With a friend, on Saturday afternoon, I went sailing on the Charles River in Boston. Wind blowing from the north-northwest (about 320 degrees for you compass enthusiasts out there) at 10 knots with gusts to 18 knots – a brisk breeze blowing diagonally across the river from the Cambridge side of the river to the Boston side of the river. We went out in a 17-foot keeled boat with jib and reefed mainsail. Without thinking too much about it, as in, for no particular reason at all, we chose a tack that took us up the Boston side of the river, maybe 30 yards from shore.

The shore bends and curves a bit. We reached a point, just about at the Hatch Shell (think Boston Pops Orchestra, the Fourth of July concert you may have seen on TV) at which the river bank curves into the river toward Cambridge which meant we had to turn with it…. which meant turning more into the wind. Most sail boats don’t move well when they’re tacking closer to the wind than 45 degrees; we were well inside that and losing speed.

Almost before it was too late, we had the thought to come about to starboard, away from the riverbank and across the wind, toward Cambridge and the middle of the river… but there was another sailboat there and we concluded that, if we turned, we would impede their progress and, possibly, collide, depending on how quickly they reacted. Not a good option.

During that moment’s hesitation, our bow turned almost directly into the wind and we were “in irons” – no momentum forward, bow just slightly to the left of the prevailing wind. Which meant, with the jib up, the wind pushed us broadside toward the river bank. I released the jib so it was flapping loose but…. it was too late. We ran aground on the downwind side of the river with no options other than one of us jumping into the water to push the boat away from the shore. Also, not a good option.

We pulled down the mainsail. Within about five minutes, the Dockmaster was behind us in his launch to pull the boat back into the middle of the river for a restart.

So, Nick, what’s the moral of the story? Well, obviously, don’t sail so close to the downwind river bank. Yes, that’s a good one. Note to self, thank you.

More broadly: Sailing (or selling) completely in the moment, enjoying the ride, reacting to what’s immediately in front of us, can get us into trouble – we don’t anticipate what’s ahead and we get caught without margin for error when conditions change. Anticipating and planning – developing quarterly plans, monthly plans, weekly plans, daily plans, call plans, relationship plans, territory plans, and business plans – helps us think several moves ahead so we don’t, at the last minute, discover that we’ve sailed or sold ourselves into a headwind with no momentum, no options, and a lost opportunity for a good sail (or sale).

As one of my sales manager clients (here in the Dockmaster role) said to his team: “If you don’t plan and we don’t talk about it, I can’t help you.”