First, now or later?

If when stopped, the engine doesn't clunk into 1st, there's a good chance it will pop out of gear up under load. You should ALWAYS let the clutch out in neutral before engaging 1st to ensure it will clunk, including (especially) on start up. Changing into 1st while the bike is moving seems to avoid the risk of popping out of gear.
 
$hitcan that heel shifter!
NEVER jam/jerk the lever into gear (a fast shift can still be done without a jam/jerk).
Bring revs up to meet your downshifts.
These are a few of my favorite things . . .
 
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