The One Question Every Writer Dreads




For most of the past three years, when someone asks me, “so, what do you do?,” I’ve answered, “I’m a writer.”

Usually, they follow-up with, “Oh, that’s kind of interesting, but what do you do to make a living?”

My stomach turns, I question my entire life, nearly have a panic attack, and then go into a lengthy explanation of everything else I do pay the bills — which kind of feels like having to prepare my taxes (which are a nightmare) in front of a stranger at a bar.

For the first time in three years, my answer to that second question is the same as the first. I am making (most) of my income from my writing and speaking. So when I tell someone, “I’m a writer and speaker,” and they then ask, “Cool, so how do you make a living?,” I now answer, “Motherfucker, I just told you. I’m a writer and a speaker.”

This is a beautiful feeling. It kinds of feels like the first time you learned how to ride a bike. You’re like, “Holy shit, I GOT THIS! I’m riding my bike! There are no training wheels on this thing! I’m still alive!”

It may not last forever — it may not last for much more than a month or two, but right now, I can say that I’m paying my rent from my art.

We need a better way of supporting artists, creatives, and entrepreneurs with their work. We also need a better way of openly discussing side-hustles and how to make money while you get started as an artist or creative. First off, if you meet someone, and they tell you they are an artist, writer, musician, creative, or entrepreneur; do not ask them, “So, how do you make a living?”

Who are you, the IRS? Trust me, not a day (or hour) goes by in an artist’s life that they are not freaking out about how they are going to pay their rent. If they are not stressing about it this month, they are stressing about it next month, and if they aren’t stressing about it next month, they are stressing about how they are going to support their family. Artists have enough anxiety in their lives. Don’t fuel the fire. It’s all a writer can do to sit down in the morning to write; they don’t need your buzzkill ass to remind them about the financial futility of their pursuit.

Second, try to engage them about their passion and their dreams. If I tell you I’m a writer, why would you ask about what else I do? Instead, ask me about what it is I’m writing. Ask me why I write. Ask me what it feels like to write. Ask me what I’ve learned from writing this year. Ask me what’s exciting me about my work right now. Increase my creative energy, don’t soak it up. When I meet someone who has just launched their first business, I never ask them, “Cool, so what’s your other job that pays the bills?” I ask them about their idea, I ask them about their business. Why did you start? How’d you get the idea? Where do you see it going in a few months, or years? What’s been the craziest thing you’ve experienced since you started? What’s been your biggest success? Mistake?

Listening to an entrepreneur tell me about their business gets me excited about my work. It creates creative energy for both of us. This is not to say that asking artists about money is off limits. It’s matter of tone and framing. Instead of asking, “So, what’s your other job that pays the bills?,” try, “How do you find time to balance your creative work with making income? What side hustles are best for making some money on the side, while still providing time and mental energy for creative work? Do you recommend quitting a job and pursuing your art full-time, or does the balance of having other part-time or full-time work actually benefit your creative pursuits? What strategies do you recommend for people looking to turn their creative work into a business?”

The answers to these types of questions will support creatives, and empower everyone in the conversation to have the courage to take more creative risks and keep creating, which is what it’s all about.


Smiley Poswolsky is the author of The Quarter-Life Breakthrough: a guide for millennials to find meaningful work. Follow @whatsupsmiley and get free resources at smileyposwolsky.com.