15 essential writing tools for Pencil & Pen lovers with an expeditionary mindset

wtf is an expeditionary mindset?

When I was in the military, I walked a lot. An expeditionary mindset is one that always asks the question: am I willing to carry <whatever> for 20 miles? – before packing it into a rucksack. This page is a very short list of writing tools that I own and love, assembled for my friend Dave.


Pencils & Pens


Paper (for writing)

First off, MLK wrote his Letter from a Birmingham Jail on scraps of toilet paper. So if you think that buying fancy paper is going to make you into the next Hemmingway, it’s not. With that said, here are a few sensible tips you can bank on.

In general:

  • Avoid artisanal pulpy-looking paper that looks fancy

  • Use acid-free paper of any quality – there’s no need to agonize over the hundreds of possible variations

What to buy (fancy & cheap)

Do pencil marks degrade over time?

Not as much as you’d think – below is a penciled journal entry from May 1998.

Penciled journal entry from 5/25/1998 (on acid-free paper). This was written with an Alvin Draftmatic .5mm mechanical pencil using HB lead.


Notebooks (various sizes)

The teeny tiny one is small enough to fit inside the top left breast pocket of my winter jacket.

I use a combo of cheap and fancy notebooks.

Canson (cheap)
Available at any Blick or Pearl. These are durable hard cover sketch books that can be beaten up and treated roughly. The largest one is a 14” x 11” (108 sheets). The next size down is 8” x 11”. I fill them up with lists, diagrams, pseudo code, and doodles.
Blick link

Moleskine (fancy)
For the 2 smaller sizes, I go fancy with Moleskine’s notebooks (hard cover). I love the quality of the paper, and the smallest one (3.5” x 5.5”) is just a bit shorter than a mechanical pencil, and is compact enough to fit inside my winter jacket breast pocket.
Amazon link


Pencil Sharpeners

Hands down, the Carl Angel 5 is the best pencil sharpener I have ever owned. If you’re the kind of person who gravitates to expensive Swiss or German made tools, the Carl may strike you as a cheap looking Chinese knock-off , but compare the $19 Carl to the $195 Caran d’Ache butterfly sharpener, try and think like a person who earns $20/hour, then answer the question which one is the right sharpener.


Thoughts on pencils – from Henry Petroski

✏️ The pencil, the tool of doodlers, stands for thinking and creativity, but at the same time, as the toy of children, it symbolizes spontaneity and immaturity. Yet the pencil’s graphite is also the ephemeral medium of thinkers, planners, drafters, architects, and engineers, the medium to be erased, revised, smudged, obliterated, lost – or inked over.
— Henry Petroski

The above quote is taken from The Pencil: A History of Design and Circumstance – a book I cannot recommend highly enough.