Foxes, rogues, thieves, and rapscallions; main chancers, devious miscreants and craven opportunists: That’s what we were when Adam Smith wrote The Wealth of Nations back when the Industrial Revolution was still an unidentified force of human nature, still fluid.

In fact, the word “entrepreneur” was not Smith’s coinage; it was his acolyte’s, one Jean-Baptiste Say, a 19th century French economist who defined the term, according to investopedia.com’s rather liberal paraphrasing, as “an individual who, rather than working as an employee, runs a small business and assumes all the risk and reward of a given business venture, idea, or good or service offered for sale. The entrepreneur is commonly seen as a business leader and innovator of new ideas and business processes.”

Frankly, I prefer the former, rather more unsavory iteration. Who wants to hang out with the stable and sane among us, when the madmen and women among us are more than willing to bend our ears and soothe our souls with tales from the front lines of self-employment? Who, but the certifiable, would comfort us about our safe decisions and tedious routines?

Who, indeed?

“I’m not sure about your partner over there, but I’m getting the impression that the only reason you want to incorporate a company that has no asset value, whatsoever, is that you think, somehow, your big mouth is going to make you rich,” the lawyer said rather testily on a chilly March afternoon in downtown Halifax precisely 23 years ago.

“Of course, dear sir, of course,” I replied jauntily. “Let us make it so. I shall get rich, my partner shall get rich, you shall get rich in the process. Then, we shall all repair to the Bahamas to get well and truly stewed thanks to our fabulous wealth.”

The thing is, I actually believed the words that were coming out of my mouth on that fateful day. And as I trudged down Hollis street, figurative diamonds embedded into the soles of my size-nine brogues where folds of newspapers kept the street salt from ruining what was left of my feet, I was happy. Deliriously, crazily happy.

I was in business. Four years later, I was out of it.

“Look, I’m really sorry, but I have to give you this,” the process server, who was also a lawyer, and also a neighbour who lived across the street, said to me on a certain December 24 afternoon. He was a Buddhist and he was having trouble handing me the document that effectively terminated my ownership of my house, my car and every other chattel my creditors deemed worthy of redeeming. “Um,” he finished, “try to have a good time this season, a family time … Oh, by the way, you need to vacate the premises by February 14.”

I mused out loud, “you mean Valentine’s Day?”

“I guess so,” he said. “I don’t recognize pagan holidays.”

I closed the door and laughed harder than I ever had before and have since. Fundamentally, though, I recognized my own culpability in my fate. Arrogance, stupidity, laziness and negligence had brought me to this low place. I had trusted too many who were untrustworthy and mistrusted too many whose advice I should have cherished. I had been an “entrepreneur” in name only. Rapidly – in the way that having no money galvanizes the senses – I began to realize what self-employment actually entails.

Since then, my personal rules of engagement in the entrepreneurial life stipulate certain fundamentals, and I’ve done pretty well by them.

Be mindful of your friends and family, for they are your greatest assets. When they tell you you are venturing down a dark path, heed them. In most cases, they know you better than you know yourself.

Take the long view. The short one only leads to momentary gains, at best, and long-term misery, at worst. Ask yourself: How many minutes are left in your life; how many are you prepared to devote to worthless, unsatisfying tasks; how many are you prepared to invest in your children, grandchildren, great-grandchildren?

Finally, never stop being a rapscallion in business, never stop pushing to achieve the main chance.

Never kid yourself, though: Attitude is a poor substitute for intelligence.

Sure, be crazy, but like a fox.