Irrational Optimism: The Truth About How to Succeed in Sales

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Ken Kupchik
Ken Kupchik


The following is an excerpt from The Sales Survival Handbook, the funniest sales book of all time. You can order the book here.

Unless you've actually spent time in a sales role, you have no idea how challenging it is.

You're constantly being rejected by customers, pressured by management, antagonized by your coworkers, undercut by your competitors, all while trying to get through a proverbial minefield to close a deal. You would think that no one in her right mind would want to put herself through it.

But it's important to remember the upside. In sales, you can make more money than in almost any other job. There are people making millions of dollars a year selling things, and the best part is there's no ceiling on your income. You are in control of how well or poorly you perform. It's like playing sports, except you're allowed to be fat. 

But there's only one way to get past all of the pressures, the distractions, and the negativity, and that's to adopt an irrationally optimistic attitude. This goes beyond just smiling more or brushing off setbacks. You truly need to believe, beyond all doubt, that you will be successful. You basically have to become borderline delusional. Only when you've adopted an irrationally optimistic mindset will you be the best.


You might be wondering what irrational optimism is. Merriam Webster sums it up as "Hopefulness and confidence about the future or the successful outcome of something," and I'd add, "hoping despite a mountain of evidence to the contrary, and multiple, seemingly insurmountable roadblocks standing in the way."

Things Irrationally Optimistic People Say

You can usually identify irrationally optimistic people at work by how well they're performing. Those at the top have convinced themselves that they have what it takes to get there, despite all obstacles. Here are some things you're likely to hear an irrationally optimistic person say:

  • "I don't care if I have to show up at their doorstep in the middle of the night covered in raccoon blood, I'm closing this deal!"
  • "So what if the customer said 'no' the first time? There will be lots of opportunities for them to say 'yes' after I call every single day for a month straight."
  • "I don't mind working the entire weekend. Not only do I get the opportunity to make more money, but my family doesn't like me anyway!"
  • "Sleep! Who needs to sleep? This is sales, not a mattress research center."
  • "I'd rather be rich and tired than broke and well rested, and if I don't hit my goal, I'll be broke and tired."
  • "You miss 100% of the shots you don't take, and close 1% of the leads you call."

How to Become Irrationally Optimistic

Contrary to popular belief, you don't need to be born an irrational optimist. Like any other skill, you can develop it through practice. Here are some tips to get you started. 

  • Instead of focusing on obstacles, focus on the opportunities. For example, don't think about the fact that your clients don't have enough in their budget to afford your product. Instead, help them think of local banks they can rob to get the money.
  • Never dwell too long on your failures. Failure is only temporary, unless you don't hit your sales goal, get fired, and then experience a series of financial setbacks that you're unable to ever fully recover from, in which case it's permanent.
  • Optimism grows out of gratitude, so be appreciative of what you already have. Also be appreciative of the things you don't have, like that multimillion-dollar waterfront mansion where the jerk who owns your company lives, which you'll never be able to afford, ever.
  • Always learn from your mistakes and use those lessons to become better in the future. If you lose a deal to a competitor, ask the customer where you fell short and accuse her of being a complete moron who just made the biggest mistake of her life. 
  • Focus on the big picture instead of getting bogged down by things that don't really matter. Think about where you want to be a year from now, and then remember that you will probably still be here, at this same job, doing literally the exact same thing you're doing now.
  • Let go of things that drain your energy. Keep toxic people out of your life as much as possible. This means you'll probably have to avoid your sales manager, but do the best you can.
  • Laugh more. Studies have shown that laughing releases endorphins, which make you feel better and lead to a more optimistic attitude. If you want a really good laugh, just take a look at how much of your paycheck you get to keep after taxes.
  • Invest in yourself. Do things that will help you with your spiritual fulfillment. Read a book. Pick up a new hobby. Print out a picture of your biggest competitor at work and set it on fire in your sink.

Remember, the only thing standing in the way of success is your own mind -- and the quality of your marketing department's leads, the state of the economy, your company's products and pricing, and a host of seemingly other random factors over which you have absolutely no control.

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Topics: Sales Humor

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