Dress Right, Pack Light, Parent Smarter

Hey Pops,

It’s Monday. The kids are home, sticky and bored. You’ve answered “what are we doing today?” three times—and it’s still before 9am.

The weekend was a blur of sunscreen, snacks, and somehow being responsible for everyone’s packing except your own.

I don’t need a break. I need a second brain that doesn’t argue or spill juice on my keyboard.

Enter AI.

Here's what we're diving into today:

• Dress better without turning into a try-hard
• Skim parenting books like a genius, not a slacker
• Let AI pack your suitcase without overthinking it

Let's get after it.

THE SITUATION:

You’ve got a family dinner or a last-minute invite to something “casual but nice.” You want to look decent, but everything in your closet is either a free T-shirt or suspiciously wrinkled.

ASK CHATGPT:

"Help me choose outfits based on the weather, what’s on my calendar, and what’s already in my closet. Keep it dad-appropriate, low-effort, and avoid anything that screams ‘midlife crisis cosplay.’"

FOLLOW-UP PROMPT: "Now help me build a capsule wardrobe: versatile basics I can mix and match without thinking. Bonus: suggest replacements for worn-out items and where to shop that won’t make me feel like I wandered into Gen Z TikTok."

REALITY CHECK: Nobody’s asking you to start caring about “aesthetics.” You just need an outfit that doesn’t make your partner immediately sigh when you walk downstairs.

THE SITUATION:

Your partner handed you a book on “gentle discipline” or “raising emotionally intelligent toddlers,” and you swore you'd read it. That was three weeks ago. It’s now functioning as a coaster.

ASK CHATGPT:

“Summarize this parenting book into five bullet points like I’m a tired dad with 30 seconds of focus left. Skip the fluff. Give me the key insights I need to know.”

FOLLOW-UP PROMPT: “Now turn this into a cheat sheet I can actually use—examples of how to apply these ideas in real life. Like, what do I say when my kid hits their sibling with a juice box?”

REALITY CHECK: You already are a good dad. This just helps you sound like one when you’re too tired to think of anything but snacks and silence.

THE SITUATION:

You’ve got a trip coming up. You’re juggling kid gear, work stuff, and whatever’s clean in the laundry pile. You want a system that keeps things efficient and saves brainpower for more important things—like remembering which kid still needs sunscreen.

ASK CHATGPT:

"Help me build a personalized packing list based on where I'm going, how long I’ll be there, the weather forecast, what I’ll be doing (work, family, leisure), and if I need to pack for my kids too. Keep it efficient but complete—no overpacking, no forgetting the essentials."

FOLLOW-UP PROMPT: "Now turn this list into a checklist I can use on my phone. Group items by category, flag anything I need to buy, and add bonus dad-specific items like kids' snacks, phone chargers, allergy meds, and backup outfits for surprise barf situations."

REALITY CHECK: You’re fully capable of packing underwear. This is about saving time, not proving your competency. Let AI handle the checklist so you can focus on the actual chaos of getting out the door.

Tool of the Week: Shortwave

Gmail is a mess. Shortwave makes it tolerable.

It takes your long, messy email threads and gives you clean, AI-generated summaries. You can actually see what matters and reply faster—with less “Hey, just checking in again…”

Perfect if your inbox is a mix of birthday invites, work drama, and forgotten school emails from last Tuesday.

🔹 Works with Gmail. Free personal plan available.