Port books for navigating ambiguity

There’s a quote from Pirates of the Caribbean: Curse of the Black Pearl that sparked my curiosity -

Will Turner: “How can we sail to an island that nobody can find with a compass that doesn’t work?”
Mr. Gibbs: “Aye, the compass doesn’t point North. But we’re not trying to find North, are we?”

It got me thinking about the history of sailing and navigation. You see, up until 1730, when John Harrison completed his chronometer, sailors had no way to accurately measure longitude (one’s position on the east/west axis of the globe).
This was no small achievement by Harrison - it took him 4 attempts and most of his life to produce a chronometer that could accurately keep time onboard a ship. The cost of setting sail without one was not to be underestimated - in 1707 the British Navy lost 4 warships (and between 1,400 and 2,000 lives) off the Isles of Scilly because the fleet was unable to accurately calculate their position in stormy seas.

As I was reading about this naval disaster, another question occurred to me - in the face of such an extreme unknown, how did these intrepid sailors set off and manage to arrive at their destination at all?
And is there something in their methods for navigating the unknown that we could learn from, to live up to our values and work towards our goals? Or as Mr Gibbs put it, can we find a compass that doesn’t point north for our own lives in the annals of sailing history?

The answer, as it turns out, is a fascinating piece of nautical history. The sailors of classical antiquity navigating in the Mediterranean Sea and beyond would use handwritten notebooks known as “portolani” - port books - that contained sailing directions built around landmarks such as ports, coastal features, and the distance between each one to the next.

In one you could expect to find:

detailed physical descriptions of shorelines, harbors, islands, and channels,
notes about tides, landmarks, reefs, shoals and difficult port entries,
instructions on how to use navigational instruments to determine position and plot routes,
calendars, astronomical tables, mathematical tables and calculation rules (notably the rule of marteloio),
lists of customs regulations at different ports,
medical recipes, and actual recipes,
instructions on ship repair,
illustrations of ports and coastlines as seen from seaward,
and more. Whatever the navigator thought might be needed to bring the ship to port safely went into their port book.

To compensate for the lack of a longitude measurement, sailors would use the crude system of dead reckoning - using a piece of driftwood and a rope, they’d estimate their speed. Coupled with an hourglass, they could calculate roughly how far they’d travelled on a given heading, thus placing themselves on a map.
The large amount of extra details found in the surviving examples of portolani is telling. Dead reckoning alone wasn’t enough - navigators need more observations to confirm their position, essentially acting as an error correction mechanism.

It’s worth noting that these books were almost always written for personal use. The majority were passed down through families. The few commercially available port books were tightly controlled by guilds and merchant organisations - they were worth their weight in gold.
In spite of the rough level of accuracy afforded by these books, they were enough to build empires - or destroy them. One prominent example of the latter was the breaking of a century-long Portuguese monopoly on the East Indies by the publication of Reysgheschrift by Dutch sailor Jan Huygen van Linschoten in 1575. This single port book enabled the Dutch and English to compete in the spice trade, previously a closely guarded secret of the Portuguese.

Personal port books

Medieval sailors would use their port books to increase the accuracy of their dead reckoning calculations. Better estimates of position meant they were more likely to arrive at their destination intact.
We can use the idea of these port books to help us avoid succumbing to the museum of the almost. By keeping one, we too can adjust the dead reckoning of our own fallible memory to better keep us on track to reach our goals.

Avoiding the museum of the almost

The museum of the almost is the collection of started but never finished projects, goals, and ideas that we all accumulate in life. It’s the half built ruins of our dreams, littering the out of sight places of our homes. Reminders that we almost finished a project, almost achieved a goal, almost lived up to our values.

We shape our buildings and afterwards our buildings shape us.
– Winston Churchill

This is far from ideal. We should be building metaphorical cathedrals, not collections of rubble. Churchill’s quote may sound familiar - a paraphrase is often attributed to Marshall McLuhan – “we shape our tools, and afterwards our tools shape us”. the tools and environments we shape for ourselves have a pervasive and constant effect on the course of our lives.
Whether you are deliberate about them or not, every decision shapes the course of your life. If we are to build our cathedrals, we will need to be intentional about building ourselves a set of tools and a practice for using them. Like Jack Sparrow’s compass, they help us set a dependable direction to achieve what we set out to do (with a little luck).

Why keeping a personal port book helps

The truly worthwhile goals in life are rarely easily achievable (for our individual circumstances). Maybe you’ve set out to keep to a personally defined “rule of life”. Maybe you’re starting a business so you can be more in control of the creative work you live for. No matter what you dream of doing, there’s not a “for dummies” guide that is perfectly tailored to your situation, skills, and circumstance. Even if there were, the seas of life are out of our control, and never do they calm to the point where we have no problems facing us.

