Streamlined Solopreneur: Helping solopreneur parents stop checking email at the playground

My 4-App Travel System That Saves Hours of Trip Planning

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Jun 16, 2025

Tune in for a deep dive into an effective travel system that transforms trip planning. Discover how Flighty keeps you ahead of delays, while Apple Notes organizes all your vital information. Learn about the 'New Trip' shortcut that simplifies everything from calendar events to personalized packing lists. Hear tips on navigating airports smoothly, especially with family, and find out why checking bags beats carry-ons. Plus, insights into Southwest’s changing policies impact family travelers!

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ADVICE

Flighty Transforms Flight Tracking

Use Flighty app for real-time flight tracking with AI delay forecasts before airlines notify you.
It also tracks connections, terminals, and has helpful widgets and Apple Watch integration for travel convenience.

ADVICE

Apple Notes for Trip Organization

Use Apple Notes to organize all trip info in one accessible note with reservations, confirmations, and itinerary.
Share notes with travel companions for collaboration and quick reference during trips.

ADVICE

Automate Trip Planning Shortcut

Use a 'New Trip' shortcut to automate trip planning: add calendar events, generate packing lists, and create project templates.
It reduces cognitive load by automatically customizing packing and trip tasks based on trip length and type.

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I'm recording from Kit Studios in Boise while attending conferences, which got me thinking about something crucial to my business success—my travel system. As someone who travels frequently for networking and conferences, I've developed a streamlined approach that keeps me organized and stress-free on the road.

My system revolves around two essential apps: Flighty for flight tracking (which often knows about delays before airlines do) and Apple Notes for keeping all trip information in one easily accessible place. But the real magic happens with my "New Trip" shortcut that automates the entire trip planning process—from creating calendar events to generating custom packing lists based on trip length and type.

I also swear by checking bags instead of dealing with carry-ons, mainly because I travel with items that can't go through security, but also because it lets me move through airports quickly with just my backpack. Plus, I share some thoughts on Southwest's recent policy changes and how they might affect family-friendly travel.

Special thanks to Kit for letting me record in their Studios! I highly recommend them for email and newsletters!
Get my free automations database at https://streamlined.fm/automation (powered by Kit, natch)

Top Takeaways:

Flighty is a game-changer for frequent travelers — it provides real-time flight tracking with AI forecasting that often alerts you to delays before airlines do, plus it tracks connections and terminal transfer times
Create a "New Trip" shortcut to automate trip planning — mine calculates trip length, adds calendar events, generates custom packing lists, and creates project templates in one tap
Set up dedicated travel and conference focus modes — customize your home screen with essential widgets (time at home, flight info, maps) and silence non-essential notifications

Links

My iPhone Focus Modes
Flighty - Flight tracking app with AI forecasting
Apple Notes - For trip organization and quick reference
Widgetsmith - For custom widgets (QR code display)
Whisper Memos - Voice note recording
Ticci Tabs - Bookmark manager app
Todoist - Project management for work tasks
Apple Reminders - For packing lists and personal tasks
MacSparky - David Sparks' site (source of packing list shortcut inspiration)
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