Perfect will of God vs Permissive will of God

Back in the day, I remember I had a pastor (ThG, Tennessee Temple) who from time to time would mention the Perfect will of God and the Permissive will of God.

(since this was a military church, I will use that example)

Suppose in a "military church" overseas there are two men, John and Sam both believes that the Lord wants them to go to Bible college to be a pastor
But at the moment, they both have 16 years of active duty and its time to ETS.
John thinks that that with one more re-up, and he will have his 20 years with full retirement.
By having that full military retirement - it will be easier for him to complete school as well
would be able to pastor a small church or even serve overseas - (less need for full mission $$ support)

Sam believes the Lord is calling him now - he gets out of the military to attend Bible college.

So by John waiting - (lets assume) that is Gods "Permissive will"

From his point of view - it does make sense

So is it possible that the Lord would not bless John as much as he would Sam,
as Sam followed what he believed to be the perfect will of God.

I HAVE NO IDEAL WHAT DIRECTION THIS DISCUSSION Will GO
So go for it!