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How to Get Exponentially Better at Generating Ideas

A Framework for More Original and Productive Thought

It is impossible to overstate the importance that thinking has on our work and life. Being able to think well is the single most important factor in being more productive, less stressed, and achieving worthwhile goals.

The great tragedy is that when we’re busy (which we all always are), focusing on our thinking is the first thing we abandon. And this is, indeed, a tragedy. When we fail to set aside time to think — really think — about our work and our lives, we fail to live and work intentionally. When that happens, we fail to achieve the things that would truly fulfill us.

Even if we set aside time to think, if we don’t do it in the right way, we can still fail to harness the benefits of it. In order to do the kind of thinking that will boost productivity, engagement, and yield original ideas, we need the right framework. We can’t simply “think deeply” or “think differently”. We need to structure or way of thinking in a certain way. We need to think wide at times, and deep at others. We need to change the way we think about thinking.

So, thinking deeply is one thing, thinking broadly is another, and thinking differently is yet another. But in order to do that, we need to think freely. And doing that is not as simple as it may sound. I intend here to dive in to exactly what I envision that to be, and how to begin doing it.

Going Beyond “Deep”

I’m a fan of Cal Newport’s book Deep Work. There is a lot of great material in it. Among the heap of tips for doing great work is something called a “Roosevelt Dash”. The nut of the concept is this: when you want to do a task or project, you can force deep focus on it by taking the time you’d estimate it would take and reducing it substantially. Then just get to work, and don’t move away from that work until you’ve finished.

Using the dash effectively requires you to do a few things: take your deadline seriously, and remove yourself from the natural flow of distractions, hunger, thirst, stretching, etc. Basically, when you go, you go hard. This, Newport says, will force you to also go into a deep focus on your work.

I love this idea, but it doesn’t exactly work when you don’t have your work defined for you — when you need to come up with ideas. Here’s something that I realized in that regard: going deep is not the answer to coming up with cool new ideas. In fact, going into deep focus is antithetical to coming up with new ideas.

In short, it does no good to go deep if you haven’t gone wide.

Going Wide

Focus is great for most of the work that we do. That’s because most of our work is by and large already defined — we know what we have to do. There is a spectrum of how well-defined work is. Some is pre-packaged — read to just do. Other work requires a lot of thought and preparation before even beginning it. But usually — no matter the type of work you have in front of you, it has pretty clear constraints.

For example: You may not know exactly what the end-game is for the presentation on Q2’s profits, but the constraints are clear that it has to say something about Q2’s profits. Deep focus can help you here because you have an idea of where you’re going. Most destinations on the map are not live options . You’ve got a general location of your destination, you just need to find the route by which to travel there.

When we are just trying to drum up ideas, the map is totally open. Any place on it is a potential destination for us. The more we can align our thinking to reflect that, the better we’ll be at generating ideas. As I have heard David Allen say many times, trying to brainstorm with the focus of having a “good idea” is actually counterproductive. Simply put, aiming for a “good idea” is actually a terrible idea.

The Practice of FREE PLAY

So here’s a better approach: free play.

The concept is simple: wander around in as wide a mental space as possible, as freely as possible for some designated amount of time. Encounter as many thoughts as you can, noting as many as you can. As you end your time wandering, select the ideas you’d like to try on.

I’ve laid out a structured account of Free Play elsewhere, as it applies to teaching kids to think creatively. But the simple gist of it is that it is:

  • self-directed (not mandated by some goal, activity, or other person)
  • focused not on results but on exploration
  • imaginative, non-literal, and removed from demands of the rest of the world
  • involves an active, but unstressed (not under the gun) frame of mind

I intend to write just a little about this process now, with more to come later. Mostly, I’m doing this because I’m teasing out the idea of free play in practice, but also because it’s got a lot more to it. Here are some components worth noting.

Freedom is hard

To really reap the benefits of free play, you need to get your mind to be as free as possible. This is the most difficult part of the process — by far. Our minds are very good at retaining and juggling ideas, goals, desires, needs, etc. Ask anyone who’s ever attempted meditation, and they will tell you. Getting those things off of your mind is exceedingly difficult.

Thoughts, not ideas

The term “idea” carries a lot of weight. Usually, part of that weight is the weight of ownership. After all, the phrase “whose idea?” comes right to the fore when we talk about ideas. Thoughts, on the other hand, don’t seem to have this weight. We have thoughts all the time, but we don’t seem to equate them with a commitment or ownership. So when you’re looking to leverage free play, be sure to wander around encountering thoughts, rather than ideas.

Encountering vs. Having

In line with the use of the term “idea”, try to think not about having thoughts when your’e doing free play. Think instead about encountering thoughts. They’re not yours — you didn’t create them, and you’re not responsible for them. You can take or leave them, so act accordingly.

You’re “trying on” ideas

Most of us wouldn’t feel great buying clothes without trying them on. This is the way we need to look at ideas as well. After a session of free play, when you’ve got some thoughts recorded, keep a list of thoughts and ideas you’d like to try on. That’s the takeaway of doing free play. You’re looking for ideas to try on. That trying on period can be hours, days, months, or years. It all depends on what the idea is.

The great thing is that (to further stretch the clothing metaphor) you can take the ideas into a tailor to have them altered to suit you and your goals. Every person you bounce the idea off of (including yourself) can make alterations to it over time. But at the end, if you’re not happy with it anymore, you can leave it behind — no questions asked.


Make no mistake about it — thinking is the most misunderstood and underestimated work we do. But it is also the most important work we do. The more we can learn to do it better, the more productive we will be. Think wide, think freely — but most importantly, give yourself the right space in which to think. Your mind will thank you for it.