iOS Today 766: Task & Project Management

Podcast: All TWiT.tv Shows (Audio)
Hosts: Micah Sargent & Rosemary Orchard
Date Recorded: August 19, 2025
Published: August 21, 2025

Episode Overview

In this episode, Micah and Rosemary dive deep into the world of task and project management on iOS, iPadOS, and beyond. They break down the complexities of keeping on top of tasks, highlight essential apps (OmniFocus, Things 3, Apple Reminders), and provide tips both philosophical (how to approach projects and tasks) and practical (features, automations, app comparison). The episode also addresses audience questions on automation and location-tracking, covers recent Apple news, and wraps up with their current "App Caps"—recommended apps they're loving.

Key Discussion Points & Insights

1. Philosophies of Task & Project Management

• Breaking Down Big Tasks

  • Micah: Large projects feel overwhelming unless broken down into small, actionable tasks.
    • “It feels incredibly daunting… but if I just thought of [projects] in the smaller steps that actually make it up… it’s actually much simpler.” (04:04)
  • Apps ideally help users structure these smaller steps, making big tasks more approachable.

• Getting Things Done (GTD) Method

  • Rosemary: Adopts elements like the "two-minute rule"—if a task takes less than two minutes, do it right away.
    • “If you can do it right now … just do it now.” (03:35)
  • Emphasizes always knowing "what is the next step?" rather than keeping vague, intimidating project lists (e.g., “clean bathroom” broken down into granular tasks).

2. Deep Dive: OmniFocus – Rosemary’s Go-To App

Comprehensive Feature Review ([03:35]–[12:30])

• Tagging & Contexts:
  • Powerful for linking similar tasks (e.g., all tasks requiring a steam cleaner).
• Defer Dates & Repeat Options:
  • Defer tasks until a specific date so they don’t clutter your list prematurely.
  • Highly customizable repeats (e.g., “third Thursday of every month”).
• Time Zone Support:
  • Critical for coordinating across regions (OmniFocus can assign due dates a specific time zone).
    • “Your due date can be assigned to a particular time zone… everything just appears automatically at the same time.” (08:49)
• Project Types (Parallel, Sequential, Complete with Last Action):
  • Flexible structure: sequential projects reveal tasks step-by-step.
  • “Complete with last action” marks whole projects complete when final task is finished.
• Project Statuses:
  • On Hold: hides for now.
  • Completed: marks all tasks done.
  • Dropped: archived but not deleted.
• Notifications:
  • Set reminders relative to due date or at fixed moments.
• Customization:
  • Estimated durations, notes, tags, folder structure.
• Platforms:
  • Available on iPhone, iPad, Mac, Apple Watch, & web.
• Rosemary’s Caution:
  • “You need to find the task manager that works for you… Omnifocus works for me, but it might not work for everyone.” (11:53)

3. Alternative Apps: Things 3 & Apple Reminders

Things 3

• Micah: Used and enjoyed in the past.
• Similar core functionality to OmniFocus but may come down to design and personal taste.
  • “I think it boils down to kind of design choices rather than functionality.” (12:31)

Apple Reminders ([13:07]–[21:00])

• Great for beginners and everyday users.
• Key Features:
  • Date, time, location, and when-messaging triggers.
  • Repeats, tags, priorities, flagging, images/URLs.
  • Subtasks: “You can sort of see making a bit of a project right there in the Reminders app.” (18:59)
  • Printing lists for those who prefer checking things off physically.
• “For me, reminders ends up being a lot of what I need… but knowing the other tools are out there… I can hop into those and do even more.” (20:19)

Notable Listener Call-to-Action

• Listeners invited to email in their favorite task/project management apps or tips. (20:49)

Notable Quotes & Memorable Moments

• Micah on project anxiety:
  “It feels like [a project is] something I can't do… if I just thought of it in smaller steps... this is actually much simpler.” (04:04)

• Rosemary on practical automation:
  “If you can do it in less than two minutes, don’t put it in a system to do it later, just do it now.” (03:35)

