As many men my age do, I believe, I occasionally want to tell the world to stuff it and go off and do something completely different. At what point is it too late? Is it ever too late? And if it is, what's the time or age that you reach that point, so I can warn my 20 year old son? Not really looking for personal answers here, understand, just wanted to start a conversation, but hey you never know...

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Too late to enjoy yourself and a new challenge? I don't think it's ever too late.

Too late to have time to build it into a career, I'd say anytime before 60 is ok.
I have been contemplating going back to school and starting a new career in teaching. I think the whole "teach an old dog new tricks" thing depends on the individual. I've seen both ends of the spectrum.
as a soon to be 25 year old, i've been wondering this myself. I realize that there are certain things that I probably can not do anymore, now that I have a family to support. But that my be a limitation not necessarily directly connected with age. Can someone be too old to go into a field that requires you to be "hip" or to bring "fresh" ideas, probably. Can someone be too old to go to medical school and become a surgeon, probably. Depending on ones past I would say that there are many professions it can be too late for such as Military, Show Business, Design, Medical, Technical.
I'll disagree with show biz, and design - I can think of many exceptions, enough to where I think the guideline is less useful.

And re: hip and fresh ideas - at the rate we are recycling decades (is it the 80s that are hip again now? or are we already up to the 90s) older ideas and an outsider perspective are valuable in design. Especially if you can argue for "timeless" instead of hip.
In my opinion, it's never too late to do anything new ... professionally or otherwise. A new move can open up exciting and achievable things that can be surprisingly successful. However, the possibility of that success will probably be greatly enhanced if the "new" thing is built on or related to what one already knows and has built on from previous schooling and life experiences ... rather than beginning totally over again from scratch. So, I think a good thing to ask oneself when contemplating a change to a new profession is, "What do I already have in my toolbox that I will be able to use in that profession?"
Well, I'm 60 years old and I am on my fourth career. I wake up everyday and try to find a new opportunity. It started back in 1966 as a photographer out of high school, then I was called to be in the US Army Intelligence with a tour in Vietnam. After that I was a Government agency with my career changing to Law Enforcement and Intelligence, I then took a position outside the Government with my own company and did industrial counter-espionage, security, security circumvention, crisis management (continuity for you new guys) and dealing with hard entities overseas. After that I got into the wine and spirits business and from there I went into the gas and oil business. While running fashion, publication, importing, exporting, and warehousing companies. I want you to know that I was sucessfull in all of these ventures making at ALL times in the 6 figures. This is a long way of saying to Jamie that instead of programming...maybe you could have let the old guy do something else. He had probably been around and maybe knew enough about business to where he could have sold, done planning, or administration. Experience is a comodity these days. But, I understand if he can cut it...he can cut it. Which also brings up managing and leading people. Anybody can manage good people...but your managing leadership abilities are not seen until you have to lead or manage bad people. But, off of that...I enjoy everyday of my life and I believe you can learn from both old and young alike. "Stay thirsty my friends"...I'm still in the wine business.
It is never too late... Heck, I was 40 years old before I figured out where to begin.

I don't think you need to "warn" your son, but rather encourage him to try many different things and to follow his heart and do what makes him happy or to follow jobs / careers that capture his interest at any point in his life.

You will always be his father and he will always be your son, but as he gets older, try being his friend more than his father and support his decisions. Just my opinion, your mileage may vary...
Thanks everybody for the intelligent, insightful replies. We have a great group of men here and it's always a pleasure to hear everyone's ideas.
In the Immortal words of the Worlds most interesting Man. "It is never to late to start beefing up your obituary." (he actually said "its never to EARLY, but same difference.)

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