Brainstorming Tips for Freelancers

I am often asked where my ideas come from. I joke that coming up with ideas is easy. Coming up with good ideas is hard. Coming up with ideas good enough to sell? That’s extremely difficult. But it is a required skill if you want to thrive as a freelancer in a creative endeavor.        

Sometimes ideas pop into my head unprompted and I’m at a loss to explain where they came from. More often, my ideas come because I intentionally seek them out. Brainstorming is essential to that. Here’s how I do it.

Set aside time for it

I don’t follow a strict schedule of, say, brainstorming every Tuesday at 1 p.m. or anything like that. I block off a few hours on my calendar a day or two in advance, use that time to come up with a whole slew of ideas at once, sell as many of them as I can, work on them for a while and then start over. Some days, for reasons I can’t explain, I feel drawn to brainstorming. I indulge that feeling when it hits me.

Stay ahead

I have found it useful to brainstorm while I’ve still got plenty of work to do. If I wait until too long to brainstorm, the ideas feel panic-driven and it’s much harder to evaluate them.     

Start with an end in mind

The term “brainstorming” suggests a loose, follow-your-muse way of thinking. But I format my sessions fairly rigidly by focusing on a very specific topic.

If you’re a songwriter, maybe you start the process by thinking of the artist you’d like to perform the song. If you’re a painter, maybe you start by imagining whose home your painting will hang in. As a freelance magazine writer, I start by focusing on the client I want to sell a story to. That gives me guard rails to stay within.

The narrower the subject matter, the easier it is to stay focused while brainstorming. For example, I write often for NASCAR.com. If I brainstorm for them and come up with an idea that doesn’t involve four tires and a steering wheel, I set it aside.

For this story, I basically turned a to-do list item into an idea: “Brainstorm Indy ideas” became the idea itself.

The reason I do it this way is that an idea is useless until I can imagine where it will be published. Last year, I visited my 50th state (Hawaii). I had been working toward that total for years and had long wanted to write about it. But it remained an unpitchable idea because I couldn’t figure out which magazine to sell it to. Finally one day the idea morphed from a travel story to a goal-setting story. SUCCESS Magazine is one of my best clients, and the editor loves ideas like that. This process justified my narrow-focus brainstorming philosophy: I wrestled with trying to figure out what to do with the 50 states idea for months, and from the time I thought of it as a SUCCESS Magazine story to selling it was less than a day.       

Clear your mind, put your phone on airplane mode, move your body

I do my best brainstorming when I’m either hiking or riding my bike. I go to familiar trails/routes because when I hike or ride on an unfamiliar route, I use up valuable brain power in following the trail and absorbing my surroundings.

Before the hike or ride starts, I decide which client I will brainstorm for. I think about recent stories I have written for them, conversations I’ve had with the editors, and any other foundational issues (lead time, style of writing, how they use art, etc.) to get me thinking about the target publication. Once I start moving, I focus on ideas. My brain flits around, of course, but I try to catch an idea and examine it as closely as possible.

Use prompts

To kickstart my brainstorming, I often ask my editors questions. What kind of story haven’t you had that you want? Or what theme issues do you have coming up that I can think of ideas for?

For my sports clients, anniversary research is an endless source of ideas.

Other prompts include, but are not limited to:

What do I want to learn about?

I am a Theodore Roosevelt fanboy, so I sold two stories about visiting the area of North Dakota where he once lived. I’m fascinated by organ transplant, so I have written several in-depth stories about it.

Where do I want to go?

I write for several regional magazines, so I focus on places in their coverage areas.

What’s on my bucket list

I learned by selling a story about trying to get my first hole-in-one that a successful bucket list idea requires brainstorming two things at once. There’s what the story is about, lowercase, which was trying to get a hole in one. And there’s what the story is ABOUT, uppercase, which was persevering toward a hard goal. (Full credit, I first heard the two explanations from Tommy Tomlinson, a friend who is an extraordinary writer.)

Those ideas aren’t going to remember themselves

I used to carry a notebook with me everywhere I went so I could jot down ideas when they occurred to me. I’ve stopped doing that only because I use my phone instead and send myself emails. I leave them unopened so they stay at the top of my queue until I do something with them—either pitch them or ditch them. I’ve heard of writers who keep notebooks next to the shower because they get so many ideas in there. You can also try Indy's tasks tool to keep track of all your ideas. Write each idea down as a task and leave it until you do something with it.

Review your previous work

Think of past ideas like stepping stones. By standing on one, you can plot what your next step will be. Ask yourself two questions: How can I make another rock similar to this one? And where can I go from this rock? If you’re a clothing designer, maybe that means fashioning pants to go with your most recent shirt. If you’re a novelist, maybe it’s a sequel or a spinoff.

The best example I have of this is the brainstorming I did after I wrote about the crazy things NHL dentists see. After that was published, I pursued two separate tracks, each of which answered one of the above questions.

After I asked myself, where can I go from this rock? I sold a profile of one of the NHL dentists to his alumni magazine.

After I asked myself, how can I make another rock similar to this one? I profiled the doctor who travels with the Professional Bull Riders and the physician’s assistant who takes care of NASCAR drivers and pit road crew members. Next up, I hope: The people who work in the medical tent at Tough Mudder, Spartan races, and other obstacle course events.

Imitation is flattery … and a productive way to brainstorm

I got an email newsletter from a financial planner about a month ago. The subject line was something like, “The To-Don’t List for Investors.” My first thought was, that’s a clever subject line. My second thought was, how can I borrow it? I quickly brainstormed ideas. I settled on a story that would fall under the headline, “The To-Don’t List for Freelancers,” which I turned into an assignment for this publication. There’s a line between borrowing and stealing. Don’t cross it.

Reward yourself

This is difficult but crucial work. The rewards — the solid story, the paycheck, the acknowledgement of a job well done — don’t come until much later. I “pay” myself for good ideas. If I come up with something I’m fairly certain will sell, I’ll extend my hike or bike ride so I can keep enjoying the outdoors, or treat myself to a mocha on the way home, or knock off work early and take my kids to the park.

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