Luckily, we don’t need to know the entire course from A to Z in order to navigate towards it. Actions taken need not be perfect, but they do need to be guided by our prior efforts. Our memory is limited, fallible, and prone to errors and omissions that make relying solely upon it less than ideal.

It is really true what philosophy tells us, that life must be understood backwards. But with this, one forgets the second proposition, that it must be lived forwards.
– Søren Kierkegaard

The solution is to leverage tools - in this case, your own personal port book - to pick up where your memory falls short. Recording a log of your observations as you progress through life extends your working memory over a distance of days, weeks, and months, instead of just minutes. These observations, thoughts, and ideas can be reviewed, and reshaped to help guide your present actions. It becomes a tool that allows you to, as Kierkegaard put it, understand your life backwards while living it forwards.
In doing so, we become like those medieval sailors - adjusting their dead reckoning with observations so as to set a more accurate course. Our own observations, kept in a port book for ourselves, become a similar error correcting device for our lives.

How to create your own

If I’ve convinced you of the value of keeping such a book, you might now be wondering “what do I actually put in one?”. The question of what goes in your port book is deeply personal. After all, it’s there to serve you. No one else will read it, it doesn’t have to become some kind of performance art. It can be messy, with false starts, dead ends, and genuinely enlightening entries.
A simple journalling practice is a great place to start. There’s no need to limit yourself to just that when the port book can be much more to you. Here’s a list of ideas for your inspiration -

For reflection - a weekly review, your own personal framework, values you hold dear, life lessons, shower thoughts, and ideas that have stuck in your head
For planning - to-do lists (using bullet journalling, dash/plus, or something entirely different), project planning, project task boards, and bucket lists
For memory - poems, quotes, theatre tickets (and your thoughts on the experience), polaroids of loved ones & mortal enemies
For expression - sketch-notes, sketches, badly drawn maps of real places, perfectly drawn maps of fictional places, deliberately misheard lyrics
For your future self - Anything else you want to keep for your future self to remember - the highlights, lowlights, and sidelights of your life can all find a place in your port book.

Start with the easiest option

So far, I’ve refrained from talking about the specific mechanics of keeping a port book for yourself. It’s the question of our age - do I use an app for this, pen and paper, or something in between. The answer is fairly simple but not universally definitive.

Use what’s the easiest and most accessible for you and your goals..

If either option is going to be a chore to use for you, it’s the wrong one. You should look forward to using your port book, if the form it takes is a hassle, it defeats the point.
If you’re still stuck for choice, here are some of the pros and cons for each solution:

Pen and paper
- Pros - tactile, doesn’t need charging, private, offline, can’t be hacked, easy to add inserts such as photos or tickets, easy to stumble across old entries
- Cons - Can be hard to carry with you when you want it near, cannot be easily backed up/duplicated, less accessible, can feel messy without structure
Note taking app
- Pros - easy to have on you at all times (via your phone), you probably already have one, easy to add pure digital content such as video or audio, can be easily backed up
- Cons - can be stolen by a wider array of villains, easy to lose entries without structure, low discoverability of old entries, hard to add physical inserts such as polaroids or concert tickets.

Personally, I use a hybrid solution - I have a specially created note for temporarily holding thoughts for transfer to my port book. I try to keep things mostly analog, but this is a personal preference. I enjoy writing with pen and paper - it feels like an extension of my mind in a way that a digital app has yet to replicate. I also find great value in stumbling across old entries as I flip through to find something.

At the end of the day, there’s nothing wrong with either option. You can also try both, or transition from one to the other at a later stage - nothing is ever locked in. I actually started with an app and transitioned to an A5 notebook later.

Concluding thoughts

This post has been more theory than practice. That’s by design - there’s never any one framework that works for everyone. Some people find bullet journalling to work for them. Others might use something a little more idiosyncratic. I use a mix of bullet journalling, weekly review (with a personal framework), and semi-structured entries.

The value is not found in the specific framework, it’s in the continued use of it as a tool to help you along your path in life. Humans are storytelling creatures - we’re not just “bullet journaling”, we’re navigating the unknown seas of life. It sounds more exciting, dramatic, and romantic. We’re more likely to keep at it, and see a benefit if there’s a story involved.

It’s not the large decisions that shape the course of our lives. It’s the small choices we make on a daily basis. Crafting a tool such as a port book helps us guide those choices by extending our working memory, and keeping us accountable to our values, goals, and ideals. With the world drowning in ambiguity right now, there’s never been a better time to start one. Like the sailors of old, we can chart our own course through history by building a practice for observing and adjusting our course.