From Ninety Years to Monday Morning

I heard someone talk about writing a ninety-year plan recently. My first reaction was that this was ridiculous. Ninety years is an absurd amount of time to plan for, and I will not be here for most of it.

Then I sat with it, and I think the absurdity is the point.

A ninety-year plan is not a forecast. Nobody can predict nine decades. What the horizon does is stop the next deadline from setting the direction. It forces a different question than the one I usually ask on a Monday. Not what is due this week, but what all of this is supposed to add up to.

A plan is a decision, not a prediction

This is where I think most long-horizon planning gets dismissed. People treat the plan as a claim about the future, watch the details turn out wrong, and conclude the exercise was a waste.

The details being wrong was always going to happen. That is not the failure. The failure is building efficiently in a direction nobody chose.

I think about it as a road. If we never decide where the road should lead, we can spend years laying good pavement toward somewhere we never wanted to go. The plan is not a prediction about the terrain. It is a decision about the destination.

That reframe changes what a goal is for. A goal is not a guess about what will happen. It is a decision about which future gets my attention today.

Different horizons have different jobs

Once I stopped treating the horizons as competing systems, they got easier to hold at once.

The long horizon decides what the work is supposed to add up to. The annual view picks which progress matters this year and, more usefully, which progress does not. The quarter converts that into something measurable. The week decides what actually gets done.

Long-range goals keep short-term urgency from running my life. Short-term goals keep the long-range vision from staying a fantasy. Neither one works alone, and most of the frustration I have had with goal setting came from asking one horizon to do another one’s job.

What I liked about V2MOM

I spent part of my career at Salesforce, where the company ran on a framework called V2MOM: Vision, Values, Methods, Obstacles, Measures. Marc Benioff wrote the first one for the company in the late nineties, and it stuck. What made it work was not the five headings. It was that everyone wrote their own, and those were visible across the company, not just handed down a level at a time.

That last part is the whole thing. I could read my leader’s V2MOM. My leader could read mine. The Obstacles section in particular was unusual because it asked people to write down in advance what was likely to get in the way, and it made that admission a normal part of the document instead of bad news you delivered later.

I have kept the habit of naming obstacles up front ever since, and it shows up in how I write specs. A flagged unknown is worth more than a confident guess.

Alignment is a sightline, not a cascade

The failure mode I have watched most often is goals that get chopped up on the way down. A company objective becomes a department objective, becomes a team objective, becomes a ticket. By the time it reaches the person doing the work, the line back to the original outcome is gone. The work still gets done. Nobody can explain why it matters.

Cascading is a delegation chain. Alignment is a sightline. The test is not whether the goals decompose cleanly on a slide. It is whether the person closest to the work can point up and name the outcome their work serves.

Leaders set direction. Teams decide how they can contribute to it. That distinction sounds small. It changes everything about how people relate to the goal, because contributing to an outcome and receiving an assignment are two different experiences.

In practice this runs on a few loops. Weekly or biweekly one-on-ones with each person, which are short and mostly about what they are working toward and what is in the way. Then a monthly check-in with the whole team together. That one matters for a different reason. Most of the work happens independently, and the all-team meeting is where people see how the independent pieces fit together. A one-on-one cannot do that.

Yearly goals set the finish line and the dates. Some of what we commit to in January runs the entire year. Some of it lands in the first quarter. Both are real goals and both get a date attached.

The quarterly review is where the direction gets tested, not just the progress. Markets move. What customers need changes. Sometimes the thing we committed to in January is no longer the right thing to build by June, and a review that only asks how we are tracking will miss that completely. So the quarterly question is really two questions. Are we making progress, and is this still where we should be going.

That is how a plan stays flexible without losing focus. The yearly goal holds the direction. The quarter is where we are allowed to change our mind about how to get there.

Back to Monday morning

The weekly practice I run comes from Tony Robbins, and it is called RPM: Result, Purpose, Massive Action Plan.

You start with the result. Not the task list, the result. One specific outcome you could judge as done or not done. Then the purpose: why do I want it? That step looks soft and it is not, because it is what carries the plan past the first week when motivation runs out. Only then do you write the actions. Robbins calls it a system of thinking rather than a time management system, and I think that framing is right.

The order is what makes it work. Every to-do list I have ever written started with the actions, which meant the actions were never tested against anything. RPM refuses to let me start there.

That is the same discipline I use at work. A PRD comes before an epic, and the bet and the measure of success come before the execution plan. Start with the result, name why it matters, then decide what to do about it. The horizons change. The sequence does not.

A ninety-year plan will be wrong in its details. Annual priorities will change. Quarterly goals will expose assumptions that were never true. Some weeks fall apart entirely.

That is not failure. The point was never to predict every turn in the road. It is to decide where the road should lead, and then keep checking that the one I am building still goes there.