What’s this about?

T-5 days to Iceland, and over the past few weeks in NYC I’ve been catching up with friends and colleagues I haven’t seen for years. I can mostly chalk it up to basic neglect as I focused on building my business. Most of the dinners/coffees had a common pattern: The seven years after leaving NYC where I stumbled into Silicon Valley, growing a business, contending with the usual and drastic ups and downs. Then I explained the past year where there was a perfect storm of being torpedoed by a customer, several deals evaporating, and stomaching the incredibly long sales cycle in enterprise software.

It is around this time I would start to feel flush, my eyes would well up and I’d begin to cry. Sometimes fighting to hold them back, other times letting them flow. No real shame in doing this, but I surprised myself time after time with the emotion that poured out of me. For the first time in eight years I don’t need to compartmentalize work from leisure, and the result is an unfamiliar, but not uneasy feeling.

Then I explained the future: take a professional sabbatical to explore what is next, personally and professionally. Attend festivals, stay in Airbnb rentals, join group tours, travel with reckless abandon and other things I would rarely consider. My plan for the next months (or years) is to open my eyes, ears, mind and heart to all that there is. For those of you who know me, you may think I’m in the early phases of ‘going native,’ and you might be right. But I’m going to allow me to guide me.

On my travels this summer/fall/beyond I want to remain somewhat engaged with the world I lived in for so long–learning from other entrepreneurs by sharing my story, helping them and whatever else comes along.

I’ll be updating my whereabouts on my LinkedIn profile, but my first wave of travel includes the following:

  • Iceland (four day trek and time in Reykjavik)
  • Sardinia/Corsica (no idea yet where I’ll be or what I will be doing!)
  • Sailing cruise up the Dalmatian Coast
  • Attend the Ars Electronica festival in Linz, Austria
  • Time in Munich and Berlin and the retune festival
  • Dublin for The Summit and to see family
  • Lisbon and southern Spain
  • And much not  yet decided!

I’m writing this to help me, inform friends and satisfy that insatiable vicarious quality that inhabits everybody I know and meet the unmet. If there’s something you want to know, please speak your mind!

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