I’m a boostrapper by nature. I typically look for low magnitude outcomes with a high probability of success that I can tackle with a small team. Today’s software world is full of these, ripe for the picking.

Lately, however, I’ve been thinking about the other end of the spectrum.

Audacious goals are low probability but, at their grandest, have the potential to effect high-magnitude systemic change in the world. They’re also notoriously slippery beasts; it’s hard to see their shape at the outset.

To grapple with the biggest challenges, I find myself asking two simple questions:

  1. Assuming success, what should be quantifiably true of the world tomorrow that is not true of it today? (A single razor-sharp test is ideal but can be hard to find; a small set of slightly duller tests, some high percentage of which ultimately prove true, might suffice.)

  2. What separable pieces can be built today that will likely be accretive toward the final goal?

By taking small concrete steps while holding the desired quantifiable outcomes as our North Star, perhaps it’s possible to slowly illuminate the shape of the beast. Then, one day, when it’s least expected, we can grab it by the tail.