(#022) Tokyo9 Act II (revised)
DISCLAIMER: This is one of two articles that were originally published as a single piece titled #003 Tokyo9, Act II: A bridge across.
The original article covered the second of my nine trips to Tokyo which I took in 2024, as part of my Tokyo9 project.
Given how life-changing 2024 has been for me — and how pivotal my trip to Tokyo was in this transformation — the first draft of the article evolved into a story of self-renewal, rather than a travel journal.
Later, I took the advice of my dear friend ‘K’ (the same most influential friend I often mention in my articles) and decided to split the original article into two standalone, yet deeply interconnected, parts: one focused on my personal cycle of self-renewal (now published as #003 A bridge across), and another centered on my days in Tokyo — an extension and revision of the original article.
The latter — still a work in progress — is the one you are reading.
Preparation
My Tokyo9 project was originally conceived as “a nine-year exploration of Tokyo’s inspirations, interwoven with my new quest for a life renewed. It was going to encompass and symbolize everything meaningful I am lucky to have — and be — dedicated to the woman I fell in love with and married in 2018.” (Verbatim from my account of the first trip last year.)
That first trip felt less like the beginning of a meditative exploration and more like a particle accelerator, spinning me close to 299,792,457 meters per second before jerking the trajectory into a head-on collision.
So yes, I had reason to be anxious this year.
What if I panicked again? This project was supposed to keep me tethered to Asia — to the world I discovered in 2004 and led me to everything I’m proud of: my confidence in crossing the globe and setting up a new life, connecting meaningfully with people and places, being a force of creation, and building realities from visions.
What if all of that had been compromised? What if I’d lost the ability to travel — and my mojo to connect? What if, when I left China, I also left behind the ‘me’ I was proud to be, and the life I had painstakingly learned to navigate?
What if, when I left Asia, I left the adventure behind?
Luckily, the craving to stay connected was stronger than the fear of failure. So I started planning early in the year — even before I finished writing the story of my first trip (which you can find here, but wear your helmet You have been warned.)
The early preparation days covered all the usual suspects: photography locations, cuisine must-tries (including an A-to-Z ramen list), specialty coffee shops, nightlife venues, stationery meccas, and logistics.
But despite the growing list of targets and attractions, the trip lacked a defining identity.
As often happens, the breakthrough came during a workout session — when your mind is oxygenated, and your thinking turns laser-sharp.
On April 1st, while taking a sauna after an intense chest day, several neural pathways finally lit up and connected:
Why not combine the blue-ocean search for inspiration behind Tokyo9 with the focused sense of purpose that Jam Nation— my new business venture — was bringing to my life? After all, one of the tenets of my search for new business adventures was that they would take me traveling to the places I love most.
The conjunction felt perfect: blending my nine-year project in Tokyo with my recently launched start-up by making Japan one of its primary markets. What better excuse to reach out and connect — to open doors, spark dialogues, meet people, and establish ongoing collaborations?
But wait, there was more.
I wouldn’t just dip into the local music scene, research live venues, explore schools and communities, and connect with musicians online.
No.
I was going to bring my trumpet. Hit clubs. And play.
∞
I booked my flights and hotel — October 4th to 13th — and began my outreach.
I wrote to every music school I could find online. Whether prestigious institutions the like of Senzoku Gakuen College of Music, Showa University of Music, or Yamaha Music School; modern international programs like the Tokyo International Music School; or individual private teachers offering their services on various platforms.
All the messages followed a similar line:
“Good morning!
My name is Luca Ferrara; I live in Milan, Italy, and will travel to Tokyo between October 4th and October 13th.
I have been studying jazz trumpet for the past four years and am intermediate in level (I just finished my first year at Civica Scuola di Musica in Milan: https://musica.fondazionemilano.eu/).
I am looking for other jazz students — ideally those with a comping instrument such as pianist, guitar, bass, or double bass — to arrange for jam sessions during my time in Tokyo.
I am sure this is a wonderful opportunity to enjoy music practice and make friends from around the world!”
I knew these were messages in bottles — tossed into a storm, Force 12 on the Beaufort scale — and I wasn’t expecting much. If anything. But when you’re trying to create something out of nothing, you’re playing a game of odds. You have to trust the power of big numbers.
You only need one.
Next, I spoke to the concierge at my hotel. I described my project and asked if they had any suggestions.
I researched music studios and rehearsal spaces — figuring that’s where local musicians gather and possibly network. I identified two major chains: Studio Penta and Studio Noah. I connected with them via LINE (I downloaded it just for this), and asked if they could put me in touch with musicians, schools, or any relevant communities.
