Journey to Reclaim: How a Messy Calendar Hunt Resulted in AI-Fueled Sanity

I have spent the bulk of my grown-up life managing too many calendars, too many concepts, and too many Chrome tabs as well as brain tabs. Staying companies, consulting, startup mayhem, family responsibilities — all while attempting to defend those hallowed windows of profound work prior to being nuked by context-switching.

For people like me — entrepreneurial creative types with ADHD-precarious attention spans and a proclivity for overcommitting to "just one more thing" — a calendar is not just a planner. It's life support. The rickety scaffolding that keeps the whole circus afloat.

I was a Fantastical guy for years. I enjoyed it. Clean, elegant, uncomplicated. But then it ballooned up — code rot and feature creep set in. Menus inside menus, features nobody requested, the kinds of "innovate or die" fixes that reduce simplicity to muck. Somewhere along the line, I caught myself: my calendar application had become the very thing I was fighting with it to avoid.

And so began my Calendar Quest — a quest for something shinier, more streamlined, and really handy. Something that valued that my life was not a straight line and wasn't demanding one job, one inbox, or one brain setting. I was looking for AI that wasn't pesty — but merely helped silently.

1. Fantastical Breakup: Year One of the Great Hunt

Fantastical used to be a precise tool. It slowly became a Swiss Army knife with 48 plugins — clever, but mostly something I'd never use.

Natural language input was magic to start — I could just utter "Call with EA next Friday at 3" and voilà, done. By 2024, though, I was drowning in widgets, calendars, integrations, and onboarding balloons regarding "new features" I'd never asked for.

Every session was a scavenger hunt. My patience snapped around "now syncing your weather feed" and "enable Fantastical AI Copilot." No thank you.

I needed something that learned from me — not another platform begging me to learn its ways.

Mental note: find something minimalist, graphical, and quietly intelligent — not yet another dopamine-vacuuming dashboard pretending to "optimize" my day.

2. Curiosity Turns to AI (and a Rabbit Hole Forms)

The breaking point was from another call to mind: AI note-takers. I started experimenting with some and thought, why can't my calendar do this?

A quick search for "AI calendar tools for multi-calendar chaos" flung open the floodgates. Now I was weighing Reclaim, Clockwise, Motion, Morgen, Amie, and some optimistic startups I can't even remember now.

• The filters were unforgiving:

  • Must sync 5+ calendars (Google + Microsoft universes) without meltdown

  • Need to auto-swat "focus" time but not share it

  • Need to control context switches without annihilating the day

Reclaim bubbled to the top for me. The tagline — "defend your time like a bouncer" — resonated. My lone holdback? It's a Dropbox company, and my track record with them has always been love-hate. (Every creative has that one "Dropbox moment," right?)

But reviews were great — real ones from human beings with brains such as mine. Average 4.8/5 on G2 for reducing meeting overload by 25%. Good enough to pilot.

3. The Shortlist Stress Test

I put Reclaim to the test against the other big boys.

Morgen: sharp, snappy, had the feel of having been designed by someone who understands design minimalism. But the AI sorcery was understated — more of a quality adhesive than an adaptive scheduler.

Sunsama: actually very sweet. Soothing rituals, great for self-reflection. But $20 a month for essentially guided time blocking? Felt like a spa day when I needed an ER triage nurse.

Amie: cheeky, lively, high-energy — but perhaps a little too sunny for someone trying to keep five calendars in sync.

And then Reclaim.

Five calendars on day one. No conflicts. No "authorize again" loops. It automatically shielded deep work blocks, optimized for family chaos (hello, grandson), and didn't make my personal time "available."

Within a week, I spent 2+ hours of actual creative flow — the kind where your head stops screaming and starts building.

4. Take Back in Action: Hands-On Flow Triumphs

Installation: ten minutes.

No scavenger hunt for tutorials, no wizard of twenty clicks. Just:

Connect calendars

Set priorities (startup > consulting > family buffers)

Let AI guide

It's freakily good at keeping you in focus. Keeps out 90-minute "heads-down" blocks, reminds you gently when you're overbooked, and rearranges itself when life surprises you.

The biggest gripe was always "no desktop app." That's sorted — as of late 2025, there are snazzy, native Mac and Windows apps that feel smooth and offline. The other grievances i had were from individuals trying to force their way into my heads down time and getting rejected…LOVE IT!

Come on? It's the anti-Fantastical. It doesn't try to impress you; it simply cheerfully gets on with it.

Reclaim.ai: The Plate-Spinners' Deep Dive

With a right balance of sanity and automation as a creative entrepreneur, Reclaim is perfect.

Price: Free for individuals (with all AI), $10/month for teams.

UI: Minimalist, smart, designed by someone who clearly understands flow. Color-coded layout keeps visual noise at a minimum, yet still enables you to spot priorities in a heartbeat. Blue for startup work, green for family, red for "don't call unless the building is on fire."

Time Blocking: The secret sauce. Automatically schedules 90–120 minute "flow blocks," shields them from invites, and dynamically re-shuffles when life becomes unmanageable. I gained about 10 extra hours of uninterrupted focus in the first month.

Quick Priorities + Stats: The "gentle accountability" feature. Tags tasks, tracks category time, and warns about fragmentation. No shame. Just feedback.

Pros: Web-first roots mean there are a few beta quirks in the desktop app. AI gets too overbearing unless you adjust your "hands-off" policies. And yeah, the Dropbox integration still makes me nervous — please, Reclaim team, don't ruin this with bloat.

Verdict: 9/10. The sanity in my madness.

The Runner-Ups (A.K.A. Great, but Not My Fit)

Morgen (7.5/10) – Blissfully straightforward, coordinates all. Perfect if you love organization but do not need AI tweaking. Somewhat sterile for creative mayhem, however.

Sunsama (7/10) – The zen daily planner. Beautiful flow, but pricey and perfect for people navigating one lane at a time. Too structured for my ADHD brain.

Amie (8/10) – The celebration. Reminds me of Slack combined with calendar combined with confetti cannon. Brilliant design, but too frivolous for five concurrent universes.

They each have their audience, but if your life is a startup sprint and then a school pickup line, Reclaim wins.

Last Thoughts: The Quiet Conductor

Reclaim doesn't plan time — it protects it. It knows how innovative ADHD brains actually operate: spurts of energy, bizarre hours, self-guilt over whatever isn't accomplished.

It adapts instead of questioning.

It is more of an aide than an additional task.

I no longer end my day looking at my calendar wondering where the hours went. They're there — defended, planned, and largely intact.

Imperfect, but on the verge of being counted as progress.

And in my world, that's gold.