Updating your skillset is great, but the trick is, how do you define "update"? It's incredibly easy to pick the wrong technology. You're trying to predict the d

Updating your skillset is great, but the trick is, how do you define "update"? It's incredibly easy to pick the wrong technology. You're trying to predict the distant future, and if you're not (i.e. you're only chasing trends), you're always in direct competition with the cheapest labor on the market. For example, I can guarantee that any 20-something "specializing" in Javascript anything right now is going to be in a world of hurt in a decade. Even if you spend the bulk of your off-hours staying "updated" on the latest in JS development, you're highly likely to be wrong. So what do you do? Do you leave it behind? When? What do you do instead? Having a deep background in something can help, but that takes time, which carries an inherent risk: if you spend N years specializing in X, you're in extreme danger of being the person who gets laid off because X isn't in demand anymore.