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Its pretty clear to me that once you're considered old, you're done when it comes to the computer profession.

Hate to disagree but I definitely do.    If you want to work into your 50's, 60' or 70's you can.   It requires a couple of things.

*  Forget programming.   Get into a skill set the 20 somethings generally ignore like project management or business analysis.
*  Persistence - NEVER give up regardless of how many times you have been put down by the young turks.    It is a numbers game.   The more things you apply for, the more likely you are to get a job.
*  Absolute confidence during an interview.   You are better than them and you can do the job like none of the young turks can.
*  Concentrate on some specific industry.   Once you have experience in that industry, it will get easier and easier to get a job.

I happen to have concentrated in banking and financial services when I go for jobs or contracts.  In my own private consulting with SMB's I generally do legal and other systems like that.

But it can be anything.   Pharmaceuticals, insurance etc.   Pick your poison.   It might take you a couple of years to get the first gig but keep plugging and you will eventually get the first one.

After that, you will be scanned and picked for similar gigs by the headhunters.

Here is a very specific suggestion.   Linux admins -These jobs are out there and quite a few are remote where you can work from home.   Most corporate Linux systems are Red Hat.   But work with CentOS on your own system which is actually Red Hat Enterprise.   There are plenty of courses on Udemy for Linux Admin at 10 bucks on sale that would qualify you for it and get certifications.   Salaries range from 85K for a beginner to 150k  for a well qualified Linux admin.   Gorn, check this out if you can stand the thought of working for a big corporation.  You have shell scripting chops and lots of other skills which would apply. 

When you are working from home, they have no idea how old you are and couldn't give a crap anyway as long as you can do the work especially if you are on a contract.

I am working right now on a 2 year gig at a major bank.    And I am older than anyone working at the entire bank.   Don't want to say how old I am ( or I would have to send Louie from South Philly after you to pay you a visit) but I was working at Cape Canaveral in the space program as a radar and telemetry engineer during the Mercury program.

So get off your butts and forget your age!!

Only one thing I can add:

It can be truly mystifying how to identify an entry point to do this. IE, some kind of work that you feel like you can add value in.

What I mean is that most of us don't know where to start.

Example: If I have been programming or in tech work for decades, how do I reposition for project management or business analysis? I don't have a track record in either.

I disagree about programming. Just take anything you can get.

There is an older mainframe dude floating around here.

Pxsant is trying to say to develop a specialty area where you aren't competing head-on with young dumbasses. And that will generally, not always be something peripheral to technology and not implementation.

That's why he's saying not programming. If you program you are in competition with young turks.

Mainframe and related older in-demand tech is the exception to that rule. Older guys and gals know that stuff and are competitive.

But I don't even have that skill set. What Pxsant says applies more to me, but I don't have a clue where the entry point would be for me.

I have a couple of suggestions on how to start to reposition yourself.

Do an advanced search on job boards like Dice or Careerbuilder or Indeed for keywords you might be interested in to see how many jobs there are and how many are remote.   A few possibilities assuming you want to stay technical and you can accept working for a big corporation.   Most will be contracts but that's life in the technical fields today.

*  Python - lots of python jobs out there
*  Linux - Linux admin mainly
*  SQL - Very good jobs where your SQL skills are very high - Use Oracle since that is what all big corporations use.   You can download a free version from Oracle.
*  Big Data - lots of big corporations have moved to big data (NoSQL etc) for certain things.   Very few candidates are out there.
*  Data Analytics - Again this a big one where there are few candidates.  You need to take courses in the R programming language which is what most big corporations use for analytics.

Once you identify a candidate, then go to Udemy to find out what courses are available.  Don't pay full price.   Virtually every course on Udemy is available on sale for $10 or $15.   Join and get on their mailing list and wait for your courses to be on sale.   Might take a month but they will be there.

Take as many courses in your chosen field as you need to become expert.   That might take a couple of months but that's the price.   Then start flooding jobs with your resume which you will have modified to show appropriate experience with the language.    Keep at it until you start to get telephone interviews. 

You might crash and burn your first few interviews but so what.   Consider it a learning experience.   Eventually, you will start to ace interviews.

As I said before, it is a numbers game.  The more you flood the jobs with resume's the more likely you are to get a job.

Attitude and persistence have a lot do with it.   You have to believe you will eventually score a job.    Don't worry about being rejected.   You might be rejected 99 times before you find that one interviewer willing to take you on.

You didn't mention cybersecurity.  That might be a good specialization for a sysadmin to have.  When I left the last company I worked for more than 1/2 the reqs. were for people with information security experience.   The only problem with that is there seems to be a bit of a cattle call going on at the moment.   Where I live, some local colleges are persistently running ads for their infosec programs.

