Brigolante holiday rentals in Assisi, Umbria

Self-catering apartments in Assisi's town center and nearby countryside.

Winning the Lottery: My New Job(s)

I have something to tell you. Yes, you.

Either you’ve been reading my ramblings here and there online for the last decade, or you’ve stuck with me on this blog for the past year and a half, or you just happened to stumble upon this post today. Regardless, you’ve taken a minute out of your busy day to stop by, so you are the first person with whom I want to share my Big News.

I have a friend who plays the lottery with religious fervor and scientific methodology. He’s been playing for years, and every once in awhile he’ll actually manage to cash in (though, truth be told, I suspect he doesn’t even come close to recouping his losses from the past decades). He is perennially (and quite amusingly) ticked off when he reads about the blessed souls whom fortune has kissed each week. “Look at this!” he’ll snap the newspaper in front of my eyes, “Can you believe this joker won!?! Says here it’s the first time he even played the damned thing. Says here he let his little boy choose the numbers. Says here he forgot he even had the ticket in his wallet until he was searching around for some coupon.” And he’ll storm off, muttering to himself about probability and systems and beginner’s luck.

The thing is, he’s not upset that someone else has won…he’s upset that someone else undeserving has won. Someone who just plays for fun, with no foresight or mathematics or gravitas. A dabbler.

Getting a paid gig blogging, especially travel blogging, has roughly the same odds as winning the lottery. It just doesn’t happen that often, and when it does it’s because there is a writer out there who has played the game with religious fervor and scientific methodology. These writers are certainly talented, but–more importantly—they are also born networkers, motivated, and tirelessly dedicated to working the system by massaging their Google rankings and updating their WordPress plugins and attending seminars on the latest in SEO. Accordingly, they get their testimonials.

And then there are bloggers like me. Writers who write for the sheer frivolous joy of putting words down on a page. I couldn’t find my Google ranking if it bit me on the butt, don’t bother with plugins unless my webmaster makes an executive decision and puts them in (which often leads to a panicked phone call to long-suffering Marcel, who explains that everything is fine and I just need to keep on doing what I’ve been doing), and am so indifferent to SEO that I don’t even put tags on my posts. I am a dabbler who, if the universe were a completely fair place, would never win the lottery. But guess what.

Yep, that’s right. You are now reading the words typed by a paid travel writer and blogger (I may bill you…I haven’t decided yet.). Not only did I win the lottery, I won it twice over by picking up two incredibly fun and challenging new gigs in a way so effortless and seemingly happenstance that it still feels very surreal—and a little tenuous. This is how it happened:

This past spring a number of Italy travel apps for the iPhone were published through Sutro Media, many of which were authored by people I knew. I thought to myself, “Huh. That would be fun…to write a travel app for Umbria.” A short while later, I learned that the formidable travel writer Alex Leviton (who wrote the Umbria guide for Lonely Planet) was writing the Umbria app for them, so I went on with my life. Apparently, destiny had other plans, as I ended up meeting Alex through a mutual friend not a month later and we immediately hit it off personally and professionally…to the point that Alex said, “You know, I could really use a writing partner locally in Umbria to make this app rock.” (She actually said that. She’s from California. They say rock and totes a lot.) “Are you interested in coming on the project?”

And so, just like that, I found myself hired to co-author of the Umbria Slow:  Food, Culture & Travel iPhone app, which does, indeed, rock. Totes.

This past spring I was invited on a weekend blogging trip promoting Umbria called “Umbria on the Blog”. It was fabulous fun, and I ended up meeting other bloggers from around Italy and a few local movers and shakers in the social media marketing world. I thought to myself, “Huh. That would be fun…to write for an official blog about Umbria and be able to meet with bloggers in and out of Umbria more often.” But the weekend ended (a huge success), and I went on with my life. Apparently, destiny had other plans, as the brains behind the Umbria on the Blog project contacted me soon after to tell me about an ongoing blogging project in the works and ask if I would be interested in writing and curating their English language content.

And so, just like that, I found myself hired to blog for Umbria on the Blog in English, which has the amazingly wonderful side benefit of being able to collaborate with others just as passionate about Umbria as I am (but with much better contacts. These are people who can actually come up with press passes.).

So, what does this mean for you, dear reader? Nothing, really. (Except, of course, you now have just one more excuse to fill your glass with Sagrantino and toast to the randomness of life.) If you like the tips and suggestions I’ve been throwing out here on my blog, you may want to consider downloading the Umbria Slow app, which includes lots of the same stuff but in a much less wordy way and with groovy Google mapping so you actually know where the hell you are going. If you like the “slice of Umbria” posts here, check in at Umbria on the Blog where you’ll find more of those style posts (I post twice a week, plus there’s a photo blog and a bits and bobs section called “What I’m Loving”. There are lot of bells and whistles over at UOTB, but it’s still me behind the curtain.).

