I take it you're just talking about the central heating circuit?
I don't turn mine off to re-pressurise the CHC. I don't do it when the boiler is actually running either, but I don't think it matters tbh.
Most boilers have a dial or readout that tells you the pressure - also I'd not get too bothered by over-pressurising your boilers central heating water system... unless it's some kind of antique death trap, it will have a pressure relief valve that vents excess pressure to the outside should you over fill the system (when it gets hot etc) - but so long as you keep an eye on the pressure gauge as you fill, you should be ok, fill it a bit at a time if you're not sure. The dial on mine 'bounces' slightly when I fill it. Ie. when you turn the fill tap off, the pressure drops a bit.
If it has lost pressure, I'd be looking for a leak somewhere.
It might be worthwhile bleeding your radiators when you pressurise the system too - fill, bleed, fill, bleed until there's no more air in the system. The only place I usually have to bleed air from is the upstairs radiators after I've run the boiler for a bit, then let everything settle down. Might take 2 or 3 days to do this, checking for air once or twice a day, just to make sure.
Unless you're messing about with the gas supply, you cannot really break your boiler just filling it up with water.