the toughest year of my life

Wow, nearly two months have passed without a word written.

Time to get this sucker rolling again.

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As the title prefaces, I have been thinking over the state of things as I approach the 365-day mark (September 1), when I moved to Milan and henceforth lived through the toughest year of my life.

It has, in essence, been a year of self-reliance. No one to fall back on (money aside), no one to push me. Just me to push myself, or not in some cases.

Without a doubt the most prominent psychological and physical challenge for me was the death of my mom, which I have documented here many times previously, but which remains still so powerful and present. I don’t dream about her as much as I did, during the worst times, when all I wanted was to sleep and for her to still be present. But I do get that sting, somewhere between my chest and my stomach, when I see her picture, or get to speak with one of her friends.

Tonight her friend (my Aunt) Barbara sent me some photos of her yearbook from Lake Placid High School. She was so beautiful at seventeen, and already so wise and compassionate. She, I quote, willed her eyes to the blind, teeth to the dentist, her hair to the wig factory, and “the rest to science.”

A week ago, I received a package from my other Aunt (Sydna), which contained a fantastic album of English family photos, including early ones of her and my dad before I was born.

The entire journey so far leaves me with no better clarity or answers, just the truth, that she of all people would have exclaimed to me in my moments of wallow, that I must live and move on. Meet new people, love new people, and share the memories of her with those she and I both love.

The amazing thing about death is it tends to create a vacuum, and humans eventually adapt in such a way to fill the vacuum, not completely, but in small but significant ways.

My immediate family is closer—that is me, my dad, and my brother. And I am cultivating more direct relationships with those in the extended family for whom she was the primary contact, not me. For instance: her brother, my uncle, Tim, his wife Kim, and their daughter Tai. I met up with them in Amsterdam last month and it was genuinely fulfilling to see and be with family.

More dramatically and in a way I always knew lurked under the surface all along but never quite saw fully, is the network of friendships I now pick up from her, with quite a few amazing women. She had plenty of male fans and friends, but it was the women she loved and befriended that collectively show her legacy. You all know who you are, no use in listing you since I would inevitably forget someone.

It’s funny, I feel more like her every day, too. Not in obvious ways, though people used to say we looked quite alike. But like this summer, I’m interning for a professional training company that focuses on negotiation skills, doing their communications and marketing. Writing, designing here and there. Researching and doing some analysis. And learning plenty about negotiation. In the process, reading a bunch about how women approach negotiation differently, why that exacerbates the gender-pay gap, etc.

Turns out, I behave and think far more like a woman than I do a typical male. In negotiation, women tend to be win-win oriented, and want to see value creation for both sides. Men tend to be more adversarial, and are more self-concerned. In reading these articles, along with a lifetime of careful observation of myself and those around me, I am still realizing how she was and how I am are clearly parallel.

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While I wish I had some of her best qualities, like being an early morning riser, I am unfortunately a member (biologically anyway) of the English male subset, which is known for its slothfulness. This is only made worse by living alone and battling mild depression, which has been another ‘challenge’ of the past twelve months.

I can’t tell you that I have been formally diagnosed, but it is evident to me. I seem to require more sleep than the average person. I get tired easily, needing to rest. I have hours and days when I am cranky and feel lots of mental toxicity, for no other reason than I wake up and feel toxic.

For a long time, perhaps most clear to me during the winter months, I really felt impotent at the gym, so the thought of going there to face people (and myself) just seemed too unpleasant in contrast to a warm couch and Netflix. This particular gym was also cramped and lacked many basic implements one uses to exercise the entire body.

In part, it was a cyclical spiral. The less I went to the gym, or the less good I felt physically, the more cranky and depressed I seemed to feel. Around the beginning of the summer, I joined a bigger and better gym, and was immediately happier to have a place to go that fulfilled at least the bare minimum to get a good full-body workout. Over the last six weeks of my internship, I have had a regular schedule, more or less, so getting back to a regular gym routine has been easier too.

Briefly, in the beginning of this year and for the time between gyms more recently, I worked out at home using a yoga mat and some small weights. This suffices for a while, but what I lack in early-morning pep I make up for in a curious desire to do all manner of household chores as soon as I begin a home workout.

Referencing this general fatigue and laziness, I also began to question a medication I take daily, Venlafaxine, which is a mild anti-anxiety pill originally prescribed by my gastroenterologist when he thought I might have Crohn’s disease a few years ago.

It was great for awhile, but now I wonder if it inhibits me. My sex drive seems low, even for me. I have never been a hormonal, animalistic person sexually. I just don’t have that desire very often.

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Which brings me to another challenge: Italian men.

Aside from the language barrier, which is more apparent than you might think, Italians are very sexual, and as I learned very quickly, they wear their desire to jump into bed on their sleeves.

