Things vs Microsoft To Do for AI-Assisted Work

The fast answer for founders and freelancers

Choose Things if you do your best work by deliberately shaping a small set of projects and want a calm personal home for them. It rewards a planning habit.

Choose Microsoft To Do if client requests, team follow-ups, and commitments usually begin in Outlook or Microsoft 365. It cuts handoffs.

Neither app will independently run your business or choose every priority for you. A useful productivity assistant lowers capture effort while preserving enough context that, after a client call or an interrupted afternoon, the next sensible action remains visible.

What AI can actually improve

AI can reduce repeatable friction in knowledge work, especially around email handling and document drafting, rather than creating extra hours from nowhere. That is a narrower promise.

A six-month randomized field experiment involving 6,000 workers found that access to generative AI in familiar work apps was associated with less time spent on email and moderately faster document completion, while meeting time did not significantly change. Read the Microsoft Research summary. The result is limited but useful because it shows that tools can speed up work you control without repairing coordination that depends on other people.

Microsoft conducted the research, so it is best treated as evidence from a particular rollout rather than a universal productivity guarantee. Buy for the workflow you have.

For founders and freelancers, the better test is whether an app turns incoming work into an unambiguous next action and helps you resume it after a disrupted afternoon. Those two moments determine whether a tool earns its place.

Compare the workflow, not the feature count

Feature counts are a distraction when your task system is supposed to support execution instead of archive intentions. Workflow wins.

My view is firm: choose the app that handles where commitments originate, rather than the one with the flashiest automation demo. Most task systems fail at the front door.

Things is a deliberate personal command center

Things works well when you want a private control panel for projects, errands, follow-ups, and creative work instead of an extension of an office suite. It favors judgment.

That restraint helps when your daily challenge is protecting attention from a long list of plausible tasks that all seem worthwhile. You decide what deserves today.

Its AI path is external rather than native

Things can work alongside AI-assisted workflows through Apple Shortcuts, its URL scheme, and AppleScript on a Mac. The core app stays hands-on. Its official guidance says it currently has no direct connections to tools such as ChatGPT or Claude, and it warns against unsafe third-party methods that access the Things database directly; see Things’ guidance on third-party AI tools.

This setup suits people who want AI upstream, such as using it to turn a messy voice note into a short project plan before reviewing the result in Things. AI helps with preparation. Things is less suitable if you expect the task manager to infer your workload and select actions for you throughout the day.

Choose Things when intentional planning is your advantage

Use Things if these statements sound familiar:

• You work mainly on Apple devices and prefer one personal system for independent work and life.
• You can spend a few minutes reviewing projects, selecting Today’s commitments, and keeping that list small.
• You want automation to speed capture or project setup without giving outside services ongoing access to your task database.
• Your bigger risk is overcommitting to interesting work instead of losing assignments inside corporate communication.

Capture freely, then plan the next day before shutting down. That short decision prevents a long morning negotiation.

Microsoft To Do is strongest where requests already arrive

Microsoft To Do makes the most sense when your workday begins in Outlook, because tasks and calendar-linked follow-up signals stay close to the messages and meetings that created them. That proximity reduces context switching.

Microsoft’s support documentation describes To Do inside Outlook with smart lists such as My Day, Important, Planned, Assigned to me, Flagged Email, and Due Today, plus details including steps, notes, reminders, and due dates. Microsoft explains the Outlook integration here. This is useful when work arrives through messages and meetings.

What its assistant value really is

Microsoft To Do’s useful assistance is largely organizational, keeping actionable follow-ups visible as you move between email and task views around your calendar. It helps you keep track. That differs from a system that interprets the changing circumstances around a personal project and recommends a tailored next action.

For an agency owner replying to clients or a consultant managing Outlook-based deliverables, reliable capture may be the immediate problem. For a solo founder with dozens of self-directed possibilities, the difference is substantial.

Choose Microsoft To Do when communication drives your workload

Microsoft To Do is the stronger fit when you regularly need to:

• Turn flagged client emails into follow-ups without retyping them elsewhere.
• Review meeting commitments beside a daily task list.
• Keep personal execution connected to a Microsoft 365-based business.
• Use shared and assigned work as input to your personal day.

Set up My Day as daily triage, not as a second permanent backlog. Move over only work you can realistically advance before tomorrow.

AI assistant myths that lead to bad tool choices

Myth: An AI connection automatically creates better priorities

An integration can create or reorganize tasks quickly, but priority still depends on current deadlines and the capacity left after plans change. Judgment remains yours.

Keep a brief daily planning checkpoint even when an assistant fills in task details. It reveals trade-offs.

Myth: More automation means less mental load

Poor automation can create duplicate tasks or noisy reminders, then bury intended commitments among suggestions you never approved. That adds mental load. An automated rule should remove one repeated step.

Start with a high-frequency workflow, such as converting a flagged email into a follow-up. Review it for seven days before adding another rule.

Myth: A polished task list is an assistant

A list can look beautifully organized and still leave you stuck at 3:30 p.m. when you are tired, behind schedule, and unable to choose the best use of the next 20 minutes. That is the usability test.

Judge the system during low-energy moments rather than during a motivated Sunday reset. Those are the moments that count.

Run a seven-day fit test

You do not need to migrate your entire work life before deciding between Things and Microsoft To Do. Use one as your active daily layer for seven days while keeping existing records available in the background.

For more on flexible restart points after interruptions, see why a perfect day plan breaks down. Build those points into this trial.

1. Capture every new commitment in one place. Include client requests, business ideas, personal administration, and work that emerges from meetings. Use concrete wording.
2. Plan one realistic day at a time. Start with three outcomes that matter, then add smaller work only when it fits.
3. Track recovery after interruptions. Each time you return to work, check whether the app makes the next action obvious within one minute.
4. Review missed work without blame. Identify whether it was never captured, buried in the wrong context, too vague, or simply more than one day could hold.
5. Measure friction rather than streaks. The better tool is the one you will still open when your backlog feels uncomfortable and your attention is thin.

At the end of the week, count missed commitments and notice how often you avoided choosing what to do next. Keep the system that reduced both.

Choose the system that protects your attention

Pick Things when you want a focused personal workspace and are willing to make the final call on what belongs in Today. Pick Microsoft To Do when Outlook and Microsoft 365 are already the river your work flows through.

If your central problem is selecting the next worthwhile task from a large mixed backlog, a recommendation-first tool such as OwnTime may fit better because it can surface work based on timing, effort, importance, and the context you provide while still letting you adjust its suggestion. It saves another round of list-scrolling.

Whichever tool you choose, schedule a 10-minute review before shutdown for the next five workdays. A good assistant returns enough attention for the decisions only you can make.