Choosing a Location
Choose an area with lots of foot traffic. If you're going to maximize your earning-potential, you'll need to go to a place in which you'll encounter a lot of different approachable people. It helps if you're both on foot at the same time. For this reason, by far the most popular locations are subway stations, metro stops, truck stops, urban campuses, or the areas around other commuter zones. Placing yourself directly outside of the entrance to a subway station is a high-yield opportunity. Different people will pass through every couple of minutes, so the turnover is high. Centralized downtown locations are a safer bet than malls or shopping centers, because commercial zones are typically worked by security staff who are typically unwelcoming of your endeavor.
Choose an area with lots of auto traffic. If you've got a sign or the materials to make one, posting up in a traffic median near an interstate on-ramp or a busy downtown street corner ensures that you'll be seen by lots of people in lots of cars without having to move or even speak. This requires the least amount of effort on your part, but it's also easier for people to ignore someone while in a car. This works best during spring or summer months when people drive with their windows down.
Avoid wealthy neighborhoods and expensive restaurant districts. While it may seem intuitive to go to where people have lots of money to give away, the wealthiest segments of the population are statistically the least likely to give to panhandlers. People in these areas are also more likely to call police, even if you're being courteous. Stick to downtown commercial districts and middle-class areas.
Keep moving. Posting up outside the same neighborhood coffee shop every day will likely get you into some heat with the staff and you'll quickly wear out your welcome with the patrons, making the likelihood of an uncomfortable confrontation too great. Besides, at that point, you'll have stopped making any money. Aim to hit up the same place no more than once a month. If you're not tied to a location, you might develop a circuit or a route based on the weather. If you're in New York in the summer, say, make your way to Boston for the early fall, Baltimore for the late fall, and get down to Florida for the winter and sleep on the beach. Keep track of the places you visit, the places you sleep, and friendly areas to work.
Choose a city friendly to panhandlers. Increasingly, when neighborhoods once commonly friendly to panhandlers become gentrified, the laws and population will change significantly, making it difficult to stay ahead of the game. Medium-to-large cities are typically friendlier to panhandlers than smaller towns. College towns, however, can be a good bet. They're full of young idealistic students who are often flush with disposable cash and susceptible to a good story. Pick a place with good weather. If you're going to be outside all day, rain or shine, pick a place where it'll be shining at least.
Asking for Money
Be polite. If there's one thing that's guaranteed to fail and get you in lots of trouble, it's demanding money from strangers in a rude or confrontational way. Smile, be courteous, and thank people whether or not they choose to give you anything. Thanking people will lay the groundwork for developing a reputation in your area. If you develop a good working relationship with the people in the areas you solicit, they'll be more likely to give you money the next time. It's not worth telling someone off in the long run, even though you might be feeling frustrated.
Be believable. Whatever your tactic in asking--if you choose to tell people the whole truth, or if you spin a yarn to get some change--you need to sound like you're being honest. If you're asking for money to get a bus ticket because you really need a bus ticket, it won't matter if the person you're asking thinks you're going to buy booze. Tailor your story to your location. If you're going to ask for a bus ticket, it helps if you're right around the corner from a bus station and have a bag. Name a specific location you need to get to, somewhere faraway and strange, like "Ohio." Make sure your appearance matches your story as best as it can. If you're playing the lost traveler, it won't help your story if it looks like you've been sleeping outside for the past couple months, even if you have been.
Be specific. Some panhandlers believe the key to success is in asking for a very particular amount of money for a very particular reason. "I need 40 cents to get a bus ticket, can you help me out?" tends to be a more effective approach than "I need to get a bus ticket." If you ask for a very specific amount of money, it increases the believability of your question. If you ask for a dollar you may get some spare change, but if you ask for 40 cents, you may get a dollar.
Be clear and concise. To avoid intimidating people or making them frustrated and unlikely to give you anything, just come out and ask for what you're looking for: "Excuse me sir, I'm sorry to bother you, but I need some change to get something to eat." Ask for one thing and give one reason: "I need ____ for _____." Using a sign can be the easiest way to panhandle. All you need is a piece of cardboard from a recycling or garbage dumpster and something to write with. Make the lettering bold and clear so it can be read quickly. Alternatively, depending on your verbal skills and your experience, being as evasive as possible can be a good way to confuse someone and make them want to get rid of you. This works especially well on "out-of-towners" or college students: "Excuse me sir, how you doing tonight? I'm sorry to bother you, but my cell phone is dead and my girlfriend's stuck up on 34th St. with our kid in the car and they got in a little accident right after they ran out of gas (you don't have a cigarette do you?) and my mom would usually pick them up but she's in the hospital with chronic fatigue syndrome and my battleship's taking off tomorrow and I'm already in the doghouse about that (you know what I mean) so I was just wondering if you had change for a twenty or just had a couple dollars or something so I can get something to eat? You got three tens?"
