#3 A conscious challenge
Do you count the number of people you speak to each week?
from Unsplash Priscilla Du Preez
Hello friends and strangers, Welcome.
For this newsletter, I will steal Jason Fried’s approach: ship fast and iterate later. My goal is to share observations, thoughts and learnings every week, via this soon-to-be old-school communication channel. Hopefully one tiny thing from the letters would spark a quick thought and turn into something meaningful for you. At least that’s the hope.
I have another website to host longer articles, which frankly I rarely proof-read either. If life is a series of games and you can choose which ones to play, then this is my playground.
Welcome to the playground.
1. Challenge accomplished
I met a person named Tony at badminton drop-in last Tuesday. Tony was kind enough to fill me in the rules of badminton so that I got a chance to play a game that day. After chatting with Tony, I made a mental checkmark - my challenge of the week was completed.
My challenge of the past week - and the past 2 months - was to talk to at least 5 strangers each week. Living in a big city like Toronto and working (prdeviledgly) a remote work in tech, it is surprisingly easy go through a day without interacting with anyone outside of work or my friend cycle (The front desk receptionist at my building has already become my friend. Hi there Inisha!) .
2. Conscious attention shift
I noticed as the summer ended, there had been less outdoor events that would drag me out naturally, so I decided to make it a conscious goal to talk to more strangers. I set the threshold at 5, for it’s slightly higher than past average but also within my comfort zone. If I spread it out over the week it’s less than 1 person per day. However, it would still require my conscious effort to initiate conversations. There is also a 1 month trial period - after 1 month if I don’t like the experience, I’ll shift my attention to another challenge without feeling defeated. As I’m sharing my experience now, it has been way past the 1 month mark and I’m happy to continue this challenge (more on this later).
3. Good strategy, bad strategy
The plan has two parts. In order to reach the goal of 5 strangers, I would need to attend enough events with a considerable amounts of strangers. On top of that, I would need to remember to initiate conversations while I’m there.
The first part is fairly straightforward. One of the perks of Toronto is the endless events, as long as you know where to look. I mostly looked for events/interactions at the following categories:
- Experiences/interests/hobbies
- Shows/performances
- “Scratching my own itch” -> tech meetups
- Team sports
The second part is more of a challenge to me. I’m more comfortable when I have one on one conversations with people I’m familiar with or communicate via text (you’re reading my newsletter after all) but I thought it’d be a good opportunity to practice small talks.
As it turned out, small talk is a skill that you can practice with techniques. Based on Jen’s advice (YouTube), I chose to focus on exploring one thing: what makes the other person smile everyday.
I like this advice as it’s a great shift of perspective - having small talks is no longer about exposing my insecurities. It is about discovering a positive piece of information of the other person.
4. Final thoughts
During the challenge I participated events that are 100% outside of my comfort zone and talked to more strangers than I ever consciously have. Although none of the small talks turned into a followup conversation (0% conversion rate if you will), this practice has made me much more comfortable discovering passions and drivers of other people.
For the next 2 months, I’ll pivot into activities that I’d like to double down - bouldering, art, and restaurants.
The challenge may or may not stay a challenge in 2 months, but the journey going there will for sure be interesting.
Until next time.