Imagine their surprise when they meet me on a date or at a bar, and I am the most tightly-wound, Anglo, never-direct-in-confrontation kind of guy. For whatever reason, it feels very different here than it did in the U.S., in the not charming kind of way. There’s just no game, no coyness, no gentlemanly decorum. Definitely no desire to “date” in the classical sense.

Spoiler: I have been on a handful of dates (day-date lunches, drinks, dinners), most of which concluded with me dodging his desire to come upstairs. This is another way I feel like “the woman.”

My mom was one to preserve her integrity, especially in relation to how others treated her. I am no different, and I feel it is under assault here.

All this stunted romance experience has made me feel even more prudish and cold than I usually do. In Tampa, I was never busy every night of the week, but I had a handful of good experiences, and had fun in the process.

I did pick up a bit of wisdom from a friend that I made here at the very start of my time, who I like a lot and had lunch with recently: while traditional dating makes logical sense, it can often mean you fall in love with the personality or the humor, and when the time comes for sexual interaction, the dynamic falls flat and the chemistry isn’t there.

After a few of those, he says (and he is older by a decade or so), it’s genuinely just easier and less painful and more efficient to sleep with people you’re attracted to, because after all we are men (“and we have needs” which I find sexist, but anyway), and if you actually like him after the act, then maybe you go to the cinema or have pizza and gelato all romantic-like.

My friend may have a point, and I appreciate that his rationale was more thoughtful than “I have a penis and it needs somewhere to go, so…”

To be completely honest, I have always found overt sexuality, in a way that seeks validation, or attention, or is just desperate and not self-respecting, to be distasteful and sad. Cue Jane’s influence again.

I am trying to wrap my mind around a different paradigm however, and I wonder if it isn’t just the old curmudgeon living in my brain that’s saying this, because I haven’t been with someone I actually liked and felt comfortable with in a long while.

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In a wider sense, normal socializing has changed for me too. Combined with the depressiveness and perhaps, Milan’s cold nature (though I would bet all large cosmopolitan cities can be difficult), the simple act of making friends anew has been challenging.

It’s not that I haven’t met anyone, but rather it’s slow getting to the point in a relationship where you have history and the interaction is seamless. I prefer organic relationship growth, over time, as the universe would prefer. Being dropped into a school program, much like summer camp, where no one knows each other, the bonds form somewhat arbitrarily. Like baking a cake too quickly and in a too-hot oven, the exterior seems done but the inside is still a work in progress.

The easiest people to get to know and enjoy being around within the SDA Bocconi community have been North Americans, from the US, Canada, and Mexico. We have the same humor, same need for alone time.

To be clear, I have met some very fun, friendly Italians, that I keep in good touch with and enjoy seeing regularly. Alessandro, Roberto, my Italian teacher Susanna, and a non-Italian from Panama, Jose. It’s perfectly fitting too that many of my enjoyable, gratifying interactions are with store salespeople, who I would certainly count as friends. Yiqin, Nicholas, Cristina, and Katherine at Bottega Veneta. Salvatore at Prada. Paolo at Burberry. Hilary, Matteo, Irene, and Imma at Bivio (my favorite resale/consignment boutique).

My Tampa friend John William posted an article on my Facebook wall recently, and it was spot-on: moving to a new place alone signals the beginning of a lot of time spent by oneself. Not necessarily “lonely,” because I am a very gifted and satisfied introvert sometimes. I have plenty going on in my brain to keep myself entertained. It’s only when I spend too much time alone, letting mild worry and self-consciousness get the better of me, that I begin to feel crippled by doubt and truly feel neurotic. And this is not a fun place to be.

In Tampa, with my plentiful mature friendships, I could always count on the impact of their behaviors, suggestions, advice, and insistence that I get out of my house to keep me connected to the real world. Here I have very little of that external influence.

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Looking ahead, a big challenge for me, or so it feels now in anticipation, is breaking into the world I came especially to Milan for: that of luxury fashion, retail, etc.

I have learned some things in the past year that necessitate a slight change in course. For example: many big brands here, even if they are publicly-held, are quite old-fashioned and parochial. “Meritocracy” as it exists in other working environments is less present here, so it tends to be more about who you know than how capable or passionate you are.

To boot, Italy virtually starves many of its fashion and retail workers. I’m not referring to retail only, but also to corporate and back-end jobs. Simply put, fashion businesses don’t fully appreciate business education or the premium of an MBA, in part because the Italian education system means that many people have master’s degrees and are overqualified. Add to that the popularity of the industry, I suppose it shouldn’t be such a surprise that companies are happy to offer low to mid salaries for new graduates who lack extensive experience.

