The lead up to leaving San Francisco

#MessinaOdyssey, Part 2

On March 3, I began my #MessinaOdyssey, taking an extended leave of San Francisco for the first time in nearly fifteen years. My rough itinerary for the next six months in can be found in Part 1.

Since publishing Part 1, I’ve been inundated with tips and offers of support and housing — I’m feeling energized and optimistic!

Absent from that post was how I came to my decision, so let me now fill in the backstory.

It would be foolhardy to attempt to reduce my last decade and a half in Silicon Valley into a taut list of perfunctory milestones, so I won’t. Things happened — both beautiful and painful. I’m a wholly different person than when I arrived in 2004; I’m more integrated in myself — grittier; and the deepening of my crow’s feet evinces the amusement and fun I’ve had too. (Trust me, I’m goofier than you probably realize.)

But over the last year, I’ve felt a growing discomfort within, like my bones had grown too big for my skin, or like that of a street-lining tree’s roots, compressed and inhibited beneath immovable concrete sideway slabs. I still haven’t pinpointed the origination of my discontent, but the pang to break out and shake free my root soil grew relentlessly. I had to make a change.

And then last November I got a letter informing me that my rent was going up 20% in February and I knew it was time to move.

I loved the city and still do, but it values something that I don’t have to offer right now, and that’s ok. It’s taken me a long time to develop the inner courage to leave relationships that aren’t working and it was time for me to leave. We’d grown apart.

You may not know this, but I quietly left Molly last April after Demo Day. My co-founders Esther and Ethan shut it down earlier this year and launched a new product called Squad. It seems to be doing well and although I’m no longer involved, I’m rooting them on.

After Molly, I explored starting something new (in the dating space no less), but the universe wasn’t having it, so I dove into the virtual avatar space for a hot minute and consulted for Facemoji, but that too didn’t quite stick for me (yes, virtual avatars will be everywhere in the future, but the current use case remains elusive). And then I received a series of invitations to speak abroad and decided to bundle them into a month-long trial to explore the nomadic lifestyle — starting in Lisbon with a panel at Web Summit, followed by a TEDx talk in Izhevsk, Russia and finishing off with keynoting MailUp’s conversational marketing conference in Milan.

Although I’ve traveled the world, I’ve never planned or traveled solo for an entire month, so this trip tested both my logistical chops and perseverance.

Within the first 10 days of my trip, my Airbnb was broken into at 5am by three thieves while I slept. They stole my laptop, cell phone, wallet, shoulder bag, and a friend’s Gucci bag and high end camera and lenses. The thieves were only scared off upon entering the bedroom where I’d been sleeping and realized that the apartment wasn’t empty.

No one was hurt, they missed my passport, and my renter’s insurance eventually covered the items that were stolen, but my digital life was significantly imperiled. Since I had enabled two-factor authentication on most of my accounts and both my phone and laptop had been stolen and I hadn’t printed out the backup codes (I know, I know), I was locked out of my most important accounts (Google, Twitter, Facebook, Instagram, my bank and credit card accounts — FUUUUU…). And since most services fall back on SMS to restore access and there are no AT&T stores in Lisbon and they wouldn’t ship an American SIM internationally, things looked pretty bleak.

Feeling a little lost in Bairro Alto

I’ll spare you the details about how I eventually recovered and re-secured my accounts (a worthwhile story for another time), but I took away several useful learnings, including:

1. Stuff is just stuff and can be replaced; personal safety is invaluable.
2. After the break-in, I flipped into triage mode, calmly recording the sequence of events and inventory of items taken while it was still fresh in my mind to expedite the police and insurance processes. This proved critical to a speedier recovery.
3. People were willing to pour out help and generosity if I just asked —including strangers who I’d only just met.

