In the wee small hours of the morning, I woke up abruptly in a cold sweat, muscles twitching and thoughts crashing around in my head. Our self-imposed deadline of April 2007 to move aboard the boat full time loomed a mere six months ahead. Six months to sort, sell, throw away, store or move on to Don Quixote nearly twenty years of accumulated goods. Six months to prepare the house for rental. Six months during which I would also be working fifteen hours a week for my clients, twenty hours a week for my husband’s practice, and twenty-five hours a week as a home school teacher. (Add ‘em up, folks!) The prospect was sufficiently daunting to cause anyone with a heartbeat to waken in the middle of the night in a panic.

Six months was also so much less time than the original eighteen months envisioned when we set the deadline. It’s funny how that works. You look out into the future and set arbitrary goals for yourself, giving ample time to accomplish all the many tasks necessary to make a dream come true. And like any student, you procrastinate your way straight into an impossible situation. Like most freshmen before finals, I lay rigid in my bed – alternating between an absolute state of panic and a depressing sense of futility.

The advantage I have over your average college dropout is that I’ve spent decades working with some of the finest project managers in the software industry. I studied this subject for years. I was bred of a brilliant program manager, born by a single mother, and polished to a fine survivalist shine by years working with phenomenally incompetent senior executives. I immediately directed all that nervous, twitchy energy into scoping the project, setting the time line, and assigning resources. Right there. In the middle of the night. In bed. Then I went back to sleep.

It occurred to me as I sat on the stick-to-your-butt-cold head the next morning, that in the event of a future middle of the night panic attack during which I lay out a six month project plan, I should make a point of pulling out the laptop and getting it all down. What seems so clear in the night as you listen to the wind make the mast vibrate takes on a dim, fuzzy vagueness in the cold light of morning.

I do not recommend using Microsoft Project to plan your live-aboard cruising transition unless you are both incredibly anal retentive and a complete program management wonk. Otherwise, you’ll find you spend all your time trying to get the tasks to link correctly… never mind the complete waste of energy devoted to leveling your six year old daughter. However, for those of us familiar with controlling the world through a Gantt chart, there is no reason to give up those basic skills just because we are fleeing from them like leaves before the wind.

Note to fellow program managers: I did consider scrumming the project, but first I knew that my husband’s capacity for estimating his work effort is non-existent, and second, absolutely no one in the family would agree to attend daily scrum meetings. I have enough trouble getting them to sit down long enough to divvy up weekend chores.

But whether you use Project, Excel, Google apps, a Wiki or *cough* paper, the first and most important step is to write it all down. All of it. Everything you must do and everything you think you should do. There are house chunks, boat chunks and kid chunks. You probably have a few “relative chunks” and endless numbers of paperwork chunks. You might have a business to dispense with or cars to sell or property to offload. Write down absolutely all of it.

Use a tool you can sort, stack, and categorize. If you don’t (or won’t) do this on a computer, then my recommended tool is sticky notes. Because what you need to do after writing down every possible task you can think of is to start grouping them into manageable chunks. Okay, maybe the tasks aren’t manageable. Maybe they are completely overwhelming. You have to start somewhere, however, so start grouping them into their categories and then lining them up in priority order.

Figure out if you have any task dependencies. Do you have to move out of the basement before you remodel it? Do you need to “accidentally” release your spouses’ pet canaries into the wild to be eaten by raccoons before you can possibly live on a boat with him? Make these connections and sort your tasks.

Then despair.

Really. Give up right then and there.

There is no possible way to get this done before your target date. There just isn’t. It’s as if you are working for an American company during the dot bomb, and they’ve laid off 60% of the work force but they want you to work smarter and get the same amount of work accomplished in less time. Face the fact that you are not going to get all of it done and half of what you do manage to tackle will be done half-assed.

But who the hell cares? You are leaving, my friend. You are cutting the lines and sailing South. And when you come back – if you come back – you are SO not going to give a rat’s ass that you failed to pack the crystal in bubble wrap and instead opted for the expedient newspaper. The crystal didn’t move the entire time you were gone. And now that you look at it on your return, you most likely wonder why you kept it.

Most of your life here is non-essential, overpriced, and way too commercialized. You are leaving it for a reason. Throw it all in a bunch of U-Haul boxes, stuff it in a storage space, and call a cleaning service to prep the house for a tenant. You’re going to have to repaint when you get back anyway. Let the tenants in their “real world” deal with the crayon on the walls.

YOU will be sipping rum, ginger ale and lime juice off an atoll in the Caribbean.