Remember when it was possible to not know something? A time not so long ago when over dinner, someone would ask a question or try and recall a fact and the entire table would discuss what their memory of the topic was and perhaps even a debate about who knew what would ensue.  A time not so long ago that when everyone had shared their thoughts, the conversation would progress without a definitive conclusion and later, on the way home, "I was actually right" statements would be made and the conversation might progress again and new opinions might surface. But, now with Google in our pocket, these conversations are much shorter. The debates don't carry on, an answer can be presented and factually laid out by the fastest search engine connoisseur.  Facts can be known in the blink of an eye, no one has to remember anything, and unstructured conversations last only moments longer than they statement, "someone google it."

What kind of toll is that having on our ability to think outside of the box and beyond what is "known?" On the older end of the millennial generation, I still remember life before I got my first cell phone (2002) and Facebook (2004).  I remember a time not too long ago when I used to be able to have a clever thought and not worry about whether it took more than 140 characters to say. In fact, this blog post it self only is now 243 words long because I couldn't figure out how to say this thought in one tweet.

But what about kids that are in elementary school now that learned to type their names before they learned to write them? What about a generation whose attention span is now too short for Facebook but prefers images that disappear after 10 seconds?

In a world that moves this quickly and where not knowing isn't a viable answer to a question, where does wonderment and naivety fit? Are we always to know everything and react accordingly? If we have an idea and think there is room to develop it into something bigger, are we brave enough to do so without checking to see if someone else already had the idea or bought the domain?

Pendulums swing even as the world moves forward. The question I am now asking myself is where does it swing back to from here.

Perhaps I've mentioned this, but, the past few months have been wild. June: Waze sold to Google

July: Leave Waze, Start BOND

August: Move to Brooklyn

September: Elope to Paris

October: Launch BOND, Wedding Party in NYC

For effectively the past 6 months, I've been in the process of prepping for and hyping a future event. Most of my thoughts have been around making sure the right people know what they need to know before everyone else can know.

But now it is November and there isn't an upcoming event that I'm thinking of ways to get people to attend, write about, or show up for. Tomorrow might be the most boring Monday in recent memory.  And while I am absolutely okay with that, I am some what pensive about the way in which I operate in an un-hyped month.

For 10 days in September, Annie and I were about as unplugged as we've been in a long time. The pace of life we lead during our trip to Paris was just about perfect. It was, honestly, the first time I've ever thought about retirement and how awesome a land line telephone and owning a cheese shop could be. A couple times throughout our stay, Annie and I split off to go explore on our own. It is always good to have some alone time to wander the streets and observe life for no other reason than your own enjoyment. One afternoon, I found a small side street with an alcove patch of grass and three identical looking cafes on each side. I sat down at the one in the middle and ordered a Bordeaux. As I slowly sipped the generously poured glass of wine, I took in the conversations and group make up at each of the tables around the square. No one except the Americans three tables over had their phones out. Everyone seemed to be genuinely enjoying just the people they were with and, though I don't speak French, I am pretty sure trending topics, Vine vs. Instagram video, and Buzzfeed articles weren't the conversations of the day.

As I walked to meet up with Annie later, I couldn't help but think about the joy I'd felt being anonymous that afternoon. Not a single person knew who I was. I didn't understand a word that they said. But smiles and my three poorly pronounced words I know in French were enough to have a wonderful time. It then got me thinking a little bit harder about the life we live in public and what that looks like in the next five to ten years.

I am not bearish on social networks as we currently understand them. Facebook and Twitter are baked far enough into every other part of the web that they'll continue to matter, but more as piping and less as destinations down the road.  So if that is true, the bet is not to short them, but to consider what kind of true conversation will we want to take place with ourselves and the real friends we have in the future? What is the bet to make that isn't the demise of what is currently hot (except for Frontback, make that go away) but instead, where are things headed in how our behaviors and social norms have adapted to living life in public and understand each other only though the carefully curate highlight reels we share online?

What is the typing point where earning the chance to unplug and be alone is the new logged-in?

Recently, I've read a couple people's blogs where they were complete honest about how hard life is. They actually admitted to their readers that sometimes, life isn't always awesome.  And as I reread my recently blog posts, tweets, and Facebook statuses, I realized that I am full of shit. My posts have been about eloping and starting a new company and the cool pocket squares someone sent me. All of those things were in fact good, but where online have I talked about how hard moving from Manhattan to Brooklyn has been or how awful my former landlord has been about returning our deposit or all of the tough things that have happened in the early days of my new company? My online posts are just a touched-up highlight reel of life that apparently has led people to believe nothing wrong ever happens. That, some how, amongst all of the truth that we all know about how hard things are in reality, I magically have avoided all of that and only live in a world of fairy dust and perfection.  For that complete misconception of which I am 100% responsible, I am sorry. I love the life that I am living and the people I am living it with, but, there is a lot of rough stuff mixed in with the occasional highlights that I have most recently shared.

“I don’t hit publish unless I am scared I’ve gone too far.” - James Altucher

I aspire to have Jerry Colonna to be my professional coach.  We swapped notes last year and he told me he is at full capacity and isn't accepting any new clients. I've gotten to know a couple of entrepreneurs to have made it on his client list before he closed it and they've told me that I am in fact missing out. So, when Jason Calacanis had Jerry on This Week In Start-Up, I was intrigued. After I pressed play, I took three full pages of notes and became even more determined to earn a spot on Jerry's client roster int he future.

I considered posting my notes here, but then reconsidered as each of the pieces of wisdom that Jason and Jerry share is incredibly and refreshingly personal.

I know that 90% of you reading this will not invest the 90 minutes to watch this in its entirety, but for those of you that do, I know that you will see the adventure ahead differently.  When you're finished up, shoot me a not or leave a comment below, would love to hear which piece of the discussion jumped out to you most.

UPDATE: Jerry mentions a talk he gives called The Crucible of Leadership. I found a great summary he wrote about that talk over on Fred Wilson's blog HERE. Another great piece of thought provoking questions and deep thoughts worth pausing to explore.