I had three really great conversations this week.

I have been leaving myself on Skype more lately because otherwise I’m essentially shut off from the world. I’m ‘derekshanahan’ there if you’re looking for me.

Twitter is one thing, but twitter is a different beast.  That’s a place to get information, reach out to people quickly, and get eyes on pieces of conversations.  Never the whole thing.

These weren’t geek conversations though.  These were my best friends an my little sister.

Cha-rule’s been my girl since I knew what girls were, and when she left Chicago I really felt the earth move.  Man we were rocking Chicago for a while; concerts a few times a week, late weeknights and early work mornings.  I met my last girlfriend through her, even.

She’s in Denver now and she loves it.  We laughed about how weird some of the people we’ve known turned out to be, and how much love we have for them.  We marveled at our friends having babies and what a different it makes when you don’t have to wear a coat outside in February.

Murph called me last night, and he misses me.  I miss him too.  It was a whirlwind, leaving Chicago, and in large part because it coincided with my acting as his Best Man in January.  Having attended the same school with him since 3rd grade, and subsequently living in Chicago (together for a majority of my time there), this is kind of the first time we’re not in the same place.

It was interesting to hear his take on my decision to chase dreams.  We laughed about how my Dad probably still hasn’t told me his real thoughts at first hearing my ideas.  How his Dad would have said, “Derek, you’re being stupid”, in the way only his father could without it being mean or demeaning.  Haha…my poor father was probably thinking the same thing.

We pretty much laughed the whole time.  Laughing via Skype usually means a laptop bouncing around your lap…a use case I wonder if they looked into.

And my sister and I chatted, finally…my little little.  She’s in Denver as well, loving the face off of her internship there and trying to figure out what’s next.  She’s headed to Notre Dame (bite my tongue) in the Fall, but last weekend was flown to NYC to partake in a youth summit/internship interview type thing with Goldman Sachs.  Not. Shabby.

We laughed about our kooky parents and contemplated the question marks in our futures.  She has friends going to SXSW so I had to explain that I was going to the Geek Bonnaroo, not the music part that normal people attend.  She gave me a video tour of her crash pad down there, and introduced two of her roommates who were hanging around.

She’s so good at life.

I’m scrambling to get things ready to go down to Austin for SXSW, and these conversations were all exactly what I needed before a geek scene.  I guess it’s ironic that Skype brought such wholesome, real connection into my lap before four days of ‘location-aware apps!’ and ‘geo-spatial data!’ and ‘foursquare vs. gowalla!’ but in the end I’m just energized at the timing of it all.

See you in Austin?

At the end of September, I moved out of my apartment on Division Avenue in Wicker Park and in with one of my best friends, Braden.

I haven’t lived in a place I’d call my own since.

Living in the domain of other people is something you get familiar with in college.  It’s a unique experience for most; those of you who went to boarding schools or those fancy East Coast prep schools were rocking the roommates even earlier.  Maybe boarding schools and prep schools are the same thing, actually…honestly I’m just a Midwest guy who played soccer and passed Calculus.

Either way the Rules of Life’s Trajectory usually dictate a point at which you don’t live in another’s domain at some point in your mid-twenties.  I did rent on my own in Wicker Park starting at about 25 or so, and I did love it…I reached the point of no return on living with roommates.

I thought so, anyway.

Ironically, living with Braden was a lot of fun.

It was kind of like a vacation in some ways, and at that point I had quite a bit of uncertainty in my life and couldn’t have made it through that without his generosity, so if you’re following him on Twitter I wouldn’t be upset if you sent him naked pictures or money.  Back then we were already spending most of our free time together and it saved us the four blocks walk between our places, which is pretty significant once it’s December and Chicago is frozen solid.

Since arriving on the Left Coast I have stayed in three different places (as of this weekend).  I’m still transient, and it’s been so long that I’m pretty darn comfortable with being transient.  It’s amazing the way life just sort of happens, and you can get comfortable with the way things were or you can let Change influence tomorrow.

My tomorrows are largely dictated by the almighty Change, as it were, and at thirty years old I feel a combination of irony and comfort with the whole thing.

