Will he, an executive before, have the required patience and humility to start at the bottom rung again, to e.g. step into a company with 20-year olds that know more than he does? 20-year olds that may not always be as kind as he would like them to be?
If I were in his shoes my answer would be no.
But the solution I would consider: have him build his own product.
He's of a certain age, so he probably has experience to areas that us younger folk have no idea about. Is getting medication a pain? Is there an app he'd wish he had on his phone or on the web to help him with various activities? Something friends of his age would like? Or something he could build for the children of older parents that could help them out?
If you're saying that he used to be an executive, I imagine by this point he's got enough savings to be comfortably retired. So, he can spend some time learning ruby on rails and pick up some front end stuff and start hacking away at a product he would like to see in the world.
Expose it publicly (the "hey I'm 61 and here's my side project" is bound to get a lot of clicks) and then go from there.
But that's what I would recommend. I wouldn't necessarily recommend he learn a stack and apply for jobs.
Beyond age-related things to solve for, his experience as an executive probably has a much more niche range of everyday inconveniences that a lot fewer people out there are building or have tried to build for. Maybe things that CEOs don't necessarily have to do themselves, but that he's noticed his EAs always spent an inordinate amount of time on, and for which a product could make them more effective.
Will he, an executive before, have the required patience and humility to start at the bottom rung again, to e.g. step into a company with 20-year olds that know more than he does? 20-year olds that may not always be as kind as he would like them to be?
If I were in his shoes my answer would be no.
But the solution I would consider: have him build his own product.
He's of a certain age, so he probably has experience to areas that us younger folk have no idea about. Is getting medication a pain? Is there an app he'd wish he had on his phone or on the web to help him with various activities? Something friends of his age would like? Or something he could build for the children of older parents that could help them out?
If you're saying that he used to be an executive, I imagine by this point he's got enough savings to be comfortably retired. So, he can spend some time learning ruby on rails and pick up some front end stuff and start hacking away at a product he would like to see in the world.
Expose it publicly (the "hey I'm 61 and here's my side project" is bound to get a lot of clicks) and then go from there.
But that's what I would recommend. I wouldn't necessarily recommend he learn a stack and apply for jobs.