I could go on and on ad nauseam about the advantages of freelancing, but then I’d be a terrific bore, and what’s the point of that? Suffice it to say that I feel lucky to have choice, right-of-refusal, and the chance to take extended vacations when body and soul seem to require them. The ugly side of the same coin is that sometimes you find yourself up against projects, clients, and financial realities that render the job somewhere on the scale of “thankless” to “mind-numbing.” Throw in a different country, culture and language and the toss of the freelance coin gets even more complex.

I’ve been really fortunate to have some relationships that have sustained me for a long, long time, and which have given me, in their own way, an anchor in this city. I’m still an American, and work is part of who I am, so knowing that every now and then, I will trod familiar sidewalks to fulfill my DNA’s desire to say “I’m gainfully employed,” is a good thing. Just last week, I had the opportunity to walk, for the umpteenth time, into the agency for which I have done the most work in Milan—the London-headquartered Leagas Delaney.

Every time I go to their offices, I feel like I’m striding through the halls of a fairy tale. The work in question may be more or less fulfilling with more or less potential for brilliance (the advertising climate isn’t exactly a joyride right now for anyone), but the 100 steps it takes me to get from the sidewalk to their frosted glass door is almost worth whatever awaits on the other side. They are located in a lovely old Palazzo at Via Pontaccio, 12, and they share the red-carpeted floor with an auction house. One of these days, I’m going to miss my “deadline,” rush down the stairs, losing a crystal slipper, and arrive on the street only to discover that my carriage has turned into a warty old pumpkin.

But until that happens, I’m grateful for the chance, every now and then, to feel exhilarated by surroundings that have nothing to do with me or my upbringing. They may, however, have much to do with who I have—quite without planning it—become. Antiquity isn’t my native milieu, and this agency isn’t my professional “home.” But I am the person who walks through it comfortably, knowing that had I planned my life myself and adhered to that plan, this exact joy would not necessarily have been an integral part of it. Maybe the goal of life is to not obstruct the unfolding of the mystery, to see what will happen if you let it.