One of the saddest things about our education system is that children are under enormous pressure to give answers that are safely within the boundaries of conventional wisdom. Unfortunately, the fear of being wrong is constantly reinforced and carries into adulthood.

I feel I was fortunate in this respect, because I apparently inherited a penchant for taking risks that might result in my looking foolish. At a very young age, I understood that it was okay to speak out and risk being laughed at. Nor was I afraid to try something novel at the risk of failing.

My memory takes me back to an incident that occurred in chemistry class when I was a sophomore in high school. The teacher (Coach Smith, who also coached the school’s basketball and football teams) asked the class, “Can anyone give me the technical definition of cold?” What a great moment for me, given that I had just read that definition in my chemistry book the night before.

Up went my hand. Coach Smith nodded in my direction and said, “Okay, Ringer, let’s hear you define cold for us.” To which I replied, “Cold is the absence of heat.” Yikes! The way the class erupted in laughter you would have thought I was a standup comic. “What a dumb ass thing to say,” the future Ivy Leaguers in the front row must have been thinking.

Coach Smith quieted the class down and, to everyone’s astonishment, said, “I have news for you. Ringer’s definition is exactly right.” Dead silence. What a beautiful and quick vindication. It was approximately the same satisfaction I would have gotten had I been given permission to roam through the classroom and randomly mess up the hair of the supercilious, would-be Ivy Leaguers.

I never forgot that exhilarating experience, and I believe it helped me when I ventured out into the real world and did a lot of things that today seem audacious even by my standards. A great example of this came early in my business career, after I had anointed myself a men’s outerwear designer. Nobody gave me permission; I just did it. I was an aspiring Tommy Hilfiger before there was a Tommy Hilfiger.

At some point in this particular career, I came up with a crazy idea for a poncho that featured two hoods. It consisted of nothing more than a large piece of vinyl with two holes in it and two hoods that a couple could wear while sitting in inclement weather at an outdoor sporting event.

But then, as now, it all got down to marketing, so I scoured my brain trying to think of ways to get some exposure for my strange looking masterpiece. Sitting in my hotel room in New York, I came up with a wild idea to try to get my two-hooded poncho on The Tonight Show.

It was in the early years of Johnny Carson’s reign, and, as unbelievable as it sounds today, I took a taxi over to NBC’s headquarters, then simply walked in off the street and sat down in the darkened studio theater to watch the rehearsal for that night’s show.

I can still remember Johnny Carson walking onto the stage to practice his lines, and my thinking how amazing it was that no one had tried to stop me from entering the theater — or even bothered to ask why I was there. While watching the rehearsal, I decided I would try to talk to the producer about using my two-headed poncho in some sort of comedy skit, but I knew I’d get escorted out if I went backstage and tried to corral him.

So, instead, I dashed outside, zipped into a phone booth, and put some coins in the slot. In those days, all you had to do was call information, get the number of the company you wanted to contact, then call and talk to a live receptionist and be directed to the party you wanted to speak with.

Just like that, I was immediately put through to an assistant producer. I introduced myself, described my two-headed poncho, explained that I thought a good comedy writer could build a funny skit around it, and asked if I could come in and show it to him. To which he responded, “Sure, when can you be here?” (Try getting that kind of response in today’s world of impenetrable gates and gatekeepers.) I quickly answered, “I can be there in a couple of minutes.”

I then went back inside, walked through the lobby, took the elevator to the associate producer’s floor, and entered his office. (Today, of course, the super-militarized lobby guards would probably mow me down with a hail of machine gun bullets.) I don’t recall the details of the meeting, but the bottom line was that I left a sample of the two-headed poncho with the associate producer and he said he would “see what he could do.”

That night I made it a point to watch The Tonight Show, and, to my delight, Ed McMahon and Skitch Henderson (the show’s bandleader at the time) actually put the poncho on together and clowned around with it. It was classic time-filler shtick. And even though it had zero impact on my sales, I’ve always thought it was amazing that a kid could walk in off the street and get his product shown on national television just by taking the initiative and asking.

I suspect this is the kind of thing Mark McCormack had in mind when he wrote his classic bestseller What They Don’t Teach You at Harvard Business School. The fact is that they don’t teach initiative, risk-taking, or audaciousness at any school. It’s strictly on-the-job training, and it involves a lot of rejection, disappointment, and embarrassment. But it’s worth it, because, thanks to the law of averages, it’s just a matter of time until it yields results.

All this mind travel had me fantasizing about how great it would be if schools at every level were compelled to teach initiative, risk-taking, and audaciousness. But, alas, where would they find teachers who had even the slightest clue as to why these skills are important in real life? Answer: nowhere.

That being the case, it’s wise to be proactive and homeschool your kids in these life-functioning skills, preferably before formal educators mold them into conventional little automatons. No disrespect to William Shakespeare, but I’ve never known of a deal that anyone closed by employing his storehouse of knowledge about English literature.