• Micah on personal preference:
  “Ultimately… it’s about the one you end up using, right? And that’s the most important thing.” (12:31)

• Rosemary's app loyalty:
  “The fact that their [OmniFocus] app icon is purple definitely plays into it.” (11:48)

• Micah on Reminders subtasks:
  “You are able to see those different subtasks and check those off. And upon checking all of them off, the main task… is completed.” (19:56)

Top Apps Highlighted

| App | Best For | Features Noted | Recommendation By | |---------------|---------------------|------------------------------------------------------------|---------------------| | OmniFocus | Power users | Advanced projects, tags, defer/repeat, time zones | Rosemary | | Things 3 | Visual/design fans | Elegant design, similar core features to OmniFocus | Micah (past user) | | Apple Reminders| Everyday users | Built-in, flexible, easy subtasks & automations | Micah (current use) |

News & Feedback Segments

Apple & Tech News ([21:56]–[30:04])

• UK Government drops demand for iCloud encryption “backdoor”
  • Rosemary: “If there is a backdoor, it’s just going to be hammered by hackers… it just causes greater security risks for everybody.” (22:38)
• Apple Watch Blood Oxygen Sensor Workaround (US only)
  • A consequence of a patent dispute: iPhone now handles measurement so Apple can legally sell these models.
  • Result: Feature is back—but visible only in the iPhone health app, not directly on the watch.
    • “This is a US-specific thing… now your phone can tell you your blood oxygen measurements again.” (23:57)

Listener Questions & Shortcuts Corner

1. Reminder Location Delay Issue ([30:04]–[34:54])

• Bob reports slow activation (up to 10 min) for arrival-based reminders.
• Troubleshooting:
  • Check if Low Power Mode is enabled—this can delay location services.
  • Try resetting network settings for more accurate triangulation.
  • Create a Shortcuts automation triggered by WiFi or location to help debug.
• Rosemary’s Tech Tip:
  • “Resetting your network settings… can often clear out the cobwebs for a lot of random issues.” (32:18)

2. Focus Mode/Shortcuts Automations ([34:54]–[43:53])

• Listener Dustin wants better automation between work/personal focus modes depending on time and location.
• Rosemary’s Advice:
  • Start with native Focus Mode schedules in Settings before jumping to Shortcuts.
  • For more complex cases, use Shortcuts Automation to check day/time and set the right focus mode.
  • Utilize formatted date/time and conditional logic in Shortcuts for more granularity.
  • “Do 90% of the automations in the Focus Mode settings and then leave this [complex] one to Shortcuts.” (41:33)
• Micah's Reflection:
  “When you have a hammer, everything looks like a nail. Sometimes you need to remember you have a whole toolbox.” (44:26)

App Caps: Host Favorites ([45:39]–[55:43])

Micah: Product Hunt (App & Website)

• Discover new tech products, apps, and services—mainly tech/AI focused.
• Community upvoting surfaces the most interesting daily launches.
• “I have found some really nifty apps and services on here over time that I still use to this day.” (45:39)
• Free. Multiple login options for participation.

Rosemary: Bridges – Link Formatting

• A $1.99 app for organizing links into folders/sections, sharing them formatted as plain text, Markdown, HTML, or JSON.
• Also auto-loads favicons, hero images, and provides notes.
• “You can be as organized or as disorganized as you’d like with Bridges.” (50:23)
• Especially useful for people who frequently share or organize large sets of links.

Additional Resources & Contact

• Email the show: iostoday@twit.tv
• Rosemary Orchard: rosemaryorchard.com
• Micah Sargent: chihuahua.coffee
• Ad-Free Episodes & Community: Join Club TWiT ($10/mo or $120/yr for ad-free shows, bonus feeds, Discord, and more)

Conclusion

This episode equips listeners with both high-level strategies and granular, app-specific tactics for conquering digital clutter and mastering one’s to-dos. Whether you’re a GTD devotee, automation tinkerer, or someone just trying to remember to water the plants, you’ll find enough recommendations and troubleshooting tips to level up your productivity on any Apple device.