Category: Reviews · Stage: Decision

By Max Beech, Head of Content

Microsoft To Do is free with Microsoft 365—deep Outlook integration, cross-platform sync, enterprise-ready. Chaos is AI-native—£8/month for intelligent prioritisation, context-aware scheduling, minimal manual planning.

After 30 days testing both in real work environments: Microsoft To Do wins for Microsoft ecosystem users; Chaos wins for AI-first productivity.

Philosophy Comparison

Microsoft To Do's approach: Ecosystem integration

"Work where you already work. Sync with Outlook, Teams, Planner. Free for everyone with Microsoft 365."

Chaos's approach: AI-enhanced efficiency

"AI handles prioritisation and scheduling. You handle execution. Move fast without manual planning overhead."

The fundamental question: Do you value deep Microsoft integration (To Do) or AI automation (Chaos)?

Feature Comparison

| Feature | Microsoft To Do | Chaos | |---------|----------------|-------| | Price | Free (included with M365) | £8/month | | Outlook integration | Native (bi-directional) | Limited (calendar import) | | Teams integration | Built-in task assignments | None | | AI assistance | None | Extensive (priority, scheduling) | | My Day planning | Manual selection each morning | AI-suggested, one-tap approve | | Shared lists | Yes (family, team lists) | No (individual-focused) | | Recurring tasks | Full support | Full support | | Mobile app quality | Good (Microsoft design) | Excellent (fast, gesture-based) |

When Microsoft To Do Wins

1. You're Deep in Microsoft Ecosystem

If you use Outlook, Teams, and Planner daily, To Do becomes your task hub.

Integration benefits:

Flagged emails → automatically appear in To Do
Tasks assigned in Teams → sync to To Do
Planner tasks → visible in To Do
One ecosystem, zero friction

User quote: "I live in Outlook. Flagging emails creates tasks instantly. No need for separate app." — Operations manager, 38

2. Budget Constraints

Microsoft To Do: Free (included with Microsoft 365 subscription) Chaos: £8/month = £96/year

ROI question: Is AI prioritisation worth £96/year when To Do does basic task management for free?

3. Team/Family Shared Lists

To Do supports shared lists—assign grocery shopping to partner, delegate team tasks to colleagues.

Chaos is individual-focused—no collaboration features.

Use case: Family task management, small team coordination → To Do wins

4. Enterprise Requirements

Microsoft To Do meets enterprise compliance (data residency, security, admin controls). IT departments approve it by default.

Chaos is newer SaaS—may require security review for enterprise deployment.

When Chaos Wins

1. AI Saves You Planning Time

Microsoft To Do workflow: Review tasks → manually pick for "My Day" → drag to time slots → reprioritise when priorities change

Chaos workflow: AI suggests 3-5 priority tasks for today based on deadlines, calendar, patterns → approve with one tap

Time saved: 10-15 minutes daily planning (Chaos AI automation vs To Do manual planning)

User quote: "Decision fatigue was real with To Do. I'd spend 20 minutes planning my day. Chaos suggests priorities—I just approve. Massive mental load reduction." — Developer, 31

2. Context-Aware Scheduling

Chaos suggests when to work on tasks based on calendar availability.

Example: Meeting-heavy morning → Chaos suggests deep work tasks for afternoon block. To Do shows all tasks equally—you decide timing manually.

3. You Don't Use Microsoft Ecosystem

If you use Gmail, Google Calendar, Slack (not Microsoft tools), To Do's main advantage disappears.

Chaos integrates with Google Calendar, Apple Calendar, generic email—platform-agnostic.

4. Speed of Capture

Chaos voice input: "Remind me to email Sarah tomorrow" → task created in 3 seconds with AI-suggested time.

To Do: Open app → tap "Add task" → type title → set due date → assign to list → done (25-40 seconds).

Winner: Chaos (8× faster capture via voice)

Real Usage Patterns

My 30-Day Microsoft To Do Experience

Week 1: Appreciated free price. Outlook integration worked seamlessly—flagged emails became tasks automatically.

Week 2: "My Day" planning ritual felt tedious. Manually selecting 8-12 tasks each morning took 15 minutes. Often picked wrong priorities.

Week 3: Tried skipping "My Day" and working from full task list. Quickly overwhelmed—too many tasks visible, no clear focus.

Week 4: Returned to "My Day" ritual, accepted it as necessary planning overhead. Finished month with solid task capture but wishing for smarter prioritisation.

Verdict: To Do works well if you commit to manual planning and value Microsoft integration. Prioritisation is entirely on you.

My 30-Day Chaos Experience

Week 1: AI suggestions felt strange. "Can I trust this to pick my priorities?" Overrode AI frequently.

Week 2: AI accuracy improved (learning my patterns). Started trusting suggestions—fewer overrides.

Week 3: Rarely overrode AI. Morning planning became effortless—review AI suggestions, approve, start working. Decision fatigue vanished.

Week 4: Appreciated not paying "planning tax" daily. Questioned whether I'm too dependent on AI automation.

Verdict: Chaos works if you trust AI assistance and value time savings over manual control.

Integration Ecosystem Comparison

Microsoft To Do connects to:

Outlook (flagged emails → tasks)
Microsoft Teams (assigned tasks sync)
Microsoft Planner (project tasks visible)
Cortana (voice task creation on Windows)
Microsoft 365 apps (Excel, Word task creation)

Chaos connects to:

Google Calendar (native sync)
Apple Calendar (native sync)
Email (manual forwarding to create tasks)
Voice assistants (Siri shortcuts, custom integrations)

Winner: Microsoft To Do (if you use Microsoft ecosystem); Chaos (if you use Google/Apple ecosystem)

Pricing Reality Check

Microsoft To Do: £0 (included with Microsoft 365 Personal £5.99/month or Business subscriptions)

Chaos: £8/month standalone

Cost comparison scenarios:

Scenario A: You already have Microsoft 365

To Do cost: £0 additional
Chaos cost: £96/year additional
AI value must exceed £96/year to justify Chaos

Scenario B: You don't use Microsoft ecosystem

To Do cost: £72/year (Microsoft 365 Personal subscription required)
Chaos cost: £96/year
Only £24/year difference—AI features may justify premium

Migration Considerations

Moving from To Do to Chaos: Export tasks from To Do (Settings → Export), import CSV to Chaos. Recurring tasks require manual recreation. Allow 1-2 hours setup time for 500+ tasks.

Moving from Chaos to To Do: Chaos exports standard task formats. AI prioritization insights won't transfer—expect adjustment period relearning manual task organization.

Key Takeaways

Microsoft To Do = free (with M365), deep Microsoft integration, manual prioritisation
Chaos = £8/month, AI-powered prioritisation, fast voice capture, platform-agnostic
To Do wins: Microsoft ecosystem users, budget constraints, team/family shared lists, enterprise compliance
Chaos wins: AI-first productivity, decision fatigue reduction, Google/Apple users, speed-focused workflows
ROI decision: Is 10-15 min daily planning time saved worth £96/year? (Yes for high-value knowledge workers)
Choose based on ecosystem: Microsoft 365 user → To Do; AI automation priority → Chaos

Disclosure: I tested both genuinely for 30 days. Currently use Chaos (AI automation matches my work style).

Try Chaos: 14-day free trial →

Chaos vs Microsoft To Do: AI-Powered vs Ecosystem Integration