This post on Idea Generation is the 2nd post in a series of no-nonsense tips for starting a revenue-generating side project from scratch. Subscribe to receive more of these.

Years ago a group of friends and I interviewed a seasoned entrepreneur. He regaled us with war stories of launching startup after startup, each one more successful and interesting than the last.

Ideas oozed from his head like a damn entrepreneurial Oracle at Delphi. So many ideas – too many ideas – that he started throwing some to us with like Oprah throwing away cars. You get an idea! And you get an idea!

Eventually it became too much for one of my friends. He blurted out:

“But where do you get your ideas from?!?”

We erupted in laughed. What a stupid question!

But did we really know the answer? Where do ideas come from?

A decade later, I’m more empathetic to my friend. Having helped lots of people start their own entrepreneurial endeavors, most hopeful founders I meet fall into three Idea camps:

  1. “I have too many of ideas. Which one do I pick?”
  2. “I have this one great idea that’s going to be huge. How do I make it happen?”
  3. “I have no ideas. Where can I find some?”

If you fall into camp #1 – too many ideas – my previous article Rule #1: Don’t Start From Scratch might help clarify which ideas you should run with now. (In short: start with an idea in which you already possess some of the skills / connections / interests.)

If you fall into camp #2 – one big idea – hang tight. I’ve got a post coming for you. (But in short: start building the first embarrassing version of your idea today, don’t get too hung up on the idea itself, and focus instead on solving a problem. And stay open to how you might solve it. In other words: ruin the perfect idea in your head as quickly as possible. Otherwise you’ll risk spending years waiting for your perfect moment with not much to show for it.)

And if you’re like my friend and fall into camp #3 – no ideas – this post is for you. Let’s demystify idea generation and help you generate a few exciting ones.

where do ideas come from

Idea Generation: Where do ideas come from?

Steven Johnson dedicated a season of his life to researching this very topic for his book Where Good Ideas Come From and TED talk of the same name. (Here’s a 5-minute video recap.)

Blinkist summarizes his book in two sentences:

“…Innovation thrive(s) in collaborative networks where opportunities for serendipitous connections exist. Great discoveries often evolve as slow hunches, maturing and connecting to other ideas over time.”

In other words:

  1. Create environments to encourage serendipitous connections, and
  2. Be patient – some ideas just take time.

Insightful, but what a buzzkill! What if we don’t have time for “slow hunches”? What if we don’t have the resources or desire to create environments for serendipitous connections? What if we want to start something now?

I come bearing good news. We can speed up the process of idea generation. Not by serendipitously and slowly generating new ideas, but by taking old, crappy, boring ideas and creating something new with them. Not over years, but in seconds.

If Rule #1 of Starting a Side Project: Don’t Start From Scratch is good news, Rule #2 is better news: We don’t need to make something new.

Start Your Side Project Rule #2: Don’t make something new.

By all means, if you have a Zero to One idea that will revolutionize the world and help it move forward, please go build that. 

But I’m here to let you off the hook: It’s okay if you’re your side project doesn’t occupy space beside Musk, Curie, Bezos, and Thiel. It’s okay if your project doesn’t seek to change the world. It’s okay if your project simply aims to shift your world.

Revolutionary is overrated. After all, most “new” ideas aren’t exactly new; they’re a combination of two or more existing ideas combined in unique and different ways.

“Truly groundbreaking ideas are rare, but you don’t necessarily need one to make a career out of creativity. My definition of creativity is the logical combination of two or more existing elements that result in a new concept. The best way to make a living with your imagination is to develop innovative applications, not imagine completely new concepts.”

–Stan Weston, creator of GI Joe
This is a real thing. The Roller Buggy (Bored Panda)

Examples of not-new new ideas

Stan Weston created GI Joe by combining two unrelated things: Dolls x Boys (& Guns) = Action Figures.




GI Joe

This seems to be the rule rather than the exception. Look around and most “new” ideas are simply “two or more existing elements” combined to create a new concept.

What is Sofar Sounds other than intimate gigs in people’s homes? 



What is Tony Chocolonely other than chocolate with bold branding that gives a shit?

side project chocolate



tony chocoloney

What is the Zero Waste Christmas Market other than a Christmas market for earth lovers?

christmas market


zero waste


zero waste christmas

And what is Writers’ Hour other than Peloton-style accountability for writers?




writers hour

Idea Sex: Coming up with your “new” side project

“Wit is the sudden marriage of ideas which before their union were not perceived to have any relation.”

–Mark Twain

Mark Twain calls this “marriage of ideas” wit. James Altucher calls it “idea sex.” And he swears by it to “Make billions. Help millions. Make people happy.”

Let’s experiment with idea sex and generate some ideas for you to run with.

Your turn:

  1. Take the lists you’ve already generated in Rule #1: Don’t Start From Scratchwho you are, what you know and who you know – including interests, frustrations, skills, experiences, networks, and communities you’re connected to.
  2. Rewrite each item you’ve listed on a separate post-it note. Place the post-it notes in front of you and shuffle them around.
  3. Pick two or three random post-its. It doesn’t matter which they are.
  4. Brainstorm a list of 10 wild, weird, and wonderful (or terrible) things you could create involving two or all three. How might you combine those together to create something “new”? Don’t stop until you hit 10 ideas. (Can’t generate 10 ideas? Then generate 20. Bad ideas are good ideas too.)
  5. Repeat this with other items on your list. Don’t stop until you hit 100 ideas of things you could start.

Congratulations! You’ve just had idea sex.

By smashing a few unrelated things together, you’ve generated a list of “new” ideas you could run with.

And it’s exactly how London’s Zero Waste Christmas Market came about.

Christmas x Sustainability x Running Events = ???

Melanie Fisher loves Christmas. That’s post-it #1.

Each year at Christmas, she’s torn between her love for buying gifts for her friends and family and the negative impact consumerism has on the environment. She cares about the sustainability of Earth and is frustrated that we’re destroying it. That’s post-it #2.

She also has experience organizing large-scale events. That skill is post-it #3.

Christmas x Sustainability x Running Events = Zero Waste Christmas Market.

Mel’s “idea sex” idea: What if I created a pop-up sustainable Christmas market in London? Host independent brands who are participating in the circular economy and invite individuals who care about shopping sustainably?

What started as a wild idea turned into hundreds of earth-lovers showing up to shop sustainably, and the spark of a new career for Melanie.

Tips to Build Your Idea Muscle

Still struggling with this idea generation stuff? Two things might help:

  1. Find an idea buddy or small group of friends to generate ideas with. Seth Godin and Chip Conley – before either of their fame and success – famously met weekly for idea brainstorming sessions in college.
  2. Strengthen your idea muscle with practice. James Altucher recommends generating 10 ideas a day on random prompts to strengthen your idea muscle.

Or take Austin Kleon’s tip:

For your side project, don’t create something new.

Instead, combine a handful of things you already care about, assets you already possess, people you already know to create something unique, valuable, and most importantly, interesting to you.

Coming up with new ideas isn’t magic. It’s multiplication.

But are any of these ideas any good? We’ll explore that next.
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✍️ Written during Writers’ Hour

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