Do a hair test first. That's the easiest way to take the plunge and still stay a bit safe. :P I have naturally dirty blonde hair so I made sure to test first because it was a huge change. Granted, I started with LUSH henna so it wasn't as great of a change. But now I use Yemeni (also from Henna Sooq; good stuff!) and I love it.
There's no use dying your hair with the box dye before you henna because I'm assuming you're not going to do that each and every time when you need to do your roots. Just try to do a test first, such as hairball from your brush, or if you're kind of a rebel and not too worried, you could just do a strand on your head to see how it'll turn out.
Good luck! Take before and after pictures!
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