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A suggestion for implementing gratitude journaling is to use Happy Rambles.

What it does It sends you an email every day at 8pm, asking you what you're grateful for (this is by default; both the time and frequency of the emails can be changed). You reply to the emails as often as you want to. You can view your past entries by going to the site. It takes less than 30 seconds to sign up.

Advantages The main advantage is that it makes gratitude journaling a behaviour that has an environmental trigger, and so you don't need to use your system 2 to get yourself to do it.

Drawbacks It doesn't send you a random past journal entry in your daily email as the site claims.

You can measure your happiness using the measures that positive psychologists use, for free, here: http://www.authentichappiness.sas.upenn.edu/