The Inevitability of Failure

Jim Vassello
The Farce of the Sale
4 min readJun 24, 2018

I sat at my desk, staring at the computer screen showing the latest scenario I came up with for a customer.

“Does this even make sense?” I thought to myself. “What if it doesn’t work and I wasted all of this time on something that never had a chance?”

I was given a scenario by my manager to help this person trying to refinance their home. There were questions about some of the renovations that could be made to her house within the financing. I had done my homework, studying the ins and outs of renovation loans and doing my best to structure the deal in the best way possible. Renovation loans are not easy to do, so most loan officers avoid them at all costs, handing them off to other bankers.

The numbers worked out. The changes were within the guidelines. I did my research and applied it accordingly.

I walked into another loan officer’s office.

“I don’t think I can handle a deal like this. Why don’t you do it so I don’t screw it up?”

Not wanting to turn away the deal himself, my colleague obliged and did the loan.

A month and a half later, when the deal closed, I asked the other loan officer how he did it, and he showed me the exact steps that I had taken but forgot a few key points. The underwriter eventually noticed those points and got the deal done.

Not only did I give away my own commission check, but I gave it to someone who knew less about the product than I did. I just didn’t trust myself. I was poking holes in the process before ever putting it into practice.

Even as I was writing my book, I consistently hesitated to put content down for others to read, poking holes in my own work while they were still just ideas in my head.

Humans are risk averse by nature and opening yourself up to be vulnerable isn’t exactly a conservative action. However, in the long-run, this resistance is detrimental to progress.

Hesitating and doing nothing is a great way to not accomplish anything when doing improv. Having the courage to will yourself in front of the group or on stage and perform is something that can be learned, but we have to practice regularly for it to become habit.

In sales, it’s the same. Hesitating and doing nothing is a great way to ensure you don’t close the deal. There’s no pamphlet or guide for each individual prospect that tells you how to close the deal for them. You have to be okay with the possibility of it not going well, then move on and learn from it without dwelling on the negative.

My hero, Matt.

The beauty of putting yourself out there is learning who is around to lift you up when the deal goes south or when you completely bomb on stage.

My first time trying longform improv was during a show. The suggestion was “broomsticks.” I didn’t really understand the rules to this game. As a matter of a fact, I did not understand the rules to it at all. I had no idea what we were doing, not even a little bit. And when you watch longform, there’s no structure to it for the audience either. It’s not like the short form games, where we explain the rules beforehand.

I had no idea what was happening. The very first scene was just somebody using a broomstick to sweep up their little coffee shop. When that scene ended, I felt like I needed to do something, so I got on a big broomstick and acted like Harry Potter, which really just left me nowhere to go with that.

Bombing on stage is akin to jumping into the deep end of the local swimming pool without knowing how to swim. You think you’re going to drown in front of the entire town and fear the embarrassment more than the actual drowning.

Luckily, my friend Matt is a brilliant improviser.

He walked at the front of the stage, put up his middle finger, and says in his British accent, “Fuck you, Reginald,” without breaking stride to the other side of the stage. End scene.

Harry Potter became a central theme to the show and, “Fuck you, Reginald,” evolved into a recurring moment the audience ate up.

Get your ideas out there and stop worrying about them not working out. Good or bad, you learn from the experience and learn who you can rely on for support. Your initial failure has the potential to be the team’s success.

Get The Farce of the Sale today on Amazon.com, a guide to improving your sales mindset through improv techniques and tactics, including our YES AND methodology. Jim is available for improv sales consulting, or just a guy who doesn’t mind a good laugh, a good beer and an improv game that combines the two.

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Jim Vassello
The Farce of the Sale

Improv enthusiast, neuroscience hobbyist, digital marketer, and proud father of a labrador/shepard/tasmanian devil puppy.