A few days ago someone was asking about live tracking and productivity hacks this is my response to them.
I use timers on my phone, Google calendar, and a spread sheet. All portable tools that have there versions on just about every platform/system. (IOS, Outlook, etc) First, everything goes in to my Google calendar, every appointment, every meet up, every time I go to VHS, every time I meet someone up for dinner, everything. I don't trust my own ability to remember anything so I use Google calendar to help me remember. Google calendar also has the ability to add email/pop-up reminders, you can get an email a week out from the event or a popup on all your devices 1hr before. I believe the default is a pop up 10 mins before. This has been tremendously useful for far out deadlines, that are 6 months to a year out as I can email reminders every other month. With Google calendar you can also add in the location of events and my phone will auto map to these places and tell me when I need to leave to arrive on time. At the end of the day or week I also back update my calendar with anything I randomly did that is not in my calendar. For example if I randomly met up with a friend on the street and went for dinner, I will update my calendar for this past events. I been doing this for ~4 years now and because of it I rarely miss appointments with people and I have this beautiful log of everything I have been doing. I can tell you with a reasonable certainty where I was a year ago.(Dinner with my Sisters, where we talked about xmas gifts for my parents) or two years ago (Trip to Seattle for work) or three years ago (Dinner at Joeys Stake house, followed by a movie at Scotia Bank theater, then drinks afterwards). This is a beautiful data set of my life, and also a good alibi if I ever need one ;) Next. I have two repeating alarms on my phone. Bed time 10pm Monday-Thursday and wake up time 8:30am Tuesday-Friday. (I don't work Mondays) The 10pm bed time is just a reminder that I should be cleaning up and getting ready for bed, I rarely go to bed at 10pm but it helps me get started to thinking about it. You could do the same thing for dinner or lunch to make sure that you eat a regular intervals. (super important) Last, The feed back loop, and self improvement. I use a spreadsheet to count points for doing good things. Along the top are columns for the date, and along the side rows are categories and things I want to track. When I brush my teeth AND FLOSS more then once a day I get a check mark in a column for that date. When I eat a vegetable, or go for a run or walk, or zero my inbox, or say something nice to my significant other, or read of an hour, cook something that is not box food, Filling out the self improvement chart, etc... I put add a check next to the date. I also put checks next to negative things, such as playing video games, watching TV/Netflix, or eating candy, etc... Each item is worth a different amount of points. The amount can be negative for bad things, negative for missing (like brushing teeth) or positive for good things. The amount can change per week as well as thing become more or less important in my life. At the bottom of the sheet there is a score for the day (total of all the points). With this score I can chart myself for each week or month so see if I am in a upwards trend or if I am in trouble. I did this for a year and my results where mixed. It was too much effort to fill in the spread sheet every day. I tried to automate it but creating a jabber chat client that would ask me questions about my day near the end of the day (did you eat a vegetable today?) and recorded the answers in to a database for me but I also found that annoying (fuck you, your not ma Mom!). I gave up on my spread sheet after i built the app and when the app got annoying i never went back to the spread sheet. Regret Anyways, I highly suggest that you NOT build a new system for this on the raspberry pi. Use existing tools that can be moved from one system to another. Don't focus on the technology, focus on the results. Start by using the tools that are available right now and use it for a few months, after 3 months, reduce an refine the process and maybe automate some of it. Also look in to the "Quantified self movement" where you will find a huge amount of research on this topic and tones of tools that other people are using. Good luck.