I even cold-emailed people seemingly connected to Tokyo’s jazz scene — authors of books or columns, curators of jazz websites, jazz-themed podcast hosts. I won’t name names, but I cast a wide net.
Then I waited.
Days passed. Then weeks.
Silence.
Not surprising. This might’ve been the first time they’d ever received a message from a complete stranger saying, “Hey, I feel like making some music and that’s why I’m flying halfway across the world just to jam with a stranger — wanna meet?”
Give up? No sir.
I knew how to recharge my inspiration. And so, on June 10th — yes, in the sauna again — I had another idea: why not hire someone to help?
Back home, I posted a job on UpWork:
“I seek a smart, young-at-heart, and disciplined personal assistant to help me with selected arrangements during my trip to Tokyo in October this year. […] I am eager to meet other jazz music students who share my passion and arrange to meet up and jam together. […] I need help to: Identify jazz music schools in Tokyo or similar aggregators of jazz musicians […]; Open a channel of communication with students/musicians of jazz; […]; Inquire if they have an interest in setting up a jam to play together when I am in Tokyo; […] I am looking for students or musicians who love jazz music and would love to meet other music lovers from around the world and play together. […] As a SIDE NOTE, I am also the founder and CEO of Jam Nation (https://www.jam-nation.com), a platform aggregating music students and musicians for playing together. […] My trip to Japan also explores opportunities to bring my business to Japan. […] I look forward to hearing back from you!”
This wasn’t like my previous mid-tier job posts on the platform — where I would usually be swamped with bids in minutes, if not seconds.
This time responses were few and slow.
Until, two weeks later — June 25th — this message landed in my inbox:
“Hi, Jazz Trumpeter!
My name is Makoto.
I am excited to apply for the personal assistant role to help with your upcoming trip to Tokyo in October.
Although I am not young, I am also an amateur jazz pianist familiar with Tokyo's vibrant jazz scene, I am well-equipped to assist you in making your trip both productive and enjoyable.
Hope you find this link to see my piano.
[…]
My favorite pianists are Oscar Peterson and Michel Petrucciani.
Beyond music, I can provide advice on itineraries and offer local insights to enjoy Japan food, nature and culture.
I look forward to the opportunity to assist you and help make your Tokyo experience extraordinary.
Best regards,
Makoto”
Bullseye. A Japanese professional, English-speaking, amateur jazz pianist with time and enthusiasm to help.
Makoto and I had several clarifying exchanges, and four days later I hired him.
Almost two months into my prep, things finally began to pick up speed.
Over the following weeks, Makoto over-delivered: he dig out three major music schools, ten smaller independent ones, 21 venues with live jazz, all hosting jam sessions, resident jazz clubs at Tokyo’s top three universities, dozens of jazz-focused social media groups, and even jam events hosted by a co-working space chain.
The number and range of options quickly became a logistic puzzle. Makoto and I agreed to meet first thing in Tokyo to confirm every item on the agenda. He suggested the day after my arrival — to leave me time to rest — but I insisted to do it over dinner on the very day of my arrival, Friday, October 4th, not to lose one beat. And that’s how we arranged.
Then came the next breakthrough: July 2nd.
After almost a month of my letter to him, Simon — the President of the Tokyo International Music School — replied.
Not only did he reply, he invited me to play at their big band rehearsals.
Now I was fired up. I wasn’t ready to sight-read new scores on the fly — not yet — but just being invited felt like a huge karmic green light.
Simon also turned out to be an ideal person to ask about Jam Nation — an insider of the music education industry in Japan and an entrepreneur on his own: I made sure besides the “musical” encounter we had time to break bread and entertain the idea of working together in some capacity, and booked his time for an evening together.
And finally, I managed to schedule a private lesson on jazz improvisation with a Japanese music teacher who replied to one of the inquiries I left on an educational platform.
My problem soon shifted from finding events… to finding time over the course of 10 days for them all.
∞
Then there was the photography side of my mission.
This time, I decided that instead of writing a story about my trip, I’d turn the trip into a video — a properly scripted and produced one.
The fact that you're reading this tells you that didn’t quite happen. (More on that later.)
Videography only recently started making its way into my creative toolkit.
Like many photographers, I had resisted. It's staged. It disrupts the moment. It goes against the grain of a documentary photographer’s craft (my genre of choice in photography) i.e,. capturing spontaneity while hovering invisibly between participation and observation.
I spent hours, days, trying to reconcile how one can live an adventure and capture it on video — the way you can with the photographic medium, if you exercise that specific ability.
I never got to a satisfactory solution. (Until this very day… something I intend to write more extensively about.)
But I couldn’t deny the power of video: it brings time into the frame, music, immersive environmental sound FX, and — of course — scripting.
