Challenge #8: Buy a Stranger a Drink

You can read more about this social skydiving/rejection therapy experiment here.

I think as humans, we should not be constantly focused on only what we can get, but also on what we can give to others. Tony Robbins once said that in life we receive value proportionate to what we give. So if you want to get more, focus on giving more.

With that in mind, today I went out to buy a stranger a drink (only after them consenting to it). This is what happened.

Filming this video was interesting. I was sitting on the bench inside the mall, about to shoot the introduction to the video, when a couple of ladies sat down on the bench near me. I thought okay, I’ll shoot the introduction after, and do the challenge now, as I didn’t want to miss a prime opportunity (we were right next to the vending machine, so it would be an easy transition to buying them a drink).

It was a success first try. And the ladies were surprised and very happy about the experience.

After saying goodbye, I plopped back down on the bench ready to check my footage when…

Oh no, the camera had got flipped around.

Eight solid minutes of my chest and audio only.

What a frustration. But I had to do it again. It actually took me a couple more tries before I could get a Japanese person to allow me to buy them a drink.

I figured this would be the case. Although buying a stranger a drink sounds like an easy task, part of this challenge was that the person has to consent to me buying them a drink first. In other words, I couldn’t just walk up to a random person and hand a drink to them.

Anyway, after a few failed attempts, another success!

I saw a couple of young gentlemen working at the hair salon. They were just standing around and chatting at the front register. There were no customers, so I knew I wouldn’t be interrupting their job.

I was hesitant to approach them. All these thoughts in my mind feeding me excuses to not do it. But then I felt my nervousness and realized that…

That nervousness means I HAVE to do it.

If it wasn’t something that I wanted to do (something that mattered to me), I wouldn’t feel that nervousness in the first place, right?

I think we should strive to constantly monitor our emotional state for instances where the thought of doing something makes us nervous, and make it a consistent habit to always do that thing. This way, we are constantly getting outside of our comfort-zone, growing, and acquiring new skills and experiences.


What went well with this challenge:

  • This was my first challenge that was based on a pure random act of kindness. I really felt good and enjoyed doing it. I’ve decided to do more of these kinds of challenges in the future.


  • Despite suffering a disappointing camera issue and losing the first set of footage, I decided to ride it out and challenge again. Even though it took me a couple times, I eventually got the outcome and footage I was looking for. In the end that gave me more time to spend outside my comfort-zone, which results in an accumulation of more social courage, confidence, and experience.


  • As usual, I felt myself pacing in circles, trying to figure out ways to avoid doing the last approach (the successful one). But in the face of that, I realized it was something that I HAD to do. On one hand, avoiding doing it would cause me to make avoiding my nervousness a habit. On the other hand, doing the thing that makes me nervous trains the exact opposite habit – the habit of continually placing oneself in situations outside their comfort-zones, and building up that confidence.

What I would like to do differently next time:

  • Having my camera flipped around and missing good footage is a technical issue I’ve had before (the police challenge). I need to make an effort to be mindful, even when I’m feeling nervous about doing the challenge, and make sure the camera is pointing in the right direction.


  • My situation usually doesn’t allow for this, but it would be nice to get more footage of me doing the challenge from a third party simultaneously. This way, I could get an accurate image of what kind of vibe I’m projecting when I talk to people. For example, what is my body language, nervous and closed-off? Or open and confident. What is my level of eye contact, appropriate for the situation? What are my facial expressions, constrained? Or open, smiley and friendly. I would like to become aware of these habits as well and correct them when possible.

Considering the effort I put into today’s challenge and the nature of it being a purely value offering challenge, and the enjoyment of giving to others, today’s challenge was a lot of fun. I want to do more challenges like these in the future!

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