350 good questions | Q 1-8 / by Chris W. Hubbard

One of the most common pieces of feedback I’ve been getting about my podcast is that I don’t interject myself into the show enough. Apparently, people want to know what I think about things. But I like the show the way it is for now. So I need to find another way. And I think I’ve found it.

I was googling around for interesting questions I could ask guests on my podcast when I came across this list of 350 good questions to ask. I loved it. I found myself reading all the questions and then answering them in my head. I realized this could be an interesting way for me to share some of what I think.

So that’s what I’m going to do. This is the first of what will inevitably be 43 or so articles, 8 questions at a time, till I answer all 350 questions.

I encourage you to participate. I get emails and messages every single week about articles I’ve written, so I know you’re reading. But perhaps join me by sharing your own answers to each question as well. You could do this by leaving them in the comments, or in a FB comment. Up to you.

Let’s begin.

Here are my answers from the first 8 questions of 350 good questions to ask.

1 - When you are old, what do you think children will ask you to tell stories about?

This is probably obvious, but I’m pretty sure they will ask me to tell stories about my decision to leave the US and travel the world, live abroad and become a kind of digital entrepreneur. I shared a lot of this story on one of my very first—and admittedly least refined— podcast episodes. You can listen to it here.

2 - If you could switch two movie characters, what switch would lead to the most inappropriate movies?

When I was little, I remember watching the original ANNIE a LOT. I mean, over and over and over. It was one of my little brother’s favorite movies. He would watch it a thousand times and never get bored. He memorized all the songs and would sing them in his sleep. It drove me a little crazy. But I secretly loved that movie, and the songs, as well.

I think it would be interesting to switch the characters of Daddy Warbucks and Annie. Little rich girl adopts an older man orphan. How about that? Reshoot scenes to show a bunch of aging old men living in a group home and singing about “tomorrow.” Feels strangely relevant these days.

3 - What animal would be the cutest if scaled down to the size of a cat?

A giraffe duh. Although I’ve always loved the idea of even smaller cats. Kitten sized cats, that stay mini forever. Somebody has actually been doing this, but only with the legs.

4 - What inanimate object would be the most annoying if it played loud upbeat music while being used?

First thing I thought of for some reason was a toothbrush, but instantly realized what a genius idea that might actually be. Pick up the brush and it not only cleans your teeth but gets you pumped for the day? Keys would great if they did this too. Obviously, a pillow that did this would be problematic.

5 - When did something start out badly for you but in the end, it was great?

Quitting my job recently FELT pretty bad. I’ve been planning to write an article or two about this. I went through a bit of a crisis. But now I’m feeling amazing and have realized I never want to go back to that kind of situation. I don’t know where the “end” is, but things are turning out to be much better than I ever could have expected.

6 - What weird food combinations do you really enjoy?

Durian. With whatever. I just love Durian and that’s enough to weird people out.

7 - How would your country change if everyone, regardless of age, could vote?

I live in Taiwan, and if that happened here there would be a complete revolution. They would ban bushibans, overtime, excessive homework and testing. They would reduce the work week to about 20 hours /week and raise the minimum wage x20. Weed and gay marriage would be legal and everyone would get 3 months of vacation time—paid for by the government—every single year. However cartoon culture might get out of control.

8 - What are some red flags to watch out for in daily life?

Anyone who approaches you with a “problem” they want to point out and connect you to as the cause. These people are everywhere and like vampires, they attempt to infect you and turn you into one of them. That’s how they multiply. Just run, as fast as you can. These are toxic people who want to ruin your day with absurdities. It’s not that it’s implausible you did create a problem, it’s just that 9 times out of 10 the problem lies with the other person. If you simply avoid people who regularly have “problems” with you, things you said or did, you will quickly discover you don’t have any problems and aren’t creating any.

Thanks for reading.
Come back next week
for questions 9 - 16.