Twenty years of trying tools

• I’ve used Gmail since early 2006, when you still needed an invite to join. Most tools since then left a receipt or a sign-up email, so this page comes from my inbox, not from memory.
• I try tools early and I let them go when they stop earning their place. Many lasted a year or two. The few that lasted much longer each did one job well.
• I was paying for an AI writing tool in 2020 and an AI image tool in September 2022, two months before ChatGPT came out. AI is the newest wave I’ve tried, not the first.

• 2006
  files

  My inbox as a hard drive

  GmailFS, then Google Docs & Spreadsheets, later Dropbox

  tried

  Before Dropbox existed, a small program let me save files into my Gmail account and open them on any computer. The same year I started sharing plans as Google Docs instead of email attachments.

  kept

  The idea, not the hack. Dropbox replaced it in 2010, and I still write in shared documents.

  learned

  I wanted my work on any machine. The first tool that does that is rarely the one that lasts.

• 2008 to 2011
  phones

  Two phones in one pocket

  BlackBerry for work email, an early iPhone for everything else

  tried

  Bought an early iPhone in late 2008 and carried it next to the work BlackBerry. From 2009 I was the trainer who taught a call centre each new iPhone before the launch queues formed.

  learned

  Using a device on my own time first is how I learned to teach it to people who had to support it.

• 2009 to now
  show, don’t tell

  Recording the screen to explain things

  Jing and a Camtasia trial in 2009, Snagit from 2012, video editing apps later

  tried

  Short screen recordings in place of long written instructions. Snagit came in 2012 and I’ve upgraded it twice since.

  kept

  The longest-running paid tool on this page, and the habit behind the explainer videos I make today.

  learned

  Two minutes of showing saves a page of telling.

• 2009 to 2010
  switching

  Moving to a Mac without leaving Windows

  Mac mini, then a MacBook Pro, with Parallels Desktop to run Windows

  tried

  Moved my own computing to a Mac, and kept the Windows programs I still needed running alongside.

  learned

  Run the old and the new side by side until the new one covers the whole job. Nobody has to switch overnight.

• 2011 to 2019
  learning

  Paying for my own lessons

  Kelby Training (monthly, for photography), Udemy, Lynda.com, Coursera, edX

  tried

  Online courses on my own account, years before any employer asked me to.

  learned

  A course sticks when I use it on a real job the same week.

• 2007 to now
  notes

  Where my thinking lives

  MindManager trial, MindMeister, Evernote Premium, Notion, now Obsidian

  tried

  Mind maps from 2007. MindMeister stayed eight years. Evernote Premium came and went twice, Notion lasted a year, and in 2026 I moved my notes to plain files on my own computer.

  learned

  Notes outlive the app they were written in. Keep them in a form you can take with you.

• 2020 to 2023
  early AI

  AI that did one small job

  Wordtune (2020), ClipDrop (2020), Midjourney (2022), Otter.ai, QuillBot, ChatGPT Plus (2023)

  tried

  Rewording a sentence, cutting out a background, transcribing a meeting, making an image from a description. Each did one narrow thing.

  learned

  Trust AI with one small, checkable job first. The big promises can wait until the small ones hold up.

• 2025 to now
  private data

  AI that stays on my own machine

  AI models that run offline on a laptop

  tried

  Running AI models on my own laptop, with nothing sent out, for documents that shouldn’t leave it. The full story is in choosing the laptop.

  learned

  Not every job needs the biggest model. Some just need one that stays at home.

Letting a tool go isn’t a failure. It usually means another tool now does that job, or the job changed.

• start with one job

  Name the task that eats the most time. Pick a tool for that, not a tool for everything.

• try it on real work

  A month on the actual job tells you more than a demo.

• keep your files portable

  If you leave the tool, your work should come with you.

• mind the data

  Customer and staff records go only to tools you’d be comfortable telling those people about.

• cancel without guilt

  Check before each renewal. If nobody would miss it, let it go.

The same habit with cameras: I learn by trying things. The latest wave: six months of teaching myself AI. The tools I use now: toolkit.

Built from my own sign-up and receipt emails, 2006 to 2026. Games, films, music and devices bought for family are left out.