Vagabond Life Lesson #1 — Generosity

Pictured above: A beautiful day at sea in Santa Barbara which is graced by the Santa Ynez mountains.

It’s been almost a year since finishing my six-month Vagabond Adventure throughout the U.S. and Canada. I’ve had time to reflect on this incredible experience which surfaced 10 life lessons along the way that have stuck with me. Over the next few months, I will write about each lesson and how it’s impacted my life.

One of the key takeaways from my Vagabond Adventure (aka Vagaventure) is that people in my life are exceedingly Generous. During my travels, a myriad of long-time friends, distant cousins, and mere acquaintances opened up their homes and hearts to me; often on short notice and without all the details pertaining to my stay.

As I take a trip down memory lane, I’m immensely grateful for the generosity I received. I’ve typically never been one to impose or ask for help unless I really needed it. There were far too many instances of hospitality and generosity to mention including folks who put me up for a night or a week, treated me to home-cooked meals and local faves, offered me their car to use to get around town, and provided me work space so that I could meet (virtually) with my coaching clients during the day. What follows are two of the grandest gestures that still has me feeling awestruck.

During one stretch of my travels, I had taken the train to Santa Barbara and rang up an acquaintance I had met at a mastermind retreat, Poppy, and remembered that she had moved there some time thereafter. I was surprised to learn that she lived on a sailboat in the harbor. Without hesitation, she invited me to stay in an extra bedroom she had available on the boat. How cool is that? Her generosity didn’t stop there. I was planning to visit my best friend in Spokane, Washington for the next leg of my trip. To my utter amazement, she gifted me a free ticket on Southwest Airlines so I could visit him and skip a long train ride (she informed me that she had become a flight attendant in the years since we had initially met). I was elated. Unfortunately, my excitement was short-lived. My buddy called and informed me a couple hours before heading to the airport that his son came down with Covid. I had to cancel the flight. After some creative problem-solving, I decided I would head up to Portland, Oregon instead. After taking a bus to Oakland the next day, she was able to get me a ticket from there to Portland. Thank you Poppy for being so thoughtful and kind!

A second gift of generosity took place in Brampton, Ontario (near Toronto) via Olga, a friend I had made during a personal self-development program many years before. As if providing me with my own room and healthy, deliciously cooked vegetarian meals wasn’t enough, Olga and her fiancé had welcomed her ex-husband’s pregnant new wife into their home for the last few months of her pregnancy. Apparently there wasn’t good medical care available in the remote region of Canada that this woman and Olga’s ex-husband lived in. I was astonished by the extraordinary level of generosity and graciousness she extended to this woman. It was clear over the four days I was there that Olga genuinely cared for her as she joined us for all of our outings and conversations. It opened my eyes to such a level of selflessness that I myself couldn’t conceive of offering had I been in a similar circumstance. Thank you for being such an inspiration, Olga! You’re truly precious!

How their Generosity influences me today

Upon reflection, I continually find myself astonished by how generous others were with me. While I’ve consistently given of my time to help others over the years and volunteered for various causes, there’s a part of me that is stingy if I have to be honest with myself. I’ve been inspired by how freely friends and especially acquaintances who hardly knew me opened up their doors and who’s hospitality instilled in me a desire to step up my game.

Since then, I’ve challenged myself to become more generous in my daily life. Sometimes it’s small gestures such as treating friends to a meal for no particular reason. I’ve also increased my charitable donations for various causes I care about and am investing even more of my personal and professional time to help others. As such, I volunteer at a local nonprofit community farm one or two days each week, lead networking walks for nonprofit and philanthropic leaders in San Diego twice a month (for free), and continue to mentor students at the start of their careers to name a few. There are additional endeavors I’ve set my sights on as well.

Now that I’ve settled into a modest apartment in Oceanside, California, I look forward to the opportunity to pay it forward and host others who are passing through. It’s all a work in progress. 🙂

How about you? How do you experience and express generosity in your daily life?