Be sympathetic. Some people are more willing to donate if they recognize that you're in a dire situation and are truly in need of help. Whether this is a lie or the truth, try appealing to their sense of empathy and morality. If they think it's their obligation to help you, they'll be more likely to do it. Saying that you're a veteran or that you were injured in a construction accident and stuck with huge hospital bills are likely to appeal to a person's sense of injustice and make them willing to help you. If you find a broken wheelchair in the trash, use it. Be very careful about elaborate lies intended to appeal to sympathy. If you claim to be a veteran and you're not, running into real soldiers with a fake story could be problematic.
Be funny. Often, appealing to someone's sense of humor rather than their sense of empathy is a more effective tactic. A sign that says, "I know where Bin Laden is. Need $ for a flamethrower and a ticket" or "Why lie? I want a beer" might make someone chuckle and donate who would normally be unsympathetic or unwilling. In a college town, humor can be particularly effective. Stay abreast of current events and local culture to get a sense of what might go over well. Singing "I'll stop singing for a dollar" to the tune of a Lady Gaga song might help rake it in or it might get you arrested.
Remember the regulars. In the old film "Treasure of the Sierra Madre," Humphrey Bogart plays a down-on-his-luck American in Mexico who accidentally asks the same American for money three times in the same day. "I never looked at your face," Bogart says when the American becomes annoyed. Don't make the same mistake. If you see the same people on their way to work every day, learn their names and greet them. If they know you're there asking for money, you won't have to ask and you know they'll give it if they feel like it. They'll also be more likely to give if you're a friendly face on their commute each day and not an inconvenience.
Remember: It's a numbers game. Don't become irritated or rude to people if they choose not to give you anything. Thank them and let them move on. Someone else will be passed in another couple seconds if you're in a good location anyway. Moving quickly through your routine is a much more effective method than dwelling on lost opportunities. Be consistent and you'll make some money.
Staying Safe
Learn the laws in the area you're planning to panhandle. Some, once popular with panhandlers, have outlawed begging in certain areas. Portland, OR, for example, no longer permits panhandling in traffic medians. Some cities have likewise restricted panhandling to particular areas or at particular times, outlawing panhandling during public events like parades, street fairs, etc. You need to learn the rules governing panhandling, so you're not arrested or ticketed.
Be a good neighbor. Your relations with nearby businesses and other panhandlers can make or break your efforts. Be courteous and cooperative to business owners and their customers. Show your appreciation for their tolerance by patronizing their shop if you can, and if you’re asked to leave or asked to stand a little further away, do so without argument. Always be friendly to other beggars, as well, and avoid territorial disputes. At the very least you’ll avoid dangerous and unsightly squabbles and you may even get some good money-making tips and make some friends. Watch for "No soliciting" or "No loitering" signs. Be cautious to avoid areas even informally labeled with these tags. You don't want to draw the ire of anyone who'll call the cops, confront you, or make for an uncomfortable scene. Keep moving and be courteous. If someone tells you to move, just move. Especially if you're alone and vulnerable, avoid possibly-dangerous confrontations at all costs. Staying on the move is a good idea in general, so if someone becomes annoyed by your presence, it's time to go elsewhere.
Stash your money frequently. Panhandlers are frequently the target of robbers. If you've been working all day, you might end up with a fair amount of spare change and cash on hand. It's not a great idea to carry it around with you all the time and attract the attention of unsavory characters. Find a spot to stash your cash, or at least a hidden lock-box or instrument case in which you might keep your money. At the very least, keep your money in different places on your person. Some in your shoes, some in your pockets, etc.
Exhaust other options before relying upon panhandling to make a living. Local churches, non-profit organizations, soup kitchens, shelters, and related services that are designed to help you get back on your feet. Panhandling is at best an inconsistent source of income and at worst a difficult and dangerous profession. Make sure you investigate all the options available in your area.
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