My calendar used to be a disaster. As a professional juggling multiple projects, my weeks were a solid wall of blue meeting blocks. “Back-to-back” wasn’t just a phrase; it was my default setting. This left me with zero time for the actual work. I’d finish a day of calls and then start my “real” job at 5 PM. I knew something had to change, and I wondered if AI scheduling tools were the answer or just another layer of complexity.
I decided to run a real-world test. For 90 days, I would use three popular tools back-to-side, one month each: Reclaim.ai, Calendar.com, and Dex. My goal was simple: to find out if they could genuinely save me time or if they were just more digital clutter.
My name is John Michael, and I’ve spent the past few years exploring how AI can help in our everyday lives. After working in the professional world for over five years, I’ve become passionate about finding tools that actually reduce friction, not just promise to. I’m not a fan of hype. I want to know what works, what doesn’t, and how it feels to use it day-to-day. This isn’t a lab test; it’s a breakdown of my 3-month journey to take back my calendar.
The Ground Rules: What I Was Trying to Fix
Before I started, I set four clear goals for this test. A tool would only be a “success” if it could help me with these specific problems:
- Stop the Email Tag: I was losing hours each week to the endless “What time works for you?” email chain. I needed a tool to handle this for me.
- Protect My Focus Time: I desperately needed to block out time for deep work—writing, analysis, and planning. My simple “Focus Time” blocks in Google Calendar were the first thing to get booked over.
- Reduce Meeting Overhead: It’s not just the meetings. It’s the prep before and the follow-up after. I wanted to see if AI could help automate or at least buffer this time.
- Manage My Habits: I am terrible at taking a lunch break. I wanted a tool that could intelligently schedule my personal habits (like lunch or a short walk) and defend that time like a real meeting.
Month 1: Reclaim.ai – The Time Defender
I started with Reclaim.ai because its promise seemed to match my biggest problem: defending my time. It claims to be an “intelligent calendar assistant” that works for you, not just for the people trying to meet with you.
Setup and Learning Curve
The setup was surprisingly fast. I signed up and connected my Google Calendar. This took about two minutes. The real work was in the settings. I told Reclaim:
- I want at least 90 minutes of “Focus Time” every morning.
- I must have a 30-minute lunch break between 12 PM and 2 PM.
- I need 15-minute buffers before and after any client call.
- I also connected my task manager (Asana) to let Reclaim schedule time for my to-do list items.
All in, I spent about 30 minutes tweaking these “Habits” and “Tasks.” The learning curve was minimal. The tool lives in the background. You don’t “use” it so much as you “unleash” it on your calendar.
The “Aha!” Moment: Flexible Blocking
Here’s the thing that changed everything: Reclaim’s flexible blocking.
When I used to block “Focus Time” on my own, it showed as “Busy” to everyone. This meant colleagues couldn’t schedule important, urgent meetings. But Reclaim’s blocks are flexible. My calendar, once that solid wall of blue, was now speckled with new color-coded blocks. My “Focus Time” was marked in green.
Crucially, Reclaim marked this time as “Free” (but with a note) to my internal team. If a high-priority meeting had to happen, my focus block would automatically move to the next available slot. But as my day filled up, Reclaim would “lock” the block, changing its status to “Busy” to protect it. It was like having a personal assistant constantly shuffling my schedule to ensure my priorities were met.
Did It Save Time?
Yes, but not in the way I expected. It didn’t reduce the number of meeting requests, but it dramatically increased my productive hours.
- It created time. I suddenly had 2-3 hours of protected deep work time every day.
- The Slack integration was a huge bonus. It automatically updated my status to “In Focus Time” or “At Lunch,” which naturally stopped colleagues from pinging me.
- It saved me from myself. I could no longer just “eat at my desk.” Reclaim had a 30-minute lunch block that would move around to find a home, but it would not be deleted.
The main downside? It’s not really built for external scheduling. Its “Smart Links” for booking are fine, but they aren’t as polished as other tools. Reclaim’s focus is clearly on you and your internal team.