I never thought I’d be thirty and living in a new city with a bunch of question marks sitting on my calendar.

I also can’t say I’d feel any more comfortable with an alternative path.

When I think about a few years ago, in a serious relationship (with a wonderful girl) and trying to put together pieces of a future in Chicago, I know that even that life was chock full of question marks.  When I read all of the wonderful bloggers I’m fortunate enough to follow; people of all ages and walks of life; I see one common thread…tomorrow’s not always what you thought it’d be.

I’m not knocking stability.  I do wish I had more, sometimes.

Yet, there’s nothing traditional about the lives of the people I know.

Even the people I know who have traditional jobs or traditional love lives or a measure of habit and repetitiveness in their days.  Even my parents, who’ve been in St. Charles for more than twenty years, still manage to face total chaos somewhat regularly.

People get pregnant, sick, fired, and bored.  They write books and get promoted and take vacations that change their lives.  They get into grad school and drop out of college and follow their instincts.

The only thing that remains constant is how mixed up and crazy the world can be.

If you’re not sure what Bonnaroo is, it’s the mecca of current music festivals.

If you are aware of Bonnaroo, and you just got your pants all bunched up because you think Coachella or Lollapalooza or Lilith Fair takes the crown as the mecca of music festivals, I’ll just say that you should try to avoid getting pants bunched up in general, and that Bonnaroo really re-ignited the concert scene for a large portion of the concert-going scene the first time it came around.  Agree to disagree.

Anyway, at the end of this week in Austin, South By Southwest kicks off with their Interactive session, which what they call the geeky stuff.  South By Southwest actually transitions from the geek scene into the music and film sessions with lots of overlapping, but all in all the first few days are what I’d call Geek Bonnaroo.

And I get to go.

The blogger network I have the great fortune to run on my free time is built on top of the social networking platform that a company called Ning created.  Ning announced a very late contest offering to take a handful of their Network Creators to the conference, and I applied thinking that I’m the kind of person who never wins contests.

I was wrong.

I found out a few days ago that I did indeed win, and that I’d be joining Ning at Geek Bonnaroo to spread the word about their platform and to basically meet thousands of other geeks in a never-ending party of tech, music, food, and dry Texas sunshine.

Sooo, yeah…I’m heading to Austin, Texas on Friday to attend a conference I’ve wanted to attend since it was first conceived.

I’m beyond pumped.

I actually won a contest!

Have you won a contest before?

Do tell!

Are you going?  If you are I’m sure we’ve already connected on twitter or plancast, but if not definitely reach out.  One place you should find me is the Glass + 20SB Happy Hour on Sunday at the Ginger Man.

It’s Friday night which means no one will read this.

I’ve been doing things other than blogging which means no one will read this.

I’m still gonna write it.

Vancouver’s been a pretty crazy experience, as I think you all know because I’m sure you watched at least five minutes of that little party they call the Olympics.  I had hoped to blog about that while it was happening but I apparently didn’t.  Someone forgot to tell me that being in Vancouver during the Winter Olympics was not just a totally incredible experience, but that it’s something you could potentially share with your friends if you took five minutes to write about it and share your photos.

I didn’t get to an event.  I took picture of people and I rode buses with foreigners and I sat in bars with wide-eyed visitors who spent hours and money and travel on a chance to surround themselves with one of the world’s most unique and incredible two-week parties.

Check out photos here.

If I had to sum up the Olympics in Canada, I’d say that it was truly inspirational to watch a nation rally around their athletes the way this one did.

Granted, that came with some very unique representations of their national spirit, be it a somewhat home-grown approach to reporting or a mid-Olympics sense of nervousness around their athlete’s success…but when they won their first Gold Medal on Canadian soil and continued winning Golds, this party was off to the races.

The hockey game was something I’ll write about separately.  That was NUTS.

Really, though…Vancouver was a tourist destination for two weeks and as such was filled with such nice people and such raging fun that I started to forget that it wasn’t like this all the time.  There were a few snafu’s; demonstrators tangling with police, long lines at bars and stores, and my commute definitely became more of a pain, but all in all I feel privileged to have been in town for the whole thing.

Seriously, though.

Did you SEE that hockey game?

