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Based on what I've read so far, you're in a really comfortable position, so don't shift specializations.

Capitalize on your rich experience with embedded hardware and software development. At 50 I'm pretty sure you have a wealth of contacts from people in that field (people you consulted for, past work buddies, etc.) warm them up and make contact: you now have a client/referral list. Ask them how they're doing, take them out for coffee. Discuss what they're currently doing and what they need help with. Start with one tiny project.

Ask your wife for a little help, ask her for some contacts. Talk to others in your field, take them out for breakfast or lunch, offer to speak in an event, you can offer consulting or training workshops.

Go back to building a business, it's your best bet, and you've done it before. Outsource the bulk of your work into your other known contacts that can refer you to high-end consulting shops in the South-east asian or Indian region. Disclaimer: I'm from the Philippines. It's 2013, there's so much more tools for remote collaboration than it was a decade ago, you'll get a good english speaking/writing workforce for less than US salary rates.

Don't study unless you really really want to. 4+ years is a lot of time. You could have made another business up and running at that amount of time.

Don't shift specializations just because of current market trends. Who knows, hardware might boom in the next decade. Honestly, currently, the web itself and all mobile app stores are over-saturated with everyone trying to make a dent.

The point is, no one can predict what is going to happen in the next 10 years, just stick with what you know and what you can do to answer a need from your contacts. If a specific "solution" you're offering picks up traction, "productize" it and put a little more focus on that, but don't bank the entire consulting shop for a product unless it dwarfs your consulting revenue by 3x-5x. Consulting cultivates client relationships, and business is all about building professional relationships that would earn you more money.

I'm not 50, I'm only 26, the 50+ year old people I know end up in three ways:

- Teaching (writing books with their knowledge, offering workshops, teaching in universities, etc.)

- Retired

- Business

Again, I'm only 26. Take the input with a grain of salt.

Well, retirement isn't for me. I will never stop working on something so long as I have the physical and mental ability. That's just how I am wired.

Teaching at universities is out because, well, I don't have a degree. Ironically, I am a pretty good teacher. I've conducted seminars in the past with audiences in the hundreds of people. I enjoy it and I do have a knack for making complex topics accessible.

I have been thinking about perhaps authoring a webinar or two or launching some kind of an engineering-related educational effort. I have one idea that could be an interesting Kickstarter project for young (and not so young) engineers. Thinking about all options right now.

Well, that would be combining business with teaching. Maybe that's a good option for me.

Maybe you can make some video tutorials on your expertise. Saying, I'd be interested in how CNC works.

I would definitely go for the teaching option. Maybe you could start like this:

1: If you have a little runway, start by learning some teaching basics, especially regarding teaching adults. Or K12 if that is what you'd like. Start by doing some of the MOOCs, coursera, edX and some others have some good education courses. The benefit of this is that not only will you learn some of the theory behind teaching, you will find out what works and doesn't work for students in an online learning format. This will be valuable for part 2-

2: set up a blog with a learning management system (LMS) to offer some short video or screencast (my favorite style of delivery) based courses for free. Use this as an R&D and market research site to see which courses get traction, how to prepare materials, interact with students, etc. Your blog posts are there to show off your knowledge and experience which should get people interested in trying out the courses and help you build a mailing list for part 3-

3: with the data from 2 above, plan a book release and some more in depth for-pay courses. Use your business skills to sell online+book+in person training for enterprises (you may find it easier to partner with a training/consulting company who may already have contacts with potential clients - less money in the beginning, but as you build your reputation you can eventually go independent) Which leads to meta-business point 4-

4: Document your journey through the above points, and sell a new book and online training course targeted at people who are in your position (ie me) so that we can all join you by buying private yachts from all the money we make :-)

5: post results here on HN for support and inspiration for others

This is what I'm doing (albeit half-assed at the moment) and I have 15 years of teaching under my belt, but no degree (by the way, I have gotten teaching posts at universities based on the strength of my teaching skills, so give up on that route just yet!) If you want to reach out for info on where to start with learning teaching (I'm the head teacher and a teacher trainer at a school in the Czech Republic) me email is in my profile, I am more than happy to chat with you about it and I have a lot of resources I am more than willing to share with you for free.