I will still be blogging here. This is my home, where I come and put on my saggy-ass sweatpants and sprawl on the couch and let it all hang out. I can do stuff here that I can’t over at the office (like swear, name specific businesses, and bitch about my in-laws). That said, I may be here a little less over the next few months while I try to get a system going with all this new writing-for-pay business going down.

In short, this post wasn’t about tooting my horn (okay, maybe just a little tooting) or trying to get you to buy my app or read my posts (okay, maybe just a little promoting) or any of that. It’s about thanking you—yes, you—for reading my words for the first time or, perhaps, for the 100th time (There are 134 posts on this blog! Yikes. No wonder my house is such a mess.). If it hadn’t been for you, I would have quit this writing pipe dream ages ago and my life would be that much less rich and full right now. So, thanks.

Now, go read my stuff at!


  1. helen |

    Congrats girlfriend!! No wonder you have been in hiding 😀 Definitely well deserved 😉

  2. Katja |

    Oh dear, I do understand your friend. But you’re not anything like these people out there who play once and win it all. You truly *rock*! So much great, witty and inspiring writing on your blog. Or were the boys involved too in your case? The two of them secretly writing it all up over the years and you not telling anybody?
    Good luck with your new ventures!

  3. Laura Saleggia |

    bravissima….quando si fa un buon lavoro con passione e divertendosi, non si possono non avere che buoni risulatati, congratulazioni…;)

  4. Marybeth |

    Tanti auguri! I’m not surprised! I’ve been an avid reader of your blog for several years, due to your unique style and excellence in turning a phrase. Being validated with these new opportunities is well-deserved and will offer more readers the chance to enjoy your slice of life in Umbria. Complimenti!

  5. Erica |

    I was expecting this.
    And I am also hoping you will write a book about your amazing funny sayings and universal wise words of wisdom.

  6. Barbara |

    At last the rest of the world is discovering what some of us have known for a long time – you’re funny, very funny, and sometimes informative too. OH, and a great writer. So congratulations not so much to you, but for the rest of the world for finally recognizing your talent(s)! And thanks for taking the time to write about someplace we love too – Umbria!

  7. Sharon Johnson |

    Congratulations to a very talented writer!!! I have been enjoying your posts on Slow Trav and here for years, and now have even more to look forward to!

  8. Toni DeBella |

    Rebecca, Congratulations! You are living my dream! I’d be jealous, but as you said in the beginning of your post, I could only be envious if you were undeserving. You are a talented writer and I am very happy for you. Looking forward to meeting you soon. (I’ll be back in Orvieto on November 28). Hugs.Toni

  9. Willemijn |

    Wow Rebecca … congratulations! Now I do not agree on the winning the lottery bit, you really deserve this (and lots more!!!). You are an excellent and very entertaining writer, keep up this good work (and happy to know you will because you are onw also getting paid!).

  10. Marzia |

    Dear Rebecca, I cannot tell how happy I am to work with you, not only because of the fun of doing things together (it felt so lonely before) but also because you are inspiring to me, as a writer, as a woman, as a mother. I really look up to you.

    Thank you for reminding me I won the lottery with this job – sometimes I’m so overwhelmed with social network restless interaction, the posts I have to wright by 11 o’ clock in the morning (inspired or not), and the freaking analytics curves, that I lose sight of a fact: this is a dream job.
    Thank you for this post, and I look forward to be out there with you again, collecting contents, photos, good laughs and very nice memories.

  11. Jessica |

    Auguri, Rebecca, that’s great news! And you totally deserve it, too. I’m glad the universe is looking out for you. 🙂

  12. Monica Fischbeck |

    Love your ramblings and congrats on Umbria App.. I just spent another Christmas in Assisi and of course had your app. way before I knew you had anything to do with it. Yes, I am an American who loves this country but considers Umbria a close second. Love the people and the beautiful country, food is fabulous and the people in Assisi are the most friendly and kind I have met in all of Europe.

    Love your stories on Expat site……I know being a transplant is not that easy but I believe you have done the best anyone could do…making the most of the situation. God Bless You! Pace e bene

  13. Marilyn Kearney |

    Hi Rebecca,
    Well done!! We are both delighted to hear of your new job/jobs…..we are particularly delighted to hear of the iphone app which will be of great value to us and to our guests here in Italy.
    From the very first time we met you at Brigolante and your continuing friendship, we have loved following your blog. We will indeed download your app (which we hope is available on our Australian phone) and look forward to hearing more terrific news about our favorite part of the world.
    Ci vediamo a Gualdo
    Marilyn & Barry


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