This trip has been in the planning stages for the better part of two years, but it’s been a vision of mine for over 30 years. Two things I realized early on: I’d have to wait until I retired, and I’d have to find someone compatible enough to join me on this wacky adventure. I’m happy to report that both conditions have been met.

Most importantly, Leah and I have been together for nearly 12 years because we forgive each other’s most embarrassing moments and tolerate each other’s most defining idiosyncrasies. We have become formidable collaborators regardless of our separate opinions and talents. Our curiosity knows no boundaries, and our appreciation of the “great outdoors” is a driving force to explore the outer limits.

We spent four weeks together last summer romping through Alaska and Yukon in preparation for this trip. Our objective was simple: to still be talking to each other by the time we returned home. While there were some tense moments along the way, it was always the laughter that eased every crisis. By passing this test, it allowed us to set our sights on bigger goals.

Of course, all of this became possible by my retiring from the NYC Department of Education after eleven years of teaching high school to students with special needs. Teaching Special Education was not a calling; it was an assignment. By enrolling and being selected into the 2006 cohort of the Teaching Fellowship, I was introduced to an urban population of teenagers that collectively knew the struggles of academic failure, the isolation of being different, the limits of parental/guardian support, and the epic challenge to be better than everyone’s expectations.

It wasn’t easy. There were a few victories along the way, but way too many disappointments made more disappointing by a system that lost its way. Too often, colleagues of mine were reminded by administrators that “It’s all about the kids,” yet the rhetoric always exceeded the reality. I’ve seen my share of budget misappropriations, bully pulpit principals, invisible discipline accountability, and city denial. I’m sure it wasn’t always this way, because I’ve met so many great teachers during my tenure who would do anything for their students, and leverage their students’ successes in order to continue teaching. Yet, it was enough to make me weary and yearn for more.

This trip is all about yearning for more. It’s about discovery, reflection and purpose.