Lessons on Planning


Most of you were not following during the last two summers, when we lived aboard and sailed.  At times, I become wistful, thinking of the bright morning sunshine in the marina in Bay City, two years ago, or our adventurous escape from Thunder Bay and the week we spent “stuck” in Presque Isle, around this time last year.

Sometimes, our sailing adventures and challenges seem so small, compared to the events of the past year and our current endeavors.  Yet, I have always considered sailing to be a metaphor for life, and I think there is one very important lessons to take from our adventures on Moonraker:

The lesson of planning and overplanning.

As humans, we love to plan.  We like to make plans, when we are in that “stuck” phase, when we can’t yet move forward.  Sometimes, plans make us feel like we’re moving forward.  We did a great deal of planning, during the three weeks we spent anchored in Thunder Bay.  I wrote so many posts about plans, and changes of plans.

If planning brings hope, that’s wonderful.  But there is a darker side to planning, and obsessing over plans.

First, planning can bring anxiety.  When other people don’t understand your plans and your direction, they can introduce doubts, which can lead to overthinking, fear, and anxiety.  As you try to explain and justify your plans, you begin to doubt yourself.

Second, being overly attached to plans can cause you to miss out on opportunities for happiness.  Our first year sailing, I had my heart set on living aboard all summer.  Which led to my being absolutely devastated when the boat was out of commission for a month and a half, after running aground in Misery Bay.  Not only did I worry and miss out on enjoying the rest of the summer, but my worrying was for naught.  In the end, we had an exciting return trip and a great adventure story to tell.

Last summer, we were constantly amending our float plan, due to the randomness of the weather on the Lakes.  We had intended to spend two nights anchored at Presque Isle, then proceed to Rogers City.  But, when we tried to leave, we found that we were unable to make any progress in the strong headwind.  There was a small craft advisory, and racers were coming into the harbor, for refuge.

We were going to have to change our plans.

So our two nights at anchor turned into a week at a marina slip.  We climbed the lighthouses, explored the area on the free loaner bicycles, and got to know the other boaters (including two absolute characters who had dropped out of the race and were docked next to us).  It really ended up being one of our favorite memories, during the summer.

So, of course we need to plan.  Make a tentative “float plan,” but don’t obsess over it.  Don’t let other people cast doubt–trust that, whatever comes along, you have the skills to make things turn out wonderfully.  And be open for those “small craft advisories” in life, those changes in the plans.

Because the unexpected changes just might lead to something even better.


15 thoughts on “Lessons on Planning

  1. Marvy post, Bethany! The higher the expectations, the harder the fall. Plans are nothing more than predictions and none of us are clairvoyant, so there will be many missteps in planning. So your advice to keep planning without obsessing over it is very reasonable.

  2. In my employer’s sphere, it’s usually put “No plan survives contact with the enemy”. That doesn’t mean they are worth having…

  3. As a compulsive planner and list-maker, I am almost always frustrated by my “failures.” My mind doesn’t function without a set plan, but life doesn’t really allow for plans. At some point, I’ll find the balance.

  4. What a beautifully written post, and I love the last paragraph. I’m so glad we humans have the ability to plan, but I am right there with you that it can take over and you miss out on those little moments.

  5. Thank you for your thoughtful words. It reminds me of the great Seth Godin. He suggests you don’t follow a detailed map, something that either you or someone else has obsessed over every detail of, but rather simply follow your compass, and let the world and your experiences guide you.

    I definitely live my life with a compass in hand and burnt the map when I gave up chasing arbitrary goals.

  6. Bethany, I have never been one to stick to rigid plans, it would be too devastating to fail. Instead I like to have a goal and then take the winding road life throws at me in the process of reaching the goal. I can see how your plan of living on board for an entire summer would be too rigid to be able to enjoy the disruptions.

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