Whew! Now that my Unemployment Anxiety resting heart rate has dropped below 120, I feel comfortable speaking authoritatively about travel writing again and ditching the blog post I was preparing on how to break down the sandwich prep station at closing time at Jimmy John’s (as if they’d have me).

As my Twitter followers already know, I’ve once again tip-toed off with update duties for the next edition of Lonely Planet Tuscany & Umbria. Needless to say, this is one of those jobs where food, wine, photo opps and bragging rights make research a squillion times more fun than the actual writing. Indeed, Tuscany writing is equal parts smug euphoria and controlled nervous breakdown. Being that 50,000 writers have already written 584,937 articles about Tuscany, the pressure and challenge to not regurgitate 134,485,832 clichés is powerful. Also, the knowledge that Tuscany guidebooks outsell the Bible (rather, they would outsell the Bible if I were God) is a little unnerving while you’re trying come up with 15 synonyms for ‘tasty’ every day.

So it is with a happy heart, a monstrous thesaurus and several nerve-soothing bottles of wine that I begin my pre-pre-research trip preparation. (Oh my god, what will I wear?)

In Freelancerland, guidebook gigs are no small commitment. They tend to be rather lengthy and all-consuming meaning usually you’re pledging to do that job, and only that job, until the job is done. So every time I’m considering a guidebook job, even one as coveted and lucrative as Tuscany, I go through a veritable tornado of indecision and doubt. Do I really want to invest three months in this thing? What if something better comes up? Am I too pretty for guidebook work? Did the statute of limitations expire from that thing that happen the last time I was there?

Unlike the easy afternoon that it takes to prepare for a 1,000 word magazine article, getting your head ready for an encyclopedic, 50,000 word guidebook job can take anywhere from three frantic days in the corner of a hostel in Florence (not recommended) to a slightly more serene two weeks in the privacy of your own home, a setting delightfully devoid of cleaning ladies cussing you out and splashing mop water on your maps. Text from the previous edition needs to be reviewed; requirements/requests/suggestions from the editor need to be absorbed; in the case of Lonely Planet, a giant sleeve of maps needs to be organized and marked up; and, depending on the destination, dead language skills need to be revived.

Further to the latter item, I like to walk around telling people (women) that I speak (butcher) Italian. I can get away with this because less than two years ago I lived there for eight months, coping with day-to-day tasks and eventually researching the current edition of Tuscany & Umbria, relying heavily on my rudimentary, but adequate Italian language skills. However, that was two years ago. And Italian is my newest and weakest language. Having not uttered a complete sentence in Italian for so long has resulted in what feels like a complete memory wipe. Furthermore, in the meantime I’ve been called upon to speak copious amounts of Spanish and Romanian, pushing Italian even further into the shadows of the thickly canopied surface of my cerebral cortex. As I’ve already discussed at great length, trying to keep track of three foreign languages that are so closely, confusingly, maddeningly similar is not one of my strong suits. I can still read Italian and even listen to it with difficulty, but I couldn’t cobble together a grammatically correct sentence right now even if you dangled a $500 bottle of Brunello di Montalcino in front of me.

In addition to all the above excitement, I’m also getting my affairs in order at home to be gone for so long. Things like stopping the mail, emptying the fridge, stocking my bags with the right clothes/meds/tech/books, setting up ‘Emailio’ (my email auto-responder and Bolivian astrological advisor) with a snarky message all have to be attended to with precision timing and obsessive-compulsive detail.

Also, since this is Italy, there’s the genuinely serious matter of clothes. I struggled with this last time, trying to strike a balance between comfort, utility and not looking like the village hobo. Since I’ll be hitting the ground in March, the issue of shorts versus pants shouldn’t be a problem this time around, but I have more nuanced issues to deal with, namely shoes. I walk anywhere from three to nine hours a day while I’m researching a guidebook. The idea of choosing style over comfort is ludicrous – unless you’re in Italy. The fact that I have been forbidden to shop for my own clothes since 1997, only exacerbates the situation. Any suggestions for non-punishing Italy guidebook author attire will be greatly welcome.

Finally, I’m seriously considering putting a call out for travel companions for this trip, who can act as expense-sharers, navigators, and personal protection. I spent much of my last Tuscany guidebook research trip lost and coping with batshit crazy people and I think these predicaments would be greatly eased by having a second and/or third body around. More on that when I actually have travel dates set. Though if you’ve got the money and time off in March/April, you should start updating your resume now. Not quite the best job in the world, but you could do worse.