I ride at night fairly regularly. I've found that a good handlebar mounted headlight is made better by complementing it with a helmet mounted forward light, like this one:
This allows me to use it in strobe mode at dusk or in diffuse evening light, and on a steady beam in darkness. Having the ability to point your light "into" a curve, or directly toward side approaching vehicles is an advantage. It's something different that get's the driver's attention.
Also, as mentioned above, don't neglect rear lighting. I use a PB blaster rear blinking light on the bike, and a different rear light blinking on the back of my helmet. Plus, I select outerwear with reflective strips designed in, and add reflective ankle bands.
There are also city tires with reflective sidewalls that really glow when headlights fall on them.
in the end, you'll just have to develop your own sense of how to ride safely, with awareness, and just enough confidence to get out there and do it. But not too much confidence...