What is the best company/industry to retrain for when you are 50 plus and only have 15 years or so left of working?

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That's a tough question. I suppose it makes sense to focus on fields that are bound to have growth going forward, such as cybersecurity or cloud computing. Perhaps getting certifications in those areas could be helpful. There's still a problem with ageism in business, and that's an obstacle that's hard to clear. But upskilling, combined with previous experience and transferable skills, may position you well.

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I'm doing exactly that, sidestepping into cyber. A years worth of certs and still couldn't break in as my experience was with specific vendors. Found a junior role to gain the missing experience, all skills transferable, the future is bright.
Ageism is a real thing sadly.

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If you have a degree, teaching. Without a degree, you can still teach in private or religious schools or as an adjunct at a community college as long as you had a long career.

You will have less ageism problems and some flexibility in schedule.

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uber driver, flex hours

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Your own company is the best choice. Find a partner or two with complimentary skills.

I had to do just that, and chose my field for it is the most highly lacking in employees, and has the biggest future of any profession that I can see getting into later in life...there is enough technical skill to make it interesting, and enough demand for a job to be waiting when you finish school.

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