TLDR: Take a well thought-out customizable Pomodoro timer, combine it with 2-way calendar sync and powerful automation capabilities, and you have Session. Just know that although the automation is “powerful”, getting anything more than simple automations set up may not be something that most users are capable of or will want to invest the time into.
I first tried Session when I was testing out pomodoro timers. I successfully used it for a few months, enjoying the elevated pomodoro experience that allowed me to follow scheduled time blocks and also log the actual time and tasks that were worked on and reflect on the day’s work. I also got into using some of the more simple automation capabilities like turning off the lights in my office at lunch time so I wouldn’t work through my lunch. Eventually I switched back to working in an office so couldn’t take advantage of the home automation anymore. That, and with the difficulty of managing multiple systems (calendar, work project management, work time tracking, and Session), I decided to stop using Session.
Well, it’s about a year and half later and I’ve found myself back testing out Session again. I’ve been trying to add a lot more structure to my day, and could really benefit from adding back a calendar-integrated pomodoro system. I followed up on it to see where development had gone and the example uses on the website sold me on giving Session another shot. Two of the specific example uses shown on the website that got me excited were: that Session can now set the Session duration based on the length of the calendar event, and that it is possible to have Session start and stop other time trackers too (like the one I use for work). I envisioned using Session for my morning routine, wind down routine, work tasks focus, making sure to take breaks and so on. (ADHD? You guessed it!)
Here are some of the ways I had hoped to use Session:
- Get a notification from my calendar for a scheduled event (as I already do now)
- Hop into Session to see my event there and the event in Session, with the start and end time all set up
- Prompt and reliable 2-way calendar sync. If I move a focus time-block or a meeting in my calendar, then it updates in Session
- Pomodoro Timer
- Use my iPhone or iPad as a dedicated Pomodoro timer to visually display time getting smaller and remind me to stay on the focus task
- Remind me when time is almost up to so I can start to wrap it up
- Remind me when the time is up
- Keep recording time after time is up, visualize how much I have gone over time, and provide continuous notifications in intervals until I end the session to help make sure I’m aware of what I’m doing and not off in outer space.
- Live syncing my timer across all my Apple devices so I can use it for all types of tasks regardless as to whether I’m working on my computer, or I just have my phone or watch on me. Also so that I can get up and walk away from my desk during a break and still get a notification to come back.
- Triggering the start and stop of other time tracking tools to help mitigate the issue of having too many systems to keep up to date (hoping I can get it to work with Harvest which I use for work)
How Session fell short for me:
- As I experienced previously, the Pomodoro timer is exceptional. The only feature I would request would be the ability to make the clock bigger on iPad so that it is easier to see the time visually.
- Calendar sync is very slow to update for my work calendar (Microsoft Exchange). This in itself is a dealbreaker as I often update same-day events. If I was using iCal for work as I do for personal, then maybe this would be ok?
- No Apple Watch app. This was a big oversight on my part. I just expected there to be one. Without an Apple Watch app I can’t leave both my phone and computer. So no use to me for morning routine, bedtime routine, breaks between sessions at work, etc.
- The automations I was hoping to set up, such as using Session to start and stop my other time tracker, are complex and do not have guides from Session on how to do them. You’re on your own and I just don’t have the time to invest in this currently.
So, I’m back to not using Session. Still giving 5-stars as this is an exceptional app for the right person. Hopefully some of the points I mentioned see improvements as I have high hopes for this app.
***Update, I forgot about the automation capabilities for blocking apps and such. Might revisit.
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