It’s transporting. But it’s also far more complex than photography.
I spent August buying gear and doing test shoots around Milan — picture me biking with a selfie stick, tripod, mics, and camera gear, talking into a lens — uncompromisingly idiotic. I’m not a YouTuber. And I’ll never be the type who works on creating content to please an algorithm while implementing the latest audience monetisation strategy. But the experience gave me deep respect for the nerve and drive it takes to publicly monologue to a camera without flinching.
I also started building a production sheet. As I said, you can’t improvise video. Run-and-gun only works in limited doses, and even then, it has to be intentional. Otherwise, it’s just noise.
By late September, I had a six-pages breakdown of scenes — dates, times, locations, equipment, narration, everything.
I was pumped.
Until…
The day before the departure
The first scene on my production sheet was scheduled for the day of departure.
To ease into the experience, I thought: why not shoot it the day before? That way, I’d have the peace of mind that, if anything went off-plan, I wouldn’t miss my flight or jeopardize the trip.
So, on October 2nd, I gathered all my equipment, set up camp in the living room, and started shooting.
It went disastrously.
Setting up each shot took forever. Properly exposing the light — far from an art, let alone a science — felt like solving a riddle. (In my defense, while photography books cover exposure in about a chapter, in videography, mastering exposure is one of the aspirations of a cinematographer’s career.) Capturing clean audio alone would have been overwhelming — shotgun mic or lav? Gain levels? Low-cut filters? Then there was the performance itself, the timing of movements. Action. No. Action. No. Action. And again.
Meanwhile, I was piling up gigabytes of footage, adding to the hours I'd need to process later in post.
And this was just me, at home, in the comfort of my apartment. What was I going to do out in Tokyo?
I was floored.
(By the way, imagine all this happening during weeks of classic Milanese gloom — cold, damp, rainy days. That doesn’t help.)
The trip wasn’t supposed to be only about making a video. But I had placed so much expectation on telling the story of my journey through that format that, when I realized I’d bitten off far more than I could chew, I spiraled into a mini-depression.
I even considered cancelling the trip altogether.
I had to make a decision.
I could either power through — insist on documenting every step, tolerate the apparent chaos, possibly hating every second of it, and hope I could edit it all into something with a sense…
Or I could give up on the video entirely.
The latter felt like such a failure. Months of preparation, so much work done, such high hopes — and now, barely 24 hours before departure, everything for nothing?
In hindsight, I realize I was trying to prove something to myself. Letting go of the video felt like defeat.
But there was also a less “negative”, more constructive and inspirational note to my unwillingness to let go.
I have always felt that there is so much more in documenting your life than the vanity of watching it again or (even worse) showing it to others.
Documenting your life expands it, stretches it left and right, allows you to accent the positives, dial down the negatives, process the experiences, discover new details and nuances, even completely reconsider your very own initial impressions, retain and remember more and in exactly the way you desire and need to remember, and eventually live more, for how can we live a large life if what we live through is lost the moment it’s gone?
But then, it was the softest voice in my head — the one I rarely listen to — that said: “You’re making this harder than it needs to be. With the preparation and agenda you’ve lined up, you already have more on your plate than most movie protagonists. Maybe you won’t come home with an epic film. But you’ll live the story — and that’s more than most get to do. Relax. You’ll be the star of the adventure. You’ll get to be the director some other day. Enjoy the journey.”
I’ll admit, I remained skeptical of that voice.
I kept looking back every single following hour and until the next day, wondering if I was making a huge mistake by putting the camera down.
But I also felt a burden lift.
My focus shifted back, undivided, to the journey ahead.
Departure day
The next morning — October 3rd, departure day — the rain continued. Cold, wet, loud, punishing.
What can I say — even more reason to leave.
The trip to the airport was uneventful. So was the first leg, Milan to Rome. Uneventful enough that I had the energy to pull out the camera again and record a few spontaneous thoughts. Not as part of a grand narrative — just fragments. Some were fun. A few insightful. Others, plain horrendous. (Nothing worth assembling as a document of the trip.)
After landing in Rome, I strolled through the international terminal at Fiumicino and made my way to the gate.
The flight was delayed. Seven and a half hours.
Perfect.
When your intercontinental flight is delayed that long, your first thought isn’t about how to rearrange things on the other end — it’s if you’ll fly at all.
I had no lounge access, no business-class seat to look forward to, and nothing remotely healthy or decent to eat. (Airports really require advance survival planning if you’re trying to stay healthy.)
So I started to wander the terminal, regroup my thoughts, and look for inspiration while stuck in this “half floor” between the basecamp I left behind and the adventure in front of me.
