In 2005, Jonathan Coulton did something most of us only dream about: he left his day job in the name of rock. (Okay, folk rock.) A lifelong musician and computer programmer by trade, Jonathan quickly gained a following with songs about coding, science fiction, and geek culture. (If you need an introduction, check out this acoustic version of his song "Code Monkey.") As a champion of music industry reform, Jonathan makes his music available for free download and use under Creative Commons. According to him, "I give away music because I want to make music, and I can't make music unless I make money, and I won't make any money unless I get heard, and I won't get heard unless I give away music." So far, he's been able to support his career this way (unsigned) for nearly a decade. How does he do it? Ask him—he's chatting live for the next hour.


Update: The q&a is closed. Thanks for all the great questions!

Name: Jonathan Coulton

Occupation: Singer, songwriter, internet superstar

Location: Brooklyn, NY

Current computer: 3 GHz Duo Core iMac; old 15" MacBook Pro

Current mobile devices: iPhone 4S

One word that best describes how I work: Reluctantly


What's apps/software/tools can't you live without?

It would be hard for me to switch from Pro Tools, which is what I've been using as my main recording and production software for years. Ableton Live is an essential little brother to it, and I frequently dip into it when I need something that sounds weird or dirty or random or electronic-y. Superior Drummer has become my new favorite MIDI/Library drum substitute package.

For live performances, even though I only use it for one song (Mr. Fancy Pants), I'd be very sad if my Zendrum ever went away. Oh yeah, [and] my guitar. I mainly play a Martin 000C GTE-16 I bought new about ten years ago, and a Nash fake Tele electric. My latest obsession is the Kaossilator, a little battery operated device with a touch pad that makes crazy sounds. I can spend hours messing around on that thing.

Besides your phone and computer, what gadget can't you live without?


It sounds crazy, but my TV remote. I spent so many years with multiple remotes and universal remotes that were too complicated for anyone but me to use, and then I found the Harmony series of remotes. I've got a bunch of stuff hooked up to the entertainment system: cable, AppleTV, Xbox, Wii, Sonos, a Mac Mini, NAS devices for storage. Anyone who has ever had to maintain a system like that will tell you it's a house of cards. Even the technically challenged grandparent generation can come to my house and, with only a couple of pointers, figure out how to use the television. That's a huge victory.

Pictured right: Jonathan's iPhone homescreen.

What's your workspace like?

A mess. I've got the whole parlor room of a Brooklyn townhouse as my office/studio, and unfortunately it's often filled up with boxes of CDs and t-shirts, along with guitars and cables and the standard studio detritus. My desk is an Anthro, and it's gone through a number of configurations as I've moved the studio from place to place. It functions well as an "answer email" desk and a "record a hit song" desk. I've got a small 4x5 sound proof booth for recording vocals and acoustic instruments, and a pile of guitars and keyboards and gizmos that I can dig through when I'm looking for inspiration.


Pictured above: Jonathan's workspace.

What do you listen to while you work?

I can't listen to music while I work—much of what I do when I'm working is music, so it sort of messes me up. But when I was writing code for a living, I would spend hours going from CD to CD, all kinds of stuff. The other developers and I had stacks and stacks of stuff that we'd trade throughout the day.


What's your best time-saving trick/life hack?

No question, the best decision I ever made was to hire someone to deal with my inbox. At a certain point, my email volume became completely unmanageable. I was spending more time answering emails than I was doing creative work. Now I have someone (I require that they refer to themselves only as "Scarface") who screens my inbox, answers the frequently asked questions, and makes me deal with the important stuff. It's been a challenge to learn how to delegate and let go of things like that, but as a life hack, it's hard to beat hiring someone to do your work for you.


What's your favorite to-do list manager?

I am terrible with to-do lists. When I have a day that really requires me to execute a bunch of stuff, nothing beats a piece of paper on the desk next to my mouse. For long term project management stuff, my assistant and I use Basecamp.


What everyday thing are you better at than anyone else?

Lovemaking. Shhhh.

What's the best advice you've ever received?

Be nice. It's more important than you think.

If you want to catch Jonathan live, he's on tour now! Check out tour dates here.

The How I Work series asks heroes, experts, brilliant, and flat-out productive people to share their shortcuts, workspaces, routines, and more. Every Wednesday we'll feature a new guest and the gadgets, apps, tips, and tricks that keep them going. Have someone you'd kill to see featured, or questions you think we should ask? Email Tessa.