Are Timelines the Same as Deadlines?

Getting ready to go cruising involves a lot of background work that sometimes looks a lot like “regular life.” Things like buying school supplies and cleaning the junk drawer. Working on the budget and reallocating money. Scheduling contractors to come look at the house for painting. Buying plywood for the bunk project on board, or buying siding pieces to replace rotten ones on the house. Dreaming on Pinterest for counters and sinks for the boat. Deciding if a rental truck or a POD storage container makes more sense for us next year. Figuring out how the 529 disbursement process works for college costs. Helping child #2 negotiate the senior year course selection minefield and decide on colleges.

Siding replacement, anyone?

Siding replacement, anyone?


There’s a timeline we’re shooting for over the next year. Parts of the timeline have deadlines, and other parts don’t. How do we reconcile all the moving parts with the very real knowledge that cruising is about flexibility?


There are, of course, some hard and fast dates. If we know what’s happening around them, we can plan out far enough ahead to make it work, whatever THAT means.


October 4-8, then 8-11: Annapolis Boat Show (I'll be at the L&L Pardey Publications booth AND at the Good Old Boat booth!) and Cruisers University (I'm teaching 2 classes). Also Fall Break for Julian, so figuring out his transport home is important.

November 22: Thanksgiving. Julian is home! Do we go to Vermont for the holiday, or do we host here?

March 9-16: Julian spring break. 

April 1-5: Spring Break for Bee and me. College visits? Boat work? House work?

June 5: Bee graduates from high school.


March 2019: Put house on market. The idea is to sell, then rent back from the new owners to take us through the end of the school year. We live in a neighborhood linked to a very desirable elementary school in a school system that’s highly ranked nationally; people tend to like to lock in where they’ll be for the school year. We’ll see how that plays out.

June 2019: Move out of the house. Store any items we’re keeping somewhere to be determined. Find a place to rent/housesit at the river so we’re close enough to Calypso to work on her easily.

August/September 2019: Get both kids settled in college, wherever that is. 

College option?

College option?


There’s a lot of wiggle room in the timelines, which can be a blessing and a curse. My advice to anyone getting ready to go cruising is to set a date and go, because the boat will never be completely DONE; why is it so hard to follow that same advice when it comes to land decisions? Putting the house on the market will depend on a number of factors (contractors and projects and weather), but if we put it off too late we’ll miss the best time to sell. But if we decide we’re putting the house on the market the day after Julian goes back to college in March, might that focus our energies? What happens if the buyer wants to move in immediately? Where do we go from there? And why am I worrying about the hypothetical demands of a hypothetical buyer?


Timelines are not deadlines, but sometimes deadlines help timelines stay on track.