He makes the interesting point that having a concrete or objective cruising goal can give people a sense of accomplishment that having subjective, fluid cruising goals does not.
Friends of ours aboard SV Bella Star had the goal of visiting 100 islands while they were in British Columbia on their shakedown cruise which I thought was a great excuse to get in the dinghy and go exploring.
As with many things, I think the best answer to the “A or B?” question for us is “both”. I like the fun-to-suck ratio because it focuses us on our own desires and dislikes rather than someone else’s. What is fun and what sucks can change over time so we don’t end up focused on an outdated goal. Of course, you can change your objective goals as well but that fluidity is built into the ideas of the fun and the suck.
Still, I also like the accomplishment of achievable goals. We haven’t set them specifically because they seem to occur naturally in cruising. For example, making your first multi-day passage or arriving in San Francisco after dreaming about it for years.
It’s very individual and I often analyze things to death (this is part of the fun for me). Do other people think in terms of goals like these or do you avoid the analysis and just go DO IT?