Separation anxiety depends on number of times left alone?

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So I feel like I've read every thing about separation anxiety, but wondering if anyone else has had this experience. Or if this is just a coincidence.

I've worked up to leaving my puppy alone for 5 minutes at a time. I do this a few times a day and watch him on camera when I leave. It seems like no matter what I do (treats, exercise, play time, training, toys, whole cut up hot dogs), the first time I leave for the day, he can only go 5 minutes. Totally ignores the bully stick and very high value food and treats. Starts pacing so I know the barking is coming.

Later on in the day, he starts chewing his bully stick and could probably chew for an hour without caring. Even if I don't give the stick, he seems to just not care and naps calmly near the door. He does watch me leave but goes pretty much right back to sleep/chewing.

Is number of times being left in a day a "thing" with separation anxiety? Where the first time I leave in a day he's freaking out but the second time he's ok? Like he forgets that I come back but the second time he remembers. Has anyone had this and if so how did you handle going to work?

Separately, I've been watching him with bully sticks and just outside so I could come back if anything was happening. So far so good. But…Is it ok to leave him with a bully when I'm back at work?

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