What Our Planning Looks Like

We had only really intended to sort out things through August, but we ended up planning for much farther than that. We've liberated our mental calendars and will shift that mental effort to actually accomplishing our plans, rather than constantly fibrillating in contingency mode.

What Our Planning Looks Like

A couple of days ago, Shiela, my mom, and I all sat down to sort out how the next few months should play out, in general. We had only really intended to sort out things through the end of August, but we ended up planning for much farther than that. Ultimately we spent about two hours writing things down in a printed paper calendar, just to make sure we keep things organized (thanks mom!). As a result, we've liberated our mental calendars and will shift that mental effort to actually accomplishing our plans, rather than constantly fibrillating in contingency mode.

We loosely and informally use the four categories of planning: Strategic, Operational, Tactical, and Contingency. We've only named them here so we can share with you the framework we use. I'm going over the categories here so you can build your own mental picture of your planning cycle.


Strategic planning is the collection and execution of Operational and Tactical plans which lead to the conclusion of some pre-defined goal.

Back in 2015, while traveling for work, I started planning for a goal five years away in 2020. While the plan now is a little different than at its inception, it has overall remained the same:

Save as much as we can until 2020, cut off superfluous expenses, generate income from a business/businesses which do not require our physical presence, stop laboring, live aboard a sailboat with our children and manage our businesses from abroad.

Strategic planning pretty much happens as you (a) define the goal (as above), and (b) make tactical plans and accomplish them (next sections).

Planning for Two Plus Crew started in 2015 as a plan to sail The Great Loop in the US in 2020. This one-page document is now 37 pages of notes, plans, and goals. The scope of it now covers sailing the world.

If you look at the revision history for our Two Plus Crew planning document, you'll see small incremental updates over the span of four years. At first the updates came nearly every day; now they come about once per month. That's because most of the heavy planning is already written down. Occasionally I go back through and re-read the whole thing just to see if there is anything I can accomplish today – be massive.


Operational planning are the steps and procedures you go about on a daily basis. Everything from getting out of bed and brushing your teeth, to meal planning. Your Operational planning should include all the things you normally have to do, plus working on your Tactical plans (more below). I make it at least a weekly effort to focus on Two Plus Crew. That's the bare minimum. Most weeks I spend 4-8 hours on this plan, even if it's just to recap what more needs to be done and/or actually doing it.


Tactical planning are the steps and actions you must accomplish –in addition to your Operational plans and actions– in order to achieve your Strategic plans and goals. For Shiela and I this meant doing things like assessing and arranging our finances, generating and implementing business plans, making reasonable investments, and saving by not dining out. We also had to learn to sail, purchase sailing reference materials, learn details about homeschooling, and even start to consider what sailboat we want, and where we want to go. Some of these things are simultaneously Tactical plans and Strategic plans – and that's ok.

If Strategic planning is what needs to be done, Tactical planning focuses on when it needs to be done.

Our initial sailplan has us departing Fort Lauderdale and sailing the Bahamas and the Greater and Lesser Antilles.

Shiela and I sat down and determined that we ought to begin our sail from Fort Lauderdale so we can move through the Bahamas relatively close to our home turf. From there we'll hit The Greater and Lesser Antilles, before moving west toward the Panama Canal, probably via Colombia.


And, of course, not everything goes according to plan. Sometimes it's as benign as a hiccup in your day (Operational planning), sometimes you have to make accommodations in plans you made on when to start sailing (Tactical planning), like we did on account of hurricane season. And sometimes you encounter something which voids your goal altogether (Strategic planning). In each case, it's important to have Contingency plans.

In each of our planning categories, we try to consider the alternatives just in case we're not able to proceed as planned. We all handle day-to-day contingencies. An example of a contingency for Operational planning: Wake up late for work? No breakfast, then! As a personal example regarding Tactical planning, we had originally planned to sail in March 2020 from Fort Lauderdale. However, as we did the research, we were reminded of hurricane season which starts in June. There's no way we want to be in the Bahamas as a new coastal sailor during hurricane season. So we modified it to leave that December. It might seem like a setback, but the result is now that we have a bit more time to practice and find a sailboat.

And the big question with contingency planning – what if we can't do this at all? No problem! I still love being an airplane pilot, and Shiela still loves styling hair. We each can make excellent incomes by simply returning to our respective careers. We even have a contingencies for contingencies; as everyone should, like what if I can't be an airplane pilot anymore?

I work in a software company designed and structured an app for field staff. That day we made a tour of our flow and could not miss a shot of our work :)
Make your plans the way you need; write them, put them in videos, or use a line board – Photo by Alvaro Reyes via Unsplash

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