In college, you’re often told that companies will be less likely to hire you if they read your resume and see that you’ve done many different things (as opposed to specializing in one and getting a Master’s or a PhD) that don’t complement each other in an obvious way. While my experience with the job world is still far too limited to confirm this, I wouldn’t be surprised if it was. And if it is, this means, as you said, that schools, universities and companies want to groom us into one-trick ponies. It’s a scary thought.
I have this plan of starting to work not too far from now and studying on the side since I already have two or three values up my sleeve. I’m lucky enough to live in a country where college and classes in general are virtually free (though creating a business is conversely full of hurdles over here). And with the abundance of evening courses you can take when you’re busy by day, it is a realistic plan indeed. To this foreign reader, your previous post about the liability of student loans is a fairy tale, fortunately. I suppose being single is an advantage in this scenario.
Now, the hard part is choosing values that multiply well, and to find HOW to multiply them well, HOW to ‘connect the dots’. Steve Jobs and you are right on that count.
I’ve noticed that it isn’t different skills you have that scares employers, it is if those skills are entrepreneurial. They want to leverage you.