And then I saw it: Ajisen Ramen. A chain I’ve had a long-standing relationship with, dating back to my early days in China — twenty years ago in Shenzhen. It had been a staple of my diet.
I treated myself to a heartwarming bowl of ramen and took advantage of the half-empty restaurant and big tables to dive into a much-needed journaling session.
By the time I finished, the ramen had lifted my mood, and the writing had helped me process what was going on — inside and out.
Then I remembered a promo email I’d once received from my credit card provider about airport benefits (a subject I used to be a guru of. Now barely an afterthought.) I fumbled through the necessary portals and forms on my phone and, to my surprise, managed to gain access to one of the MasterCard lounges. I surveyed the place until I found a hidden enough corner, laid down on the floor, took my shoes off, and put my feet on the sofa (primitive, yes, but also very regenerative.)
Later that evening, we finally boarded — around 10:30 PM.
My seat felt even smaller than usual for economy, but I managed to doze off a few times. I stuck to my routine — kept my diet clean, drank plenty of water, avoided too much screen time. These small, healthy habits don’t just compound in the long run — they create an immediate sense of agency and intentionality. And that’s powerful for your mood and motivation.
Originally, I was supposed to land on Friday, October 4th, at 11 AM. With the delay, the new ETA was 5:30 PM — still enough time to reach the hotel, freshen up, and meet Makoto for dinner.
The arrival
I finally landed at 6:51 PM.
There was still immigration to clear, bags to collect, and transportation to figure out — though thankfully, I’d flown into Haneda, a mercifully short 30-minute ride from my hotel. But my roaming plan wasn’t working, and I ran into issues registering for the airport Wi-Fi. I couldn’t get a steady connection, which meant I wasn’t able to reach Makoto properly.
I was painfully aware that he had agreed to meet for dinner purely out of kindness: reviewing my weekly plan wasn’t part of his job, nor was he compensated for it — and now, he had to deal with the uncertainty of my delayed arrival, all while barely hearing from me. I tried to communicate and suggest regrouping the next day.
But Makoto, in his usual grace, made no fuss. No stress. No time constraints. He simply replied that he’d wait for me — not at the restaurant, but at the hotel, to welcome me at check-in.
His calm generosity was a balm for my travel-worn spirit. There was comfort in encountering a person — and a culture — that instinctively knows when and how to ease the emphasis on schedules, performance, and the relentless to-do list we so often glorify back home. Instead, they attune to the essence of things: the beauty of connection, shared moments, discovery, serendipity — and true hospitality.
I cleared immigration, collected my luggage, and was out of the terminal by 7:34 PM. I allowed myself the luxury of an Uber to save time, and let Makoto know my ETA was 8:16 PM.
Things were slowly clicking back into place.
Then I pulled out my camera, checked a few settings, and hit record.
The footage I captured from the backseat of that car — it changed everything.
Let me be clear: it’s bad. Technically, it’s awful. The exposure is off. The sound is thin. The image is shaky (and not in deliberate ways). The lighting is harsh. It looks like the work of someone who’s been run over by time zones.
And yet… it’s raw. It’s real. It’s present. It’s honest. It’s mysterious. Dreamlike.
It captured exactly where I was: two hours of domestic travel, eight hours of delay in Rome, thirteen hours of economy-class flight. I was entering a week packed with high-adrenaline events — including public jam sessions — while quietly mourning the defeat of the “perfect video” I had dreamed of making.
And so, that imperfect, clumsy clip — that was me. That was the moment. Flawed, exhausted, vanishing, but true.
I still revisit it from time to time.
The clash of a grand soundtrack with blurred, out-of-focus imagery. The sense of being in a space station, watching distant clusters of light. The loss of control over space and time — and yet, the certainty I was flowing toward exactly where I wanted to be.
By most standards, it was a failed shot.
In my book? A resounding success. Among everything I’ve captured, this remains the most powerful window back into that journey.
I arrived, stepped out of the car, and made my way to the front desk. After introducing myself and showing my ID, I scanned the room for Makoto.
There were barely any guests in the lobby. Perhaps the hotel was lightly booked — or more likely, the staff were so efficient in their welcome, check-in, guidance, and problem-solving that no one lingered long. Either way, it was easy to spot Makoto.
I asked him for one last inch of patience so I could freshen up, ran upstairs for a quick two minutes, then came down with a single, focused craving: food.
Unlike the usual warm-up period that comes with meeting someone in person for the first time, I felt immediately at ease around Makoto — almost energized. I believe that the feeling of having “made it to the other side”, despite the setbacks and physical hurdles, naturally focused all my efforts on one priority and one priority only: seizing everything there was from every single instant and live as a celebration.
