Healthy Pessimism

Putting your worst foot forward turns out to be a great negotiation tactic, but more importantly, an excellent thinking process to get what you want.

That is how Rufus Griscom raised $3.3 million dollars from investors, and eventually sold his company to Disney for $40 million dollars.

Instead of flaunting his strengths and minimising his weaknesses, he leads meetings with “top five reasons not to invest in my business” and “Here’s Why You Should Not Buy Babble.”

This way of selling doesn’t only make him seem sincere and empathic, but also smart and realistic.

Unbridled optimism can come across as slimy salesmanship, making us seem dishonest and as a consequence, met with skepticism. It is a form of delusion, the inability to look at reality without bias. Too much of it can be catastrophic.

Ironically, by acknowledging and thinking about the most serious problems, Rufus disarms the investors, opens the possibility to plan for business risk, and get people on his side to solve these problems together.

Of course, being optimistic makes us happier. But every once in a while, it’s time put away those rose-tinted glasses and look at reality for what it really is.

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