Writer Wednesday: Jack Cheng

Some people are born to set roots and others are born to roam the world. Jack Cheng is of the latter kind and you just need to see his Instagram to see how much of the world he has explored. It’d be enough to recognize that Jack is a talented writer, his first novel These Days is a great example of how well and real he can write. The thing is that writing is just one aspect of Jack and his professional trajectory and life journey is as interesting as his stories.

Here’re a couple of questions so you can get to know a little more about Jack.

1. Hi, Jack. So happy to have you as part of Writer Wednesday. Why don’t you give us a quick tour of what your professional trajectory has been like so far in your life?

Every career I’ve had started as a hobby. In college I was studying communications and economics but goofing around on Photoshop contest websites like Worth1000, and that helped me land an advertising internship (which was how I met you!). I moved to New York after I graduated and while I was working as an art director I spent a lot of spare time blogging and building websites. I quit my last ad job in fall of 2008 and freelanced for a while, then started a small design studio building websites and apps with a couple of friends. Around that time I also started working on a novel. I’d come home from work exhausted and spend an hour or two in front of the computer and then pass out in bed. At some point I realized I enjoyed writing so much that I’d be willing to move back to Michigan and live out of my parents’ basement to keep doing it, and I couldn’t say that about my day job.

I was telling all this to a friend over ramen and he was like, Why don’t you quit? And I was like, Why don’t I quit? At that point I had a second draft of my novel and was ready to launch the Kickstarter campaign to fund a print run. The campaign was a success; I hired an editor and went pretty much full time on the book, and shipped it to my backers nine months later.

I’m working on my second novel now, living in Detroit (though I do have my own place) and I freelance every once in a while to pay the bills.

2. What places have you visited in the world and which would you recommend as your top 3 places people should visit?

I was born in Shanghai and go back pretty often with my mom and brother because my dad’s job has him there for most of the year. Recently we’ve been doing a family trip every Christmas holiday, and most this past year went on a cruise of the eastern Mediterranean. I’ve been on every continent except Africa and Antarctica.

My top three are all part of trips that effected huge changes in my life, and as I list them I realize, maybe unsurprisingly, that they were all solo trips too: Kyoto, Japan (my first time traveling alone), New Mexico (part of a monthlong road trip two summers ago), and The Sacred Valley in Peru (in February of 2014).

3. How has being Asian impacted your life on a personal and professional level?

We moved from Shanghai when I was five and I grew up very much American. There’s discrimination, but a lot of it is unconscious stereotyping, even well-intentioned at times, and the most overt forms of it I’ve experienced have come from hormone-ridden teenagers. The new show Fresh Off the Boat is not far off from what it was like for me growing up. My parents made me go to Chinese school on Saturdays and I think anything your parents force on you at that age you automatically reject, and it’s taken me half my life to start developing a natural interest in where I come from. There are doors that I'm on the verge of opening.

4. What was it like writing and presenting These Days?

It was the best thing I’ve ever done. When you finish a monumental project like publishing a book, it makes you feel confident you can handle other monumental projects too. At least, it did for me.

5. You had a great Kickstarter campaign, how would you describe the reaction to the campaign and what can you tell us regarding that experience?

The reaction was great. When the support came in I realized how reciprocal the project was as a whole. Even though it was fiction I was writing about what I’d been living and breathing for years—advertising, design, tech—and because I was living and breathing those things, the audience for my book was an audience of people I already knew and were friends with.

6. What’s China like and how has it influenced you in the way you see life?

China is massive and bewildering. Things feel different every time I’m back in Shanghai. There is a kind of mob mentality there that reminds me at times of the Internet at both its best and worst. If you're interested in modern Chinese culture, I recommend reading China Smack, which posts a daily story that's trending in Chinese social media (along with comments) translated into English.

7. If you could transport yourself into a book by touching it, which stories would you like to visit and why?

My gut reaction here is to say sci-fi because OUTER SPACE. But I’d also like to go the other direction, feel what it really felt like to live in the past. It’s like, Thoreau complained about newspapers and gossip but did it feel as out of control back then as the Buzzfeedy internet does today? These are things I would like to know.

8. You’re a super hero and you have a super-secret lair. What’s in it and how do you access it?

If I were a superhero then I would able to fly, and if I were able to fly then my lair would either be in the clouds or on a secluded mountain with a view overlooking a valley. It would have a desk, something to type on, a notebook and pen, and a supply of healthy delicious food. In other words, everything I have now in Detroit, minus the flying.

9. You’re commissioned to design the most ridiculous obstacle course in existence, what are the five obstacles people have to face and what’s the prize at the end?

1. Voltron of all your ex-partners
2. Ten hours in a room with your biggest vice
3. Being in an episode of Black Mirror
4. Michigan winter
5. Writing a novel

The prize would be the fortitude gained from finishing the obstacle course.

10. If people don’t know Jack and want to remedy that, where do they find you and what’s next for you?

Every Sunday I send out a weekly newsletter, usually three or four paragraphs on something that pertains to whatever I'm writing or learning. I’m also @jackcheng on the tweets.


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Some people live life on autopilot. Jack is exactly the opposite of this. Thanks to him for taking the time to let us get to know him a little better and to you for reading.

Cheers,