Even when we don't know exactly where we're going

We can know exactly how we'll get there

“I don't know exactly where I'm going, but I do know exactly how I'll get there.”

It was an quip in a longer conversation, so quick it slipped by me before I had a chance to record who said it. But it clicked, clicked in the way that ideas sometimes do. When you're not looking sometimes you find something.

I know that sentence flies in the face of much recieved wisdom in strategy circles. You should always know precisely where you're headed because otherwise you're wasting effort. You've got to have an aimpoint, a target, an intended destination, and a well-articulated end state.

To this point, the paraphrase often trotted out from Alice in Wonderland’s Cheshire Cat, is that if you don't know where you're going, any road will get you there. That's not actually what the crazy cat says in the book, but it's what so many strategists like to point out as evidence that we must never acknowledge that we won't know the destination very well.

But do we really know with certainty where we're headed from the outset?

Imagine a conversation with George Washington the day he took command of the Continental Army. Do you think he would have been able to tell you much about how the British surrender would come about?

Or Ulysses S. Grant, as well, in 1861, would he have visualized that three to four years later he would be grinding down the Confederates in Virginia?

Take Ike: Dwight Eisenhower could hardly have known when the war began how it would look to end it, and he had arguably the largest share in ending it in Europe.

Step back from war and the same sight emerges. Imagine a runner that knows some basics about a particular race. Distance, the course’s ups and downs, likely weather, and a little about the competitors also toeing the starting line.

If we're talking about a track meet or a one-mile race across pure flatness, then our runner can diligently plan a pace with a great deal of specificity.

But many races aren't so simple.

This year I'm running a series of four, 6-stage, 155-mile races in the 4 Deserts Grand Slam (sounds insane, I know, but my reasons can be found here). At the first of these events, in the Namib Desert, the world's oldest desert with giant sand dunes, the race course took me to the top of one of those dunes.

It was likely the tallest dune in that desert and you could see quite far, far across the khaki-colored wasteland.

But even there I couldn't see the finish line. And as I paused there I realized I was not far off from the "Wanderer above the Seat of Fog," an early 19th century German painting I've long admired for its ability to capture the strategist at the moment the strategy is made.

The "Wanderer" in the painting looks out over an unknown terrain and cannot see his destination clearly. There is presumably some rough path below, thick cloud cover, and jagged rocks to navigate. All obscure the ultimate goal.

Standing atop my dune, I realized I was the "Wanderer." While I had some mental sketch of what the ultimate goal, the finish line, would be, I had never traveled this stage course in Namibia before. If I was honest with myself, I knew very little about what achieving it would be like.

So I learned to lean on a technique in the ultra runner's toolkit called rating of perceived exertion, or "RPE." It is, in part, as it sounds. A simple calculation of perceived exertion. A check-in on how your body is doing in a given moment. The shorter the race, the higher and hotter you can burn—aim for, say, an 8 or even a 9 out of 10. The longer the distance, it's much more prudent to aim for a 5 or a 6.

In a desert race that goes on for 6 days and 155 miles, in an unfamiliar, harsh land, you can't know much about getting to the finish. You can't forecast if you'll twist an ankle in mile 23 of a 25-mile day, or that you'll run through a heat-sink in a rock maze that will raise the temperature to 131 degrees F (which really happened). Because at the start your vision of the finish is more a mirage than truth, you have to lean on something certain.

That certainty is you. RPE. A continual evaluation of yourself. How am I, right now, right here, given that I've come X far and still have Y to go?

It took me awhile to accept this. I didn't want to accept this. I'm the kind of guy that prefers to script out everything pre-race, that I'll run a 7-minute-per-mile pace in mile 13, for example. But there's a difference between who I think I am at the start line and who I really am in that mile 13.

None of this is to say we shouldn't have an end point we're aiming for. We should.

We simply cannot know that end point with certainty. In any difficult endeavor requiring sophisticated strategy, the endpoint will fluctuate, it will change. And so we must be prepared to lean on the much more certain variable—our ability to gauge our performance in relation to the given environment in the moment.

The more realistic we are about what we know and don't know, the better we'll fare.