The latest in a series exploring all the potential realities and futures of my favorite recurring stock photo image.

The Cure For: I Don’t Know What To Write About

Here it’s not that he doesn’t know what to write about. It’s more that he finally has half a day to indulge his own writing, free from other commitments, and opened up the Evernote document he maintains titled “Story Ideas For Later.” He’s now overwhelmed with the options in front of him, unsure of which one is most engaging or has the most potential and is freaking out he’s going to waste an opportunity.

Is Writing Your Passion? Really?

Here he’s lamenting the tendency of editors and writers to use question marks in their headlines just to make some sort of point.

Have You Ever Regretted Becoming A Freelancer?

Here he’s regretting having become a freelancer. OK maybe not that but he’s certainly becoming frustrated at the current state of freelance writing job boards, which are littered with poor quality leads looking for the lowest possible amount they can pay for work that used to be handled by an in-house. He’s remembering that all the experience he’s accumulated over the years matters not at all when the only thing people are looking for is a ridiculously low per-word rate.

For those that are struggling to write….this may help.

The key is staring at your screen dramatically. Not even kidding.

What To Do When A Simple Writing Project Becomes Complicated

Here he’s remembering there’s no such thing as a simple writing assignment. Every one is unique, takes talent to execute and is bound to involve at least some amount of confusion and frustration.

How To Answer The ‘Are You Writing About Me’ Question

The key is to mumble “no” under your breath while avoiding eye contact and wondering which one of your colleagues would be willing to publish the piece under their name so you don’t look like a liar in two weeks.