Strategists can be dreamers. We sometimes day-dream about what might come to pass, what possibilities we might achieve. I think that’s great. If we don’t dream something new, then it’s likely nobody ever gets going anywhere good.

I’ve been thinking about how it is we can estimate the far-bounds of possibility. And my sense is there’s nothing wrong with wild-blue-yonder thinking as long as it’s tempered somewhat and grounded in cold-hard-reality.

So here’s what I’d suggest. The next time you want to think through how far you can push your organization or yourself towards the far end of strategic possibility, draw an hourglass shape with an open part in the middle.

At the very top, write out that wild-idea. What you think you might be able to accomplish, what dream you want to run down. How far do you think you can push yourself in competition, versus an adversary, against a marketplace competitor. Ask and answer: What might I accomplish?

Then, at the bottom, what’s the track record look like. Have you done something like this before? What’s the base rate comparison? Have you faced this adversary before? If so, how did it go?

Finally, in the middle of the hourglass: what are your current assets and liabilities that are pertinent to this competition.

If the gap between the top (stretch) aim and the bottom base rate is enormous—maybe you’ve got some asset ammo laying around that you think can help get you from the bottom to the top. Or maybe you see a time period where a lead-weight-liability won’t be a factor and you think you can gain some ground.