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Yasha Krasnov
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I use Trello for life planning as many of people here :)
It's a good idea to build something more people-oriented in life planning. But, I love Trello (and I'll still use it) because of its flexibility. For example I didn't find the way to create month/year goals column on Caltra.
+ if you wanna be more human-friendly, you should improve your UX. For example highlight milestones on-hover...
Caltra
Trello for humans, not companies