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Book Brew 154: When Your Font Betrays You: Lessons From a Gibberish PDF

Book Brew

Apparently, fonts have the power to humble you. I learned that the hard way.

The Human Edge
(backstory cuz I can’t help myself)


Back in August, Damien gave a presentation with HubSpot titled “The Human Edge in an AI World.” In it, he presented the attendees with a Writing Style Guide Template that we then gave to them for free as a thank you for attending and participating in the session.


The presentation was fantastic, because Damien.  Lots of the attendees downloaded the template.


Enter: The Gibberish Files

“When you only share your wins, you create distance.  When you share the struggle that led you to the win, you create connection.” Justin Welsh


Then the “oh shit” moment happened.  


I received the following message from one of the attendees (who also happens to be a friend, former co-worker, and the amazing owner of Petals and Pearls Craft Designs, who designed my beautiful wedding bouquet)

 A screenshot of a text message conversation. The top message says, "I got the template!" and the bottom message says, "But the download looks like this-". In between the messages is a screenshot of a mobile phone displaying a document titled "Writing Style Guide." The subtitle reads, "Your AI Tools don't write like you because you didn't tell them how." The rest of the document, which lists the guide's contents and uses, is corrupted with garbled characters and gibberish, indicating an error with the file display.


“Failure becomes cheap education.” Justin Welsh


Well, that’s not at all what it should look like.  


Turns out, despite testing the file across multiple desktop and handheld devices, we never tested it out on any Apple products. 

The font we used was not a WebSafe font (these are the fonts that are pre-installed on the majority of devices and operating systems….think Arial, Times New Roman, Georgia). So when it loaded on a device that didn’t have our chosen font (Playfair Display), it loaded gibberish.  Yay.


Don’t Bitch, Just Fix It

“Whatever it is - if you gotta do it, don’t bitch about it.” - Matthew McConaughey 


I followed McConaughey’s advice and fixed it…no bitching needed.  I reformatted the entire document.  Reuploaded to our website.  And then manually sent messages to each of the attendees who downloaded it, giving them the corrected version.  Not exactly how I had wanted to spend the hour following the session.


Customer Service > Ego

(that’s a "greater than" symbol for anyone who is rusty on their math)

“Never make the customer do what I could do for them.” - Justin Welsh


I could have been an ass and just told them that it was a paid resource we spent hours painstakingly creating that we gave them for free, so suck it up, buttercup.  But we aren’t those kinds of assholes (don’t get me wrong, we can be assholes, but not when it comes to customer service and integrity).


Growth by Gibberish

“Growth demands discomfort.” James Clear


Did I enjoy “failing” in this moment? Not really.  


But did I embrace it as a moment of growth? Absotively posilutely! 


Because, as Lucy Hictchcok wrote in one of Steven Bartlett’s 100 CEO’s newsletters:

If you’re not able to self-check and look at your own weaknesses, you’ll never be able to have a healthy business in all areas.” 


Rules for Surviving Fontpocalypse 2025

  • Check Yo’ Work → Then check it again. Fonts are sneaky little gremlins.
  • Failure = Tuition → If you don’t have room for failure, you don’t have room for growth.
  • Web-Safe or Bust → Use fonts everyone’s devices recognize (sorry, Playfair, you’re pretty but a liability in documents).
  • CSS Is Your Friend → Always set a backup font family…this is your safety net against chaos.
  • Laugh, Don’t Lash Out → A good belly laugh beats beating yourself up.
  • Don’t Be an Asshole → Fix the problem for your customer, even if it’s free. Integrity > Ego.
  • Blame the Capybara (Optional) → When all else fails, pass the buck to an adorable rodent.

Ponder This

  1. What’s your most memorable “facepalm” moment and what did it teach you?
  2. How do you handle mistakes: denial, deflection, or ownership?
  3. Would your customers say you fix problems or hand them more work?

Books/Newsletters

  • The Saturday Solopreneur - Justin Welsh
  • 3-2-1 - James Clear
  • Lyrics of Livin’ - Matthew McConaughey
  • 100 CEOs - Steven Bartlett

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