The Secret To Making A Living As A Writer: Work For Free

Penelope Trunk writes,

High performers work for free. The difference between working for free because you’re a loser and working for free because you’re a high performer is what you get from the deal.

People often ask me how to become a writer. The answer is to write for free. You won’t get paid for years. I wrote for decades before I saw any money from my writing.
- How to decide when to work for free?

I guess this is what you would call a long term plan for writing success. On the other hand, if you've written for years--blogging, journaling, scribbling on the walls, whatever--you can count that as part of your unpaid apprenticeship.

In any case, let's say someone approaches you with a project, it's something you wouldn't mind doing, but you would be expected to work for free. How do you know whether this opportunity would represent a stepping stone or just one more thing to take you away from that novel you swore you'd finish this year?

I'm reminded of Neil Gaiman's recent commencement address where he compared ones goal, whatever it is, to a mountain. He said, and I'm paraphrasing: If you have a choice to make ask yourself, If I do this, will it take me farther toward, or farther away from, the mountain?

Simple, huh?

What follows is an unholy mashup of Neil Gaiman and Penelope Trunk. Here are guidelines on how to tell whether working for free would take you farther toward, or farther away from, your mountain.

1. Is the path to your mountain jammed with other people or is it an empty thoroughfare?

The more crowded the path, the more attractive free work becomes because it allows you to build your resume.  Penelope writes:

But you know how you can tell when it’s a job no one else wants? It’s really easy to get. If you are having trouble doing the work you want to do then it’s a pretty good bet that it’s not easy work to get.
- How to decide when to work for free?

If it's not easy work to get then working for free can help you fly about the crowds as you work you way closer to your mountain.

2. This job will get you closer to your mountain, but will you starve along the way?

Do your research. Make sure the path you are on really does lead to your mountain and not into a quagmire.

If you're a photographer, taking free pictures for Penelope Trunk's blog makes sense. It's read by thousands of people, potential customers, who will see your work. It's great advertising.

On the other hand, taking pictures for Jane Doe's blog who has 1 subscriber, someone who is currently lost in the subarctic, doesn't make a lot of sense.

3. Will this job help you establish contacts with other people who are heading in the same direction you are?

Everyone is the hero of their own journey and every hero needs a mentor. If working for free will help you meet people you can learn from, perhaps people who would be valuable business contacts for the rest of your professional life, then what are you waiting for?

4. Is the mountain your mountain?

Sometimes we think our goals are the ones we chose when they're really the ones our parents picked out for us, or our society wanted us to have. Perhaps we got swept along a certain path without actively choosing it for ourselves.

Say you want to go into business for yourself. Taking a free internship that will allow you to observe business leaders in action, that will allow you to learn about various aspects of an actual business first hand, could be great experience. Not only if you keep entrepreneurship as your goal, but perhaps as a test to see if going into business for yourself really is your mountain.

Best of luck on your journey toward your mountain.

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- Penelope Trunk Discusses Time Management
- Pixar: 22 Ways To Tell A Great Story
- Kristen Lamb: Don't Let Trolls Make You Crazy