I came to Vancouver without a place to live.

The time leading up to the decision to pursue an uncertain life, in another country no less, was not a lot of time.  It didn’t leave much wiggle room.

In fact, it basically wasn’t enough time to make any real decisions.  It meant saying goodbye to my closest friends, my family, and the massive network I’d built up around Chicago could barely even happen.   It wasn’t the kind of thing most people would probably accept as a phase in their adult experience.

I’m fairly confident means that that I’m crazy, and I’ll look back on the whole experience and wonder what lead to my being the kind of guy who would move to a foreign country without a work permit, a place to live, or enough time to really say goodbye to friends and family.

I’ll wonder, but I won’t really doubt the decision.

I don’t say that because I’m sure that things will work out.  I just say that because I know that even if I decide that I could have done things differently, it won’t be because I made the decision I made; to come here and take a shot at doing something really significant.

Yeah…you do things like that because you think you’re right.

You think you’ll look back on it and look like an idiot savant.

And failure means the ’savant’ part gets tossed.

So you work hard, and hope that a savant you remain.

It’s as good a reason to work as any, I suppose.

What are you working for?

I’ve spent my whole life surrounded by incredible women.

My mother, bless her, is the epitome of pure love.

She’s a woman who’s conquered every inch of her heart and shows everyone around her what it means to really be human.  She loves harder than anyone I know, and she raised me to do the same.

My darling sisters attack life with wide open eyes and unabashedly caring hearts, the spark in every room they enter.  They radiate the kind of beauty Kings built Empires for, and every day I’m not around them I miss a little piece of myself.

If you only knew the kind of people I got to call family.

I have some thirty odd cousins, maybe more, and an overwhelming majority of them are women.  The kind of women they write books about; women who cut through life with love and rigor and a fierce prowess that demands nothing but goodness and a grounded sense of humor.  They want to know you, everything about you, because they want to know how to love you.  Everyone in sight is family, in our family.

I boast adoring Aunts, quirky and matriarchal, overflowing with wisdom of the heart.  Their undercurrent is fueled by an innate sense of family and homestead; life is life, and it’s nothing without the people you love.

My truly magnanimous grandmother, sharply navigating a long and storied life of deep belief and tradition, left cancer in her wake and walks among the Saints, a maven of Queens, New York.

Might we all live a life as full as hers.

To that I add a circle of girlfriends to slay dragons.

The most beautiful, caring, hilarious and intelligent women this planet’s got skipping around it.  World changers and nurturers, all of them show me on a regular basis how simple life really is.

I believe that the entire history of mankind’s battle between heart and mind is running through every woman alive, and the few that I’m fortunate enough to call friends each in their own way reveal the savviest navigation of that balancing act.  My heart beats for you, misses you dearly, and would stop in its tracks without each of you in my life.

You women shape my world.

You women frame my expectations.  You women shine a light on how we got here, and what tomorrow looks like.

You women are my heart and soul.

You women are my Valentines.

I spent four hours explaining myself to a stout customs agent, and walked out of Vancouver airport into a brisk late evening surrounded by the kind of bustle you’d expect at a mid-sized American airport, with unfamiliar signage the only hint that I was dragging my belongings over foreign soil.

Temporary permit aside, I was actually in the next stage of my life.

I was walking towards a new home.

That’s something you do a few times in your life, at most.  I’d imagine most of us can count the places we’ve called home quite easily.  I know I can.

I was born in New Jersey, gained a sister in Connecticut, and spent the following thirteen years in St. Charles, Illinois. My little little was born in Illinois, and I entertain a hunch that moving somehow equated with children, so we stayed.

College in California, back to Chicago.

Bam.

Aside from stints in other places that mostly relate to soccer, and certainly don’t qualify as homes, that sums up my living locales over the last thirty years.

Yet here I was, hopping in a cab because my ride couldn’t outwait an overly inquisitive border patrol, skimming through a city I knew almost nothing about aside from the facts purged from a visitor’s guide I’d received from my adorable mother when plans began to formalize around my move.

Loonies and toonies.  Stanley Park.  Kits Beach.

What are people like in Vancouver?  What will I really miss from Chicago?

