The Journey Begins

I had been contemplating the possibility of traveling around the world with my boys for a few years, dating back to just after my wife died in early 2014. I held the notion close to my heart, but yet far enough away from my head so as to allow a sense of excitement to rise without being attached to any of the myriad external realities of making it happen. That was not something I did consciously, but rather out of necessity; a survival mechanism that afforded me the opportunity to escape the deep pain that I was in. Any thought about what it would actually take to execute such an endeavor threw me into a tailspin that instantly derailed the fantasy. Having traveled extensively, though, I could envision the situations we could be in. I could imagine conversations with other travelers. I could taste the sense of freedom of traveling for extended periods of time. I could feel my curiosity swelling with each new place we visited. The thought of entering each day without regard to the first-world responsibilities and challenges of single parenthood was incredibly alluring.

The concept of world travel started as a singular notion during the apex of my grief. It was a moment of ostensible reason substantiated by all my prior world travel experiences and forged with the catalyst of deep suffering. However, I had no ground under my feet to take such a thought seriously. There was no perspective for me in which traveling around the world made any sense at all. If I ever had context and meaning in my life, I surely lost it when Shira died. I was free-floating. Untethered. I didn’t have any resources left to take responsibility for my life. I was laid out flat in front of forces that were much greater than me; subject to the divine.

Perhaps informed by Shira’s love, I somehow had the fortuitous sense to hunker down and maintain stability, especially for the sake of the boys. So the thought of packing it all up and hitting the road didn’t stick around for long. My focus turned to leading myself through the despair and grief towards praise for life and love. If nothing else, I did this for my boys. I understood that their ability to rise out of the ashes of loss was wholly dependent on my ability to do the same. I latched onto the idea that if I were to become the captain of this ship, I needed to take charge. I needed to take responsibility for my life. I needed to turn towards love and away from anger, and blame and shame.

Over time, as I gained greater levels of perspective and the grief-praise paradigm that I entrusted shifted its proportions, the nebulous idea of a global expedition, built loosely in my sub-consciousness, ripened to the forefront of my mind, buoyed by its potent possibility and attractive nature. The ripening was made possible by my ability to cultivate love out of threadbare fields of grief, blame, and anger. It was made possible by hope. It was made possible, somehow, by my desire to choose life; to wake up each day and put myself in front of my circumstances; to face the seemingly impossible; to try and fail, and try and fail. It was made sweeter by integrating the meaning of my wife’s life with that of my own. Her life – and death – gave me all the reason I needed to seriously entertain the thought of making such a bold move. And because I was reevaluating every aspect of my life, and myself, I began to understand that if there were ever a time to undertake such an endeavor, now would be the time.

It is said that a journey of a thousand miles begins with a single step. With all due respect to the Chinese philosopher Lao-tzu, I’m inclined to improve on the quotation by adding that the journey begins with one single step of intention. Once I connected with my intention, the train began to roll out of the station, and all my thoughts and actions began to support the idea. I began to dream up itineraries, drafting them out on maps that came in the mail from Partners in Health’s fundraising packets. I started to make lists of things to do on scraps of paper, and then into a spreadsheet on my computer. I initiated the overwhelmingly arduous task of clearing out my house in advance of renting it out – one drawer at a time. I broached the idea with my boys and spoke with close friends about it. Well over a year in advance of our departure, I was taking stock of what it would take to make this trip happen – a daunting set of associated responsibilities with extensive breadth and depth to each one.

And, with each step along the way, my intention grew stronger.

The first, and largest, outward step came in January 2018 when I posted my house for rent on the web. Then another big step in the beginning of May when I received an email from a family in Colorado who, after visiting my home in early May, sent an email stating that they wanted to rent it. I actually knew before I even met them – when I received their first email inquiry to arrange a visit – that everything was about to change. I could feel it. From that moment on, it was game on! The train had left the station and I was on for one hell of a wild ride.

