aka The Self-Inflicted PUNishment of a Dude Who Can’t Stop Drawing Puns
When I started drawing puns back in 2013, I had no idea what a tiny little corner I would be doodling myself into. Little did I know at the time, I’d be making over 2900 of them… In October 2015, I hit the 1,000 mark and figured it was time to catalog everything I’d done into a searchable digital archive. That’s where the fun 10-year journey started…
 2015: Initial attemptÂ
The majority of my first 1,000 posts on Instagram were photos of my drawings taken with my phone. There wasn’t a quick and easy way to download them from Instagram, so in order to catalog them, I had to bust out the sketchbooks and scan them one by one.
If you’ve ever tried scanning or making a copy of anything from a book, you probably know it’s a little clumsy. The binding side of the pages shows up darker in scans because they’re not flat against the scanner bed like the rest of the page. That took a lot of cleanup for drawings that were next to the binding. I fit an average of 4 drawings on each page, so there was a ton of cropping and cleanup of the scans… I see the scan to the left had a small hair on it which I’m sure I spent more time than I needed to fixing in Photoshop. Ah, good times! And then each file had to be named, and I had to figure out the dates of the early ones I did before I started putting the dates on the lower right corner.Â
I’m sure it took at least a week, but I did it, and then had no idea what to do with the scans. I found I couldn’t put them on my website without them bogging the load time of the pages down to a crawl. I know – I’ll make a book! But if I made a book (which will happen one of these days) I wanted the captions from Instagram posts under each one, and heck if I was going to copy and paste those from each Instagram post 1,000 times.Â
Between having a day job that ate up 1/3 of my day and keeping up with getting new music out of my head on top of that (2015 was a very prolific songwriting year), I hit a brick wall, and the catalog door closed, while the drawings kept on a-comin’.
2020: Back to it
Ah, good ol’ 2020. Between the plague and living in the middle of Minneapolis while the stores I shopped at were being looted and burned down that May, I had a lot of free time to kill at home. When it got to the point where I was watching Youtube videos of different ways to fold socks, I realized maybe it was time to do something more important, such as looking into how to get my drawings into some sort of searchable database again. By that point, 5 years of drawings (1,400 more) were posted on my Instagram feed. Along came 4K Stogram, an app that allowed me to download my entire Instagram feed along with a CSV file of dates and captions. Although the data was complete, it was messy. Here’s what the Instagram export file names looked like:
It included all my reels and stories, too, so the grand total was over 2,800 Insta-files with mile-long names like that. Ew. One helpful aspect was that the names contained date and time stamps, which simplified organizing them. I needed to rename the files to make them understandable. This involved manually entering each name into the CSV file and using a file renaming application to remove unnecessary numbers and rename the files to make them easily sortable by date and searchable, like this:
Once I started digging into that, I realized I was in for another uphill battle. After spending countless hours dealing with the file name piece, figuring out how to clean up the captions was the last thing I wanted to do, plus, I was consumed with moving back to NYC… and so the punny catalog door closed yet again!
 2025: Captions, and 500 more new punnies to deal with
In January 2025 I felt it was high time to get my art off my much-neglected social media accounts and onto my website. Social media just isn’t as fun to me anymore – it’s far more invasive than it is enjoyable. My feeds are cluttered with ads and content I don’t want to see (much of it from accounts I don’t even follow – don’t get me started on those stupid reels… people I follow whose content I actually want to see seem to be harder to get to. Instant messaging always annoyed me too with how the second I read a message, it’s visibly marked as read on sender’s side. I got tired of trying to keep up with it all. This meant it was time to sit down once and for all to get this shit done. By that point, I had about 500 new punnies, so instead of 2,400 I now had 2,900 to deal with. Ugh!
See all those light grey areas and cute lil emojis? For years, Instagram didn’t allow line breaks in captions, so the workaround was to paste in a string of invisible code to create the illusion of a line break. Those characters, certain emojis, and other things like commas and quotation marks when trying to convert all 1,435,219 caption characters to a CSV file for Lightroom.
There was no single search & replace function or script that completely stripped that crap out, and until that was done I couldn’t import the captions to to Lightroom without all that crap causing crashes and import errors. It took a lot of experimenting and a combination of different tricks, but I found the magic combination. If I ever had to do this again, I honestly have no idea what I did! Thankfully, this is a one and done thing and I’ll never have to deal with this type of large-scale conversion again.Â
In addition to that, I spent a lot of time figuring out how to best optimize the images so they didn’t cause significant slowdowns with page load times on my website. Load times are still a little pokey, but it is now at a stage where it can be shared and I can start shutting down my Facespace and Instagland pages.
I’m not even close to done drawing puns; my punny-do list is still a mile long. Now that this cataloging challenge is in the rear view mirror, they’ll be posted here on my site instead of social media. There will be an option to comment for anyone interested in that. There’s still a lot of work to be done (such as a shop and figuring out an order form for custom GuyWhoDraws wallpaper) but 12 years into this, I feel like I’m finally off to a good start!Â
Feel free to sign up on my mailing list to get a heads up whenever the new punnies drop and other stuff pertaining to my art!
Â
