Response Crafting

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San Francisco

I love the irregular rises and falls off your body; the beautiful little ridges and peaks and valleys. Your toe bones and knee joints and hips. Your small stature so unadorned, bare shoulders still exposed beyond cloth.


I love the roughness of your heels, your skin that’s cool to the touch, the soft gray of your eyes and the real tone of your hamstrings that you hide. I love your ugly, pilling socks; your stretched-out woolen sweater. And I love the looseness of those curls.

I love that deep little scar across your sternum, right over the hollow of your heart. The broken, disjointed stretch of skin that some of your less worthwhile lovers call imperfect. That is one of my favorite spots.

I hear that scar has a dark history and this only makes me love it more. I watch as you raise your hand to shield it, and I want my hand to be there with yours too.

They tell me that I’ll tire of you – that you’ll break me or bore me before we even crest “forever” – but I don’t believe them. Some things, you just know.

Some say you make us soft – that you go too easy on your lovers; boost egos; string us along too long.

They tell me you’re no better than your painted ladies, luring farm boys in with smokescreens and empty promises that they pay – too much – for the chance to believe.

But those farm boys, they are laughing.

“Even under the terrible burden of destiny laughing as a young man laughs, laughing even as an ignorant fighter laughs who has never lost a battle, bragging and laughing that under his wrist is the pulse, and under his ribs the heart of
the people,

And so while others may prefer to stand on the sideline and sneer at the spectacle – tell us that you’re no good and we’re no good and we’re even worse, on top of that, for our naïveté in the ring – they don’t know what they don’t know.

That this is who we are and why we’re here. This is part of why we love you.

That, and: the irregular little rises and falls of your body; the cool roughness of your touch; the intoxication of those soft gray eyes.

You won’t be my lover forever, but you are the one I’ve most loved to love.



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Chicago, San Francisco and New York: why we love one and don’t like the other two


Chicago is happy and happy to be happy. Easy-going and easily eager (fair-weather fans and lovable losers, anyone??) and if you express any other emotions, Chicago fields it by fetching you beer. Or bacon. Or burgers. Or boats. Or sports.

Let’s be honest: Chicago is pretty much a golden retriever.

I liked Chicago. I was never crazy for it – never got gaga over it – but I could never bring myself to hate Chicago in the same way you can’t really hate a golden retriever. Even if you could, his simple-minded pleasantness would make him immune to it.

Don’t get me wrong, Chicago is smart enough. Hard-working, too, and plenty trainable. It’s just that at the end of the day, he’s no more complex than a roll in the park and a belly rub. (And what kind of person are you, really, if you don’t like those?)

People always say that the best part about Chicago is that it’s “right in between west coast and east coast – not just geographically, but politically, personality… pace.” They’re right. It is a little bit of everything.

But that also means it’s also not too much of any one thing. i.e., anything. 

You throw the ball and go on walks and all of this is fine and well… until one day you realize maybe you aren’t getting enough out of a city that stares at you, tongue out and tail wagging, for absolutely no reason. For four years straight.

And it occurs to you to go elsewhere.

(And it ain’t you, Chicago. It ain’t you. Don’t you worry your pretty little head – you were good to me. And before you know it, you’ll have brand new friends and have forgotten all about that one girl you once knew who, crazy enough, didn’t eat bacon.)

San Francisco:

San Francisco is definitely not a golden retriever. San Francisco may be available but never even pretends to know you, let alone try to be your friend.

What I like about San Francisco – what anybody likes about it (and it seems that it’s the tourists who are especially vocal) –  is what I see as its “intoxicating subtle roughness.” It’s like a hand-woven rug or the first sip of whiskey.

San Francisco is feminine; San Francisco is cool to the touch. San Francisco is, perhaps, a bit reptilian – beautiful without the easy answer of softness or gloss. And we like it.

It’s the creativity; it’s the promise of creation. It’s existing with one foot on the edges of subculture and the other immersed in true markets (finance, tech.) Nobody likes grit and grossness, per say, in and of itself. Rather, we like that grittiness is white space; a reprieve from the Play-Doh casting of other places.

