If You Write What You Love, Will the Money Follow?

If you write what you love will the money follow?

By Randy Ross (Portions of this piece originally published on Randy's Blog, The Loneliest Planet.)



If you want to make money as a writer, you're supposed to think of yourself as a small business. With that in mind, I went to see a small business consultant specializing in artists and writers.

His very blunt advice to me:

  • You need to determine if the writing you love is going to be a nice hobby or a real job. 

  • To do that, you need objective third-party confirmation -- from people other than friends or relatives -- that you've got talent.

  • Then, you have to get out there and sell, and sell some more.

  • For most creative types, if you do what you love, the money will NOT follow.

Note: The photo above is my car, which is now old enough to buy its own beer and cigarettes. Instead of buying a new car, I decided to save the money, quit a part-time job, and spend a year trying to earn some dough writing what I love.

I've been following the consultant's advice. To date, I've had enough success to delude myself, but not enough to pay for a bag of groceries.

Got Talent?

Writers can get third-party confirmation numerous ways, including:

I have tried -- or plan to try -- all of the above. Here are my results so far:

  • I've applied to a slew of contests and grants and had no luck with any of the majors. Many of the contests cost money, money that adds up. From now on, I'm sticking with free contests and grants, such as this fellowship grant offered by the Massachusetts Cultural Council.

Note: Two friends have won the grant's top prize of $7,500. I've been rejected once, but will apply again.)

  • I've sent stories and novel excerpts to literary magazines. Though none of the major publications took my stuff, several smaller ones did. Also, I was a finalist in a small, local fiction contest that the organizers said had "dozens of entrants." I received no money, but my piece appeared in two small literary journals. 

Note: I guess in theory, I can say I'm a published fiction writer. However, the small business expert was not impressed and told me to quit noodling around with publications no one has heard of. Agreed.

  • I applied for a fellowship at the prestigious MacDowell Colony. The application ($30) was easy. The rejection I just received was less so. Here's a list of writing residencies.

  • I've been reading my short stories, naughty humor, and novel excerpts at local venues for several years. Recently, I assembled those readings into a one-man show called The Chronic Single's Handbook. Then, I pitched the one-hour show to two fringe theater festivals -- and was accept at both. The consultant was only mildly impressed: One festival chose entrants using a lottery system. The other will cost me $700.

Note: Fringe theater festivals look for new and/or experimental performance pieces. They also give out awards and you have the opportunity to earn money from box office receipts. Note: To prepare for my show, I've hired a theater director, which will cost me about $1000. Average earnings from performers at the $700 fringe festival: $1,500. Don't do the math; it’s too depressing.) A list of fringe theater festivals.

Sell and Sell Some More

The consultant and I organized my writing into two product lines:

1) Self-promotion advice for writers. (Sounds boring, but I have a background in Web marketing and enjoy writing about this stuff.)

2) Humor and naughty fiction.

Here are ways I could make money with each product line.

1) Self-Promotion for Writers


  • Sell advertising. I have a blog called The Loneliest Planet on which I sell ads hosted by Google. I'm currently earning $10 a month. (When visitors click an ad, I get some dough.) If I can increase my page views from the 3,000 a month I get now to 30,000 a month, I'll make some money. Odds of making real money: slim.

  • Sell ebooks: I plan to self-publish excerpts of my blog as Kindle Singles and write an ebook on self-promotion for writers. Odds of making real money: slim

Offline/Old School:

  • Teach/Lecture at local adult education centers, conferences, colleges -- any place that will take me. So far, this looks promising. I approached several institutions in Boston and am scheduled to teach a couple of seminars or speak on two panels. The pay rate is low: $20 per hour of teaching. One of the panels will pay around $200. This is also a good way to promote my blog and ebooks. Odds of making some money: possible.

2) Humor and Naughty Fiction


  • Sell Advertising on Youtube: I've recording myself performing around Boston and then allowed Youtube to post ads at the beginning of my videos. (I've earned $5 during the last year.) Odds: slim

  • Sell ebooks: I'll repackage and self-publish my writing into three short ebooks: humorous erotica, weird travel tales, and excerpts from my novel. I've been selling the novel excerpts off my site using Paypal. (I've made $12 so far.) Odds of making money: slim.

  • Sell audio: Recording MP3 files for sale is relatively easy. Using a mic, you dictate directly into your computer or record to an audio recorder that records to MP3 format, and then upload to your computer. Last year, I spent $80 for a Philips recorder that works pretty well. Decent recording and editing software called Audacity is free but can be a pain to use. Once the files are on my computer, I upload them to a site called, which is like Youtube but for audio. (sales to date: Zip, nadda, bupkis) I also uploaded audio to a site called that allows public radio stations to purchase your clips. (sales to date: zilch, nil, non-existent.) And finally, you can upload your recordings to iTunes for sale as podcasts. (I haven't done this yet)

Offline/Old School:

  • Readings and Performances: I'll pitch more fringe festivals, colleges, and any venue that will have me. Also, readings and performances also offer a good opportunity to sell ebooks and printed booklets of my writing. Odds of making money: possible.

  • Getting a book deal with an advance. Odds of this happening or me making real money: Ha!

The Reality

Chances are, the consultant is right, the money won't follow, and I'll be looking for a real job in 12 months. But right now, I'm having a great time, a time I'll probably look back on wistfully when I'm driving around in my new car.

(This post originally published on Randy's blog, The Loneliest Planet.)

About the Author See other articles by Randy Ross
by Randy Ross

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