Got questions for Little Bobby? Send them to dearlittlebobby@pyragraph.com.

Dear Little Bobby,

I really want to quit my day job because it’s taking away from my creative work. Financially, I’m almost there but not quite ready to take the plunge. Any words of encouragement?

—Take this Job and Shove It

Dear Take this job,

You describe a situation that most creative people empathize with. Artists, painters, musicians, writers, filmmakers, dancers and SOOO many others would love to make art instead of working a day job. To make art full time, and for that to be their only job, would be a dream come true for millions of Americans.

I stipulate that by saying “Americans”—because even though I do not know where you are—I will assume that you are in an industrialized country with enough food and clean water, and with a roof over your head. Otherwise you would not be concerned with “maybe quitting my day job” and this is “taking away from my creative work.” You and I are blessed my friend. Even if we do not believe in “blessings” (I am not sure that I do), we can still say we are “fortunate.” Most humans would LOVE to seriously contemplate what you are contemplating. I encourage you to keep this in mind, as much as possible.

To even have the ability, the time and resources to pursue creative endeavors means that certain basic needs are being met. But humans have found time and time again that when those needs are met, other needs present themselves, such as the need to express ourselves creatively. For me personally, my healthiest mental state is dependent upon me expressing myself.

The ONLY way to take the plunge and to make creativity your full-time pursuit is to actually do it: to save up financially, to have your expenses in order, and to have your creative side in its healthiest state as well. I know that if I am worried about paying my mortgage, I do not really feel like writing a good song. If I am stressed about my finances, I might want to just sit around listening to sad music (not such a bad way to spend an afternoon, but it does not pay the bills).

If you quit your day job and get on this path, you might realize the dream that so many people dream. Or you might “fail.” What is failure? I would recommend thinking about that. Not to focus on negative possibilities, but to be upfront and honest with yourself—and by extension, you will be honest with your family, friends and other artists. Is failure just falling behind financially? Is failure making bad art, yet having a stack of money in the bank? Or is failure simply not being fulfilled emotionally? For most of us it is a combination of those things and maybe more.

While you are at it, think about how you might define “success.” Or are you thinking that you’ll know it when you see it? Perhaps, but it seems more likely that if we do not know what we are looking for, then we will not know where to aim. Unless you do not want to aim. Maybe you just want to create, to live and to love. And if you are in a place to do that, then do what is most beneficial to you and to others.

But do not do this with rose-colored glasses on. If you do, you might as well have blinders on.

—Little Bobby Tucker

—“Some people work very hard, but still they never get it right”
The Velvet Underground, “Beginning To See The Light,” 1969

Dear Little Bobby…

I am a relatively young woman, 27, and I’ve been thinking about selling my used panties online. Probably on Craigslist, but I don’t know. I’ve heard about other women doing this. I just want to stay safe, in every aspect. Do you think this is wise? Is it easy money? Or is it asking for trouble?

Underwear, Nuff to Share

Dear Underwear,

You can search any social media outlet and find people who are trying to make money off of something sexual: services, nude photos, sexual videos, panties, new/used sex toys, you name it.

Is it wise for you to do this? As far as morals go, I always felt like I would have been a stripper. When I was 23 or so and went to a strip club for the first time I thought, “I would SO be doing that too if I were her.” I have always felt like I am hyper-sexual, and that could be a good way to deal with it: being sexual and making money at the same time. Win/win. But of course that ignores reality: the potential difficulties and pitfalls of actually being a stripper.

I too have heard tales told of young women selling their used panties online, through Craigslist or other vending sites. The stories I have heard have been successful, but that only means that I have not heard about the ventures that did not work out as hoped.

As far as being safe and avoiding trouble, you should keep in mind that there is potentially lots of it. How would you remain anonymous if you wanted to do so? How would you deliver an item to a buyer? How would you collect payment? Would you use a return address? Or a P.O. Box? Or use the buyer’s address as the return address?

I did read an account of a young woman who delivered the panties in person. She claimed it was safe, always in a very public, populated place with regular buyers. The comments below that story consisted of mostly “Why would you do this in person? Are you crazy? That is so dangerous! Do it through the mail!” etc., and I agree, but this potential danger could be true of any Craigslist transaction. Let us not ignore the present state of this country, where it’s getting dangerous to go to the movies or to be a little old black lady in church or a first grader in class.

Women already have increased risks of being the victims of physical violence, especially sexual violence. If you decide to do this, do not disclose your name, do not disclose your address, or even your location in the country. Maybe use an online vendor that is located on the opposite side of the country. Do not use a payment system like Paypal if your real name is associated with it.

Be careful—it’s the same thing I would tell anyone who wants to be a stripper or a cam girl or anything else like this. Whatever you decide, be safe.

—Little Bobby Tucker

—“I’d give my whole life to see it,
Just you, stood there, only in your underwear”
Pulp, “Underwear,” 1995