The Trail

Nathan A. Cunningham
4 min readAug 12, 2023


Just below/above? the scariest section of the famous Devil’s Backbone trail below the summit of Mount Baldy in San Bernadino County, CA

Its obvious and widely accepted that taking notes is important, just ask Leonardo da Vinci or Richard Branson. And I’ve written elsewhere about Notebooks, Journals, and Common Place Books why it’s generally a good idea.

But here is a tactic I use in note taking or journalling, an example, and a fatal flaw you’ll want to avoid.

I call it The Trail.

“The Trail” is a journaling method I use for capturing and organizing ideas that come to me when I’m, you guessed it, on the trail … most of the time running.

The blood is flowing, the mind is clear (works with cycling as well, and for a while I used “the road”) and it’s when I get my best thinking done — often it’s a conversation with God or at least begins that way.

While running I’m thinking through ideas … but a challenge was always having great ideas when out on the trail, but then back in the weeds of life and the hustle of the day to day I’d forget. I’d loose confidence in the idea or feel less enthused about it … i.e. reality check kicking in … often for legitimate reasons such as bad timing or flawed assumptions etc.

So I began the practice of recording voice notes or written notes immediately after my run.

I always title the notes as “The Trail” with the date.

In the future, if I remember I once had an idea and now its relevant or useful, I’m be able to look it up vs. having it cluttering around in my mind indefinitely like the infamous kitchen or desk drawer that ends up having all the junk you don’t know where else to put. This simple practice, frees up my mind for much more productive stuff. And helps greatly with recall.

I just flip through the tiny notebooks that I carry for this purpose, or search “the trail” on my Phone or Evernote / Obsidian vault and I have tons of ideas and entries and thoughts for later use. By using the “show random note” in Obsidian, often these show up in serendipitously and provide unexpected inspiration.

David Allen talks about this a lot in his books Getting Things Done and Making It All Work about [the benefits getting things out of your head and into a trusted system].

While, I’ve experimented with memory boosting techniques, such as the mind palace, for storage and recall of what I process while on the trail, I’m still preferring to keep a notebook handy and write things down as soon possible.

Keep a notebook. Travel with it, eat with it, sleep with it. Slap into it every stray thought that flutters up in your brain. Cheap paper is less perishable than gray matter, and lead pencil markings endure longer than memory.
—Jack London

An Example

Here’s an example of a thought that came during the summit push of Mount Baldy in San Bernardino county. I wrote this note in July 2020 just before after heading down that very trail shown above. It says:

Without question we all will suffer.
The question is how high will be our suffering and how high might be our joy?

A Fatal Flaw in Notetaking

I’ve learned a fatal flaw in notetaking. I’ve been subject to it for years. The flas is, if you don’t review your notes, they don’t stick. And you’re less likely to take action on them. If one of you’re strengths is “input” like mine (see Strengthsfinder for the assessment), it can be particularly tempting to just take notes, but never put the value from taking them out in the world. I need to publish regularly to counter this and it ties to one of my life-quotes:

Goods in any storehouse are useless until somebody takes them out and puts them to the use they were meant for. That applies to what man stores away in his brain too.
— Thomas J. Watson, the former President of IBM and namesake of IBM’s Watson.

Originally published on Instagram not long after some of the events alluded to above.

See also:

For further thought and future posts:

  • [How is AI impacting our note taking habits?]
  • [What are the benefits getting things out of your head and into a trusted system?]
  • [What are Smart Notes and Why Care?]