That time Saksham and I hung out with astronaut Mike Massimino

More on that: one of these strangers included Lisboan Nuno Loureiro. We met only the night before the break-in on a crypto cruise his company Bright Pixel co-sponsored and that I’d snuck on to with another new friend from Web Summit — Saksham Sharda. Although I was able to borrow a friend’s phone to call my bank and credit card company to lock down my cards, I still needed to replace my laptop and phone. Since he was local, I reached out to Nuno for advice on where I should buy Apple products. On his recommendation, I went to buy a new iPhone, but the only MacBook Pros they had in stock had Portuguese keyboards. I just couldn’t bring myself to drop $2500 on a machine with a keyboard in a foreign character set. Ordering one from the states would take weeks to arrive — long after I’d have left for Russia.

Graciously Nuno not only offered to loan me one of his company’s MacBook Pros, but also offered up his offices as a coworking spot — which I happily accepted. And after I’d exhausted all other options to obtain a new MacBook Pro, he once again bailed me out and let me keep the loaner for the rest of my journey — through Russia and Italy. Considering Nuno didn’t know me from Adam, this was an incredible act of faith and good will.

Not the worst place to prepare a TEDx talk

My next stop was two hours to the east of Moscow by plane. The Izhevsk winter reminded me of the short, cold, slushy days I endured in Pittsburgh. But Brian and Misha Capitano, two co-organizers of TEDx Izhevsk, greeted me with warmth and support and put me up in an historic rustic bed and breakfast called Бобровая долина (“Beaver Valley”). Misha had invited me to speak to inspire the citizens of her city to think expansively about economic development, especially in the tech sector. Historically, Izhevsk could be considered the Detroit of Kalashnikovs — though recently it’d become a hub for software development outsourcing. While these jobs are good, she wanted to encourage her community to design and develop more original products, so that they could reap the upsides, rather than just cheaply build products for others. Thus my talk — on the origin and philosophical inspiration for the hashtag — was meant to still an appetite for risk taking, starting small, and embracing both a willingness to fail and to work more openly (behaviors that I learned are inhibited by conventional Russian culture).

When I got to Milan, my keynote went over well and I made a fast friend in Armin ZadakBar, a fellow conference presenter. Turned out he was local to the city and gave me an enlightened tour, presented me to a class of future entrepreneurs at one of the largest coworking networks in Europe, recorded an interview, and then introduced me to the best burger in Milan, which happened to be sold at a joint he co-owned. I also occasioned to meet up with Fabrizio Rinaldi and Francesco Di Lorenzo, two developer-designers who make the Boxy series of apps (including Boxy for Twitter and Boxy Suite for Google apps). Although I’d only known them online, my ass was saved yet again when they volunteered to mail Nuno’s laptop back to Lisbon after I attempted to mail it back on the last day of my trip, only to discover that the Italian post isn’t open on Sundays! Amazon is coming for you, Poste Italiane!

The Lab’s Gourmet Burger

I returned to the United States early in December. I’d survived a month abroad, in foreign territory — my shit had been taken, I’d been violated, and yet made it through okay. The universe rewarded me with friends, adventures, and positive surprises that I couldn’t have predicted. Most importantly (probably): I didn’t die!

So I resolved to take an even bigger leap and spent the remainder of December and parts of January prepping, packing, and purging —with a brief sojourn to the Philippines for Kat Borlongan and Renaud Visage’s wedding. Once I returned, I decided against the new fancy high tech storage solution for something a bit more conventional and moved everything out of my place. I had amazing and unexpected support from new friends—without whom this whole enterprise wouldn’t have been possible. They know who they are. I dropped off my keys on February 10 and for the first time in my life, no longer had a fixed address.

P.S. I’d be remiss if I didn’t mention at least one of the two tattoos I got during this journey:

Coming Soon: Part III

So now that my odyssey is underway, all that’s left is to dig into my current area of focus — coming up in Part 3!

Also, Saksham Sharda, my friend from the crypto cruise interviewed me! Check it out:

What if the Romans had #hashtagged their written Histories?

☞ Chris eventually reads every response on Medium or you can chat him up on Twitter, send him an email, or subscribe to his seldom email newsletter. Do let him know what you think .