In retrospect, crossing paths with him through UpWork, insisting on meeting as soon as I landed, and his generosity in waiting for me — it made all the difference for this edition of my yearly trips to Tokyo.
This time, the trip began with a human connection.
Last year, during Act I of my Tokyo9 project, I was the protagonist and Tokyo the setting — or maybe the other way around.
There were no other characters. Not really.
This year, my presence was more of a nexus: connecting the people I arranged to meet, the plans for a new venture, my passion for music, and the scenes and communities it led me to.
Rather than an object moving through space, I was the force that set things in motion.
Makoto had already made plans for our dinner.
Unsurprisingly, his choice was spot on: a yakitori place beloved by locals, yet well outside tourist circles. It was ten minutes away on foot, nestled in the alleyways of the Gate of the Tiger — the elegant neighbourhood of Toranomon.
He led the way with the help of his phone.
We got lost, repeatedly. One might think this would be frustrating — especially on an empty stomach — but if I’d tried to craft an immersive, mood-setting experience to ease myself into the moment, I couldn’t have done better.
It almost felt like he got lost on purpose,
just to lighten my guilt of missing our original plan, and turn it into an adventure we were now sharing.
We zigzagged through alleys, climbed narrow stairs, ducked into side streets and small doors. Everything was so clean, so safe, so well-lit and decent and dignified — even the scent of the city felt warm and reassuring — and yet never obvious, never lacking in wonder, surprise, and adventure.
So very Tokyo.
“Irasshaimase!”
The host’s welcome rang out as we stepped through a doorway at the end of a narrow staircase that vanished into the side of the street. We took our seats, right in front of the pass-through window looking into the kitchen, a privileged vetrina into the behind the scenes.
Japanese menus — well, menus. Makoto did the ordering.
I indulged in a beer — an exception to my new, much-celebrated diet (On cholesterol and renewal). A Yebisu, brewed right here in Tokyo, near Ebisu Station, in the Taito ward.
The sense of place was already into outerspace.
The house specialty — named after the place, Tsukune — was a reinterpretation of a classic chicken skewer (also an exception to my diet). A juicy, fluffy, superb chunk of minced chicken meat held by a pair of parallel skewers.
If you wanted to design one flavor that captured everything Japan could be — lights, scents, products, rituals, excellence — pack it into an unassuming medium ready to explode left and right in your mouth, that would be the taste.
As I bit into it, I felt in my heart that this Act II would be an entirely different animal. Doubts, sadness, anxiety — all of it washed away like seashells pulled back into the ocean.
I swear I felt mist building in my eyes as my self-consciousness was perfectly aware I was part of a unforgettable adventure already.
It’s not the agenda.
People, connection, and the symbols and rituals that celebrate them — they’re what separate bliss from doom.
I felt free to speak my mind without filters or ulterior motives. I ate gloriously, drunk with satisfaction. We spoke with ease and openness. It felt like instant friendship — I don’t mean the lifelong kind — like the one I have with K — but still an uncomplicated sense of trust, honesty, and mutual respect. A genuine connection with no transactional strings.
Encounters like this — were at the very core of my renewal goals.
Once we finished everything we ordered — and reordered — and after the usual elegant exchange to see who was going to take the bill, Makoto walked me back to the hotel, agreed on a time and place for our meeting the next day (our first jam), and left me in the generous hands of one of Tokyo’s most legendary hospitality team — the Okura Garden’s.
I went to sleep shortly after settling in the room without indulging too much in reliving the day or anticipating the week ahead. There was really nothing to take away nor to add to the scene to make it perfect. Cut.
I slept with confidence and gusto.
What a difference from the first night I spent during my trip to Tokyo last year.
I don’t know if I’ll ever manage to fully recount everything that happened between Saturday, October 5th, and Sunday the 13th. Those days were overflowing — every moment packed with habits and sparks of renewal that came to define my 2024, as I devoured everything Tokyo threw my way. I walked so much each day that my legs and feet ached with real, physical pain.
Maybe one day I’ll do this story proper justice.
But for now, here’s a rough “dump” of notes, journals, and photos — a sketch of an extraordinary chapter.
One… two… One two three four!
Saturday, October 5th.
The next day began with an 11 a.m. jazz improvisation class with a teacher I had found and booked online. The lesson was at his home in Setagaya — Tokyo’s second-largest ward by size and the most populous, with nearly a million residents — located in the southwest of the city.
Even with the exact address in hand — and, truth be told, with Google Maps doing a heroic job — getting there still involved navigating directions like:
(Me) “I’m on the Chiyoda Line. I’ll text you after I transfer to the Odakyū Odawara Line at Yoyogi-Uehara.”
