🚀 Why Sunday nights feel worse than Monday mornings

“In this world, nothing can be said to be certain except death and taxes…and the Sunday Scaries.” Benjamin Franklin knew that even if you love your job of founding a country and drafting up Declarations, you might still dread going into the office on Monday.

Part of the Sunday Scaries are attributed to the sadness of the weekend ending, but it's the creeping anxiety about the week ahead and all that it might entail that truly horrifies product managers. It sucks because it makes Sundays feel less like a day off and more like a countdown.

As PMs, we're not just dreading Monday—we're dreading walking into Monday with zero context on where we left off with that critical feature spec, which stakeholder is blocking the API decision, or why we scheduled three conflicting user research sessions.

It's like being the "Outie" version of yourself from Severance—except instead of corporate conspiracy, your "Innie" self just left you a cryptic Slack thread and three half-finished PRDs.

The result? Monday becomes a scramble to piece together your work instead of driving product forward.

The 15-Minute Fix That Actually Works

Here's the two-part system that works. But if this feels like too much to start, just begin with the Sunday Check-In—it's the real Sunday Scaries killer.

The solution isn't working all Sunday (we're not monsters). It's spending 15-30 minutes on Sunday evening to bridge the gap between Friday-you and Monday-you.

Part 1: The Friday Checkout

Before you log off Friday, brain-dump these into a note:

• Unfinished business: What's half-done and needs your attention Monday? Rank by impact/urgency.

• Project pulse check: One-line status for each initiative. What's the next concrete action?

• Meeting prep radar: Which Monday meetings need prep? What decisions are you driving?

Pro tip: Do this at 4 PM, not 5:59 PM. Your Friday-afternoon brain still has some juice left.

Part 2: The Sunday Check-In (15-30 minutes)

Sunday evening, review your Friday Checkout and add:

• Weekly priorities locked: Based on your Friday Checkout, what are your three concrete priorities for the week? Slot them directly into your calendar.

• Calendar optimization: What meetings can you kill, combine, or delegate? Your future self will thank you.

• Waiting on others: What are you blocked on? Who owes you decisions, feedback, or deliverables? Note what you need to follow up on.

The AI Upgrade

Create a ChatGPT/Claude project with these instructions in the project settings:

"You're my PM context assistant. Help me with the weekly wrap-up and planning. When I dump my Friday brain contents, organize them into three clean sections: (1) Unfinished Tasks (prioritized by impact), (2) Project Status (with next concrete actions), and (3) Meeting Prep Needed. When I ask for Sunday planning based on those Friday notes, help me identify my top 3 priorities for the week and suggest how to structure/sequence them. Keep everything scannable and action-oriented."

Then use the same conversation thread each week:

Friday: Voice-memo your brain dump and it'll organize everything cleanly.

Sunday: Ask: "Based on my Friday notes, what should my top 3 priorities be this week?"

This simple ritual transforms Sunday anxiety into Monday confidence. When you start the week knowing exactly where you left off, you make faster decisions and manage stakeholders proactively instead of playing catch-up.

The Sunday Ritual Reward

After your check-in, reward yourself. Watch whatever HBO show is currently dominating Sunday nights, eat a little sweet treat, or do whatever helps you transition from "work brain" back to "weekend brain." 

Whether you're drafting the Declaration of Independence or plotting to steal it for some Freemason treasure hunt, there's no better way to beat the Sunday Scaries than with a bit of preparation. Because the best product managers don't just ship features—they ship momentum.

The Meme