WHY IS THIS THING we call Creativity, so often characterized by lack of stricture, also in part defined by structure?

My own winding career path, as a sculptor, a graphic designer, and now an independent creative director and writer has caused me to consider that question a lot.

Perhaps that varied career is one reason why I’ve been invited by the Dallas Society of Visual Communications to moderate a panel discussion tomorrow morning entitled, “Becoming A Successful Freelancer.”Part of the DSVC series Working Lunches, the presentation will feature four creative-industry freelancers: Ken Koester, Hal Riley, Ramsey Ruelas, and Karen Scamardo.A room full of creatives means anything can happen, but just in case, I’ll walk in with five cards up my sleeve, each bearing a question that on the surface seems pretty tame. But take it from me, put to hard-to-nail-down right brainers each can touch a nerve.

My five questions go something like this:

1. What’s your plan, Stan?

Our title, “Becoming A Successful Freelancer,” suggests a process, something more like a formula to be followed than an exciting, dramatic chemical reaction or a quick flash with sudden results. This first question I hope to direct at attendees, suggesting they envision their own personal point of reference to which all they hear over the next two hours can be applied.

2. Is “freelance” a word that really works anymore?

Shifting to our panel, I want to hear how the changing face of advertising and marketing has impacted their practices. If, in the new media, advertising agencies are having to retool machines originally designed to crank out disruptive messaging, has this meant more work or less? And has there been a shift to more often working directly with clients?

3. How do you feel about selling yourself on an open market?

When you became a freelancer, frog-kissing became part of your job description. And while word-of-mouth referrals have perhaps reduced some of the seemingly unseemly business of putting yourself out there, how did you get projects in the early days of being independent?

4. Good with numbers?

Estimates, contracts, time sheets and invoices. What are the tools or processes you’ve found essential to locking down a project, keeping both you and your client accountable, and then getting paid for it?

5. Will this ever end?

Is there an exit strategy? Do you want to retire, or do you, like me, plan to continue working into your golden years Stephen J. Hawking-style, in a wheelchair with a keyboard strapped to your face?