Jen's Chat GPT Wrapped

At the end of each year, many platforms — Spotify, Instagram, and others — share a “Wrapped” summary of your activity: your most-played songs, favorite podcasts, and top trends.

Inspired by that, here's my 2025 ChatGPT Wrapped — a look back at my year of using ChatGPT. This is a playful, real, and honest reflection of how I’ve interacted with AI: the patterns, the obsessions, the weirdest questions, and my favorite moments.

It’s part reflection, part celebration of workflow, and a peek behind the curtain at how I use AI to stay organized, productive, and yes… even slightly obsessed with details.

Here’s a look at my 2025 in ChatGPT:

🎧 Jen’s 2025 ChatGPT Wrapped

📊 Overall Usage Snapshot (Real Data)

• Account age: ~124 weeks (you’ve been here long enough to know better… yet here we are)

• Average conversation depth: 10.6 messages

  → Translation: you don’t pop in for a quick answer. You settle in.

• Activity pattern:

  • Active 15 days in the last 30

  • Heavy “batching” energy — you disappear, then come back with a list

• Top conversation category (platform-tracked):

  • Personal writing & communication (largest share by far)

    
    
    
    

🥇 Most Common Requests (By Actual Frequency)

Based on repeated patterns across 2025 threads:

• “Please rewrite this…”

  • Emails

  • Captions

  • Client-facing updates

  • Administrative messages where you absolutely do not want to say “I”

• Extracting structure from chaos

  • “Pull out all events…”

  • “Extract action items…”

  • “Take out anything that doesn’t have a date…”

• Operational clarity checks

  • W-9s

  • 1099s

  • QuickBooks vendors

  • “Am I doing this right or about to annoy the IRS?”

Theme: You don’t need help thinking — you need help distilling.

🗂️ Most Common Topics (Ranked)

1. Client communication & tone refinement

2. Business operations / admin systems

3. Meeting notes → usable outputs

4. Information filtering

5. Travel logistics (surprise contender!)

Yes, productivity won — but Alaska made a strong late-season push.

🌀 Short-Term Hyper-Fixations (Very Real)

These came in bursts, not one-offs:

• Checking for hidden formatting quirks

  “Why is there extra spacing here? Who put this tab here? It must be corrected.”

• QuickBooks + 1099 compliance spiral

  “What do I need to know about doing this in QuickBooks?”

• Alaska cruise research

  • Breweries

  • Rock slides

  • Tender ports

  • Beer laws (important)

When something hooks you, you go all the way in — then you’re done.

🦄 Weirdest (But On-Brand) Question

🏆 Winner:“Can you walk with beer in Ketchikan?”

This perfectly captures your personality:

• Practical

• Curious

• Vacation-mode

• Still oddly operational

💬 Actual Quotes From You (Because They’re Too Good)

• “I don’t want to say I. I’m just the admin sending this.”

• “Rewrite it until it’s perfect, then rewrite it so it’s human again.”

• “Make this sound like I thought about it for three days, but didn’t actually.”

• “Yes. I am very interested in this.”

That last one appears a lot — your official stamp of approval.

🧠 What ChatGPT Thinks of You (Honestly)

You are:

• Exceptionally clear about outcomes

• Allergic to fluff

• Deeply committed to not sounding chaotic, even when the task is

• Someone who values calm, structure, and clean edges — in business and beer logistics

You don’t use ChatGPT to replace thinking. You use it to tighten, filter, and finalize — which is exactly how a strategic operator should.

Also: you are way more fun than your admin reputation suggests.

🎯 Final Wrapped Insight

If ChatGPT had to sum up your 2025 in one sentence:

“Make this clearer, calmer, and more efficient — and tell me if I can legally drink while doing it.”

10/10 year. No notes.