This checklist is for big ideas. The consequential ones. Ideas that keep you up at night, toying with quitting your job; moving city or country; committing to a long-term relationship — whether that be with a partner, co-founder or new community.

It isn’t for the ‘should-I-write-a-blog-about-it’ ideas. Those are also worth filtering, sure — but we can’t painstakingly question every passing idea which bubbles up to consciousness.

No, these are exercises to help filter the excitement and promise of an idea from its substance and longevity.

For that reason, it isn’t easy. It isn’t comfortable, and at the end of it all, you still may not have complete clarity, certainty or anything of the kind.

In fact, you’ll never know for sure if an idea is worth pursuing — not before living it.

But you can weed out those seedling ventures which never really stood a chance. That is, you can save yourself a lot of wasted time, confusion and head-banging procrastination by investing some honest thought upfront.

Here’s a brief checklist for doing so that may help.

1. Sit With Pen & Paper, For 6 Hours, Without Distraction

It will be a struggle. It’s intended to be a struggle.

Think Neil Gaiman’s rule for writing, applied to exploring an idea. In Gaiman’s words:

All I’m allowed to do is absolutely nothing, or write.

This process forces us to confront the substance of an idea. Without distractions to escape into, 6 hours is a long time. Long enough to scratch through the exciting surface of an idea’s initial presentation. Long enough to search its contents, pick at new threads and either uncover an immeasurable complexity or run abruptly into several dead ends.

It is less about one’s interest in or affinity for an idea. Less about how agonizing or enjoyable the process was. It is simply about blocking out the full 6 hours, and arriving at the end of them, without deviation.

The real test isn’t whether or not you enjoyed the process — it’s whether you were willing to survive the struggle at all.

2. Be Brutally Honest About Your Motivations

If money or status is the driving force behind an idea, that’s fine — just learn to recognize it as such.

Then ask, ‘Is this motivation strong enough to get me out of bed during the lowest lows; without guarantee of success; when the end is always obfuscated by clouds of doubt and uncertainty?’

There are plenty of sources of motivation that burn steadily for years, decades, lifetimes. And there are as many others that burn bright then fizzle before an idea is ever fully implemented.

It’s best to identify which type is driving your pursuit before setting out.

3. Is The Exit The Goal?

This is a direct question. It should be a brief reflection.

If your idea is something you can’t wait to hand over to someone else at a profit — that’s fine, but you will always be beholden to the needs and wants of investors, shareholders and partners.

Because of these pressures, and others:

Ideas born with the exit in mind are often nudged out the door before reaching maturity.

If, on the other hand, your idea is something you can’t wait to spend as long as it takes exploring — then welcome to the club.

4. Ask Whyhen Ask It Again.

Why do you want to pursue this idea and not something else?

Okay, why is that important to you?

And why does that matter… you get the idea.

It begins to get uncomfortable only a couple of levels down — and strangely, few take the time to venture even that far. But by pushing the ‘whys’ of our ideas to their uncomfortable limits, before committing and taking the plunge, we protect ourselves against pursuing avenues we do not fully understand or appreciate.

And after all, if you are preparing to dive deep, you’ll want to know what lies waiting in the rocky depths.

5. Can You Afford To Be Wrong?

If the answer is an urgent ‘no’, this should put you on your guard.

Because you will be. Without exception. Your first iteration is guaranteed to be incomplete. And if you are in a rush to ‘make it work’ nonetheless, the deeper truth of your idea — the richest kernel of whatever inspired its original formulation — will be passed over in favor of more immediate gratifications and instantiations.

Only when we can afford to be wrong, and embarrassingly so, can we pursue an idea freely.

An Iterative Process

Unfortunately, one static sitting is unlikely to be enough. Kierkegaard’s yawning abyss which lurks beneath this question of, ‘Is it worth pursuing?’, never truly leaves us. We must return to it, time and time again, and we must produce acceptable answers at each revisiting.

And each time we do, we move forward with renewed confidence, clarity and creative energy. That is how you’ll know it’s worth pursuing — whether or not the end looks anything at all as imagined.

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