The questions were endless, and I consciously decided to ignore them completely.  I was tired, feeling a bit violated, and still extremely unsure about the near future.  Work permits, a fledgling company, and no plan as to where I’d live just seemed as if they’d still be waiting for me in the morning.

The cabbie remained silent throughout the trip across Vancouver to Anthony’s home, where I’d be holed up in the basement until I found an apartment.  I preferred his silence.  I welcomed it, actually.

I watched yellow and white lights wiggle across my window and guessed at the forms they hinted at, buildings in a city I’d soon know my way around.

This is what the edge of a cliff looks like, I thought.

Tomorrow will look nothing like yesterday.

There’s something about the kinds of changes I’ve been through lately that make me feel as if I’m on an island.

I want to assure you that this isn’t some emo blog post about being lonely, and I’m pretty sure it won’t even contain a Lost reference.*

Back in about June, I had lunch with Anthony and we subsequently started spending time with an idea that became foodtree.

I have no clue as to whether any of my old colleagues are reading this, but I want to make sure it’s clear that that doesn’t mean I’d started checking out of the financial industry.  Last Summer and this past Fall, I worked extremely hard to push my practice forward.  I’ve always been a project guy, and 20 Something Bloggers is testament to that; I spend a lot of my free time getting involved in things.

Anyway, it’s almost impossible to illustrate how quickly things changed at the end of last year, and I think that’s partly because it was often in ways that made writing about it here inappropriate.

Hell, making any claim as to what might happen in the context of something like foodtree would have been (and still would be) outright irresponsible.  We’re a startup, and every day’s a blessing even now.

As a blogger, though, I’ve spent a lot of my written words pushing for a few common endeavors within the community.  One of them is transparency; I think blogging is at it’s best when we try to be concise and honest.  The other is confidence; I think personal bloggers write themselves towards a voice that represents them, and the more they write the closer we all get to the good stuff.

Yet for months now I’ve left a lot out, and I’ve quite obviously written far less than at any point in recent memory.  If you know me in person, I’ve probably complained about this more than once over a beer.   The most uncomfortable thing I think I’ve dealt with through this process is censorship.  Initiated by me, no less.

(The second most uncomfortable thing I’ve dealt with would be an overdrafted bank account.  Sidenote.)

I feel as if I find myself on an island.

I feel that way because I can’t think of anyone in my life who could honestly answer this question:

“So…how the f*ck did you get where you are right now?”

Which makes for quite a lot of filling in, I suppose.

*Don’t get me started on Lost.  Don’t get me started on being on the West Coast where things happen later, and Lost.  Don’t get me started on Canada, and Lost.

I was beginning to doubt my odds of getting a work visa in Canada.

My two week provisional visitor’s visa was almost up.  I’d spent all week locking down my very digital and very public life, and reassuring most of my friends and family at home that I was not, in fact, totally insane.  I felt as if the whole bureaucratic ineptitude of a nation had decided to throw a tea party at my expense.  I was in Canada, but I wasn’t allowed to work…much less build a company from scratch.

It was Friday, and I was cellbound come Monday.

Quick decisions are a part of life, and as daylight ticked away late Friday afternoon I decided to make the best of the situation and snap up an inappropriately inexpensive flight from Vancouver to Chicago the following morning.  Bust out of town…come back three days later and try a novel approach.

So yeah, I bought a plane ticket at about 7pm, and got on a 7am flight to Chicago.

I arrived in Chicago at about 7pm last Saturday.

Recently I gave a Best Man speech (posted here) at the wedding of one of my oldest and best friends.  The move to Vancouver injected a lot of emotion into that wedding weekend, and into the few weeks that followed. Murph and I always seemed to end up in the same place, so my leaving was a big deal.

So when I arrived in Chicago that evening, with the help of Braden and my sister I made my way to the bar downtown in which I knew that Murph’s wife, Ash, had planned on throwing him a surprise 30th birthday party.

Have you ever seen a surprise party get surprised?

It was maybe an hour after his friend’s and family had yelled, “Surprise!” in this private funky room in the basement of this place, and just one of them (his lovely wife, of course), knew that there was more to come.  I remember nearly buzzing as I ran down the stairs and walked into the room; our friends, his family, and then he turned and nearly sh#t his pants.  It was magic.