And because it’s more than Play-Doh – or golden retrievers – San Francisco inspires much stronger feelings all around.

People who hate San Francisco:

If you Google “I hate Chicago” you get little more than a Bro Bible article wherein a Chicago native writes, in a self-deprecating but-still Chicago bro way, about the “worst” ways Chicago is annoying… like – get this – how Chicagoans actually eat at Grand Luxe Cafe and restaurant row and “try to fill emptiness by proclaiming FOOD as their passion.” (Ugh, I totally hear you. So annoying!) #goldenretriever.

Google “I hate San Francisco,” though, and you’ll get 600+ word rants on how truly deplorable this city is. A real cesspool of human depravity. The lowest of low. Worst of the worst. (It is, one person even threatened, “my least favorite big city”! Whoa, Pacha. Stand back. Anything but that!)

All the SF critics kinda cite the same reasons: dirtiness; poor transportation (public transit, parking, walking the hills.) They say that “people” (read: “girls”) are “flaky;” that people are “entitled elitists.” It’s too cold, it’s too expensive; not kid-friendly and nobody dresses up. It’s not only dirty, but also “filthy” (I found several people who cited both.) And on top of that, it’s full of lib’rals.

One person told me that what they hate about San Francisco is that “everyone has ideas.” Hearing this I was like “wuht? How are ideas a threat?” But others agree: tech bros “think they’re saving the world with their crackpot schemes aka ‘start-ups.'” Some people use the cop out: “it’s the hipsters.”

But if you take the opposites of that criticism, you can begin to shape an understanding of what the SF critics do like and look for in a city. You get things like: “Clean. Easy and reliable parking. Friendly, dependable people. Clean. Low cost of living. Republicans. Clean. Conventionality rather than new ideas or world change. Kid-friendly… Clean.”

Guys. That’s a suburb. You’ve pretty much gotchoself a golden retriever.

New York

I’ve never lived in New York and have only visited like two or three times. I liked it – though what do I know, being a tourist? But I liked it enough to feel I can say so. It’s got the economic (read: fissscal) diversity without any of that “social” shit: the idealistic or socialist or burning-man-istic bullshit. You either make money – in the ordinary ways – or you don’t. And you either work hard, or you don’t. End of story.

You don’t just work hard, play hard. You go hard. You get ready when you go out and you stay out until the early hours. Even dating is a competitive sport. Hell, even walking around is a competitive sport.

New York’s got the polish, but it’s also got a bit of the pretentiousness – and the impatience. They can be pretty and put-together when they like you, but they’re also not afraid to tell it like it is if you’re in their way.

Aren’t there sharks that eat their own siblings as embryos? That might be what New York is. Or maybe a swan – pretty, but then goes around killing people for seemingly no reason.

Don’t get me wrong – I like winning. And I like NY plenty. And maybe I could move there; I’d just have to prepare myself for zero-sum games first.

What it all means

I have heard that you either love San Francisco or you love New York. And when you love one, you hate the other.

And I started thinking about this in the context of Chicago, too – sweet kid brother Chicago (if New York is the hard-knocks older brother and San Francisco is the free-wheeling sister.)

And, more importantly, what it meant for personalities, because if cities are reflections of ourselves, then what sort of “self” does each city have?

Studies have been done on the personality spread of the United States, and they have found that there are three dominant types.

Americans living in the north-central Great Plains and the South tend to be “conventional and friendly;” those who reside in the Western and Eastern seaboards can be described as “relaxed and creative,” while New England and Mid-Atlantic dwellers are prone to being “temperamental and uninhibited.”


The study broke the states down by the big five personality traits: Openness, Conscientiousness, Extroversion, Agreeableness and Neuroticism.

The Midwest is more extroverted, more agreeable and less neurotic, but also more conscientious and less open. Both of the coasts are more introverted and less agreeable than the Midwest; less conscientious and with above average to high openness (west cost being the higher of the two.) Also, east coast is a lot more neurotic.

All of us as individuals fall somewhere on the spectrum of each of those. And it just might stand to reason that the cities we like – even love – mirror our preferences.