Lee

[Edit] for an LMS try looking at Moodle or the edX platform, both are open source, and Moodle also has a rich plugin environment including modules for payment systems. I have a lot of experience with Moodle, and I'll be trying out the edX platform over the Christmas break. There are some others out there, but these 2 seem to be the best from a no pay system

Sent reply off-list. Thanks for your pointers.

>During dinner last night my wife said she wants me to focus on finishing a Bachelors and then a Masters starting next year. She said she doesn't care if I don't work during that time. She feels this will be good for me mentally and that it will/might bring opportunities to the table at one point or another.

First? I'd argue this is as much a relationship issue as a career issue. Treat it as such. When you are down, and relying on your support network to help you out, remember that you are relying on your support network to help you out and act accordingly. I mean, every relationship is different, and I can't tell you how to act in yours, but be conscious that you are using your support network.

(this can cause problems for you as much as it can cause problems for other people; accepting help can be hard. But either way, it's something you need to come to terms with.)

Next?

>My current view is that my only way out is through entrepreneurship. I need to keep trying until I hit upon something that works. I know I have a few potentially good ones but I don't have enough money to launch them correctly. I have to boostrap from small ideas to larger ones.

See, after a business failure? I really like to work for other people. Usually when I get a full time job, people think I'm pretty great, and generally I make more money working for other people than for myself (Apparently, I am not a particularly competent business person.) Anyhow, working for other people tends to rebuild both my damaged self-esteem and my damaged financial situation.

Another thing? Unless you are going for VC? Now is the worst time to bootstrap (unless you are selling to the VC funded... and if you plan on selling the company, rather than selling a product to the VC funded? I suspect you are too late on the bandwagon.) - It is difficult to compete with people who have VC and don't immediately need to make payroll.

So yeah; were I you? I would focus on contracting and/or on getting a regular job.

Now, I live in Santa Clara, not Santa Clarita, but from what I've seen? there are a lot of old guys in the embedded systems market. Can you handle VHDL or the like? Can you handle contracting?

I'm assuming that your contacts are stale or otherwise not all that useful. (First thing? call everyone who worked for you in the past. I've found that ex-employees generally think more of me than I think they ought.)

If you really don't have contacts (or want easy work... in my experience, if I get a job through contacts, I actually have to /work/ - if I can attract a random recruiter, usually the standards are way lower.)

That is... honestly, I don't know exactly what it is. I have really, really good luck with recruiters, and I don't know why.

Part of it is that if a recruiter spams me about a job I'm qualified for (and it is spam; none of them put any effort into vetting me first, as evidenced by all the offers I get for jobs that I'm obviously unqualified for) I respond.

But... part of that is that I'm on the recruiter mailing lists, and my resume kicks off the keyword searches. I don't know why or how this happened. The last recruiter who contacted me (I wasn't interested, but I referred him to a friend who got the job.) He said that he found me on Dice... but I haven't been active on DICE for at least four years, so I don't know if the guy was lying or if the net was just that wide.

I've even gotten jobs responding to craigslist ads (posted by body shops.)

But yeah, I... don't really understand why I seem to have such luck with recruiters. But, body shops and recruiters are a good way to go if you are down on your luck and need to get your foot back in the door.

Don't make any 4+ year commitments if it's not something you truly want to do.

"My current view is that my only way out is through entrepreneurship. I need to keep trying until I hit upon something that works. I know I have a few potentially good ones but I don't have enough money to launch them correctly. I have to boostrap from small ideas to larger ones."

This seems to say it all - what you want to do/be. So do/be it. If you don't have enough money to launch it "correctly", the launch it "incorrectly" and work your way to "correct". I'm currently bootstrapping from small ideas to larger ones, and while it isn't exactly kush, it's doable. It takes awhile and isn't going to be the answer to "how do I make a quick buck?".

I read somewhere that VC's on average fund people that are 40+, it's just not sexy and thus newsworthy (trying to find source). Also, if you have issues with people with larger than average ego, then you might need to avoid VC's as well...

Edit: Also, vet your current good ideas. Talk to entrepreneurs, investors, business people, potential end users about them. Even ask the judges at the pitch competition individually their thoughts (even if there was some ego amongst them - individually they could be awesome).

