iOS Today 779: Holiday Planning
Hosts: Micah Sargent & Rosemary Orchard
Date: November 20, 2025
Episode Overview
In this festive edition of iOS Today, Micah Sargent and Rosemary Orchard dive into the art and tech of holiday planning. They explore the best apps, gadgets, and strategies for organizing everything from Thanksgiving feasts to holiday Secret Santas, all while keeping the process (and the people) stress-free. Whether you’re a meticulous planner or a “pantser,” this episode is full of practical iOS and cross-platform recommendations for invites, lists, gift exchanges, and more.
Main Topics & Discussion Highlights
1. Setting the Tone for Low-Stress Holidays
- Micah expresses his love for Thanksgiving as his favorite, least stressful holiday—recalling how it’s about “everybody gets together and we just have a fun time and it's less stressful.” (03:00)
- Rosemary, as a Brit, notes the cultural differences in holiday observance and planning.
2. Event Planning & Invitation Apps
Apple Invites App (04:30)
- Micah introduces Apple’s new Invites app for organizing get-togethers.
- Key Features:
- Fun, customizable backgrounds (fall themes, photos, colors).
- Built-in shared photo albums for event guests, so everyone can upload photos during the event.
- Integrated links for things like gift registries.
- Group playlist creation for collaborative party music.
- Guest management options, like approval of attendees and plus-ones.
- Accessibility tools like background image descriptions.
- Communication tools for real-time event updates.
“This is the thing that makes this unique… If I choose Create Album, what happens here is everyone who joins this invite is able to then add photos to this group album.” —Micah (05:30)
Partyful (08:00)
- Alternative for cross-platform and non-Apple users.
- More visually dynamic, “more Gen Z” with options like custom emojis, animated effects, and polls for finding the best date.
- Built-in payment splits (Venmo integration), registries, dress codes, food, parking details, and SMS message blasts.
- Micah emphasizes inclusivity: “Honestly, I'm very much of the opinion you meet people where they are, right? … I'll download the Partyful app, I'll use that.” (09:30)
3. Organizing Lists, Tasks, and Timelines
Apple Reminders (17:00)
- Rosemary uses Reminders for Christmas gifting and general holiday task lists.
- Utilizes sectioned lists for better organization (by recipient, task type, etc.).
- Features like date/location-based reminders, shared lists, tags, subtasks, images/notes, and assigning tasks to individuals.
“This works really well for just being like, oh, yeah, I've got this idea of this thing that I need to do. But it also works very well for planning for holidays.” —Rosemary (18:20)
OmniOutliner 6 (20:00)
- Advanced outlining tool, now in public beta.
- Ideal for comprehensive planning: nested tasks, status tracking (idea/purchased/wrapped/delivered), budgeting, and bulk edits.
- Powerful for meal preparation timing (e.g., coordinating cooking times).
- Advanced automation uses AI to help draft to-do lists for big meals or events.
“You can build something like a book list, and this is a table… You can assign them with a little dropdown to a particular person. I can show what status they're in: is it an idea, is it purchased, is it wrapped, is it delivered, etc.” —Rosemary (21:25)
4. Recipe Management for Holiday Cooking
Paprika & Crouton (24:00)
- Micah recommends Paprika (robust, cross-device syncing).
- Rosemary highlights Crouton, an intuitive, hands-free cooking app designed for smooth in-kitchen usage.
- Both easily import recipes, strip out superfluous text, and focus on usability while cooking.
5. Keeping the Focus on Celebration
“Make sure to actually remember what the purpose of your current celebration is. Is it seeing your friends and family? If things go wrong… don't stress too much. Somebody out there on the Internet will have had the same problem and will have a suggestion for you—and worst case scenario, have a frozen pizza in the freezer just in case.” —Rosemary (26:16)
6. Streamlining Gift Exchanges
Elfster (27:00)
- Micah: “None [of the other Secret Santa apps] have been as good… It knows what you need when it comes to a Secret Santa app and tries to present all of those features.”
- Features: automatic exclusions (e.g., not drawing partners), public budget setting, in-app messaging, and anonymous questions.
- Rosemary’s pro tip: Send “red herring” messages for extra secrecy and fun, and use anonymous wrapping methods for an added layer of surprise.
“These things are intended to be fun, so keep that in mind.” —Rosemary (29:00)
Notable Quotes & Memorable Moments
- “Every name in your system is a person who trusts you, and every password is a door you're responsible for locking. And when the threat comes, and it always comes, you hold back the chaos.” (Opening context, 00:01)
- “Is it designed for this sort of thing? Yes and no. Omni Outliner actually has… automatic light and dark themes for the notes or the documents themselves.” —Rosemary (21:55)
- “If something goes wrong, make it part of the fun for sure.” —Micah (26:38)
- “If you put your phone in this pocket, you have to get it back out to use it. I also feel like the likelihood of you trying to put your phone through the slot… and dropping your phone onto the floor… is way too high.” —Rosemary on the new über-expensive Apple “iPhone Pocket” accessory (36:12)
App & Gadget Picks: "App Cap" Segment
Taurus Mini Mag Power Bank (41:35)
- Rosemary’s favorite slim, 5000mAh MagSafe-compatible battery pack (~$40), great for small pockets and on-the-go.
Locket Widget (43:50)
- Micah spotlights this “private social media” app: friends share photos directly onto each other’s home screens.
- Recent feature: group “photo dump” or “roll call,” where friends contribute photos en masse, weekly.
- Free with in-app upgrades.
Timestamps for Key Segments
- 03:00 — Holiday philosophy & stress-free planning
- 04:30 — Apple Invites app demo
- 08:00 — Partyful as a cross-platform option
- 17:00 — Apple Reminders for planning
- 20:00 — OmniOutliner 6 for advanced organizing
- 24:00 — Recipe apps (Paprika & Crouton)
- 26:16 — Celebrating family, not perfection
- 27:00 — Elfster for gift exchanges
- 41:35 — Taurus Mini Mag Power Bank review
- 43:50 — Locket Widget review
Wrapping Up
Micah and Rosemary encourage listeners to focus on togetherness and stress less—tech can help, but the memories matter most. From event invites to surprise gifts, this episode delivers a toolkit for making your holiday season smoother and more joyful.
Next Week: More iOS, gadget, and app recommendations.
Contact: Email: iostoday@twit.tv
Rosemary: rosemaryorchard.com
Micah: @MicahSargent or chihuahuacoffee.com
Happy Holidays!