Can you teach an old dog new tricks?

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Footlights

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I have recently started riding a 20 year old horse who has clearly never been taught to go in an outline.

In your opinion, do you think it would be possible to teach this to him now or would it be too difficult for his muslces? Or do you think I should just let him be and let him enjoy being ridden how he has always known it?
 
Depends on what you mean by outline. If you mean "nose on vertical at all costs" no. If you mean can you teach him gradually to carry himself properly, from behind, using his back end properly, yes. But bear in mind his age and don't push it.
 
I mean working from behind and building up muscle in the correct places. At the moment he has no topline whatsoever. I would always take things very slowly considering his age and have already started walking up gradual hills which has made a big improvement already.

Has anyone else had experience of bringing an older horse back into work before? I just want to add that he has more energy than a lot of the 6 year old on my yard and really enjoys being ridden, loves jumping etc.
 
He should be able to gradually improve and build up some correct muscle, by working him in the way you have described. I would get his back checked by a physio or chiro and also his saddle as there is every likelyhood that they will need some adjustment.
 
When I worked at a dressage livery yard a lady moved there with her 27 year old horse. He'd only been used for hacking before (she'd owned him since he was 6 or 7) but the two of them learned together and competed successfully at prelim dressage :)
 
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