I'm your age, with a similar story, and completely understand where you're coming from. 25 years ago everybody wanted to hire me. Now it's depressing. I don't have a solution yet to getting hired into today's market where 6-figure income flow to kids performing skills it only took a few months to learn. Some ideas: (1) send your resume and practice interviewing with someone who will give you an honest respnose about why you're not getting offers (real companies won't give an honest response). (2) spend a couple of months putting up a free website on heroku with whatever are the "hot" products of the moment (arduino? raspbery? node? angular? go? mongo? zurb? etc...) then instead of a resume showing how old you are send a resume showing the stupid-but-well-paying stuff you can do with what's hot at the moment. (2a) put it all on github and show HN (3) go to meetups where the people you want to work with are and talk to them, show something in the lightning talk, and say you're looking for work. (4) go to hackers/founders things, buy beers, and say you're technical. (5) get tattoos, skinny jeans, and a skateboard, stop posting anything anonymously (nobody but old fogies believe in anonymity any more) and pretend you're only 20.

If ANY of those work, please let me know so I can follow my own advise.

As for school, only go if what you want to do is to learn more and if you think that's the way to learn.

Yup. Twenty-five years ago I could walk out of a job and into another within hours. Things change.

I've done the meetup thing. I'll say that most tech meetups have been a total waste of time. "I have an idea for <x>. Could you be my tech co-founder and build it for nothing?". Please.

The other aspect of meetups is that a lot of them are loud drinking parties. I don't drink. No, not some prudish thing. I just don't drink. The stuff doesn't attract me at all. And, of course, if I my intent is to meet people I kinda want to be able to hear them. So driving to a meetup an hour away, at a bar, with loud music and booze isn't my idea of something productive. Could be wrong.

Tru dat (I'm feeling more youthful already, saying something like 'tru dat'), most of these networking things will not workout, but most of anything doesn't work out, maybe you have to do 100 for that 1% chance of a chance. Yes, the kinds of alcohol-based meetings your talking about aren't the best. I'd recommend instead the educational meetings, like user groups where people are giving talks showing off their latest use of X technology. E.G an arduino group, a python group, a goggles group, whatever tech floats your boat. The people in those kinds of meetups, in my experience, are more than not serious about the tech and not just looking for a drink.

Another thing I didn't mention is the personal email to someone at some company, being honest about some real connection why you and them should be together, not in response to a job listing but just in response to why you'd think they're a good fit, or praising them honestly on something they do. I at least tend to get responses, if nothing else, from these outside-the-box attempts.

- you may get lucky and find a job where you'll be able to give all you can, but this is not probable.

- most jobs you'd get would suck one way or another, prepare for a life of pain.

- you may get a degree in CS, but this won't help at all to get a job. Do that only if you don't need to earn a living and want to have fun learning.

- but since you don't seem to be entirely "financially independant" (what would happen if your wife lost her job?), there remains only one good alternative: keep being an entrepreneur. You would be a good co-founder.

Have you ever considered teaching? With all your practical experience you could open up coaching center and start teaching? Doesn't require much investment and this is a good time too, people are realizing the importance of knowing how to code and with all the efforts being made by govt. encouraging people to learning to code, this might just work out for you. And like others, I too don't think a college degree will help you. Best of luck.

I have one comment to make. I don't mean it as advice (I don't give good advice), but as a potentially (ir)relevant semi-obvious but perhaps overlooked fact. You meet lots of people in school. You may be right the degree may be no use. But that doesn't automatically mean that getting a degree is no use.

Degrees don't help as much in getting a job after 30. Getting degrees just makes the shitty software mobsters angrier. You're going to want to find a job through personal connections. A university is a great place to make personal connections.

with all the varied experience that you have, why would you want to focus on a programming job. If you are good at sales, evangelizing tech, there are plenty of non programming opportunities where you can add significant value. Look at all the tech companies that want a community manager. There are lots of international tech companies that have good products that are dying to get a foothold in the US market. get in touch with them; tell them you help market, evangelize their product; you can help support their US customers. having a holistic business perspective is an extremely valuable skill.