You can take a test to help you decide here. Doing so might explain why you hate the cities you do. It might even save you a move to a city you subsequently deem “too dirty.” Or, rather, one that seems more “idealistic” than “ideal.”


The first week in SF

Part 1. Logistics

Arriving: I took one large suitcase and one weekender bag. I flew in from Chicago on Sunday, arriving the evening before I started my new role. (Having traveled every week for work when I was doing the consulting thing, taking the 6 am flight Monday morning and going straight to the client site, this <24 hour turnaround was fine. Plus, I wanted as much time in Chicago as possible.) What was a bit challenging was securing accommodations…

Housing. First of all, very important: It’s not really the cost. It’s the competition. You can make peace with the prices quickly enough. But being okay with what you’ll pay won’t get you an apartment…

Over the two weeks leading up to my arrival after I got my offer, I sent more apartment inquiries and responses to craigslist posts than I had sent cover letters during the job hunt – i.e., in SF, securing the apartment is more difficult than landing the job – and pretty much received zero replies. So I took the hint and figured I’d book a short-term, day rate stay and then continue the home hunt once in SF. (This approach was unanimously confirmed by everyone I asked.)

I heard this “short-term” phase, during which you are looking for the “real” place, can last as long as “a couple of months.” Because I don’t have a strong appetite for forking over ~2 months at $200 a night, I wanted the cheapest immediate option, which meant a shared room. I booked an airbnb and, because I got a weird vibe from the airbnb guy, also booked a backup, which was a hostel. Yes, like our college backpacking days.

That “weird vibe” was right:the airbnb proved flaky. Sunday night I took a cab to the city (I know “everyone” takes the BART, but I had luggage and time considerations) and I’m standing on a sidewalk, calling his cell phone periodically for about an hour before I gave up and checked into my backup, the hostel, where I bunked with 3 girls from Germany.

I’ve stayed in hostels while traveling before and have never had an issue. It’s, of course, a whole lot easier when you’re all on the same sleeping schedule – and my roommates were polite enough, though but you can only be so quiet in a 10’x10′ room. Luckily, I had earplugs to pop in.

I was incredibly – incredibly – lucky and, by some good hand of the apartment gods, landed a place the next day – my very first full day in the city. A friend of a friend was moving and she was like “if you want this place, call me immediately.” I didn’t even have to see it. I wanted it. I swung by as early as I could and, to my additional luck, this place is absolutely adorable, in a great location, and only slightly over the very optimistic (read: overly aggressive) budget I had set. Somehow I walked out of that meeting with keys. (She had had another renter lined up. I pain to think what happened to that poor girl.)

Landing a place in SF feels a little like winning the lottery. The feel of real keys leaves you on a total high that lasts for days.

And even this place is still only short-term.

None of this is forever and that’s both exciting and a little scary. Mostly exciting.

Getting around. I take the occasional cab but so far, I’ve been walking. I tried to take the bus home once, but walked pretty much the entire route home without ever seeing one pass. So I’ve just been walking since. The city is deliciously walkable, even – especially? -with the hills. It’s a lot the street width – the narrow through-ways lend a feel like one big neighborhood. Even Market, one of the majors, is easily traversed.

The only qualifier I’ll put on this is: shoes. Walking this much when you’re probably not wearing walkin’ shoes means that your feet will endure some… “conditioning.” And if you’re like me and rocking those pointy-toe flats, it’s not just blisters or shin splits – no, the bones of your feet will hurt. But it’s all part of the love.

But, as an added bonus: your legs will also endure the training – even one week in, they already start feeling amazing. (Update: after 3 months of walking my hilly 40-min commute almost daily, my legs and behind had definition like I’d never seen on them.)

PS? Remember that cliche where some grandpa would complain he walked miles to school, “uphill both ways?” It’s a joke, right? Everyone rolls their eyes? In SF, that’s actually real. Your walk really can be uphill both ways. 🙂

As expected, I love this city so far. I’d been here before, but being here now, in this way? It felt immediately comfortable. Like mine.

