This past winter break I flew back from a relaxing vacation on the West Coast and made a routine connection in the fine city of Cleveland, Ohio. Unfortunately, the situation quickly degraded into the typical travel clusterfuck with the onset of a major snow storm, soon to be exacerbated by the ensuing Arctic chill.
Airport monitors gradually moved from “on time” to “delayed” to “cancelled.” Hundreds of frustrated passengers formed spontaneous lines just waiting to argue with the helpless gate agents (“there’s not that much ice on the runway, come on, I need to get to ATL”). Children screamed and cried; people abandoned the last shreds of human decency, You know, the average airport nightmare. Despite all this, however, I managed to come away having learned the value of asking.
It is amazing how much the world opens up when you make your desires or intentions known to others. In Cleveland, my experience was made much easier by actively seeking out those in positions of authority or knowledge. Instead of blindly stumbling around the mountains of suitcases piled up in the terminal or waiting in a useless line, I asked a baggage handler to search the black hole that was the backroom luggage storage. Thirty seconds later, he emerged with my blue duffle. Later that night at around 3 a.m., after having looked at all sorts of ridiculous transportation alternatives (think a $600, 14-hour train ride leaving at 2:15 a.m.), I finally called and asked a rental car service if they would provide a vehicle to someone under the minimum age of 25. To my surprise, the company said yes and several hours later I embarked on an impromptu solo road trip home (the car had an iPod connector so, rest assured, Waka and 2 Chainz got plenty of playtime).
The point of this story, of which I am overly proud, is that proactivity in asking things of others can be a serious time saver and generally make life more manageable. If there is something you are unsure of or that you believe another can do to help you, do not hesitate to politely ask. There is no sense in wasting an inordinate amount of time being miserable because you were too timid to make your concerns publicly known.
This is not, however, a license to act ignorant, entitled or generally spoiled. If there is a problem you can resolve yourself without too much trouble, do it. Similarly, if the request would impose a major burden on another, it is probably best to refrain from asking. Personal judgment is crucial in the gray area. Always be realistic, as much as it might be beneficial. You would not expect a professor to provide detailed feedback on all three of your rough drafts, much like you would not expect the Chili’s waitress to individually calculate the checks between 12 of your friends because one guy had two Sunrise margaritas.
So what are some situations in which asking is acceptable and worthwhile? Usually anytime you are a paying customer there is a degree of obligation on the staff’s part to heed your request. Examples might include restaurants (always push for the best table possible—away from the kitchen and bathroom), higher-end transportation (airlines, boats, chartered cars, etc.), hotels (concierges can be an incredible asset) and certain retail instances where bargaining is commonplace. Also, as touched on before, when you are unsure of something or need clarification and the solution does not require a substantial commitment, go ahead and ask.
Remember, however, that the response you receive is a product of how, who, and what you ask, as well as the context. In regards to the last point: you get what you pay for. Transcontinental first class on Emirates is probably more inclined to refill your ginger ale than a Fly4less duct-tape-holding-engine-number-3-onto-the-wing shuttle from Flagstaff to Reno.
Do not be tentative in interacting with and asking of others. You most often will find that those who are in a position to assist you will be happy to help you, now that they know that you want something and what it is.
Give it a try: ask for that free upgrade—you might just get lucky.