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Working with people is compelling, fascinating, and difficult, and it has been spicing up my life for some time. It is my type of work as I love communication and people’s reactions and approaches to various matters. 
Since I turned 40, everything seemed smoother, as the scriptwriter of Mad Men was right: “Until the age of 40, you will have met all the types of people they are.” 

After almost 20 years of entrepreneurship, I have realized that Pareto was right. 80% of my earnings come from a small minority of 20% of my customers, who are decent early-paying clients.

For the remaining 80% of clients, the sky’s the limit. I was surprised by some outrageous requests at the beginning of my entrepreneurial career—so outrageous that I wrote an essay about them.
For example, if a customer asks for a tornado of sharks for a copywriting job, I ask, “White sharks?” and move on.

Lesson learned: Do business in Equilibrium.

Once a representative of a medical company called, and between the “lines,” I picked up on their willingness for 17 people to benefit from our English course but to pay for only 10 people because some of the attendants might get bored in the end, as happens at all English courses, he says, “knowingly.”.
I never take this type of approach kindly, as a lack of respect for my time and efforts translates into a lack of respect for me and my hard-crafted projects, mission, and vision. Learning a language is not for everyone, as it involves commitment and hard work, and new eyes are opened for you to see more and more with each passing class. Language is information.

Lesson learned: Set up specific protocols and keep detailed records.

Another bizarre request was to develop product descriptions for Amazon listings using unspecified American lingo on short notice before discussing the terms of the contract and payment methods. They were pooling descriptions in order to choose the finest ones and avoid paying the authors. They claimed to be in desperate need due to the approaching deadline. I almost fell for it.

Lesson learned: Consider requesting an emergency fee.

To summarize, I have very explicit terms and conditions that I discuss with customers beforehand, and I make sure to ask all relevant questions at the outset in order to determine what type of customer I am dealing with.
Not to mention that “no” is a very good answer sometimes…

Picture by the author, taken in Milan.