First Light
Most people spend more time planning their vacation than they spend planning their lives.
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Your life, one week at a time
Each dot is a single week. The Stoics kept death in view not to despair, but to spend the squares that remain.
The comparison is not exaggeration. It is arithmetic. Count the hours you spent last month researching flights, comparing hotels, mapping itineraries for a four-day weekend. Now count the hours you spent in the same month asking where the next six months of work should actually go. Most quarters close without that audit ever happening.
The vacation gets the attention because the stakes feel contained. A bad restaurant is reversible. A missed ferry costs half a day. The boundaries make the planning possible. But the year has no forcing function. There is always next quarter to recalibrate. There is always next month to re-prioritise. So the deck about strategic direction gets deferred, and the coffee chat about what you actually want gets cancelled, and by December you are six capability-building months behind a person who spent two hours in January with a blank page.
The problem is not that vacation planning is wasteful. The problem is that it proves you already know how to do the other thing. You know how to block time, reverse-engineer from a goal, say no to the less important option. You already run that process. You just run it on the thing with a departure date.
So this week: two hours, offline, with one question — if the next six months were a trip you were planning, where would you be trying to go? Not the aspirational answer. The answer you would actually book the flight for.