(Kelvin) “The Odakyū Odawara has an express, a super-express, a semi-express, and a regular line. I suggest you get off at Omotesando, wait for the semi-express on the Chiyoda Line, then ride it straight to Chitose-Funabashi. No need to transfer again.”
You get the idea.
Despite the unfamiliar location and convoluted commute, I arrived at 10:39 a.m. — one minute early for our 10:40 meeting at the station. Nothing surprising, given where I was. Still, I couldn’t help but reflect on how often I feel out of place in Italy when I arrive five minutes early, only to wait twenty minutes for others to… come downstairs.
When everyone else plays by different rules, it takes stamina — and a dash of well-managed schizophrenia — to insist on marching to your own drum.
Kelvin came to meet me at the station, greeted me warmly, and walked me back to his place.
Naturally, I began diving into his story as soon as we introduced ourselves. That was just as important to me as the lesson itself.
Living life without genuine curiosity for the people who become part of it — especially those we’ve chosen to bring into our world, for a part large or small, as I did with Kelvin — would make for a flat and narrow existence.
It didn’t take long for us to establish a heartfelt rapport. Kelvin, a Japanese national, had spent most of his life in Singapore. He returned to Tokyo during the COVID years, accompanied by his Chinese wife, to be closer to his family.
To my surprise, he was fluent in Mandarin — something I hadn’t expected — and we ended up conducting the entire lesson in Chinese.
I carry a deep sense of loss about not speaking the native language of everyone I meet, not being able to connect with them at the most intimate level. So even though Mandarin isn’t the local tongue, but it was a language dear to Kelvin, and speaking a common language other than English in that context gave the whole encounter a magical dimension that didn’t go unnoticed.
It felt like we met at a crossroads — two people not quite rooted in where they were, whose paths happened to intersect in the most serendipitous of ways.
The lesson itself was fantastic. I hadn’t set high expectations; I was mostly seeking the experience: to meet someone new, share a moment, and dive into something we were both passionate about. But I left with more than I’d hoped for — useful exercises and a renewed sense of joy in improvisation. I played with more abandon than I had in quite a while.
By the time we finished, it felt like more than just a cut-and-dry class. His wife must have sensed the good energy between us — she made a point of taking a photo of us together (thankfully, or I would have forgotten).
The magic I’d set out to cultivate in this trip — using music as a fast-track to genuine human connection — was working.
I made my way back to the hotel to freshen up, change, regroup my equipment, and head out again (a routine I repeated at least twice a day for ten days straight, whether for music performances, photographic sessions, or mission-critical stationary shopping.)
This time, the destination was a club called Somethin’ Jazz, in Ikebukuro, a district in the Toshima ward, nearly an hour north by public transport.
The weekly program at Somethin’ Jazz perfectly illustrates how deeply Tokyo’s jazz culture is embraced — far more than in any other city I know. The club hosts jam sessions every day it’s open, dividing events into “Jam Sessions” and “Jam Parties,” and running two separate stages on different floors: one dedicated to jazz, the other to funk. The “Jam Sessions” are traditional improvisational gatherings, while “Jam Parties” are designed for less experienced players, with an unspoken agreement among participants that less-than-stellar performers are also encouraged to take the spotlight.
I attended Saturday’s jazz Jam Party. Though it openly welcomed beginners, this was not just my first jam session in Tokyo — it was my very first public jam, ever.
I was nervous.
Makoto was going to join me there.
I wasn’t sure whether to feel reassured or a bit uneasy. Having someone I knew in the audience meant I wouldn’t face the stage alone, but it also meant that if I flopped, it wouldn’t just be in front of strangers — it would be in front of someone I had a connection with.
I arrived several minutes early and went looking for food. Makoto had told me it was good practice to bring something to share at these “Jam parties.” Unfortunately, I couldn’t find any open stores nearby, so I decided to head to the club first and scope it out. I figured Makoto and I could go grab our share of the buffet together later.
When it was time to play, I took the stage, did a quick warm-up to get my chops ready, and called out a few tunes — All of Me, Softly as in a Morning Sunrise, Summertime — all basic standards in a beginner’s jazz repertoire.
The club hosts provided rhythmic comping on drums and double bass.
Makoto sat down at the piano. I expected him to hold his end, but what I didn’t expect was his ability to improvise brilliantly over any tune I (or others) called — no sheet music, just pure memory of progressions and melodies, barely glancing at the keys. He was more than technically flawless and melodically eloquent — he was a virtuoso.
My first thought as I stood there after my intro and solo, was: “I’ve been corresponding with this person for four months now. We’ve been planning to take Tokyo’s jam sessions by storm, collaborating on a platform for both amateur and professional musicians. We broke bread, and shared an Ebisu beer together. And all this time, the only mention of his piano skills was ‘I am an amateur piano player.’”
