Soon after my plane touched down in Dublin, I knew my time touring and recording with Wilco was over. I travelled to record on “Mermaid Avenue” the collaboration between Billy Bragg and Wilco composing music to lyrics and poems left by Woody Guthrie, one of my heroes. It was a true honor to be part of such an historical recording and it closed out my tenure with Wilco on a high note.
On the flight back to Chicago after the sessions it sure didn’t feel like a high note. I had joined the band two years prior at age 38 to literally live my childhood dream – touring the world in a band. These were the most fun, adventurous and carefree years of my life and I was not prepared for them to end. But end they did, leaving me broke and strung out from two years of touring on the road with no plan B.
Thus, I found myself sleeping on a mattress on the concrete floor of my younger brother’s suburban home searching for my future. Day after day I listened to the sounds of “normal” suburban family life unfolding above me. The contrast with my life was jarring and extremely depressing. I had left the lucrative opportunity to franchise my guitar repair business coast-to-coast, a once-in-a-lifetime chance, to pursue this rock and roll dream. Now the dream was over.
What does a 40-year-old do when his future suddenly becomes a blank slate? Try as I may, I could not find that answer anywhere. I would have to build it myself. After hitting a brick wall for a few depressing weeks, I landed upon 3 questions that could lead me to purpose and meaning in life and thus, a path out of my brother’s basement.
When considering our futures, we often consider the barriers first. I turned that around by removing the barriers in the first question I constructed for myself – If I had millions and millions of dollars, what would I spend my time doing? Like many folks I would take care of family members, travel, and splurge on anything I wanted. But then what? What would I do when I tired of travel and buying toys? What would I do to occupy my time and fulfil me for 16 hours a day?
The second question was informed by the tragic passings of friends and family members before their time – If I had one year to live, what would I spend my time doing? Again, like many folks I would prioritize time with loved ones and maybe visit an exotic location or two. But then my attention would turn to my legacy, what I would leave behind. Or, what I could do to achieve some measure of self-actualization and reach my full potential in my final year.
The answer to the third question is very consequential because it can drive your actions and provide purpose regardless of how much money you have and how long you live – From your deathbed, what regrets do you absolutely not want to have? This is a real kicker because it forces you to address the “I-wished-I-would-have……” and the “Why-on-earth-didn’t-I…….” and the “I-could-have……” scenarios. If you have ever heard these things from people in their final chapter of life you know how terrifying it is to realize one has major unfulfilled objectives after it is too late to address them.
Once I could honestly answer these questions, my undeniable purpose came into focus as my answer to all three was the same – I needed to compose and record my musical masterpiece.
I do not know where these questions came from. I just know they arrived in my darkest hours when I most needed them. And they provided me not only with a purpose which inspired me to leave my brother’s basement, they serve as a framework that has kept me fulfilled and on track to this very day, decades later.
And so it came to pass, my brother bought me a car and gave me his bank card (security pin – 1234, seriously!) and I drove south to Mississippi to fulfil my destiny. This was one of the most eventful and consequential decisions of my life! We will certainly dig into that in future blogs!