Ask HN: How can I help my 40 year old brother get into tech?

This is what worked your someone I knew. YMMV.

1. Introduce him to one of many free online UI/UX courses and figure out if he's actually into it. If he isn't, try some other tech thing.

2. Once you've figured out what he's into, make him do one or two online courses in it, preferable from a good university (see: edx.org).

3. Work on a portfolio. Projects of his own, and contributions to F/OSS projects.

4. Add more to the portfolio. Non-profits often will give people with little previous experience a chance.

5. Apply to jobs for a junior position. Try small companies if he isn't having success elsewhere.

6. If he's finding it impossible to find work, internships are the way to go. They often make it easier to get jobs.

Does he want to get into software? Or just into tech in general. Because a couple decades of supermarket managerial experience means he could offer a wealth of insights into point-of-sale systems tech - he has been using it for years already. Don't dismiss that experience - Use it.

He could go a couple ways, either looking for an entry level position settings up POS systems, and working up from there, or could try to get into product design with insights into was has or has not worked for his teams over the years. I'd recommend getting in touch with the vendors he likely already has worked with and inquire what openings are available.