As I’m sure you can imagine, the party was really great, and the chance to catch people so quickly after I’d run out of town in the midst of my first (and somewhat frantic) move was refreshing.  I hadn’t been gone long, no doubt, but to really get another goodbye was heartwarming.

I spent most of the weekend with my family, and headed back to Vancouver Tuesday, with no clue as to where I’d actually end up.

This time around I had an application for a work visa and a bunch of supporting documents, including my original diploma from Stanford and a job offer letter from our CEO (snap!).

I was entirely unsure as to what I’d face when I walked up to the same customs line and told them I intended to work.  I had no idea if they’d pull up a record of my first experience, and begin the conversation from Skeptic Island.

I had no idea if they were following me on Twitter; I sure wasn’t risking it, though.

Approaching the customs area, though, had quickly become a very friendly place, with the city putting on a smile for its influx of Olympic attendees.

I was politely instructed that New Workers had their own line, and I proceeded to a back room (I’ve now seen all the back rooms in that airport, I’d imagine) where I came upon a very, very cute customs agent who is now also responsible for making my life infinitely easier.

Two or three questions and bam: a year-long work visa.  Thank you very much.

No…I didn’t ask her out.

I got the hell out of there.

Photo by me; that’s Rafe, Anthony’s son.

I flew to Vancouver on January 18th, and haven’t blogged since. I pushed out [two nine] to share music, and thank heavens because it’s been my primary means of connection these last two weeks.

The flight to Vancouver is a long one…I still haven’t taken it direct from Chicago so it really amounts to about six or seven hours in the air.  That’s two long naps or a short book, and thankfully it hasn’t meant a painfully long conversation with an overzealous stranger.

When I arrived I was admittedly nervous.  Looking back, some of the difficulties I’m about to share could have been avoided, but it’s not every day you pick up and move to a foreign country.  It’s not every day you call Canada a foreign country, either, but that is in fact what it is.

I guess I should take a second; if you have no idea why I was moving my rear end to Vancouver, you can snag some background on that here.  It involves food and ninjas.

Anyway, I walk off the plane and I’m presupposing the conversation I’m about to have with the customs officer.  You know how it is…you know they’ll ask you three questions and one will be specific and generally that’s it.  Why are you here?  Who’re you visiting?  When are you going home?  Have you ever been in love?

Thing is, I didn’t know how to play the fact that I was hoping to work (and stay) here.  It all felt disingenuous, since I felt as if I needed to keep the work thing on the down low, along with the part where I might not leave.  Throw in the heightened security surrounding Olympic Games and I already had myself psyched out.

So you can imagine how the conversation went.

“When do you fly home?”  “Not sure yet…it’s an open ended trip.”

The quizzical look on his face pretty much sealed the deal.  I was smuggling drugs.

So if you’re wondering what happens to drug dealers, read on.

They let you into baggage claim, thinking things are good.  Little do you know you’ve got a code on your claim ticket that says, “put this man into custody and interrogate him until later this evening”.

Which is what they did.

I almost don’t want to revisit it.

They wanted history on me, my family, and my friends.  They wanted addresses.  They took my work history, asked me if I was heterosexual, and walked into the back room over and over again for half hour dig sessions.  The questions got hairy when they came back from the report that Google had provided, which included this blog, my twitter feed, LinkedIn, Facebook, and FriendFeed profiles.  I immediate regretted this post, and half of the day’s twitter feed.  My LinkedIn profile was a dead giveaway.  Super.

Four hours later, after reciting my entire life story, including phone numbers for people in three different cities, I was handed a provisional, two-week, visitors visa that upon expiration was to result in my arrest if I had so much as a pinky toe on Canadian soil come February.

Locals claimed that they wouldn’t enforce such nonsense, which I felt might be advice I’d regret taking once I’d landed in a jail cell.  I opted for the ‘let’s get me a work visa before I’m illegal’ route.  Or I wanted that to be the plan, until the government denied my application, and I found myself looking February dead in the eye.

[to be continued]

Photo by Patrick Doheny.