It should be common sense these days - if you are working for a company for 5 or 10 years - what do you have to show for it once you get booted? WIN still re-reimburses their employees (I think they still do) for up to $5000 per year for college, or certifications like CCNA. Lot of WIN employees I know took advantage of this and they have up-to-date skills, even though they are working for a dinosaur company.
Just having on your resume you worked for WIN for 20 years don't mean jack anymore if you don't show you continued learning newer technologies. Udemy and Udacity offer lots of low cost training classes - really no excuse to be caught unemployed with legacy skills that nobody needs.
You can make excuses for not updating your skills - then your resume will be sent to the trash bin by companies you apply to because your skills are outdated.
OP by @Wvxrl4U-1euw