Enslave yourself to the chart and compass – gain the freedom of the seas. – old sailor’s proverb

Today is my first day of unemployment. It feels strange to say that. Last month, I decided to quit my job of ten years and take a leap into the unknown. It’s exhilarating to be free, but what does “free” actually mean?

One thing it means is “freedom to” focus on personal interests and goals. One of my goals is to write 500 words a day. Approximately. Maybe more, maybe less. Not every day, but most days. And let all other caveats apply.

It also means “freedom from” a set of weighty responsibilities. On the first day, I’m most struck by the huge space left by the absence of such responsibilities. A deafening silence. Like air to birds or water to fish, it’s not clear how much something surrounds you and fills your life until it’s gone.

How I fill that empty void (between “to” and “from”) will largely define what “free” means to me. Which is both exciting and concerning. Exciting because the realm of possibility seems suddenly endless; concerning because not all of those possibilities are good and choosing among them is hard.

Navigating those seas and sharing the journey will be the focus of this blog. I took the name “second sailing” from a passage in Plato’s Phaedo. It means starting anew, based on an old expression for taking to oars when the wind dies or takes you off course. It seemed appropriate for my new voyage and direction.

In the end, it’s not really about being free. Even if we forgo one thing, we still need to serve some goal, purpose or desire. And life is about choosing which goals and desires to serve and attempt to fulfill. About choosing what master to serve.

On the paradox of living free, Phillip Seymour Hoffman said it best in The Master:

Free winds and no tyranny for you, Freddie, sailor of the seas. You pay no rent, free to go where you please. Then go, go to that landless latitude and good luck. If you figure a way to live without serving a master, any master, then let the rest of us know, will you? For you’d be the first in the history of the world.