Sharing is caring!

John Challis is a designer living and working from countries such as Thailand, India, and Vietnam. He and I worked together at IBM before he started this period of remote freelance work. I had the chance to catch up with John while he was on a break from his travels and visiting family. During our talk, he discusses how he balances taking risks and taking on new challenging opportunities like World travel.

For the full transcript of the interview and links to the resources mentioned, click here. Check out more videos and interviews, check out our YouTube channel.

What drives you, and what is your eventual goal?

Yeah. So yeah, like you said, we talked about this a bit with your last blog post that we did, but I had some interest in art and some interest in business, and I didn’t know exactly for sure what direction I wanted to go with my life and with my career. So in school, I spent a lot of time exploring different options, doing different internships, different jobs, and trying and figure out what interested me.

So I spent quite a bit of time doing a variety of different things internships with startups, in-house design positions in a design agency. The goal was to try to find something that I was passionate about. Ultimately the goal was to become successful and make with some freedom and autonomy in my work.

Growing up I had seen a lot of different people in my life who were in jobs that they didn’t necessarily like

Growing up I had seen a lot of different people in my life who were in jobs that they didn’t necessarily like. Certain people weren’t passionate about their work. They were just living day to day trying to get by, but not necessarily enjoying what they were doing most of their time.

What’s your approach to balancing risk?

I think we all want some form of security, and so taking risk can be difficult. The key is to take calculated risks. Sometimes I feel like I’m not taking enough risks. To other people, I look like I’m taking a lot of risks.

So I really try to think through risks. Even though I like to do things that maybe aren’t the typical path, I also really try to think through what are the good things and bad things that might happen. And a lot of time I’ll even write that down for any particular decision.

To other people, I look like I’m taking a lot of risks.

I was reading The 4-Hour Workweek and he talks, Tim Ferriss, talks about that quite a bit. What are the worst possible downsides if I made this decision. A lot of times in our minds we think there’s a lot of super negative things that might happen. If we really sit down and analyze things, we can see things like, “I may be a year delayed if I decide to leave my job…”

We always jump to the worst case scenario, like “I’ll never have work or have money again.” But if you sit down and think about it, the worst thing that could happen is if you’ve already made it to this point, someone will most likely hire you again.

I didn’t want to just accept the status quo. So, I wanted to figure things out for myself

Have you always been this way?

From an early age, I didn’t want to just accept the status quo. Kind of I wanted to figure things out for myself. I think if you talk to my parents, they’d probably say the same thing, even a young kid. When I was a kid playing baseball and my day was my coach. He would tell me to do something. I wouldn’t it because I thought there was a better way.

You can find John online here

His blog about his work and travels, Hastyville.



Check out John’s previous interview.

Read about his adventures and lessons from living and working overseas.

Matt Eng

Matt Eng

DesignOps Manager. Based in Austin,TX. Worked with clients such as Alcatel-Lucent, Ogilvy, RBC, Deloitte, Whirlpool, Polycom, Symantec, and Pebble. Matt teaches, mentors, and speaks about design, creativity, and fostering stronger connections within teams.