Minor addition to this information - depending upon what's installed on your computer, you may not see the MyTomTom icon in the systray, but need to get to it with an extra step. If necessary, that step involves clicking on the upward pointing arrowhead in the systray. This opens a small window in the bottom right corner of the screen that may include several previously hidden icons, one of which is the MyTomTom icon. Right-clicking on that icon pops open the MyTT window described by canderson.I'm hoping this is just a little miscommunication.
Let's try this. Down in the lower right of the screen, there's the 'systray' icon for MyTomTom. Right click that. With the device connected (and it will show that it is connected or not), you should see "Add community content" right above the bar, and right below "My TomTom".
I know that hidden icons may be on a Windows machine but the OP is on a Mac. Don't know whether they have same thing.......
How about this tool:
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