_{Day 93/100}

Hey—It's Tim.

I updated the website theme the other week.

Not a big update. Just wanted access to some new layout features.
Clicked the button. Watched the spinner. Felt smug.

And then...
BOOM.

All my custom PHP — gone.
All the duct-taped logic I’d written for Penfriend. All the clever little things I built to make the site work how I wanted.

Poof. Like it never existed.

Whole thing reminded me of the only real rule of SaaS life:

Software loves you right up until it updates.

How to not implode your life when something updates behind your back.

1. Back your shit up.

Not just your site. Your logic.

• Got custom code? Save a copy in Git or Notion or a folder called “do-not-delete-this-i-swear”.

• Got custom fields in your CMS? Screenshot them. Label them.

• Got automation that only works because of one weird webhook path you found in a Discord thread in 2021? Write that down somewhere. Seriously.

Because when the update hits… it’s not just about fixing it.
It’s about remembering what the hell it even did in the first place.

I have a whole folder of things like this in my gyazo.
Shoutout gyazo. Best screenshot app ever.

I wrote a love letter to it once.

2. New update dropped. Everything is broken. Again.

Here’s the emergency checklist I now run.
(It’s taped to the mental dashboard next to “don’t ship at 5pm on a Friday”.)

1. Panic briefly. Then stop panicking.
   This step is mandatory. Let it happen. Then move on.
   

2. Revert the update (if you can).
   Stop the bleeding. You don’t need to debug chaos in real-time.
   

3. Check your backups.
   Not just the site. The logic. The config. The weird folder of half-working PHP from 2022.
   

4. Triage what’s broken.
   Focus on anything that handles:

   1. payments

   2. login

   3. forms

   4. content display
      Everything else can wait.
      

5. Tell your goddamn team what is going on.
   A Slack thread, a status page, a sticky note on their desk.
   Doesn’t matter. Just don’t disappear into the debug abyss with zero context.
   

6. (Optional but cathartic)
   Write a newsletter about it so your pain has ROI.

3. Learn the lesson twice. And then a third time

This isn’t the first time this has happened to me.

• Once I broke a checkout page because I forgot I had hardcoded a Stripe key in a theme file.
  

• Once I lost a year’s worth of testimonials because I didn’t realise my CMS purge setting was set to 30 days.
  

• Now this.

Apparently I need the lesson in surround sound.
So here it is again, in bold:

If you’re lucky, the update breaks something you notice.
If you’re unlucky, it breaks something you don’t — and your conversions quietly fall off a cliff.

One last thing I’ll add?

If your tool lets you export settings, do it.
If it doesn’t — stop using that tool. Or build your own. Like I did.
(Don’t recommend. But also… recommend.)

See you tomorrow.

✌️ Tim "Is there a personality update?" Hanson
CMO @Penfriend.ai

Same brain, different platforms: X, Threads, LinkedIn.

P.S. 
Next week might be the last one.
But between us...
if enough people reply, I might keep going.
Don’t tell anyone. Just hit reply.

Penfriend.ai
Made by content marketers. Used by better ones.