Here’s my personal breakdown of that first month. This isn’t from a marketing site; it’s just my honest take:
| My Experience with Reclaim.ai | The Good (Pros) | The Bad (Cons) |
| Core Function | Genius at auto-scheduling Habits (lunch!) and Tasks. | Not great for external scheduling. The links feel basic. |
| Best Feature | Flexible “free/busy” time blocking is a game-changer. | Can feel “too aggressive” at first. It moves things around a lot. |
| Integration | Excellent sync with Google Calendar, Slack, and Asana. | Limited task management. It only blocks time, doesn’t manage projects. |
| Overall Feel | Like a shield. It’s an introverted tool designed to protect you. | Took a week to fully trust it and not manually override it. |
Month 2: Calendar.com – The External Gateway
After a month of defending my internal time, I switched to Calendar.com. I disconnected Reclaim (which was painful) and set up my new tool. The vibe was immediately different. While Reclaim felt like a shield, Calendar.com felt like a polished front door.
Its primary focus is on making it easy for other people to book time with you. It’s a direct competitor to tools like Calendly but with a layer of AI and team analytics.
Setup and Learning Curve
Setup was also very quick. I connected my calendar, and the main task was creating my “Scheduling Links.” This is where it really shined.
I created several different links:
- 30-Minute Client Chat: Available only on Tuesday and Thursday afternoons.
- 15-Minute Quick Sync: Available to my internal team anytime I was free.
- Podcast Recording: A 60-minute slot with custom questions on the booking form.
The interface was clean, and building these links was simple. The learning curve was basically zero. If you’ve ever used a scheduling link tool, you’ll understand this in five minutes.
Where It Shined: Smart Team Scheduling
The “Aha!” moment came when I set up a team link. I needed to schedule a call with a client, our lead designer, and myself. Instead of the 10-email chain this usually takes, I created one link from Calendar.com.
It scanned all three of our calendars, found the only 45-minute slots we all had free, and presented just those to the client. The client booked, and the event, complete with a Zoom link, appeared on all our calendars. This feature alone was worth the price of admission. It completely solved my “email tag” problem for external meetings.
The “Vs. Reclaim” Problem
Here’s what this really means: Calendar.com is an extroverted tool. It’s fantastic at managing the flow of meetings coming in.
But it did nothing to solve my other problems. It didn’t create focus time. It didn’t schedule my habits. It didn’t protect me from booking back-to-back meetings. In fact, it made it easier to fill up my calendar because the booking process was so smooth. It was an amazing tool for scheduling, but a poor tool for time management.
| My Experience with Calendar.com | The Good (Pros) | The Bad (Cons) |
| Core Function | The best external booking link tool I’ve ever used. | Does almost nothing for internal time management. |
| Best Feature | Team scheduling links (finding time for multiple people) is flawless. | It’s not a time “defender.” It’s a time “filler.” |
| Integration | Great with Google & Microsoft. Clean, polished, and professional. | I missed Reclaim’s “Habit” scheduling every single day. |
| Overall Feel | Like a professional receptionist. It’s an extroverted tool. | Can lead to more meetings if you aren’t careful. |
Month 3: Dex – The (Surprising) Relationship Manager
For my final month, I loaded up Dex. And this is where my entire test went completely sideways.
I spent the first day trying to find the scheduling links. I looked for “Habit” or “Task” scheduling. I couldn’t find anything. I was frustrated, thinking the tool was buggy or just poorly designed.
Then I had my “Aha!” moment: Dex is not an AI scheduler.
The Big Misconception
Dex is a “Personal CRM,” or a relationship manager. It’s not designed to optimize your calendar blocks; it’s designed to remind you to fill your calendar with the right people.
Comparing Dex to Reclaim is like comparing a phone book to a stopwatch. They both involve time, but they do completely different jobs. I had completely misunderstood the tool.
How I Used It Instead
Once I figured out its real purpose, I pivoted my test. I had just “attended” a large virtual conference and had a list of 20 new contacts. Instead of letting them rot in my inbox, I put them all into Dex.
- I connected Dex to my LinkedIn and email.
- It automatically pulled in their info, photos, and job titles.
- I set reminders. “Follow up with Jane Smith in 2 weeks.” “Check in with Tom Lee in 1 month.”
- I added notes: “Met at the AI summit. Talked about new productivity models.”
Dex then integrated with my calendar, not to block time, but to add small reminders. A little “ping” would show up: “Time to reconnect with Jane Smith.” It was brilliant.
Did It Save Time?
No. In fact, it cost me a little time each week to log contacts and set reminders.
