Reuben Ingber

INTRO: Reuben Ingber is a front end web developer and designer based in Manhattan. He is also creator and host of the podcast How to Hold a Pencil. We scheduled a quick phone interview back in June and I asked him all kinds of questions about hosting a podcast and balancing side projects with a full-time job. His pursuits stem from a genuine curiosity for his craft and the people and ideas surrounding it. He is a self-taught developer and his podcast focuses on interviews with designers and developers with similar stories. The summary on his website sums it up nicely: 

"How to Hold a Pencil is an interview show with self-taught designers and developers. Its purpose is to inspire and empower individuals who are already learning to make things and to help others get off the sidelines. The stories are meant to help people find and explore different paths towards education, in the hopes that more people will take the bull by the horns and go out make something."

The more we talked, the more evident it became that Reuben pursues projects based on deep desires to learn and put great things out into the world.

Environment + Geography

Reuben grew up in New York, went to school in Washington D.C. and eventually moved back to the big apple. He takes advantage of being in a creative hub like New York by going to meet ups, attending events and trying to get to Creative Mornings every month. "I think being surrounded by other people who are in your industry or field is certainly helpful. And being surrounded by companies and creative companies is helpful because your opportunities are greater."

After leaving D.C., he took some time to freelance and figure out what his next move should be. "I had no idea what I was going to do. I was scared shitless, but I knew it was going to work out. I knew that I would figure something out or do whatever it took to figure that out." Looking back, he's glad he made the move and would do it all over again.

Media + Motivation

When coding or writing, Reuben listens to soundtracks, techno or instrumental music. When commuting to work or doing mindless tasks, he listens to podcasts. It isn't often that I get to ask a podcast host for a list of their favorites so this was really exciting:

  1. Build and Launch
  2. Design Matters
  3. Entrepreneurs and Coffee (a new listen)
  4. The Podcast Dude
  5. Slate's Whistlestop
  6. The Whisky Topic
  7. 99% Invisible
  8. Developer Tea
  9. The East Wing
  10. The Gently Mad

The motivation for personal and side projects stems from a desire to learn or a passion for what it is. "Whether that's development or design or writing, I have this drive to learn new things." For freelance work, he tries to find something he's passionate about or something that involves learning a new skill. "I've grown confident enough in my skills where I can say, 'Sure, I'll do that for you' even if I've never done it before."

Current Work + Process

His workload includes a full-time job at Business Insider, freelance projects on the side and How to Hold a Pencil. We related over the challenges of balancing projects and ways to carve out the time. "My freelance work is done mostly at night and on weekends. I try to do podcasting at night, in the morning or whenever the free moment exists to edit." 

When working on a big freelance project, Reuben's schedule might look something like this: 

  1. 6:00 a.m. Wake up and get two hours of work done
  2. Commute to full-time job and work an eight hour day
  3. Commute home, eat dinner and work until midnight
  4. Repeat, repeat, repeat for three weeks 

Reuben describes his work in one of two ways:

  1. "If it's my parents or my parents' friends, I say, 'I build websites.' I also tell them I'm work at Business Insider. And they're like, 'Oh, you work at Business Insider and you build websites. Done.'" 
  2. "For people our age, I explain that I build websites, I freelance, I design, I podcast, I do a bunch of stuff."

Since most of Reuben's work lives in the digital world, I was curious about any analog projects he might be pursuing on the side. "About three or four years ago, I started to run and that's sort of become my analog project. It's my time to clear my head and think. There are a lot of analog and physical projects that I would love to work on, but I live in a Manhattan apartment and I don't have the space. I would love to build things, I just don't have the opportunity to do it. I consider running an analog project. It's one of those opportunities to focus on one thing."

Biggest Surprises from How to Hold a Pencil:

  1. "The biggest surprise is the fact that people are so willing to come onto the show. That I've been able to talk to people like Debbie Millman, Chris Coyier and these people that are huge in the industry."
  2. "When I was publishing consistently, I was getting 700-800 listens per week. Some episodes have reached over 2,000 downloads since posting."

Biggest challenges from How to Hold a Pencil:

  1. "Keeping to a schedule. When you you say you're going to post a podcast a week and you're doing it on your own, there's a lot to do."
  2. "Acquiring and maintaining sponsorships. After awhile, getting those sponsorships was really difficult and took a lot of time and energy. It was a whole process and I just wanted to get back to having conversations with people."

Whether you're new to coding or just looking for the inspiration to get outside of your comfort zone and expand your skill set, How to Hold a Pencil is well-worth checking out. Two of my favorite interviews are with Lara Hogan and Lee Rubinstein

For more of Reuben's work, check out his website and Twitter.