Part 2: Exploring

The first weekend: in addition to general eating, walking and day-drinking, we rode bikes to Lands End to see about the Sutro Baths – urban ruins on the west side of the peninsula where a large, privately owned swimming pool complex built in the late 19th century used to stand. If you’re into that sort of thing, it’s pretty cool. The outlines of the original pools are still there, and the low walls are filled with totally gross, standing, algae-dense water. I dipped a toe in from a step of an old staircase leading into the water. Because I’m like that.

To get there, we rode “through” (read: over) Presidio… because we thought it was, you know, like a park park. An extension of Crissy Field or something.

It is a huge hill, guys. A small mountain, really – or feels that way when you’re noob rental-biking over. The fact that we got stuck walking bikes up the mini-mountain was my fault, because I wanted to “be in the trees.” Because I’m like that, too. That being said, it made the destination that much more rewarding when we finally battled our way over. (I believe we agreed on this. Eventually.)

At the bath-ruins, we shared a warm backpack-beer overlooking the shoreline. Afterwards, drinks at Cliff House. And then rode back – through the city, not over Presidio. A much more relaxed and reasonable route.

Part 3: More

What the first week tastes like: 

  • Magnolia beer for the first and second time. (The low hoppiness makes this one a particularly palatale beer for me.)
  • Vegetarian sausage made from butternut squash, because you’re into gastro pubs even when all they do is sausage
  • Deviled eggs for dinner because you can
  • Iced coffee, from both a.) your new Starbucks as well as b.) the little local coffee shop you guys try
  • A block of Ghirardelli dark chocolate, because you’re still new enough to the city that that’s fun.
  • The intoxicating salt of a sweaty brow; cheekbone; jawline after that Tour-de-San Fran over Presidio.
  • Warm canned beer pulled from a backpack, shared overlooking a beautifully rocky shoreline.
  • Cold reward beer overlooking the harbor, once back downtown
  • A single olive snatched on your behalf from a bar garnish tray
  • Ludicrously fresh crab meat piled on top of a Louie
  • The best sourdough anywhere. (SF sourdough really does put all the rest of it to shame. You don’t even have to like sourdough.)
  • Cheese sticks, chocolate chips and white wine from the little local market, because some things don’t change by city 🙂

What it feels like: The first week was mostly logistics – getting to and from work, getting coffee, getting groceries, getting booze. Figuring out the new role and what they want to see out of it; starting to deliver on those things. Repeat.

There’s scarcely time for reflection or really thinking about anything outside of this. That being said, there is:

a.) Some initial… “scariness,” mostly due to lack of housing / “place” in an expensive city without a local support system. Something similar to the way I felt when I flew to London a few weeks early for my study abroad, planning to backpack before the term started, and found myself without a place to store the two huge bags I’d brought for the semester while I did so. I eventually resolved this, but those first 24 hours in the city were emotionally trying to say the least. My first few hours here were a little like this, albeit less scary.

b.) Excitement! A wave of… something like “blissful relief” at finally really being here. And liking it as much as you thought you would.

c.) Setting goals for the new role. Or, rather, reminding yourself of the goals you had set when looking for it.

d.) How to transfer the rest of what you love to your new home. How life goes from here.

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How Cuba was

Note: I wrote another article on FAQ, best and worst, reviews, and tips here.



It’s a lot like small-town Central America. It’s like the places your bus stops to refuel on the way from Belize to Quintana Roo. It’s a little like that city in Mexico where I bought (or think I bought; perhaps only thought about buying) a bag of clementines for something like a dime.

And it is nothing like the rest of the Caribbean.

Think sick-skinny stray dogs trotting along the edges of streets, head and tail in low-carriage. Think streets that are paved but also dusty; think also cobblestone alleys and other unpaved side streets, narrow and pothole-riddled, entirely dust and mud. Think people walking, people driving classic cars, people waiting listlessly at bus stops, people leaning against door jambs of decrepit architecture wonders. Think the delirious deliciousness of humidity and heat.

Think the smell of diesel and dust, as well as the subtle sweetness of humidity and fresh sweat.

But, even all this considered, it’s already becoming not the place we think of.

They still have classic cars and cigars. But they also know we want them.