At a minimum, and I don’t find these requirements at all overambitious, I would like to make enough to be comfortable, pay down my student loans, and enjoy life within some reasonable limits. Not asking for six figures, but preferably more than I was making before the MBA.

So where does this leave me? One option is to leave Italy and pursue options elsewhere. But, options are limited to the places where businesses are located, like New York, LA, London, Paris, etc., and Milan is arguably the cheapest of these places to live.

If I expand my scope a bit, to not simply be brands I love and lust after, then there are other options, like e-commerce companies, branding and marketing firms, etc. I intend to investigate these.

Other parts of Europe, like Amsterdam, Germany, Scandinavia, or Switzerland could be good alternatives.

Another tip I picked up from a friend of a friend, who works for the Hermès Group company which deals exclusively in exotic animal skins and works with all the top brands, was: focus on business-to-business firms, like his, rather than business-to-consumer brands, which have cachet but are far too competitive.

And I like this advice. I have always felt more like a behind-the-scenes, low-profile kind of person more than a glitzy, glamorous one. To land a job at Bottega Veneta or Prada or Chanel would, of course, be a dream come true. Am I willing to accept so much sacrifice, like making no money, working in an outdated culture, and being offered little opportunity to advance through skill and effort? No, probably not. Life is too short, and I know too many people who are living it now that aren’t happy.

This is an interesting corollary to a more apparent, consumer-side observation I have of myself, which is: I really don’t like “trendy fashion.” Luxury brands are no longer about a standard of design or quality, or original creation. They’re machines, made to sell a lifestyle, and they are driven by trends. Being trendy means being mass, mimicking each other, and subscribing to a group aesthetic, not thinking independently.

I won’t claim that I am an outlandishly unique dresser, but I have a strong aversion to trends, and thus find myself buying things that are tasteful, even playful, but which are not tied to any current trend. The last new things I bought outside of shoes or bags were pairs of Zara jeans and sneakers. Almost all of my clothes now come from Bivio, where items are more period-imprecise, timeless, or dated enough to be cheeky or funny. And they look brand new!

So when I think about brands to work for, the list is not long. Like I said, if the conditions were right, I wouldn’t say no to a place like Louis Vuitton, Givenchy, Saint Laurent, or Gucci, but so much about “luxury” these days is almost offensive to me. It’s offensive how expensive things have become, considering their wide margins. It’s offensive that brands sell keychains for $350 and things like fur-lined loafers are now di moda. But people buy these things, and so it is.

I recently made a list of all the brands I would fill my own boutique with, and it was all quieter, opposite-of-trendy brands. Rather, ones that make consistently beautiful items, like Manolo Blahnik, Sportmax, Jil Sander, Sonia Rykiel, Tod’s, The Row, Rick Owens.

Sigh. The weight of it all can feel overwhelming sometimes. But I know deep down that someone is bound to appreciate and echo my feelings, and it is there I will feel gratified to work and flourish.

I hope.

All this said, with all of the uprooting, personal strife, and sometimes oppressive sadness, my support network has stepped up in a way I couldn’t have imagined. My dad came to Milan twice, and will be here a third time before the year is out (I graduate from Bocconi on December 17).

My best friends from Tampa have come to see me—Matt (from Zurich), Tona and Randy, Mark, Brandie, Paul, Stephen. Plus a handful of friends passing through Milan from Tampa, like my neighbor Karl and his wife Isabelle, my childhood crib pal Steven Hoffstetter, and various acquaintances who happened to find themselves here.

There have been many Google Hangouts too, e-mails, and as I am a nerd for snail mail, a whole ton of postcards and letters from here and plenty received in return. Pro tip: the Italian postal system is easy to access, but inevitably you will hit a snag and have to come back the next day, or buy stamps from the tobacco shop because the post office is fresh out.

I have however found some rhythms and routines, like the gym I mentioned earlier. A hairdresser I like a lot, at a salon that is 3 minutes from my apartment. A handful of restaurants and cafes where I am actually a regular. A proxy for Whole Foods, albeit smaller and just as expensive.

What is clear is that this year, the hardest of my time living so far, has been about facing things.

Facing the emptiness that my mom’s death left. Facing a whole hell of a lot of uncertainty and discomfort and change. Facing my own lack of discipline in certain ways. And facing new realities about the working world.

What “facing things” makes you realize, especially when they seem so damn cruel, is that you will always find a way to cope. The human brain is so adaptable and infinitely capable of modifying itself. Looking back on the past year, however tough it was, gives me the feeling I can do anything now. Move again, find a job in a tricky economic climate, prosper.

Maybe that was the point of moving, of leaving my home. To gain confidence and become a wiser person via elevated struggle…