A very thoughtful article by DHH. I think there seems to be two "goals" at work.
1. Short-term, achievable goal. Acts like a milestone and gives you momentum, feedback, encouragement.
2. Long-term ambitious goal. This is something that acts like a lighthouse in the distance.
To me, it's interesting how these two types of goals interact and how one manages them.
For example, some companies seem to be formed by the small achievable "goal" method. They start small with little ambitions. They get traction and initial success, and then grow from there. This is similar to DHH's racing journey.
However, there are other examples of people starting out with more audacious goals, like Elon Musk with Tesla or even SpaceX. The long-term audacious goals seem to drive development and the short-term milestones. Without the long-term audacious goal I don't think that there would be enough momentum/energy/vision to push through the short term goals.
I'm not sure how these two goals work together, and would love to hear your thoughts on this.
Can you just have the short term achievable "goals" and then grow from there? Or do you need the long-term audacious goal to guide your short term milestones?