Annual Review with Apple Reminders
An annual review with Apple Reminders uses a templated reflection list with year-end questions, goal carryover, life category review, and a January 1 implementation checklist.
Look, the thing about annual reviews is that 80% of people stare at a blank Notion page on December 28th for an hour, give up, then make a half-hearted resolution list on January 1 that's dead by February. The reason isn't motivation. It's that "review the year" is a vague non-task and your brain can't grip it. The fix is structure. A list of specific questions with checkboxes, stamped from a template, that you can do across 3 short sessions instead of one painful long one. The "I didn't do anything this year" feeling is mostly time blindness operating at a 12-month scale; you forget what happened in March by November because the months stop feeling like distinct chunks.
I ran my own annual review on Apple Reminders for the first time in December 2024. It took 90 minutes total across three days. Honestly, it shipped because every reflection question was a checkbox and my brain treats checkboxes like a videogame.
Why Apple Reminders works for annual reviews
Apple Reminders works for annual reviews because the templated list with subtask checkboxes converts an intimidating reflection exercise into a series of concrete, completable prompts.
The blank page problem is the whole problem. When you open Notion or a Google Doc to "review the year," you're staring at infinity. Apple Reminders forces you into one question at a time, with a checkbox to tick when you've answered it. The completed-task counter goes up. Your brain stays engaged. You actually finish.
The other thing Reminders does well here is recurrence. Once you build the template once, you stamp it again next December. The questions stay consistent year over year, which is the whole point of a review. If you change the questions every year, you lose the comparison.
"I tried Notion for annual reviews three years running and never finished one. Switched to a Reminders template with 18 questions, finished in 4 sittings. Checkboxes hit the dopamine differently."
- paraphrased from r/productivity, December 2025
By the way, this is not a tool that's going to write the review for you. Reminders holds the structure, not the prose. The actual answers live in your head or in a Notes doc that the reminder links to. Reminders is the scaffolding.
The system
The system is one Reviews folder, three lists per year, and a template you stamp in late December.
Folder: Annual Reviews (a list folder, holds all year lists)
Lists per year (3):
- 2026 Reflection - the year-end questions (December)
- 2026 Categories - the life-category audit (late December)
- 2027 Implementation - the January 1 setup tasks (early January)
Categories (the 8 life areas I review, adjust to your life):
- Health (physical, mental, sleep)
- Money (income, savings, investments, debts)
- Relationships (partner, family, close friends)
- Career / Work
- Learning (books, skills, courses)
- Creative output (writing, projects, side things)
- Home and environment
- Spirituality / inner life (whatever this means to you)
Tags (4):
#win- things that went well#lesson- things that didn't and what you learned#carryover- goals or projects that move into next year#kill- things to stop doing entirely
The reflection question set (the template, 18 questions across 3 lists):
In 2026 Reflection:
- What were the 3 biggest wins this year?
- What were the 3 biggest disappointments or losses?
- What did you spend the most time on that you regret?
- What did you spend the least time on that you wish you'd done more of?
- Who were the 3 people who most positively affected your year?
- Who or what drained your energy the most?
- What did you learn about yourself that surprised you?
In 2026 Categories (one section per life area, with sub-questions): 8. For each of the 8 life areas: rate 1-10, write 2 sentences why, list 1 thing to do better next year.
In 2027 Implementation:
9. What are your 3 themes for 2027? (not goals, themes)
10. What are your 5 specific projects for Q1?
11. What are you stopping entirely? (tag #kill)
12. What's the one keystone habit you'll add in January?
13. What's the system for tracking those, weekly review cadence?
This isn't an exhaustive list. Add your own. The point is the question structure.
Setup steps
Create the Annual Reviews folder. Right-click the sidebar, New Folder, name it Annual Reviews. Drag any previous-year lists into it. If this is your first year, it's empty, that's fine.
Build the three 2026 lists inside the folder: 2026 Reflection, 2026 Categories, 2027 Implementation. Pin them temporarily during review season; unpin after January.
Stamp the reflection questions as subtasks in the 2026 Reflection list. Each top-level reminder is a question. Subtasks underneath are optional supporting prompts (like "be specific" or "name names"). Apple supports one level of subtask nesting, so don't try to go deeper.
Build the categories list. In 2026 Categories, create one section per life area (Health, Money, Relationships, etc.). Each section has 3 reminders: Rate 1-10, Why, One thing to improve.
Build the implementation list. In 2027 Implementation, create reminders for the 5 questions above. Date them January 1, 2027 so they show up in Today on New Year's Day.
Save the structure as a template for next year. Apple Reminders supports list templates: right-click the 2026 Reflection list, Save as Template. Same for the other two. When December 2027 rolls around, stamp the template, rename to 2027 Reflection, and you're set.
Schedule the review sessions. Block 90 minutes in your calendar across 3 days in late December. Day 1 is 2026 Reflection. Day 2 is 2026 Categories. Day 3 is 2027 Implementation. Doing it across days, not in one sitting, is the difference between finishing and quitting halfway.
The definitive guide to Apple Reminders in 2026 covers list folders, sections, and templates in depth, and How to Use Apple Reminders Templates for Recurring Projects walks you through the stamp pattern in detail.
Daily ritual
Annual reviews aren't daily, obviously. The "ritual" here is the late-December cadence across three sittings.
Day 1 (45 min, mid-late December). Open 2026 Reflection. Work through the 7 questions in order. Don't skip ahead. Write 2-3 sentences in the notes field per question (Reminders' notes field is plain text and gets cramped past ~200 words, so keep it tight; long-form goes into a linked Apple Note). Tag answers with #win, #lesson, #carryover as you go.
