Retiring is a hard thing to do - it's basically a massive career change. Both of my parents really struggled with it.
There is a career book called What Colour is Your Parachute, which walks through what kind of core aspects you want to focus on for a career change. Granted they're not working but it might help them focus on what they want to achieve in the next 10, 20, whatever years. Eg do they have a service motivation (helping other people), do they have special skills they want to keep in use etc. 'What makes life worth living' is where they need to get to - core motivation stuff. It's quite challenging.
When your family was young, what did you always wish you had more time for? In my dad's case, it was classic cars - he has about 5 on the go right now and spends most days up to his eyeballs in engine grease. My mum loves reading and visiting museums, so she joined the National Women's Register. They also decorate frequently and grow veggies in the garden. My MIL volunteers in a charity shop.
Suggest they join U3A (just google for contact for their area). It is for retirees and has lots of different interest groups. My mum & stepdad belong and go to the film club, travel & photography. A good opportunity to try out new things without making a big commitment. Plus they've made lots of new friends. Some things they do together and others desperately.
what have you always wanted to do, but never had the opportunity to do? what do you regret never achieving? What skills do you wish you had? What sport would you like to learn? If you could have membership to any organisation, what would it be?
That's sort of it. They are both mid 60's, retired 5 years ago and from then on they've 'floated' from day to day, don't have focus, go shopping a lot as they 'just want to go out' and aren't able to plan/see what they want to do. They have asked DH for help as they say they want someone to tell them what they should do.
I've suggested we ask them/give them some questions to think about what they really want. At the moment they're talking about moving out of their house (after 40 years) but don't know where they'd go and it sounds like if they aren't helped they might do something rash that they'll regret.
So, if you were to change/improve your life at this age, what would help you decide what to do? The only questions I can think of are:
-What are you happy/unhappy with in your day to day life? -When was the happiest time of your life and why? -What causes you the most stress?