In 2007, Drew Houston posted his new app to Hacker News: “Dropbox - Throw away your USB drive.” The top comment is now infamous in some circles.
I signed up on January 21, 2010. Upgraded to a paid plan eight months later. $9.99 for 50 GB. Like a lot of venture-backed software, Dropbox started as a simple, lightweight app that worked incredibly well. Now it’s a bloated piece of crap whose time is up the next time I have a free afternoon to find a replacement.
But one nifty feature they added around 2017: any screenshot you take on macOS automatically lands in a Dropbox screenshots folder. I never think about it. Cmd-Shift-4, grab what I need, move on. The folder just accumulates.
I’ve been using Claude Code for everything lately, so I pointed it at the screenshots folder to see what was in there.
The hockey stick
I’ve taken more screenshots in the last three months than in 2020, 2021, and 2022 combined.
The totals:
| Year | Count | Daily Avg |
|---|---|---|
| 2017 (Jul–Dec) | 285 | 1.6 |
| 2018 | 966 | 2.6 |
| 2019 | 878 | 2.4 |
| 2020 | 549 | 1.5 |
| 2021 | 600 | 1.6 |
| 2022 | 513 | 1.4 |
| 2023 | 524 | 1.4 |
| 2024 | 329 | 0.9 |
| 2025 | 1,977 | 5.4 |
| 2026 (Jan–Feb) | 1,544 | 27.1 |
For most of those years I averaged one or two screenshots a day. Then late 2025 hit and it exploded to 27 per day. The reason is Claude Code.
The adoption timeline
I installed the Claude Code VS Code extension on October 9, 2025. For the first month I was mostly poking around. Screenshots barely moved. Then around mid-November something clicked and my weekly average went from 6 to 113. By December I was at 688 a month. January 2026 peaked at 898.
The best artifact in the whole archive is from December 14. It’s a screenshot of my terminal showing npm i -g @anthropic-ai/claude-code failing with an EACCES permissions error. The tool that would 10x my screenshot rate, captured at the moment of its own failed installation. I had to sudo my way through it.
The terminal that launched a thousand screenshots.
Once I got it working, the projects started stacking up. Hallucinating Splines (a SimCity-for-AI-agents platform that hit the front page of Hacker News), Battlefield First Edition with my 9-year-old, over a dozen internal tools and prototyping sessions at Hello Gravel. Each one meant rapid-fire screenshotting of outputs, errors, and results.
My busiest single day was January 22: 84 screenshots. I was building out RockOS, an internal tool for Hello Gravel that handles order processing and supplier management. I was trying to get the design right while also running a data migration out of Airtable. Between 10 and 11 AM I took 23 screenshots, one every 2.6 minutes for a solid hour.
A second shift
The screenshot timestamps show something I wouldn’t have noticed on my own. In 2018 and 2019, I was a textbook 9-to-5 screenshotter. Almost nothing before 8 AM or after 6 PM. Morning peak at 10 AM, afternoon peak at 3 PM, then a cliff at 5.
The Claude Code era looks different. The daytime pattern is roughly the same. But now there’s a second peak from 7 PM to 11 PM that barely existed before. The evening volume at 9 PM now rivals the morning peak at 10 AM.
After putting the kids to bed, I get a little more Claude time in!
An accidental career history
The content of the screenshots is its own timeline. My first screenshot, July 5, 2017, is a database connections dialog: PostgreSQL, MySQL, Oracle, DB2. Enterprise admin stuff.
2018 is email marketing analytics, CRM tracking with opens, clicks, sends. 2019 is Salesforce error pages and Slack channels (there’s a screenshot of a Slack message about a board dinner: “I think you earned a place in there tonight”). 2020 shifts to Plaid API pricing tiers and fintech strategy decks. 2021 is construction lending business plans, slides titled “Who We Sell To” targeting subcontractors. 2022 is sales commission spreadsheets.
Then 2025 arrives and it’s all Claude Code terminals, MCP server extensions, and split-screen workflows with code on the left and a browser on the right.
I’ve been quietly documenting my career with screenshots.
The mundane stuff
Some other things visible in the data.
macOS changed the screenshot naming convention three times. In 2017-2019, files were named Screenshot 2017-07-05 14.20.22.png with 24-hour time. Around 2020, macOS Big Sur changed it to Screen Shot (two words) with AM/PM and “at” in the middle. Then macOS Ventura around 2022-2023 changed it back to Screenshot (one word) but kept the AM/PM. This breaks the clean sorting order of the folder. I’d love to hear the thrilling insider story from someone at Apple about how this happened.
Every August vacation shows up. We do a two-week vacation each summer and the data knows it: 14-day gap in August 2022, 13-day gap in late July to August 2023, 13-day gap in late July to August 2024. August is consistently one of my quietest months even outside the gaps.
December 2023 was my quietest month ever at 14 screenshots. That lined up with some changes in my work. 2024 was the least active full year at 329 total, under one per day. The contrast with 12 months later is pretty stark.
The longest gap was 15 days in late April to early May 2024. I’m fairly sure a Dropbox update or something turned off my screenshot capturing and I didn’t notice for a couple of weeks.
Wednesdays are peak screenshot days. 1,710 total, slightly ahead of Tuesday and Thursday. Weekends barely register: 6x fewer screenshots than weekdays.
52% of all days over 8.5 years had at least one screenshot. Since Claude Code, it’s closer to 100%. All 13 of my 50+ screenshot days have happened since December 2025.
My first screenshot was a database connections dialog. 8,000 screenshots later, the only consistent thing is Cmd-Shift-4.
The screenshot that started it all. Is this DataGrip?