Day 339 – How To: Escape the Box

27 – 100 Online Brainstorming Tools to Help You Think Outside the Box

You have to be right with being wrong. If you attach too much value to never being wrong, you limit your ability to unexpectedly be right. Thinking outside the box (even if ultimately you have to act inside of it) requires letting go of your filters while you try to come up with new ideas.

And we all carry so many filters with us…



Confirmation bias is the root of all evil. And it is a natural side-effect of how our brains are wired. But that doesn’t mean I have to let myself be subject to it.

The mechanism underlying confirmation bias is ultimately the source of science. What else is science but a series of reinforcing observations that our brains build into theories of how the world works. It is how we learn. It is how animals learn. It is the filter that exposes patterns in reality to our consciousness.

Sadly, it is also indiscriminate. The mechanism throws away “minor details” that cloud the patterns so that they do not drown in the random noise of reality.

But one persons’ irrelevant noise is another persons’ evidence against conventional wisdom. Confirmation bias is the foundation of our intelligence, working against us exercising the intelligence it gave us.

And while evolutionarily, nature doesn’t mind confirmation bias, we should.

And it is hard. Because you have to stay vigilant to a subconscious voice that is trying to make life easier for you by telling you it’s okay to ignore information, “because you are right already”. You have to let go of the convenience.

You have to allow yourself to consider new ideas you know are wrong.

Especially when you are absolutely certain they are wrong.

Take comfort in the fact that if they are actually wrong, they will still be wrong after you have thoroughly investigated them. And if you yourself were wrong, then you will be a better person for having given them a chance.


Cultural and societal norms are really just like personal biases in disguise. Except, they are much harder to shift or escape. You cannot individually give up a norm, you can merely choose to ignore it and hope society will let you get away with it.

You need a certain amount of fearlessness.

Society builds these norms on tacit agreement of what is deemed right and wrong. That doesn’t make it the right right, or the right wrong. It is just the prevailing wisdom of the crowd, and it shifts like a glacier.

And sometimes that shift begins with a good outside-the-box idea that lies within a region of taboo. An idea that proves so useful that a society as a whole has to re-examine its biases to square the utility of the idea with the pre-conceived notion of a norm.

This is also a very effective tool to shift ignorant norms; just find something currently outside-the-norm that would be inside-the-norm in a more ideal future, and then find a way to make people want it. I’m sure there is a whole book in that idea alone.

Seth Godin or Clay Shirky may actually have written it already if I looked.

In any case… for the sake of good brainstorming, set all norms aside. Include in the ground rules of a brainstorming session the idea that there are no taboos, or even better, encourage people seeking out taboo solutions as part of the mix. You can always discard them later. Ideas do not have to be acted upon. They merely need to be considered before being discarded.

Sexism, Racism, Ageism, Oh My

Ah, the battle-grounds where personal bias and societal norm bleed into each-other; feed and reinforce each-other.

You grow up in a soup of societal biases that seep in through your pores throughout your youth as your brain builds a model of the world. Then, if you’re not wary, you become a part of the problem as you start acting according to the biases that society has weaned you on.

And even though I have always been a contrarian who doesn’t take much stock in the norms society has chosen to set, I’m not free of the potential effects of the biases I grew up with. And you should never feel bad for the first thought or first instinct inside your head. As long as the second thought is to challenge it appropriately.


No Stupid Ideas

I have already alluded to this earlier.

Set the ground-rules clearly up-front. Even if you are brain-storming by yourself, remind yourself of the ground-rules to give yourself permission to go far and wide for ideas. Use Oblique Strategies to widen the field further if you feel your ideas remain constrained.

Explicitly set a time segment purely for idea generation.
During this time, everything is written down and nothing is discussed.
Cut off anyone that tries to anyway.
Encourage participants to go broader, weirder, deeper with ideas.

And if you are the only participant… remind yourself!

You’ll be surprised how many ideas you can create in 5-10 minutes if you do not censor or discuss anything during this period.

Think Later

The pay-off for not “thinking” about the ideas is that you will have a lot more of them by the time you do get to the thinking. Once the new ideas dry up, or you run out of time for them, everyone gets to argue and criticise as needed.

Eliminate ideas that are clearly inappropriate. Eliminate all the -isms as quickly as possible at this stage, ideally with discussion of why they were inappropriate in the first place. This is where education happens if necessary.

Eliminate ideas that have flaws in them if nobody can think of a work-around. Eliminate ideas that are too expensive. Too ambitious. Too intractable.

But do not eliminate blindly.
Have solid reasons.
Defend others’ ideas till they can no longer stand.
Ideally record the discussion so that later you may re-examine old ideas in light of new facts.

Try, Try Again

And if for any reason you didn’t get the winning idea… don’t give up.

If the idea-generation got shut down by discussion of a pertinently offensive idea, finish the discussion, adjourn the meeting and re-schedule for later. If thinking eliminated all the ideas you came up with as infeasible, do not try again immediately, adjourn and re-schedule.

Every dead end.

Eventually you will find the winning ideas.

And you probably already do a variant of this inside your head throughout the day as you make decisions. Challenge that process to consider a wider range of ideas as well. And challenge yourself to be more critical of the ideas you came up with. If they survive they will be all the stronger in the face of any external scrutiny.