I'd also argue that certain type of software skills don't become obsolete, and that a sufficiently experienced developer shouldn't have too much trouble picking up the 'latest and greatest' technologies. It's not like it actually changes fundamentally every few years!

Unfortunately, most HR departments don't understand that. To many HR recruiters, IT recruitment is a task of ticking off the checkboxes for knowledge, as opposed to screening for skills, character traits and personality.

But if your competitors have the same amount of experience but have picked up and used the 'latest and greatest' tools in real production environment, guess which one will get the job?

Do keep in mind that if you're 40 years old, it's less likely you'll get a job by picking up the 'latest and greatest' tools. Cause most companies that use these tools often employ workers a wee bit half over your age.

The problem is most employers only care about actual on-the-job experience. You might be a strong Python hacker, but if you haven't used Python in a professional setting recently it doesn't count.

Having something to show is the obvious solution to that. Even the simplest app hosted somewhere cheap demonstrates a myriad of skills that speak volumes about your capabilities. You still have to dodge the person ticking the bullet points in HR but that is a problem that everybody has regardless of the level of expertise.

I am not discouraging this kind of initiative, as it is the kind of thing that good managers are looking for. It has just been my experience that the majority of employers will not care, even if you have something to show.