#33: Joy of Sketching
What Jeff has learned from surprising strangers with pencil portraits in Southeast Asia, and why he’s committed to spreading positivity
Welcome to this week’s edition of SEAmplified! We amplify the voices of youths and unravel our shared culture and lived experiences in Southeast Asia.
Recently, we spoke to Jeff Lai, who’s known on social media for surprising strangers with pencil portraits. From his sketching adventures in Southeast Asia to his recent life transition, Jeff shared his insights on people and spreading positivity with us.
Reading time: 8 minutes
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Right after we ordered our dinner at a cafe in Singapore’s Chinatown, Jeff took out his art kit and started sketching.
SEAmplified: “Oh, you’ve spotted someone?”
Jeff: “Yes, a Western-looking guy sitting diagonally across us who’s having his meal.”
His goal? To surprise his target with a portrait and pass it to him before he leaves.
About fifteen minutes later, Jeff completes the sketch.
But his target was leaving the cafe.
Fortunately, we managed to catch up with him just outside the cafe.
Jeff started a conversation with him, and we learned that he’s a university student from Finland who’s in Singapore for an exchange program. Jeff also recorded the process and encounter with his smartphone, and plans to upload the video onto his social media account afterward.
Such is the spontaneous modus operandi of the 26-year-old Singaporean artist, who’s well-known on social media for surprising strangers with a sketched portrait of themselves.
It all started as his friend's April Fools Day challenge in 2022, when Jeff was still a university student. Videos of him sketching and surprising strangers on trains went viral, and he has since amassed more than a hundred thousand followers on his Instagram (IG) “@playingwithpencil” and TikTok “@jeffandpencil”.
Now a full-time software engineer in an AI art company, Jeff has also begun giving in-person art workshops to give drawing tips and meet his followers in person.
I wondered what kept him going.
The Challenge
If you’ve been following our Instagram, you’d know that we challenged Jeff to sketch and befriend someone in Singapore in October. (PS: Check it out here if you’ve missed it.)
So I began our conversation by finding out what the experience was like for him—since he’s a self-professed introvert:
SEAmplified: “So, how was it?”
Jeff: “Honestly, it was so hard to find someone at Lucky Plaza. I think there’s a barrier – everyone was just rushing everywhere. They’re not shopping or relaxing, and I had a hard time trying to identify who to draw.
So I moved around for about half an hour, before deciding to draw the shop owner whom you saw in the video.”
SEAmplified: “What do you mean by ‘the barrier’? Was it a cultural or language barrier?”
Jeff: “As in, I think it’s the vibe I get. You know, when you’re an introvert, sometimes you can sense the vibe of a person. If you feel like that person is okay, it’s probably easy to start a chat with them.
But I didn’t get that feeling when I was there.”
As an introvert myself, I often feel like an invisible wall is present whenever we put ourselves into a new situation or environment, which needs to be dismantled by someone we feel comfortable speaking to.
I’d probably give up finding a profile for the video if I was in Jeff’s situation. But how did he overcome that?
Jeff: “Just do it.”
He would then share how he would often remind himself to do things in sequence.
Jeff: “First, pick up a pencil. Second, draw the face. Soon, you’ll realize that you’ve completed the sketch. Finally, you stand up, walk to the stranger, and pass them the sketch.”
However, when he reached out to the Filipino shop owner whom he featured in the video, he immediately sensed that she had her guard up. She was wondering why Jeff was recording a video of her, and it seemed that she was uncomfortable with it.
With that, he started to break the ice by sharing his personal story of how he adapted to the Singaporean culture and way of life, after coming from Malaysia at a younger age. That helped him to form a connection with the shop owner, who eventually let her guard down and agreed to be featured.
I thought that was brilliant.
Regional Observations
Apart from the Filipino shop owner, Jeff has sketched and surprised strangers when traveling around Southeast Asia. For example, he drew handsome guys when traveling in Vietnam, which attracted thousands of likes on his IG.
To Jeff’s surprise, he felt more relaxed drawing strangers while overseas.
SEAmplified: “Why is that the case?”
Jeff: “I don’t know why. Maybe because the mood is just different, like I go overseas to relax and enjoy myself, right? But when I’m in Singapore, I need to be the outgoing person sometimes.”
SEAmplified: “But do you think that the difference in culture could have been a factor at play? Did you spot any differences in reactions between the Vietnamese and Singaporeans?”
