There are 3 things that have really helped me with idea generation. Feed the subconscious, record and retrieve inspirational moments and ideas and find patterns in "good ideas".

Feed the subconscious - Spontaneous ideas are usually the best ideas and one of the best ways to fuel your brain with material for spontaneous ideas is to have many diverse life experiences swimming around in your subconscious. When you brainstorm you will have more ideas, make more connections, associations, analogies and in a nutshell you will have more "dots to connects". Curiosity, inspiration, play and discovery are essential to having great ideas. Personal work will allow you to explore, play and discover. We experience the world through our 5 human senses (Sight, Touch, Smell, Taste, Sound), so spend some time celebrating them. Do it this week! Each day pick one of the 5 human senses and focus on experiences specific to that sense. The more human senses you can engage the more memorable the experience will be.
Record and retrieve inspirational moments and ideas - The best ideas usually come at inconvenient times, such as, walking the dog, taking a shower, waiting in line at the supermarket, etc. The key is to record these ideas and moments of inspiration so you can later develop them into something great when you are in the right place and have the time. Sketchbooks are great for recording and developing ideas, but not so great for retrieving them. I wrote my genius idea in. A solution for this problem are programs like: Evernote, OneNote, Google Docs, etc. I prefer OneNote.
Find patterns in "good ideas" - By looking at various ideas we can classify them into "idea categories". We then can use these categories as a framework to help explore any particular "subject". Confused? Below I explain a little more in-depth.

Define

So say you are creating an illustration about "music piracy". First, define your subject. music and piracy. The better you define what you will be brainstorming about, the more possible associations you will have to work with. Here are some ways to help you define your subject.

Function - Does it have a function? Is that function part of its identity? example: Shovel=dig, Telephone=talk, bridge=cross, Madonna=sing, etc
Physical Characteristics - Are its physical characteristics a key part of its identity? example: water=clear, sun=fire/hot, knife=sharp, ice=cold, etc
Non-Physical Characteristics - Are its non-physical characteristics a key part of its identity? example: Mother Teresa=unselfish, Albert Einstein= intelligent, shark= dangerous, etc
Human senses - When you think about your subject in terms of the 5 human senses, Sight, Sound, Smell, Taste, Touch , are their any characteristics that have a strong association with a particular sense? example: ice=cold, grass=green, lemon=sour, jalapeño =spicy, jackhammer=loud,etc
Association - A big part of editorial and adverting illustration is playing with visual cultural symbols. What are the first things that come to mind when you think about your subject? example: racism= swastika, money=dollar sign, crying=tears, etc
Can & Can’t / Is & Isn’t - Another good way to define your subject is to think of things that are the opposite of it. example: order=chaos, peace=war, snow=sun, etc

Idea Categories

Once you have "defined" your subject you will now have lots of material floating around in your head to work with. By looking at various creative ideas we can classify them into "idea categories". With your subject in mind look at each category and see if any ideas come to mind? Are there symbols I can merge to illustrate "music piracy"? Can I change a physical characteristic of a pirate to make the association of music? etc.

Merge
Word Play (Pun,Rhyme, etc)
Juxtapose / context
Physical Characteristics
Non-Physical Characteristics
Comparison / Analogy
Function
Can & Can't / Is & Isn't
Time / Consequence
Irony / expectations / literal meaning
Parody

Note: lots of ideas have elements from more than one idea category.

Below you can see some explanations and examples of the idea categories I came up with. I am sure you can think of more categories to create your perfect idea category framework.

The real value in this exercise is to become aware and recognize patterns in successful ideas.

Browse through these websites and see if you start recognizing patterns in ideas and can come up with your own "idea categories".

Merge

In order to describe a new concept we often combine two or more familiar concepts/symbols. For example, when the train was first invented it was described as an "iron horse" ... because it was strong like iron and functioned as transportation like a horse. This helped people understand its function and characteristics. Other examples include "email, spork, etc"

Mr. E.T. by Andrew Jeffery Wright.

Juxtapose / Context

Put something familiar in a new context to give it new meaning

Advertising Agency: Güzel Sanatlar Saatchi & Saatchi, Istanbul, Turkey

Word Play /Rhymes / Puns /etc

Play with words

Focus Group & Focus Groupies By Graham Roumieu

I'm down by Lonely Dinosaur

Pentagon, Hexagon, Oregon by Lonely Dinosaur

Physical Characteristics

Change a physical characteristic. Exaggerate it, make it bigger, smaller,change its material, make it translucent, make it glow, make it rigid, make it fluid, make it shinny, etc

Advertising Agency: Grey, Santiago, Chile

Advertising Agency: JWT, Milan, Italy

Comparison / Analogy

Make an analogy or comparison to show a correlation.

It's the Hat! by Advertising Agency Serviceplan Hamburg

Function

Change the context of its normal function. Replace the tool known for a common function.

"We are already open!" Advertising Agency: TBWA\Central Asia, Kazakhstan

Spun Dry by Glenn Jones

Can/Can't and Is/Isn't

Image by Banksy

Time / Consequence

rearrange the order of events, outcomes, objectives, etc

Like boxes of shit in your house? Get a cat

by THE ONION

Irony / Expectations / Literal Meaning / etc

Clown Gun by Christian Northeast

Space Defenders by Glenn Jones

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More suggestions for creative blocks

What works for you? Leave your suggestions in the comments

change of environment (take a random bus)
exercise (run, bike, walk, gym, yoga, etc)
notice the mundane - listen to something new, read something new, eat something new, try something new, buy different brands (toothpaste, soap,etc), use your opposite hand to do common tasks
have a conversation with an old friend, a new friend, a strangers, etc
wake up at a different time, go to bed at a different time
look through old photos and sketchbooks

Thanks for reading! More articles here.

-Nate Williams

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Ideas for Generating Ideas