I don't know if this falls under your purview or if this is more DND's, but you've served in the CF and can maybe speak to it. My thinking would be that when someone is transitioning out, it's almost too late, and you should have been preparing them throughout their career.
Are there programs in the Canadian Forces that soldiers, sailors, airmen, and airwomen can avail themselves of to help them so that it's not such a shock for them, as you said, to step out into the great unknown? Are there programs throughout their careers that help them to plan financially and all the other things they may need to plan for, for their post-military life? Do those programs exist?