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

Dear Little Bobby,

I became an artist because I saw things in the world that I wanted other people to see as well, and because the creative process can be so damned amazing! 

I wanted to share that vision, but in a 25-year career as a creative, I have lost my passion and desire and feel that I am helping nobody. I always thought I was honoring my art education by working in a profession—graphic design—that utilizes many of the the skills I learned in school (“It’s technically visual art!” I told myself), but with all these years of sometimes-oppressive coworkers and client wrangling, I have lost my way. 

My passion for the work is gone, but my desire to help others see the beauty and complications of this world are as strong as ever. I am stuck and don’t know how to get out of this rut. I took a sabbatical from my work and time’s up, but I still don’t know what’s next! Help!

—Barren and Broke

Dear Barren and Broke,

You say that your passion for the work is gone but the desire to help others is still strong. So focus on THAT passion for helping others.

As far as your career in graphic design goes, you may or may not need to find a new career. That depends on your life, finances, wants, family, etc. It’s a separate question from how you’ll get out of that rut. You owe it to yourself (and to others) to, as you put it, help others see the beauty and complications of this world.

It’s true that all good things come to an end and that means eventually those of us who are artists will stop being artists. Maybe we stop when circumstances force us to stop. Sickness, age, death…eventually these things will stop all of us. But until then, we artists will always have a desire to express our art.

Obviously you don’t have to keep going, but if it were me, I would keep looking for ways to get out of that rut. I would seek out new art, new collaborators, new mediums, new methods/technologies. I might even turn to something very old because it’s new to me.

For instance, after many years of playing the piano, I became bored and complacent with it. I was beginning to wonder if I could do anything else with it. So I got out my mother’s steel guitar from the 1960s and decided to suddenly learn how to play THAT. However basic my playing may have been, it was new to me. That newness opened me up to possibilities I had never considered. I was open to a tonal quality that, until then, I didn’t even know I could harness. And then a few years later I did the same thing with the saxophone.

I believe this can also be done with visual arts. Never painted? Pick up a brush. Never sculpted? Go get some clay or maybe a chainsaw and a tree stump. I think if you even TRY to become comfortable in your rut, you will regret it, so keep trying to open yourself up. Keep trying and then keep trying AGAIN until it happens. The only things you have to lose are self-doubt, fear and regret.

—Little Bobby
“Come on you raver, you seer of visions, come on you painter, you piper, you prisoner and shine!”—Pink Floyd, 1975

Dear Little Bobby,

I’m kind of shy. When it comes to meeting girls or asking them out, I get nervous about how to actually do the asking. Is it better for me to give a girl my phone number or for me to ask her for her number?

—Dude Wondering in Austin

Dear Dude,

Dude, I’m wondering: When are ya’ll gonna finally get ’round to legalizing weed there in Texas? I mean, medicinal Cannabis is STILL illegal in Texas. This is due, in large part, to Austin—the state capital, a progressive college town, where all the cool kids live—being sliced up by Republican redistricting laws. A corrupt system which has been used, over the course of many years, to deny the people of Austin legitimate, honest representation in the politics of Texas. It is similar to the situation that exists for the citizens of Washington DC, except in THAT case, people who live in the District of Columbia are COMPLETELY denied certain voting rights, such as the right to be represented in the United States Senate. Also, their only member of the House of Representatives is a delegate who is NOT allowed to vote on the most crucial matters of law. Anyways…onto flirting with girls.

I used to feel more comfortable giving my phone number to a lady, rather than asking for hers. That is, until a best friend of mine (a beautiful young woman) pointed out that some women would prefer to be asked. I said to my friend, “But if I ask a potential first date for her number, I feel like I’m being intrusive. Whereas, if I offer my number to her and say, ‘Give me a call if you would like to hang out,’ I am being more respectful. It’s like I am putting the ball in her court, instead of putting her on the spot.”

My friend said, “You may feel that way, but how often do those girls end up calling you?”

And the answer was: almost never. Most of my positive dating experiences have been the result of me taking the initiative. I asked the person out. I didn’t wait for them to ask me out.

BUT if you are going to be the one who makes the first move, be confident in yourself. You might hear “no” just as often as you hear “yes.”

I heard “no” because the young woman had a boyfriend, or I heard, “No, thank you, I’m a lesbian,” or any number of responses…but I’ve also heard “yes.”

My point is, to avoid putting pressure on a young woman, when you take the initiative that I am suggesting, I would also suggest this: Ask for permission to ask. You could say, “Would it be okay for me to ask you for your phone number? Maybe I could buy you dinner?”

Happy dating.

—Little Bobby Tucker
Former single guy