You are correct I did forget the cyber/information security possibility.   That one might be a bit more difficult to gain expertise in.  Mainly because the tools used at big corporations may not be available to you or they are too expensive to buy.    Still, it is something to think about.   

Also, it may be a bit higher risk.  If the corporation you work at in cybersecurity has a major break in and data compromise, you may be screwed along with the security management.

"Example: Javascript by itself, not a ticket. Much more convincing: Angular.js (a common JS library used in web dev.)"

That is exactly why I said you might crash and burn some interviews.   They are using something you didn't come up to speed on.  So go out and get your hands on Angular.js and work it until you become an expert in it.   I searched Udemy and found at least 25 courses on variants of Angular including Angular 4, 5, JS, Node JS etc., all at $19 each.  Buy a course or two or three and beat them to death.  So it takes you a month or two or even longer.   

Next interview, you might run into another library or something else you didn't get up to speed on yet.   So do the same thing again.

After a bit of time, you will have more in-depth knowledge and expertise on the subject than the people who are interviewing you.  And that will come out and be obvious to them in the interview.

Also, you build an application (Web in this case) which has commercial applicability in the SMB or next level upmarket.   Host it yourself so you can show it during the interview.  When they ask who you built it for, say that you hold the copyright and do not reveal customer names because of confidentiality issues.  That is an absolute truth for me.  Virtually every private customer I have (law firms, others) wants a non-disclosure agreement, especially where I maintain the copyright.

I guess the most important thing is to go in stages and NEVER GIVE UP.  Find out through the interviews what you are short on and get that part up to speed for the next interview and the next and so on.  Ultimately you will discover you know more about the technical subject matter than the people working at the places you are interviewing with.

Then there is the issue of buzz word bingo with resumes and HR departments.   But that might be a subject for a separate post.

Then there is the issue of buzz word bingo with resumes and HR departments.   But that might be a subject for a separate post.

Pxsant, I did some checking on Indeed.com. I don't know where you would recommend to source your leads for opportunities for the kind of campaign you're describing.  Indeed.com seems as good a place as any to start.

When I'm on Indeed what I see is:

Any tech skill you want to mention is dominated by body shop listings. A FEW major employers advertising directly.

I've found that lacking the mix of alphabet soup listed in the job ad, you don't get any opportunity to talk to a human to do what you're saying.

That by itself messes with my motivation to try what you're saying. I know factually that placed in a real task environment, I may run rings around any real human. But I'm going to be weeded out long before I get that opportunity.

The body shops and most Fortune 500s won't even talk to you unless you fill out a lengthy Taleo assessment. (Note to older workers who haven't interviewed for years; Taleo is the main HR platform that forces the applicant to fill out a detailed item by item application for a job that usually takes 30 mint to an hour.)

Then (and I have found this out directly) even when you meet the job's likely needs, you don't get a call back when you have a problematic current bio (too many years since FTE, non verifiable experience with clients or employers long out of business, small shitty companies that are unknowns, etc.)

Suppose you progress to talking with someone.

They'll ask where you did this and that and who they can ask about you. NOT about what you can actually do. Again, it's not about what you can do for them, the process is still in this "we need to assess your merit" phase.

Ok, suppose one gets past this phase:

Back in the 90s, I really knew my shit about Windows application development on C++, VB and Delphi, and HR software wasn't in wide use. I  almost always crashed and burned on the interviews that were more formal and structured. 

The places I was actually able to get into were the small biz shitholes that had no formal interview process. Which is why I was always complaining about my clients.

Now, that's really my own self esteem, salesmanship, and self worth issue that I fully own and it's all my fault, I realize.

I'm just saying that even when I was at the top of a particular area of expertise with a lot of current work to show for it, I would get dissed down to nothing and rarely got invited for a follow up. That was in an area I already knew.

Tooling up on a completely new skill and building some app to show it? Maybe there's some new weird current dynamics that make that feasible but I never got that to work.

Lastly, you're saying it may take many tries. That's true and I tended to give up after 5 successive failures in a given niche.

I'm probably more persistent in the face of really discouraging odds than anyone else on this board currently.

Tooling up on a completely new skill and building some app to show it? Maybe there's some new weird current dynamics that make that feasible but I never got that to work.

I don't understand.  If one wanted to build web apps, why couldn't a person identify the most in-demand web app frameworks and tools and create something like https://www.timeanddate.com/date/duration.html and demo it to the employer?

Do you think that would not be good enough or only paid work will do?