AI assistants for planning your day: routines, nudges and memory
Which AI assistants can plan my day and remind me what is next?
Updated · 5 assistants ranked
Five assistants describe planning or preparing your day: Alfi, AVA, Caddy, Familiar and Waldo. All five took at least two of four tests (Proactive Help, Routines, Memory, Connected apps) and are ranked. Waldo averages 7.0 over all four, ahead of Caddy at 6.0 and Familiar at 5.5, but four of the five are pre-filled and Waldo and Familiar are still waitlist products. We do not test the quality of a plan.
Top picks
- 17.0
Tested on 4 of 4Best: Routines9, Memory8Time to finish 12m
- 26.0CaddyBest free option
Tested on 2 of 4Best: Memory6, Connected apps6
- 35.5
Tested on 4 of 4Best: Proactive7, Memory6
- 44.7
Tested on 3 of 4Best: Connected apps7, Memory4
- 54.5
Tested on 2 of 4Best: Routines5, Connected apps4
Top pick: highest average here. Best free option: highest among assistants you can use for free. Fastest that's still good: quickest median time to finish among those averaging 7 or more.
Full ranking
| # | Assistant | Proactive | Routines | Memory | Connected apps | Average |
|---|---|---|---|---|---|---|
| 1 | Waldo | 5 | 9 | 8 | 6 | 7.0 |
| 2 | Caddy | — | — | 6 | 6 | 6.0 |
| 3 | Familiar | 7 | 5 | 6 | 4 | 5.5 |
| 4 | AVA | — | 3 | 4 | 7 | 4.7 |
| 5 | Alfi by Text.ai | — | 5 | — | 4 | 4.5 |
How this report works
Included are assistants whose catalog description (checked 2026-10-26) mentions planning or preparing your day. They are ranked by the average of Proactive Help (speaking up unprompted), Routines (a scheduled job on time), Memory (what you told it) and Connected apps (using your calendar and tools), with at least two taken. Scores come from the published score sheet and are dated 2026-10-27. 4 of the 5 ranked assistants (Alfi, AVA, Familiar and Waldo) carry pre-filled scores, which are placeholder estimates the site has not yet replaced with its own test runs, so treat their places as provisional. Caddy is the only one that is not pre-filled.
How to choose
- Check access first. Waldo and Familiar are on a waitlist in our catalog (checked 2026-10-26), so you may not be able to use them yet.
- Look at Routines for a morning plan: that test checks that a scheduled job arrives on time with the right content and takes a change.
- Look at Proactive Help if you want it to speak first. Only Waldo (5) and Familiar (7) have a score; it is untested for Caddy, AVA and Alfi.
Can an AI assistant plan my day?
Five catalog entries describe planning or preparing a day. We test that a scheduled job arrives on time and takes a change (Routines), that it speaks up unprompted (Proactive Help), that it remembers what you told it and that it uses your connected apps. We do not test the plan itself.
Which AI assistants have the best scores for daily planning?
Waldo averages 7.0 over four tests, Caddy 6.0 over two, Familiar 5.5 over four, AVA 4.7 over three and Alfi 4.5 over two. Only Caddy is not pre-filled, so every other place is provisional.
How is this different from the habit tracking page?
That page covers check-ins on goals with Routines, Proactive Help and Memory. This one covers a daily plan, adds Connected apps and has a different set of assistants; only Caddy is on both.
What users say
My favorite way to use Caddy is to get it to help me find gallery openings + lectures… then put those on my cal 😎
Open sourceIt pushed Gmail before I asked for it - it kept pitching features instead of following the conversation - It asked too many questions back-to-back
Open sourceFrequently asked questions
Which assistant is best for this?
Waldo leads with an average of 7.0, ahead of Caddy and Familiar.
Is there a good free option?
Caddy is the highest-ranked assistant with a free plan, averaging 6.0.
How did you test these assistants?
Every assistant got the same published tests, word for word, scored from three checkpoints and the number of corrections it needed. Each test is on the Dimensions page.