They’re gearing up for tourism – have already figured out some of the ways they can make a buck or two off of visitors as we pass through. But, on the other hand, have not yet developed the finesse and ease of hospitality. They have self-awareness, but don’t yet have a broad tourism benchmark.


The tarmac is like something out of my grandparent’s era, something vintage – 1970’s – but very real. There, in old-school lettering, “La Habana,” and I’m already excited. There’s something very special about landing in places you’ve longed for or love.

There’s a driver pick-up, and in the backseat of his classic car on the way to Havana, I’m all but hanging my head out the window like a dog, lapping at the air and rejoicing in my sheer happiness for it all. I’m happy even for the refreshing authenticity of sweat that lines the entire length of my back and thighs against the pleather seat.

We pass through these incredible areas, originally built up in awe-inducing architectural splendor (seriously, if you’re into turn of the century showcases, you might die) and now reduced to little more than empire ruins.

And within them, these little shops set up behind barred windows or back alleys. Women hand-washing glassware next to hand-written signs and the occasional lonely, faded gesticulation of spray paint. Like “this is what a bar might look like” or “this is what graffiti might look like.” In another era; another world.

And it’s all like having cake smashed in your face. Stale cake, but still beautifully decorated. You go to take a bite but find yourself overwhelmed by it, and it’s impossible to take it all in.

Once there, the driver helps with bags. “Enjoy your stay,” he says. “And let me know if you want a ride back to the airport. I left my number.” He goes to leave.

“Oh, be careful,” he warns, turning back in the doorway. “This is a safe area. People are nice. But not everyone should be trusted.”

That first night:

We went for a walk. We learned that you can buy a bottled beer from any bar for about a dollar and then walk out with it to roam the streets with beer in hand.

Because Cuba, she just does not care.

This was henceforth known as “walking beer” (lovingly appendaged from a Dutch woman I met in Turkey who expressed jealously of the US for our “walking coffee.” Meaning, merely: “coffee to go”) and became the backbone of our trip.

I also found a dog. There’s always a dog.

There were tons of stray dogs – there always are – but this one had a hurt leg and was limping so severely he would only go a few steps before curling up into another tiny ball and so of course, like any person emboldened with the romanticism of being in a foreign place for the first time, we strode over to the nearest bar and, despite the kitchen being closed, negotiated the best dog-appropriate-food:dollar ratio order we could, and took it back out to offer to him.

He refused it. I urged myself to pretend it was because he wasn’t hungry.

I went back to the bar and ordered a beer.

That first morning:

I’d wanted to go to Cuba for so long that after I’d booked the trip, I told people that I was so happy to actually be going, I wouldn’t care if it rained while I was there.

And then it did.

And, true to my word, I didn’t. He wasn’t too perturbed, either.

It rained pretty much the whole time, to varying degrees – from light mist to downpour. And there was never a moment I didn’t grant Havana the space to be a real place that exists outside of my desire to be there.

I woke up to the sound of an actual rooster.

And it was only mildly adulterated by the hum of the air conditioning unit, set on high.

I got up to write, because I do that sometimes and I do it even more when traveling, but first went out onto one of the two balconies – the one facing the ocean.

There are little droplets hanging along the underside of the railing. It’s not pouring, but the light is a white-gray. It’s a delicate rain; something only discernible when you set your gaze against something dark. But it’s raining nonetheless and we’ll be out in it and we don’t care.

First on the agenda: coffee.

At some point after that? Beer.

And then mostly a lot of walking around.

And also the need for food.

Being (i.e., the answer to “what did you do?”)

Walk around. Don’t sight-see.

I mean, I guess go ahead and sight-see if you want to sight-see, because there’s probably plenty to see if you do, but if you’re willing to, just walk around.

Be. Exist.

You get yourself a bottled “walking beer” and you walk yourself around. When that one’s done, you find another bar and get yourself another.

It’s like being a local but better. Because you get to be there, on the streets, but you get to see it for the first time. And you also have the special privileges afforded with that, like feeding stray dogs leftover egg yolks rationed off your breakfast, wrapped up in a napkin.

When you get tired of walking, sit for a bit. When you get hungry, eat. Rinse. Repeat.