But what it saved was social capital. It saved me from the embarrassment of forgetting a key contact. It made me look more thoughtful and organized than I actually am. It stopped important relationships from “slipping through the cracks.” This value isn’t measured in minutes saved; it’s measured in opportunities gained.
The Final Verdict: Time Invested vs. Time Saved
After 90 days, I had a very clear winner. But more importantly, I had a new, much smarter “stack” of tools. The goal shouldn’t be to find one tool, but the right combination of tools.
Here’s my final breakdown of the time I put in versus the value I got out.
Final Showdown: My 90-Day Test Results
| Tool | Time Invested (My 30-Day Test) | Time Saved (Estimated Per Week) | My Honest Verdict |
| Reclaim.ai | ~45 minutes for setup & tuning. | ~4-5 hours saved. (This was created focus time). | The Clear Winner. This was the only tool that actually gave me back time for deep work. It fixed the root problem of a chaotic internal schedule. |
| Calendar.com | ~60 minutes to create all my links. | ~1-2 hours saved. (This was time not spent on email tag). | Essential for Externals. A fantastic tool for client-facing work. It solved my “email tag” problem perfectly but didn’t help my work-life balance. |
| Dex | ~3 hours to import contacts & learn it. | Zero hours saved. (It cost time to maintain). | The Wrong Tool (for this test). An amazing relationship manager, but it is not an AI scheduler. It’s an investment in your network, not your schedule. |
This little table is what I live by now. When people ask me what tool to use, I don’t give them one answer. I ask them, “What are you trying to fix?”
My New “Productivity Stack”: How I Use Them Now
I didn’t just pick one. I ended the test and immediately subscribed to two of them. Here is the exact system I use every day now.
- Foundation: Reclaim.aiReclaim is my new calendar “brain.” It runs 24/7, connected to my Google Calendar. It is responsible for all my internal time: scheduling my tasks from Asana, forcing me to take lunch, and building a wall of “Focus Time” around my important projects.
- Front Door: Calendar.comI use this for all my external scheduling. Its beautiful, simple links go in my email signature. When a client books a call, Calendar.com looks at my schedule. It sees the “Busy” blocks from my real meetings and the flexible “Busy” blocks from Reclaim, and it intelligently offers only the truly available times.
- Network: DexI keep Dex open in a browser tab. After a big meeting or a new intro, I spend five minutes logging the person and setting a follow-up reminder.
This combination is the key. Reclaim protects me from myself and my team. Calendar.com protects me from the chaos of the outside world. And Dex ensures the people I do meet with are never forgotten. This isn’t just about tools; it’s about the psychology of how we manage our time. Many people, myself included, struggle to protect their own schedules, a challenge explored in Harvard Business Review articles on productivity, which notes that we often sabotage our own best-laid plans. My new stack acts as an automated system to prevent that self-sabotage.
Frequently Asked Questions (FAQs)
Which AI scheduler is best for a solo freelancer?
Calendar.com, without a doubt. Your main problem is booking clients efficiently. It makes you look professional and cuts down on admin time, which is time you could be billing.
Which tool is best for a busy manager in a big company?
Reclaim.ai. Your problem isn’t getting meetings; it’s surviving them. Reclaim will defend your time, help you find 1:1 time with your team, and automatically sync your status to Slack so people know when not to bother you.
Is Reclaim.ai or Calendar.com better than Calendly?
It depends on the job. Calendly is simpler than Calendar.com, but Calendar.com’s team scheduling and analytics are more powerful. Reclaim is in a completely different category. It’s not a Calendly competitor; it’s a time manager.
Do these tools work with Microsoft Outlook?
Yes. When I was testing, both Reclaim.ai and Calendar.com had full support for Microsoft 365 / Outlook calendars, just like they do for Google Calendar. Dex is more about connecting to email and social media, so it works alongside any calendar.
Conclusion: Did They Save Time or Add Complexity?
So, here’s the final answer. AI scheduling tools are not a magic wand. If you just add them without a goal, they will add complexity.
But if you identify your problem, they absolutely save time. My 90-day test proved that the hype is partially real. These tools saved me from the complexity of my own messy calendar. Reclaim.ai simplified my internal life by creating focus. Calendar.com simplified my external life by managing meeting requests. And Dex simplified my relationships by ensuring no one fell through the cracks.
The real solution wasn’t one tool; it was building a smart system where each tool had one specific job to do.