Honestly, most amateur musicians I know — and certainly every professional one — would make their skill level the center of every conversation if they were half as proficient as Makoto was. But Makoto never indulged in that, not even close.
Everyone on stage was friendly and gracious, making me feel truly welcomed, sharing the same curiosity, openness, and joy I brought from across the world.
And I felt a deep pride for summoning the courage to be on stage for the first time — and that it happened in Tokyo.
Monday, October 7th.
(…hands down the best breakfast I have ever had in my life;)
(…my early morning workout routine, and the unexpected physical test I took at the gym;)
(…closing Volume 5 of my Stalogy journal series, the one that took me through the greatest renewal cycle in my life since 2007, when I launched my first business venture;)
(…getting coffee at Bongen Coffee and visiting Tsukijigawa Kameibashi Park — closing a circle that had to be closed;)
(…meeting Simon Beston of the Tokyo International Music School for dinner.)
I see… colors
Tuesday, October 8th.
When I founded Tokyo9, photography was the art form of choice.
Music is profoundly engaging, yes — but the interaction between artist and audience usually happens through the art itself. It’s mediated, abstracted.
Photography — at least the kind I’m drawn to: documentary, photojournalism, street — demands something different. It asks you to approach. To open up. To strike a conversation. To get close enough that people let you in. Sometimes that human contact is what separates a good image from a great one. It’s a discipline that involves technique, yes—but also empathy, timing, courage.
Becoming a better photographer means diving deeper into the moment and closer to the people in it.
I cherish both my passions, but if I had to choose one, I know where my heart would fall.
And on this trip, I dove into photography more fully than I had in years.
So transformational was this journey that…
I transitioned into color.
That may not sound life-changing. But after five years of shooting almost exclusively in black and white, the shift felt almost dizzying. For the first time, I truly saw color — not as a distraction from the subject, but as an expressive element in itself. I began to understand how color can evoke mood, deepen emotion, even become part of a visual signature. I used to find it arbitrary. Now I saw it as essential. Color is part of how we experience the world — it has meaning, whether a particular color is the product of a deliberate choice, or simply chance.
I also started to let go of the belief that every photograph had to center around people.
For years, I looked down on shots that didn’t feature a human subject front and center. Flowers, buildings, empty streets — these felt like evasions. Lazy. Cowardly. I judged every photo without a person in it as somehow lesser, even when I found it intuitively striking.
But something shifted.
A weight lifted. I began to embrace the idea that a photograph can simply be a vessel for emotion — even if that emotion is quiet, or solitary, or stirred by a scene without a soul in sight. And if an image moves someone — even just yourself at some later time — then it matters.
My technical skills grew as well. I pushed myself on multiple fronts, and I continued to experiment with video — something I had originally envisioned as central to this whole trip and this very account. I shot footage throughout the journey, capturing not just moments but motion.
Ironically, it rained on nine out of the eleven days I spent in Tokyo. And yet, I stayed out. I walked through the rain. I photographed through the rain. I ran through my agenda undisturbed — energized, even — as if under the brightest sun. (And somehow, I didn’t even catch a cold.)
(…dinner with Makoto;)
(…drinks at the SG Club;)
Wednesday, October 9th.
(…practice session at Noah Studio Ginza;)
(…shopping for stationary in Ginza;)
(…attending the rehearsals of the Tokyo International Music School Big Band;)
Also, not a day went by without a chance encounter, a reason to feel welcomed and socially engaged or to celebrate serendipity. The experience reminded me how beautiful it is when you give a chance to life and engage with others building relationships out of the blue. That is a defining part of the person I am and I do want to keep it alive.
Accounting for all social exchanges during my trip would be a daunting task, but here is one story that stands out.
During my visit to a world famous Korean BBQ joint in Shibuya I picked up a conversation on a moment’s notice with a small group of salarymen (in the best sense of the word: young driven professionals in their best outfits).
I pretended to be some kind of celebrity.
I referenced the framed signatures hanging on the wall near the entrance to suggest that one of those was mine. I must have done a real good acting job, or the sakè they enjoyed during dinner worked to my favour, either way they thoroughly believed me.
In the meantime, the small group turned into a small audience and more and more colleagues joined. By the time I broke to them the fact that I was joking, the crowd’s laugh was loud and earthy.
This eventually drew in the attention of their boss who — with the greatest kindness and most affable of ways — joined the conversation and grew an interest in my story. I returned the interest, and asked several times what his company do, to which he replied, “I work in a software company.”
