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Once I get up, my dog & I always have long adventures including but not limited to, going on a run/long walk, riding in the car, riding on the train to my work, hanging with me at my work, & then a long night (which is technically "my day").

Am I cramping my dog's style by making him a night owl? He still gets to nap intermittently while I'm working at night, but I do wake him up to take him home & he & I may not crawl into bed for the "night" until 3-5AM. Then we sleep until he wakes me up to pee & then we go back to sleep. Sometimes he wants the day to begin around 9-11AM, but I crate him until noon or 2 (on a really bad day, maybe even 3 or 4) & then our day together begins.

Should I follow his sleeping pattern instead of my own, or can I train him to live my working lifestyle?
 

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I've always been a night owl and kept similar hours to yours. My dogs have always adjusted very quickly just fine. They never even woke me up to pee. When I've had job or schedule changes or had to work a few early days a week and a few late days a week or had to wake them up early for any reason, they made it very clear they were not happy turning into morning pups and were snoring the minute they unhappily flopped into the car lol.
If I take my current dog to the field or dog park in the morning, he'll go do his bathroom stuff but won't play much. If we go in the afternoon or night he's much more active.
So I've never had any trouble.
Your dog sounds like he has a pretty good life with you so I wouldn't worry. It's better to keep a consistent schedule than keep switching back and forth. I only change when I absolutely have to for job requirements.
 

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I'm also a night owl and George came to me from early birds so there was a period of adjustment at first but now he's fine. He naps when he wants to, plays when he wants to and goes to bed when I want to. He seems pretty happy about it. Like your dog, OP, he sometimes wants to get up earlier but once he's had a pee it's back to bed. He has the occassional restless night but then, don't we all?
 
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