A 2009 Tax-Time Interview with Roni Deutch

I recently did an interview with The Agony Column’s Rick Kleffel, and provided tax tips for people who used to work in corporate jobs, and are now working as part-time artists and/or entrepreneurs. You can listen to the full MP3 here, or find the author’s summary below:

As an interviewer, I try to avoid agendas when getting ready to speak with an interviewee. If someone wants to know in advance what questions I'm going to ask, I'll inform them that they'll hear them when I speak them in the interview. I research the work, write up the questions and present them on the spot. But for Roni Deutch, I took a different approach.

It's tax time and I didn't want to have an interview that was as long as the tax law books and just as boring and unfocused. I told Roni that when we spoke, I'd be asking her about a very specific situation — I wanted tax information for those of us who had heretofore worked in pretty much simple, corporate jobs but had ended up working as part-time artists and entrepreneurs. It's pretty much a shock to go from handing over a couple of W-2s — or entering them into some horrific tax program — to keeping track of expenses, knowing what you can deduct and even just preparing to collect all the crap you need to present to person qualified to complete the paperwork for you. Deutch nails every bit of advice you need in about 20 hard-driving minutes, which you can hear via this linked MP3 file.