Eating (i.e., vegetables in Cuba):

I read, before going to Cuba, that it was particularly un-veg-friendly. And I’m not about to tell you that it wasn’t, because it definitely is.

But I will tell you that it wasn’t as bad as some say, because it isn’t.

Did I eat over-oiled fried rice? Yes. Canned green beans served as salad? Sure did.

But I knew about these things before I even got there, and by the time I was there and being served, found it entirely too easy to overlook this discrepancy between their idea of salad and mine; to forgive a country for serving – god forbid – different food than I might serve myself, and for not having Luna bars (or spin class) to sell me.

So I go, eat what they have, and still have a good time.

Pretty much all of the things I ate and some the things I drank in Cuba:

  • A lot of a dish simply called: “fresh vegetables.” Iceberg, tomatoes, canned green beans.
  • Also available fried
  • Eggs, scrambled and fried
  • Cheese cubes
  • The saltiest pickles you’ll ever taste in your life
  • Fruit – pineapple, banana, guava, papaya, etc. All sorts.
  • Toast and other breads
  • Black beans, often served too deliciously to be vegetarian
  • Beer.


Riding in cars with boys:

So. When you go, tons of drivers will try to sell you on an “hour-long” classic car tour.

Some people have come back from Cuba saying this was their favorite part.

This part nearly put a damper on things for me.

Here’s the trick, I think: make sure you negotiate. Make sure every time things change, you re-negotiate. If you strike up a conversation (and you will) and they take you somewhere else based on the dialogue, make sure you clarify the charge. If you explicitly ask to go elsewhere, make sure you clarify the charge. If you mention being hungry and let them recommend their favorite restaurant and drop you off and then wait, make sure you clarify whether or not they’re charging you by the hour as you eat.

(Looking at you, Abraham. With your entirely-too-seductive hot pink Hello Kitty car.)


Reading and Writing:

I read B.J. Novak’s “One More Thing” on the way to Cuba, because I guess I figured it’d make a good vacation read, of the books the airport carried.

I didn’t really underline anything, which is atypical. And I pressed two flowers between different pages, which was also atypical, but in a better way.

I didn’t take a notebook with me, so I jotted tiny notes on the only piece of paper I had, which was the back of some official-looking form we’d gotten from the flight attendant, field-less but printed entirely in Spanish.

I also went completely offline. Mostly because I had to.

But also because that was largely the point.

Want more on Cuba? here.

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Cuba – FAQ, best and worst, reviews, and tips

Note: I wrote more about my time in Cuba here.


How did you get there?
You still have to fly through other countries. Connections are pretty plentiful, though – you can go through Canada, Mexico, Costa Rica, Columbia, most of the Caribbean, etc. The major airlines flying into and out of Havana (“La Habana”) are Cubana and Interjet.

Is it legal now?
No, not for tourism. As of Jan. 2015, Americans are now permitted to travel if it falls under one of twelve categories. You no longer have to apply beforehand, but you may be asked to cite your reason. I was asked when booking. Official .gov wordage.

Any trouble with credit cards?
No problem whatsoever booking the flights or accommodations online using an American credit card. Not sure on using cards in Cuba – I read they still weren’t accepted and never tried. Used cash the whole time.

How much cash did you bring?
Cash is apparently hard (impossible?) to come by for Americans in Cuba, so take more than you’ll ever need. If your accommodations and flights are already handled online, I’d like to say that $150-200 per person per day should suffice. Worked for us. But use your own judgment. You absolutely want to take enough to have cash left over. Do not get stranded.

Did you have any trouble with customs in Cuba?
Not at all. Zero. As others have mentioned, the only real question going into Cuba was whether I’d been to Africa in the last 30 days.

Did you have have any trouble with U.S. customs coming back?
Still no. When they ask where you’re coming from, you tell them your connecting city. They may ask if you bought anything. Tell them yes or no. (ps – it’s legal to bring back up to $100 of Cuban cigars.)

