging community was more reflective. Slowmo was a doctor living in a mansion and decided to rollerskate to death. That’s commitment. Maybe not for everyone, but I love this film for allowing Slowmo the space and respect to articulate his choices and how he rationally came to choose his path.

  27. Damn man that was so we’ll written, I could feel your pain while reading it.

    That sucks so much you lost such a great friend… I am in a similar boat to you, I don’t dislike asking people what they do, I actually really enjoy that, but I dislike people asking me that question since I’ve kinda sorta semi retired and I’ve just never figured out a good way to talk about that without coming across a way I don’t want to socially.

    This post was a good mental push tho, I need to get over that and or find a good way to explain it, because I could be sitting on a similar “friend gold mine” and not know about it either.

    Hope the grief is not too bad/overwhelming for you man. Wish I knew of something that made losing someone close feel better, but sadly I’ve never found anything that improves it much. Life is strange, hopefully we do get to see our loved ones in some form after our physical deaths!

  28. Sam-I am so sorry for your loss. Tragic. Your words are beautiful and helped reaffirm what is most important for me. Life can be precious and your words really hit home . I’m sending my prayers and thoughts. Thank you for always being you.

    1. A rich life. You can probably never know an individual completely, but if you’re lucky you get to know the good stuff. Sending love and light.

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