Day 2 (30 min, the next evening). Open 2026 Categories. Walk through all 8 life areas. Rate each 1-10, write 2 sentences why, name one thing to do better. This is the audit pass. You'll notice patterns. The 3/10 areas tell you where 2027 lives.
Day 3 (45 min, December 29-31). Open 2027 Implementation. Now you're forward-facing. Themes, projects, the keystone habit, what you're stopping. Date these reminders to January 1 so they hit your Today view on New Year's Day. The system is now armed for the next year.
Weekly cadence in January (10 min). Open 2027 Implementation every Sunday in January. Check progress on the 5 Q1 projects. Adjust. The implementation list lives all of Q1, then gets archived once you have a working rhythm.
End-of-quarter pulse (15 min, March 31). Open 2027 Implementation, open 2026 Reflection (for comparison). Are the themes still right? Did anything fall apart? Adjust the projects. This is the lightweight mid-year check that prevents the annual review from being a one-off ritual that dies by February.
"The trick I missed for years was doing it across 3 days, not 1 evening. One sitting gives you a tired, generic review. Three sittings let your brain mull each layer. Took me 5 years to figure that out."
- paraphrased from r/getdisciplined, January 2026
Edge cases
The "I didn't do anything this year" feeling. Hits everyone in question 1. You did stuff. Open your camera roll, scroll January 1 forward week by week. Photos remind you of what happened. Don't trust your memory.
The bad year. Some years are heavy. Capture the lessons. Tag #lesson. The point isn't to celebrate, it's to extract signal. Bad years often carry more signal than good ones.
The over-ambitious implementation list. First-time reviewers list 20 projects for Q1. You'll do 2-3 well. Limit to 5 max. Unselected projects go into an "ideas parking lot" list with no date.
Reviewing with a partner. Share the 2027 Implementation list (Apple Reminders supports list sharing). Keep individual reflection private. Use @-mention to split which goal each person owns.
The mid-year pivot. Sometimes by June your themes are wrong. That's fine. Open 2027 Implementation, mark the dead themes complete with a #kill tag and a date note, write new ones. The annual review isn't sacred. It's a starting point, not a contract.
Year-over-year carryover. Goals tagged #carryover from 2025 should appear at the top of 2027 Implementation, with a note "deferred from 2026, X years." If something carries over 3 years, it's not actually a goal, it's a fantasy. Drop it.
For a tighter weekly cadence: Weekly Review with Apple Reminders handles the small-loop review that feeds the annual one. For a full GTD setup: Apple Reminders for GTD in 2026 covers how the review fits into a complete capture and process system. If you're a writer, Apple Reminders for Writers has a parallel year-end pipeline for shipped pieces and ideas archive. For year-end financial cleanup that's adjacent: Tax Deadline Reminders in Apple Reminders covers the January 1 setup.
How Ultra Reminders extends the annual review
Ultra Reminders adds three things specifically useful when reviewing the year:
AI synthesis of completed reminders. Ultra reads your Completed view across all of 2026 and clusters the patterns. "You spent 40% of your tagged time on #client-work, 18% on Health, 6% on #deep work. You completed 312 tasks in Q1 but only 198 in Q3." The raw audit becomes a 2-minute summary instead of an hour of scrolling.
True natural language input on reflection. Instead of typing "Rate Health 1-10" then tapping in the rating, you can speak or type "Health was a 7 this year, slept badly Jan-March, fixed in Q2 with magnesium and earlier bedtime." Ultra parses the rating, the timeframe, the notes. Apple's parser leaves all that text in the title.
The 10am implementation plan in January. Once 2027 Implementation is set, every weekday morning at 10am Ultra reads your themes, your Q1 projects, and your calendar, and surfaces today's most important thing. Removes the "what should I work on" friction that kills New Year resolutions in week 2.
All of it runs on-device via the Qwen 3 1.7B LLM. Apache 2.0 licensed model. Nothing leaves the Mac.
FAQ
Q: How long should an annual review actually take?
A: About 90 minutes total, split across 3 sittings of 30-45 minutes each in late December. One marathon sitting gives you a tired, generic review. Three short sittings let each layer (reflection, audit, implementation) breathe. Don't try to do it in one evening; you'll quit halfway.
Q: Should I keep last year's review list or archive it?
A: Keep it, drag it into the Annual Reviews folder, unpin it. You'll reference it next December to see what carried over, what worked, what didn't. Five years of preserved annual reviews is a small history of your trajectory. Don't delete.
Q: What's the difference between themes and goals?
A: Themes are directions (Year of Health, Year of Saying No, Year of Building). Goals are specific outcomes (Lose 8kg, Save 5L, Ship the SaaS). Themes hold up when goals fail. Pick 3 themes; goals fit inside them. Most people set goals without themes and get whiplashed when one fails.
Q: Can I share my annual review with a coach or mentor?
A: Yes. Tap the list, Share List, send to their iCloud email. Or paste the visible reminder list into a Notes doc and share that. For privacy, share only the 2027 Implementation list, not the 2026 Reflection list (which often has personal admissions you don't want anyone seeing).
Q: What if I miss December and end up doing this in February?
A: Do it anyway. A review in February is better than no review. Adjust the lists to "2026 Reflection (done February 2027)" and proceed. The calendar date is symbolic; the structure is the actual value. Many people do their annual review in late January, after the holiday chaos. Honestly, your mileage may vary.
Ultra Reminders solves a year-end review structure instead of staring at a blank page. $35 lifetime purchase, 14-day money-back guarantee, at ultrareminders.com.