How Entrepreneurs Really Handle Work Notes Across Digital Tools

Table of Contents

1. Why everyone eventually quits their first notes app

Notion was the golden child. Until it wasn’t. Early on, I tried using Notion as a full work OS — CRM, SOPs, task list, random venting space — and what killed it wasn’t performance. It was friction. A note would start as a quick drop-in idea, but by the time I’d chosen the page, the database type, and the right emoji, the actual thought was gone. That delay killed it for anything truly fleeting.

This always seems to happen with all-in-one tools. Eventually the layers you configure to structure your thoughts start interfering with the thoughts themselves. That paradox hits fast when you’re solo or running a team under ten. If you have to tell someone where to write the thing before they write the thing, it’s dead.

Also, Notion tends to silently fail syncing across devices when it’s offline. Especially gruesome if someone’s mid-meeting, goes into a tunnel, writes something they think got saved — but doesn’t. No error, no warning. Just confusion hours later when the manager says, “Where’s the call summary?” and the salesperson swears they wrote it.

2. Using Apple Notes in professional workflows until it haunts you

For a while I ran my podcast guest questions and investor Q&A prep out of Apple Notes. It was frictionless — until I needed to share with someone who wasn’t on Apple. Game over.

Sync mostly works but iCloud has a nasty pattern where the search inside Apple Notes just gives up for certain random phrases. Like it’ll find “email pitch” but not “pitch email.” And since the app doesn’t expose any sort of export or API, you’re stuck either copy/pasting or screenshotting everything when it’s time to migrate.

One bug that’s both annoying and oddly consistent: if you paste a link-heavy bulleted list into an existing Apple Note on iPadOS, it’ll sometimes strip the hyperlinks silently. Not always. Not on desktop. I still do not understand why.

3. Hacky attempts with Airtable and why they almost work

If you don’t mind things looking ugly, Airtable actually gets you surprisingly far as a note dashboard. I once built a note tracker where every row was a conversation, with linked records for related tasks. Markdown-style notes went in a long text field. I even added a checkbox column for “punchy quote,” pulled those out to an auto-summarizer in OpenAI, and sent them to Slack.

Here’s what broke it: filtering. Once I got over 500 notes, the filtering UI would sometimes freeze in Safari. Also, rich text copy/paste into long text fields would mangle formatting unless you pasted as plain text.

There’s a hidden limitation too — you can’t view linked record previews in expanded mode and edit the child record inline if you’re already in an embed (like via shared forms or apps). Had to retrain myself to open parent records manually every time — or just accept clumsy nesting behavior.

Actually useful Airtable tip:

If you need to make a fast-filtered log of conversations, use a JavaScript button field to append text to a synced “Interaction Notes” shared view. You can automate this with Make to send a digest every Friday based on who you last talked to.

4. Why most Zapier note automations break faster than you expect

I’ve rebuilt the same basic Zap 4 times: when I finish a Zoom call, create a timestamped Google Doc with the client name and meeting transcript. Every time, some part fails after two weeks.

Here’s the usual pattern:

Zoom’s new meeting webhook double-fires if the call ends and restarts within ten minutes
Otter.ai transcription webhook doesn’t always trigger predictably — sometimes arrives before Zoom call ends
Google Drive will rate-limit creates if docs are made too fast in quick succession from a shared drive; throws silent errors that Zapier hides without logging properly
Zapier Paths can’t distinguish between copied vs original doc if titles are identical, so appends go to the wrong place

A weird workaround I found: using ChatGPT’s API to generate a doc intro paragraph reduced the rate-limit errors, possibly by slowing the execution time just long enough to escape batching issues with Google Drive. No idea why.

5. Team pushback when switching from docs to structured notes

Tried to get the team to use Noteplane for structured daily updates. Immediate feedback was: too opinionated, looks like a calendar app, syncing isn’t intuitive. Also every time someone copied from their desktop Noteplan to Slack, it stripped indentation weirdly.

The problem wasn’t the tool — it was that people have note muscle memory. They’re used to Cmd+N launching a blank page in their evil comfort zone (Google Docs). Once you’re asking people to think before they write, it’s over.

Surprisingly, the only structure that stuck was a Slack shortcut that opened a form. Top field: “What happened today that someone else might need to know three days from now?” That fed straight into a Notion database via Zapier. People trusted Slack. They didn’t trust a desktop calendar-looking thing that felt like homework every time it booted up.

6. Using Obsidian with Git sync is solid until someone touches it

I had a beautiful setup where my Obsidian vault synced to a private GitHub repo every morning, just in case. For solo note-taking and daily logs, it worked perfectly. Then I handed the Git repo to a contractor who wanted to edit files directly in VS Code.

Immediately: merge conflicts, encoding warnings, and one strangely corrupted file where a Smart Quote character turned into a diamond-question-box on Mac. Obsidian didn’t show the error — just rendered an empty note. Git diff showed a bunch of duplicated frontmatter and all-numeric lines.

The platform flaw here isn’t Git or Obsidian. It’s human behavior. Nobody tells people NOT to edit synced text files with AI-enabled code editors unless you spell it out.

Also, Obsidian on iPad doesn’t consistently respect newly renamed files if you rename while editing — it’ll save *both* versions if sync hits during the rename. I lost about six outlines that way before just disabling Obsidian Sync entirely and going back to Dropbox.

7. Thin workflow using Drafts saves more than it should

I forget how long I’ve been using Drafts, but it’s the only app that’s consistently handled the tiny half-thoughts: task stub, name to Google, podcast quote to expand later. Nothing structured. Just fast and searchable.

Eventually I built a Drafts action that lets me type a short note and tap once to:

Append it to a topic-specific Obsidian daily note via iCloud write
Send the same line to a Slack channel
Optionally queue it into a Readwise highlight via their API

The catch: sometimes Drafts will crash if the Obsidian note doesn’t yet exist. You can actually bypass this by checking for the file first in the action script, but that logic only works for certain iOS versions. Behavior seems to change under iOS 16 vs iOS 17.

The biggest “aha” moment? Logs showed that when I disabled background sync and forced Drafts to run all actions manually, it became far more stable — because Tweetbot wasn’t also trying to fetch updates at the same time on iOS. Networking collisions on mobile are the hidden enemy of your fleeting thoughts.