Jeff: “I wouldn’t say that the culture would affect that much. But one thing for sure is that the Vietnamese are more shy. Probably because I don’t speak their language, hence they don’t know what to say in response.”
That’s interesting, I thought. At least he wasn’t misunderstood in Vietnam.
Apart from the Vietnamese, Jeff shared that there are differences between how Singaporeans and Malaysians would react to his act.
He used to think that Singaporeans don’t respond to surprises well, and Malaysians are more warm and receptive. He felt that Singaporeans were more conservative and less inclined to reveal their expressions.
Nowadays, he feels that it’s the other way around. Based on his judgement, such surprises are more commonly seen in Singapore than in Malaysia, which explains why Singaporeans respond more favorably than Malaysians.
Well, I’m not sure if that’s true, but Jeff’s observations reveal how being shy and reserved is a common denominator for Southeast Asians. How then did Jeff manage to step out of his comfort zone?
Turns out, it’s the mindset that matters.
Jeff: “I began with the mindset of playing with something—which was how the username ‘playingwithpencil’ came about—since I didn’t go through the professional route to become an artist.
That lowered my expectations of my art, which allowed me to focus on making people happy. Knowing that I’ve made people smile also makes my day, and that encourages me to step out of my comfort zone.”
Transition
As Jeff stepped out of his comfort zone, curiosity over how people would react to his surprise became another motivating factor.
Two years on, I wondered if his curiosity had been satisfied.
Jeff: “No, no, no. Because everyone is just different, and I don’t think I’ll get sick of it. The only thing that I’ll get sick of is probably the art that I create.”
SEAmplified: “What kind of art do you think you’ll do in the future?”
Jeff: “How about you tell me what I should do?
I really have no clue, I’m waiting for someone to tell me what to do. But as long as I’m using it as a medium to connect, I think it’s good.”
I wasn’t expecting that.
On the surface, it seems that Jeff is exploring new ways to entertain his audience. But what I saw was an influencer caught in the maze of transition, from a university student to a working professional.
He admits that the transition has affected his content creation process.
For instance, when Jeff was a university student, he used to have the freedom to take time off to sketch people locally and overseas. But becoming a working professional meant losing that freedom, and having lesser opportunities to do something creative for his social media account.
Another example would be how Jeff went from sketching strangers on trains—an act that he was initially known for—to sketching strangers in different settings. But he has remained active on social media, and I wondered what kept him going.
Jeff: “My social media followers are my greatest source of motivation. You know that there are a lot of people watching you, and if you stop, you will be letting people down. That’s why I want to keep doing it.”
SEAmplified: “Is there a timeframe that you’re looking at? 5 years? 10 years?
Jeff: “No, I’ll keep doing it, until I get … sued?”
SEAmplified: “Touchwood.”
Amidst the transition, Jeff has found new opportunities. In August, he was approached by an art community to organize a pencil portrait workshop, where he taught ten of his followers to sketch faces using a pencil.
He felt that it was a good opportunity for him to learn how to come up with a lesson plan, sharpen his techniques, and organize the session by himself.
But that’s not the main point.
While Jeff has been surprising strangers for two years, he hasn’t had the chance to meet and connect with his followers in person. He would find that he was often alone in the pencil sketching scene, and feels that it is not as popular as digital art or watercolor art.
He’s curious if there’s anyone else who’s interested in the art, and he’s currently on the hunt to meet like-minded people and form a niche community. The workshop was only his first step in this endeavor.
Spreading Positivity
So far, it seems that Jeff is quite insistent on using pencils as a medium to connect with people.
His goal? To have an avenue for relaxation and to bring joy to people at the same time. Surprising strangers with pencil portraits is a unique act, and that makes it all the more worthwhile for Jeff to pursue.
I asked if his impression of people has ever changed since he started drawing. After all, I’ve met people dabbling with art who look at humans with a critical lens.
But for a self-professed optimistic person like Jeff, approaching people to spread positivity and see the good side of them has been a key tenet for his content creation work.
Jeff: “Friends have questioned why I could accept and forgive people who’ve done something wrong, and I’d say, why not?”
He adds by saying that if one’s perception of people were to be negative, it would be less likely for them to step out and surprise strangers. To him, it’s really about believing that something is good and the desire to spread positivity to everyone around him.
Sometimes, society just needs more people like Jeff.
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