Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way.
― E.L. Doctorow
As a child I remember hating long road trips to my grandparents house, mostly because I couldn't wait to arrive. The 4 hours from Cleveland to Cincinnati seemed like days. The more excited I got to see Grandma, the more agonizing the wait became.
I've always been a chronic complainer. That must be why my parents always told me, with a faint hope of relief, to "take a nap, and we'll take a shortcut."
Software roadmaps can plague us the same way. We focus so much on the destination that we are distracted by what's happening along the way.
We strive to follow the path the crow flies, as direct as possible. But actually, the most successful trips are the ones with planned stops along the way.
I think a lot of us are afraid to aim for a point which isn't our destination - as if we would somehow confuse ourselves about where we are ultimately headed.
We can't predict accidents or traffic congestion. We might have an idea that downtown Columbus is slow between 6-8 am, but planning what lane we will be in at what speed is ridiculous. It's just too far out to know.
Maybe that breakfast burrito you ate before leaving was a bad idea and you have to make an unexpected stop for 15 minutes. Shit happens (pun intended), just course correct.
Break up your trips into predictable chunks. Schedule them into slivers where big problems cause minor inconveniences, not emergencies. Baby steps. Ship it.