Fair enough, this could have been one of millions of stories. But there was something visibly different about the way he said “I work in a software company.” And so, of course, I couldn’t let him go so easily.
I insisted that his answer was a bit too generic and doubled down on my question: “what about it? Which company?” and eventually found out he was nothing less than Hiroshi Mikitani, founder and CEO of Rakuten, one of the two or three most successful and famous entrepreneurs in Japan.
Now, I have never been star-struck by wealth and success (I met and done business with my share of billionaires in my life and, in fact, mostly disliked them) but his kind and humble ways were warm and hopeful and this made the event very special.
Eventually, I was so much into the moment that I even forgot to think about the potential upsides of a business exchange. I didn’t suggest to exchange cards and didn’t pitch my start-up. Because of this I felt like an ass for days afterwards, but the memory of the event remains one of the fondest memories I have of the trip.
Thursday, October 10th.
(…photography from iconic locations in Shibuya;)
Friday, October 11th.
(…coffee at Coffee Wrights in Taito-ku;)
(…jam at the Tokyo Institute of Science university’s jazz club;)
I also caught Kandace Springs at the Cotton Club.
Needless to say Kandace — playing along with Liany Mateo at the double base and Camille Gainer Jones at the drums — was a breath-taking show.
I didn’t feel this way about listening to music in quite some time and it reminded me of how different it is to experience music live, both for the quality of the music and for the human touch it acquires when you have direct sensorial evidence that it’s real people actually creating those melodies and harmonies you hear.
As high the quality of a recording can be, the reproduction of music will never compare to spectating its making.
(…discovering Ginza Soryu, who ended up closing the restaurant just to keep me and the other two patrons in privacy, and spending a late evening chatting and joking with total strangers — along with the chef — met at a sushi place;)
(…bar Kage, Tokyo’s best whiskey bar;)
Saturday, October 12th.
(…early morning in Harajuku;)
(…breakfast at Little Nap Stand and taking pictures of kids playing baseball;)
(…attending the Yokohama live jazz music festival;)
(…visiting and photography at the Mori Art Museum;)
(…night-time photography in Shibuya;)
Conclusions
But the greatest take away has been how all of the entire trip led me to realize that Jam Nation, my new enterprise, was already the new adventure I was seeking for to move on to my new life.
Being in a foreign land, and a land full of energy and inspiration, created the environment I needed to feel comfortable to be my new self without any resistance from the old world’s constructs that try to keep each of us as coherent with the rest of society — and our former self — as possible.
And so, throughout my trip, and through each experience — musical, photographic, culinary, social — I had the courage and ease to embrace and experiment with fully wearing my new hat, and the world reacted with nothing but positive vibes: principals and students at music schools showed their interest, bar owners and bar patrons showed their interest, and even during the most occasional of encounters I had a chance to make an impression and leave a footprint as leader of a new initiative.
My new (ad)venture was also providing me a platform where to anchor my newly built relationships and to create expectations of things to follow, news to look forward to, and opportunities to share upon the official launch and certainly at my next trip back to Tokyo (for Act III, in 2025.)
And, yes, I do feel the sense of challenge and fulfilment that comes from having chosen a course of action true to myself and being fighting for it, but this is the ultimate sense of adventure!
I had to embrace a new start with a beginner’s mind, gathering all the humbleness that comes from embarking on a journey as a novice — as opposed to an expert — while at the same time fighting the cynicism — from others as well as from myself — that kept me from dreaming big.
During the last few days of my stay in Tokyo, I felt I there was nothing I was missing about my life in Italy if not my family.
I feel deeply proud of the way I went back to an alien place and in ten days built a world around me I would feel completely at home into.
I didn’t simply feel in a comfortable trip, I felt I established all my ecosystem: human, logistics, social, and even my own sense of purpose. Just the way it happened when I moved to China twenty years before. I made myself fully acclimatised and naturalised, and this is not something to be taken for granted — it’s one of those skills I learnt in the years, and
to see that I could still move to yet another country, following my inspiration, and make a world and a life out of it without looking back or any feeling of longing was deeply gratifying.
As I was on my way to the airport, I also felt that the foundation of a bridge across my life in Italy and my adventure in Asia — through my new business — was established.
This may not be the condition of total abandonment I had the privilege of living through in the past, but my belief that something so remote could be built, using a little faith in what I was doing, a little confidence that I would find the way, and realising that my family and my close friends were in fact making my experience and my adventure even more complete and meaningful — because I could share it with them — were already working their magic.
If I look back at the events of last year — Tokyo9 Act I — it’s incredible how even the most patchy, scant, disastrous start can take you to places you would never dare to imagine.
Places so much closer to your dreams.
All you have to do is find the courage to begin again.
L.F
