How to choose a daily highlight
A good Highlight takes sixty to ninety minutes and is best chosen by your gut
A Highlight which takes too long to complete will sometimes not be completed which is not helping motivation for the next day. 60 to 90 minutes is the perfect duration for a daily Highlight.
For choosing the best Highlight for a given day, you should just trust your gut. Most of the times is will be right and if it isn't or a day is not going according to plan, a Highlight can also be changed during the day. No hard feelings.
What should be considered
There are three different aspects which can influence what kind of Highlight you choose for a day:
1. Urgency: "What's the most pressing thing I have to do today?"
Sometimes you just have to finish something because of a deadline or other pressing matters. If there is is something urgent in your to-do list, you might just choose the most pressing thing on there as a Highlight.
2. Satisfaction: "At the end of the day, which Highlight will bring me the most satisfaction?"
Think about the sense of accomplishment locked inside each potential Highlight. Look not at the urgency but tasks that maybe are perpetually pushed off because of other tasks but are important and actually satisfying for you. Use the Highlight to break the "someday cycle" of those tasks and do that one thing you meant to do for weeks.
3. Joy: "When I reflect on today, what will bring me the most joy?"
Not every Highlight needs to be productive or have a value associated with it. Some things are worth doing, just because you like doing them: Reading a fantasy novel, going for a walk, playing a game, etc. Time is not wasted by doing something "unproductive" as long as you are intentional about it.