Whether it’s landing a date, a raise or a sale, there is a lot of wisdom to the axiom, If you don’t ask, you don’t get. Usually, the worst that can happen is being told no. But that tiny word can have a huge impact, especially on those with a low tolerance for rejection. So much so that it can seem almost counterintuitive to pop a burning question (like asking for directions – who’s with me?!). However, no matter the slings and arrows one’s fragile ego may be forced to endure, the alternative of traveling down the path of least resistance is an unfulfilling, hollow existence. Conversely, how awesome and invigorating is it when you get that yes? YES! Oh baby, how we love that almost equally tiny word.

Here’s a little secret: The more times you engage in asking, the easier it gets and the more yes answers will result. It’s a numbers game where the odds improve as you go because, consciously or not, you progress in the often very subtle art of persuasion. Some psychology and being dialed in to human nature, as well as key factors like motive, determination, confidence, timing and tact (think assertive rather than aggressive) increase the likelihood of success. It’s a character-building process that imbibes a person with one of life’s most essential traits – resiliency. And while asking, particularly the hard questions, may not boost your popularity, it very likely will garner more respect.

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Many people find as time goes on, and they continue to ask, ask, ask away, that most of the nos lose their sting. At that point, asking becomes almost purely a reward system (giving is even more important, but that’s not this conversation). You become a Zen master of sorts – an asking assassin if you will. Like most, I am a ways from reaching that level of asking enlightenment, and although I may never reach that plateau I can assure you that it is within the reach of us mere mortals. The most important thing is its pursuit; break out of your comfort zone, defy the inertia and ask that woman/ man, supervisor or prospect for whatever it is you want or deserve.

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It does not have to be something big; in fact, sometimes the small things can be just as gratifying. If you’re having difficulty setting your course for Asking Avenue, then gain some momentum by targeting little victories. I submit three recent experiences where I went against the grain to ask for what was right and just, the results of which inspired this topic and I hope your own courage to step up.

The first is based on a family trip to the beaches of Florida’s Sanibel Island. There I encountered a confusing self-service parking machine that I fed a $10 bill to cover $4 of parking, only to realize it was incapable of returning change. I then canceled to get the $10 back, which resulted in zero parking time and a receipt spit out with giant bold print: NO REFUND. As a backed-up line of increasingly impatient tourists queued up behind me, I agitatedly jammed another $4 into the machine to cover our day. Far more than the money, I was outraged by the injustice.

Back home a week later, I initiated my quest for righteousness with the City of Sanibel, asking for my $10 despite overt and abundant disclaimers to the contrary. It quickly became clear that few people if any had taken on the system, as city employees seemed incredulous and unsure what to do with me. But I refused to accept no for an answer, following up my calls with a letter and always being resolute yet courteous. Guess what? You can fight city hall and win. Never did $10 make me feel so rich.

Another situation stems from a car I rented from Enterprise for a business trip. Upon returning the vehicle, a crack emanating from a minute chip high up on the passenger side of the windshield was pointed out. Thus, a report was filed to cover the damage through my auto insurance. I thought, how could they be sure – let alone prove – the source of the crack did not originate before I took possession of the car? So when Enterprise’s adjuster called to settle the case, I asked it be dropped on that basis. Within days the claim disappeared … which further proves asking is everything it’s cracked up to be.

The final example is the new associate publisher title that appears in my column this month. Was the promotion hard-earned and well deserved? You bet, but asking is still what initiated it. I urge you to enrich yourself and your career by going after that which you have every right to covet.

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