I never imagined how much form these initial actions would bring to such a grandiose and nebulous idea. I had spent so many months conceptualizing and considering it, deliberating and dreaming. The plan was starting to develop and crystallize. As with other major steps in the process – telling my family, giving notice at work, buying air tickets and insurance – the idea of travel shifted from being a probability, to a possibility, to a budding reality.

Now, after many months of intense preparations, as we depart Boston on the first leg of our journey, the immensity of what I’m doing is finally starting to sink in. Taking my two sons around the world seems incredibly ambitious! Holy shit! I’m at once terrified of the idea and absolutely excited by it. I’ve been moving on such a high-speed train towards this goal that I haven’t had time to digest its speed and direction, its potency and enormity. The locomotive seems to be well on its way, but I’m not driving anymore (was I ever?) and I certainly don’t know where it’s taking me. We shall have to wait and see.


  • Leo Luna samantha and arabella

    hi I hope you have the time of your lives!!!!!!!!!!! we will be thinking of you and following you on that map thingy today we’re helping Deborah get ready for the memorial also by the way toby you should set up a page about Albert!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! ps arabella says no more exclamation points Leo!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

  • Lauri

    Dear David, Toby and Leo, what a beautiful and inspiring blog and adventure! Gary and I wish you three a wonderful, meaningful, and exciting journey around our planet Earth. Smooth sailing and blue skies ahead! I’ll be thinking of you every day. Happy, healthy New Year 5779! L’shana tovah. Lots of love, peace and hugs, Lauri

  • Vicky Benedek

    Dear David, Toby and Leo,
    I am in complete owe of your master undertaking! I am inspired by your endeavor and look forward to following you on your journey around the world.
    Wishing you a happy, healthy and exciting fun-filled year.
    Vicky (Jewish Preschool of Lexington)

  • Gaby

    Toby, Leo and David

    I still can believe this beautiful dream is happening now, i’m so happy for you, also very curious to see and talk with you about all the adventures. Espero que sepan que los amo demasiado y que son muy importantes para mí, se que este año va a cambiar sus vidas de una manera muy especial y las llenara de mucho amor y experiencias inolvidables, con gente de todo el mundo y de todos los que estamos atentos a ver cual es la siguiente parada en su viaje.

    Leo, i love your hair
    Toby, i hope you get to see dolphins somewhere in the world
    David, mantén tu corazón abierto a recibir todo lo bueno que este viaje tiene para ti


  • Maragaret Flinter

    I have wondered several times over the past year since i first heard you mention this grand plan if you were really going to do it. I asked Toby about it at camp and he said Oh Yeah! And here you are!
    My love and best wishes go with the three of you on this exciting and i think brave, adventure. Thank you for sharing this first post, with all the pain and loss and grief that you have carried over the past years since the death of Shira, and the rock solid commitment to your boys that has helped carry you through it. I will look forward to everypost! Wishing you a safe, healthy, amazing , learning time.

  • Nancy Farber

    Safe travels on this amazing journey! Thank you for sharing your thoughts and plans so exquisitely. I look forward to following your journey…enjoy your incredible adventure! Nancy

  • albert cook

    David, you are an inspiration…….from heartache & grief you generate adventure, learning & connection with your boys and who knows how many new people. All best wishes to Toby, Leo & you for a trip of a lifetime. Much love & respect to you brother, take chances. stay safe, enjoy! And please keep us informed !

  • LIsa Kennedy

    You are doing it! I didn’t get to say “bon voyage”, but you are already across the world. I read the list of countries and I am so excited for you all. I wish the greatest growth, learning and love to come from this grand exploration together, bringing Shira in your hearts. And you are all wildly amazing to do this trip. Thank you for sharing it.

    Much Love, Lisa

  • Moti Zemelman

    I’m so inspired and moved by your journey already!! Thanks for including me. I loved getting to talk to you that night at the DNE camp store about this upcoming adventure. Can’t wait to hear more! I’m looking forward to getting to know you better through following your journey here and hopefully one of these days hanging out more in person when you return next year!

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