Key bar and restaurant reviews:

Prado No 12: cannot speak highly enough of this place. Adorable location on the acute corner of two streets, with like 4 tables, where you can tuck in real quick during a downpour. They’ll sell you some food after the kitchen’s closed so you can feed a stray dog, let you negotiate a beer with your last dollar (CUC), and then remember your name when you drag yourself in to do it all over again the next day.

El Floridita: Alright, yes. This is one of two bars where Hemingway chilled. He drank there all the time and loved their daiquiris (which, incidentally, they claim to have invented) and now he’s got a statue. Whatever. You should go. But go, have a drink, get the photo, and then get the hell out. It’s not really worth more than that.

Paladar Doña Carmela: the place your taxi or “classic car hour-long tour” driver will take you. You’re going to be irritated, maybe even suspicious. It’s actually really good – probably one of the best places in the Havana area – but be careful that you negotiate with your driver so he doesn’t charge you per hour while you eat.

La Farmacia: overlooked gem. They do this breakfast with eggs and fruit and coffee and espresso for like $4.

The best and worst of Havana:

Most expensive drinks: by far Hotel Santa Isabel, where a whiskey ran the handsome Chicago price of $15.
And maybe that’s what you get for drinking at a hotel, but drinks (and food) at many of the other hotels were reasonable enough.

Least expensive drinks: pretty much everywhere else.
Seriously, though. Everything from beer to mojitos to whiskey pretty consistently go for $1.50-$3. Prices were a bit cheaper along Paseo del Prado, the street running from the Capitol Building to the sea, and might peak a bit in some of the more touristy areas of Old Havana, but if you’re seeing big-city prices, you’re in the wrong place. 

Best deal: you mean other than most all of Havana?

Biggest rip-off: the “one-hour” tour by classic car tour, where you’re invited to pile into a classic car so a driver can chauffeur you to all his favorite tourist traps (not so subtly suggesting you buy things) for more than one hour and charge you for both the overage and all kinds of other things. Fun.

Best meal: Paladar Doña Carmela
Sigh. Yehhs, the same place the tour driver will take you… they were right.

Worst meal: The pizza, if you mistake salt for parmesan and sabotage it.
In all seriousness, I guess there might be a lot of great contenders here, if you were critical enough. But luckily they all save each other. You don’t go to Cuba for haute cuisine. Let it go. 

Worst service: Le Patio restaurant at Hotel Del Tejadillo in Cathedral Plaza, where if you stop in for a beer during a downpour, are treated like an outright derelict.

Best mojito: Europa, but only by one of the bartenders – not the others – and I don’t even remember his name. Sorry.
Confession bear: I’m not really all that into mojitos (I’m not really all that into any sugary drinks) and this was one of three, total, that I had in Havana. But! It was the also the best mojito I’ve ever had (one might even say the only one I’ve ever really liked) and I figure that counts for something.

Best daiquiri: I don’t know, El Floridita?
It was the only one I had. See: “mojitos.”

Other tips and Warnings:

  • Don’t do the classic car hour-long tour. Or do, but know that they’re going to try to charge you more . At least my driver, Abraham, with his bright pink Hello Kitty car, did that, trying to charge $100 more than what we’d initially discussed.
  • Seriously, watch out for Abraham and his bright pink Hello Kitty car.
  • In the same way that most cities have strangers on the street that try to sell you drugs, people here will try to sell you cigars.
  • If you buy a cigar – whether from a factory, a bar, or some random guy – it is almost assured that it will be ruthlessly judged on basis of quality or cost thereafter.
  • Everyone – men, women, probably children – drinks mojitos in Cuba. This does not, however, change the rest of the world’s perception of mojitos. If, still high on your mojito-sipping confidence from Havana, you order one at home, you will still get looks. Just like before.
  • Make sure you plan out your entire itinerary before booking anything – flights or hotels. Several of the airlines only fly out on certain days.
  • Make sure you check your departure terminal. There are several, and are set far enough apart that they require a taxi to travel in between.
  • If you get a late-night personal pizza from one of the many vendors, be warned that the big shaker is not parmesan. It’s onion or garlic salt. Dumping it on your pizza will render it all but inedible.

I wrote more about my time in Cuba here.


The trip after leaving a job

A week from now, I’ll be on a flight to Cuba.

