Abstract
Problem: After 30+ years of daily note-taking, what best practices has Tim Cain developed for journaling — and what would he tell someone just starting out?
Approach: Tim responds to a viewer's detailed question about his note-taking system, covering format, tools, content, and common pitfalls.
Findings: There is no perfect system. The most important thing is to start immediately, do it daily until it becomes habit, and keep notes factual. Record names, dates, and what people actually said — not your interpretation. Digitize everything for searchability and cloud backup.
Key insight: Perfect is the enemy of good — don't stop taking notes because your system isn't ideal, you missed a day, or your tool lacks a feature. Just write things down.
Start Now, Don't Wait
Tim's number one piece of advice: start immediately. Don't wait for the perfect notebook, the perfect journaling software, a new project, or the right moment. Pick up a scrap of paper, open Notepad on your phone, grab an unused notebook — just start writing down things that happened today. Waiting for perfect conditions means you'll put it off forever.
Make It a Habit
The most important thing about note-taking is doing it every single day. Once it becomes a habit, you stop thinking about it and just do it. To encourage the habit:
- On your phone: Make your notes app a home screen widget, or put it on your lock screen so you see it constantly
- Paper journal: Leave it somewhere visible — next to the TV if you sit there, on your nightstand if you write at night
- On your computer: Keep a file on your desktop or pin the app to your taskbar so it's always one click away
The key is reducing friction. If you see it, you'll use it.
There Is No Perfect System
Tim has used many different systems over the decades and explicitly states there is no one-size-fits-all journaling technique. He's tried:
- Loose leaf paper — problem: hard to keep dates and order straight when doing multiple notes per day
- Bound paper journals — better for maintaining chronological order; he liked carrying a notebook everywhere
- Text files on desktop — at minimum gets a "last modified" timestamp automatically
- Journaling software (including Obsidian) — liked the cross-referencing but stopped because of difficulty syncing across platforms
- Private social media posts — surprisingly effective: timestamped automatically, accessible from any device, could copy to permanent notes later and delete
- Audio/video journaling (blogging, vlogging, podcasting tools) — viable today but harder to search unless you also subtitle/transcribe
His advice: try something for a few weeks. If it's annoying or has problems, switch. Don't get locked into searching for the "right" tool.
What to Write Down
Record What Happened
Write down things that happened — especially anything that gives you a visceral reaction, whether positive or negative. If someone finished a task two days early, write it down. If something went wrong, write it down.
Always Include Dates and Names
Always record:
- The date — Tim considers this the single most consistent practice across all his years of note-taking
- Who was present / who said what — he deeply regrets the notes where he wrote "a designer today said..." without recording the name. You can always anonymize later, but you can't recover a forgotten name.
Stick to Facts, Not Interpretations
This is Tim's hardest but most important content rule. Write down what people said and did, not what you think they meant:
- ❌ "Bob was being vindictive"
- ✅ "Bob kept bringing up this other person and said he was going to do these things"
- ❌ "Mary was upset about this feature"
- ✅ "Mary said she didn't like this feature and said it was going to lead to these problems"
Why this matters: People will deny things. With factual notes recording their actual words, you have a record. Tim describes instances where people denied saying something, and his notes — sometimes corroborated by others who were present — proved otherwise. Interpretation can always be done later; the raw facts cannot be reconstructed.
If you really want to record feelings and interpretations, keep them in a separate journal from your factual notes.
The Manager's Secret Weapon
Tim specifically highlights note-taking for managers: when it's time for someone's review, you can search your notes for that person's name and find concrete examples of their work. Instead of vague feedback, you can say:
- "You consistently finished mechanics tasks early — you're faster than you think"
- "UI tasks took you longer than your estimates — keep that in mind"
People love hearing specific, evidence-based feedback in reviews.
Digitize Everything
Whatever format you use, Tim eventually digitized all of it. Paper notes, loose leaf, journals — everything got digitized because:
- Searchability — you can find anything by searching text
- Cloud backup — if your computer explodes or you lose your phone, everything is safe
- OCR is amazing now — modern OCR can handle printed text, typed text, and even cursive handwriting
Tim's 30+ years of digitized notes are what enabled him to create his Fallout and Temple of Elemental Evil development timeline videos — just looking through his notes and reassembling events in order.
Don't Let Perfect Be the Enemy of Good
Tim's strongest recurring theme: don't stop taking notes because of imperfection.
- Your journaling software doesn't support cross-references? Keep using it.
- You can't insert photos or video? Keep using it.
- You forgot to journal yesterday? Just journal today — write down what you remember from yesterday, date it today, and move on.
- Your notes aren't as detailed as you'd like? They're still better than no notes.
Tim himself has notes missing dates, missing names, missing context. He doesn't wish he hadn't taken those notes — he wishes he'd taken better notes. Every imperfect note is still valuable.
References
- Tim Cain. YouTube video. https://www.youtube.com/watch?v=kbHlwUS7d4k