Month #8: Starting a conversation every day

A Year of Monthly Challenges

Last week, I happened to come across a mini-documentary called Sonder. The word “sonder” is a neologism defined as:

n. the realization that each random passerby is living a life as vivid and complex as your own

— Dictionary of Obscure Sorrows

The five-minute long documentary is set on a commuter-train in Jacksonville, Florida. Throughout the short ride, the videographer simply asks the other passengers some basic questions about themselves, and in doing so captures beautiful anecdotes about their lives and personalities.

The result is similar to Brandon Stanton’s Humans of New York — it highlights the unique identities and experiences of the “anonymous” people we pass by every day, yanking them out of the scenery and into the spotlight.

This month, I challenged myself to break the “stranger barrier” in my own way. The goal was to start a conversation with someone new every day, in hopes of learning stories, making friends, discovering opportunities, or just engaging with cool and different people.

Despite being sick and stuck at home a lot for both the first and last weeks of May (allergy season 😫), I managed to talk to a bunch of people who I hadn't before:

• I hung out on the porch of my Santa Cruz AirBnb with a guy who travels around the world attending frisbee golf tournaments. He told me he’s always wanted to play at the Golden Gate Park course in San Francisco, and is going to invite me to join when he does.
• I befriended the Honduran abuela who works at my corner Walgreens. Now, we exchange cheerful greetings in Spanish whenever I stop by, and sometimes talk about restaurants or weekend plans. She also has great bakery recommendations!
• I spent a flight from PHX→SFO learning about investing in unlisted companies from Scott Hall, who dropped out of 4th grade and has forged his own path as a finance and marketing writer.

These were a few of my favorites, but there were plenty more. A lot of them were interesting, but many others were pretty mundane, and didn’t make it past small talk.

In order to have a meaningful conversation, both parties need to be engaged. Sometimes, I caught myself “checking out” once I felt like I had accomplished my task for the day; This led to stunted conversations and awkward interactions.

In general, one of the biggest obstacles for me in really benefiting from these monthly challenges has been learning to embrace the spirit of the challenge, rather than treating it as a set of tasks.

I’m still working on it.

Anyway, this was a really fun challenge. I found myself starting conversations in situations where I normally would’ve just zoned out or put in my earphones. When I did engage, I was usually glad that I did.

Now that I’m in the habit, I’ll keep pushing myself to start conversations, and hopefully experience “sonder” a little more frequently.

Month #9: Do nothing every day

Whenever I’m on a plane, I gain this temporary ability to reflect on my day-to-day life from a higher perspective. I’m removed from all of my normal stimuli — there’s nowhere I can possibly go, no notifications or functional WiFi — and I just kind of let my mind wander.

This leads me to do some of my best thinking. I’m rarely trying to think about anything; In fact, I’m usually trying to fall asleep, but I often end up having some combination of interesting random ideas, realizations about things I’ve been overlooking, or breakthroughs on current projects.

I note down these thoughts while I’m in the air, and usually land with a renewed sense of drive and direction.

I want to spend more time in this mentally productive state, so this month I’m going to try to do so on daily basis. I’ll set aside 15 minutes each day to let my mind wander. No computer. No walking around. I’m just going to sit in a boring-ass environment with my passive thoughts and maybe a notebook and do absolutely nothing.

Next blog entry to be posted on July 1st