I have wanted to go to Cuba for at least three years now, probably more.

There are a lot of really appealing things about it for me – the grittiness, the richness of the culture, the sultriness, the sadness, the heat… and all of those things have always been there. But when I really try to pinpoint the origination of my desire, there is instead another moment that stands out in my mind – the earliest memory I have – when I once offhandedly told my project manager, at a previous job (before I was a project manager myself): “I really want to go to Cuba.” And, because this is how she was, she laughed. And then said to me, because this too is how she was: “you can’t.

She really wasn’t a good project manager. Most of us, unfortunately, aren’t.

Even though this was about Cuba and not the project, that exchange right there illustrates the real problem with project managers – this adherence to The Rules As Written; this complete subscription to The Letter of The Law. The rejection of anything outside of it, even at the risk of destroying passion and ideas.

Of course, it was technically illegal to go to Cuba at that point. And yeah, technically, it still sort of is. But technically it also sort of isn’t anymore, and so now is a great time, if you really want to, to go. So even though, technically, Americans still “can’t” go, I am.

I hope that by going, I can eradicate that association with “Cuba” from my mind. And I hope that by going, I can get that much farther from that world – from her, from all project managers, from the world of project management as it exists, with all that exhaustive and exhausting Process. I hope that by going, I can carve out even more space for a manager to be a manager without being the manager who dashes unconventional thoughts. That I’ll find validation with doing so many other things that so many other people are pointing to and saying people “can’t.”

Because this isn’t, of course, just about Cuba. Travel never really is.

There’s an odd thing with travel – the way that it amplifies personalities, the way that our aspirations and anxieties emerge. The way we choose places, the things they come to represent, the things we ask of them, the way we go.

There are personalities and persona in travel:

The turn-key traveler, the one who follows guidebooks to a tee. The one who will Google “one week in wherever” and then actually use the itineraries, leaving no review or recommendation unturned and, above all, never straying off the beaten path.

The relaxation traveler, who is probably the most easy-going person you could ever hope to travel with. A little spot, a little sun, and a little quiet, and they’re set.

The luxury traveler; the braggart traveler. The one who has to stay at the best places, the one who finds themselves doing “once in a lifetime things” more than once in more places than one.

The adventurist. The humanitarian. The hobbyist.

And then the traveler who wants to sink into the real life of a place, who wants to walk the neighborhood streets, eat the street food, ride motorbikes, chase dogs. And this one, this is me.

And my point here is that not everyone uses travel to reconcile the same needs. Some of us are searching for romance, some of us want adventure, some want relaxation. Some want to check a box; some want a place without a box to check. But most all of us are looking for reassurance or soothing that we’ve long felt denied; we target a place we think will offer it.

And some of us, we want a place to tell us, because others aren’t:

Nah, girl. You different, but you ain’t wrong.

So I’m going. I am not going to the National Capital Building or the Museum of the Revolution. And no, I do not need the beach.

I want to walk the streets and be gritty and feel out of place but so deeply delighted. And when this has been exhausted, I’ll sit down to some food and a drink. And here, I guess I’ll want a cigar and any kind of pour not cut with syrup, even though the former is probably not so widespread as we think and the latter most certainly is.

Just let me really be here. Just grant me this validation of “being able to;” reassurance and real proof that one can do the sort of things they think they can.

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When architecture fails: River City, Chicago

The River City development was designed by architect Bertrand Goldberg, whose most famous work was Marina City (“the corn cobs.”) Despite a similar design and methodology, River City, completed over two decades after Marina (1986 and 1964, respectively) never saw the success of its predecessor. On the contrary, it is quite a failed project.

River City was originally intended to be a series of four towers 85-stories tall; the building as it stands today was meant to be a base to support behemoths that were never finished. In addition, there are thousands of square feet of empty retail space on the first floor; slabs of cement that have stood waiting since 1986.

River City

River City, Chicago

I recently went inside the property. I was shocked at how haphazard the design was. Within moments of entering the building, I was overcome with how “wrong” it felt. Below are the photos I took during this visit. (Apologies on quality; all I had was my phone.)