When I was 7 years old, my family had a house in Stockbridge, Massachusetts. My mom loved to drive, and I was an enthusiastic passenger. We'd take drives just to explore. My favorite was when we tried to get lost.

There was no GPS back then, no Google Maps. Just those big, unruly paper things. But we never used them on these drives. The goal was to venture beyond the familiar and see where we ended up. And once my mom acknowledged we were lost, the challenge became finding our way back.

What I remember most is asking her over and over: “Are we lost yet?”

Not yet, she'd say, smiling. She was so cheerful, so indulgent of my excitement. She loved that I loved it. Finally, after enough winding roads and repeated questions, she'd admit: “We’re lost.” And I'd light up. It's funny that, as a 7-year-old, nothing thrilled me more than getting lost and finding our way home.

What a gift it was that she played along. My mom never stopped reinventing herself. Growing up in a military family meant she was always moving — Augusta, Georgia, Marion, Indiana, Pittsburgh — then to New York for college. She spent the rest of her life in New York, but she never lost that restless curiosity.

She moved to New York with the dream of becoming a fashion designer. She had a sewing machine and was always customizing clothes for me. I remember a jean jacket she customized when I was a little kid. She covered the back with studs in the shape of stars, and added a Rolls Royce patch I had picked out myself.

One afternoon, standing outside FAO Schwarz at 59th and 5th Avenue, a man approached me, complimented me on the jacket, and asked where I got it. I said proudly, “My mom made it.” He thanked me and walked off. I turned to my dad, who looked stunned. “Do you know who that was?” he asked. I shook my head. “That was Salvador Dalí.” I didn’t know who that was then. I do now.

She designed clothes, hosted a cooking show on the radio, and even opened a dinner theater. But her passion became early childhood education, and she earned her PhD at sixty. She credited the shift in focus to me. When I was little I had a very difficult time in school. She was determined to understand why nobody seemed to be able to get through to me in a classroom, when at home she saw my potential. Working with little kids ended up being her life's work.

Looking back now, it seemed normal — that she was working with kids, sewing, sketching, hosting a cooking show on the radio, then opening a dinner theater, then back to school. I didn't think about it much then, as I was too concerned with what I was going to do. But I see the pattern now: she continued searching until she found something that stuck. As an adult I've leaned on that idea more than once. When I feel off course, I think, Okay — let's just drive and find the way.

Traveling always remained her great passion, whether in Italy — her favorite place on earth — or simply driving the winding roads of the Berkshires. She was always searching for what lay beyond the familiar.

The exact routes we took don't matter. What mattered was the bond we shared. My mom loved the game, but her real joy was in how much fun I was having. My dad and sister, on the other hand, didn't enjoy it. It made them uncomfortable to be off the familiar roads. But my mom was different. She leaned into it with me. She knew my curiosity and need to explore came from her, and she wanted to encourage it.

That instinct has never left me. Even now, when I explore a new place, I prefer to wander without a plan. I'll go to the “must-see” spots, but I think the best part is what you find on the way there — the wrong turns, the side streets, the unexpected people you meet. Sometimes I still test myself. I'll drive beyond my comfort zone in northern Westchester with no GPS, then try to find my way back. And when a dirt road suddenly opens onto a familiar street, I can still feel that childhood thrill.

Technology is taking some of that away. Phones tell us where to go, how to get there, what to see. We're gaining so much in convenience but losing the art of discovery, of getting lost on purpose. I see how people freak out (including myself) when the GPS drops out. Or if my phone loses service while I'm searching for an answer. We're losing the ability to figure stuff out. We all need instant answers.

Meanwhile, I'm still constantly getting lost — geographically, but also as a person. Who am I? What am I doing? I've had multiple careers — corporate work, small businesses, restaurants, social media marketing. But my only original goals were to write and play music. I'm giving them another shot now, 30 years later. I figure I've still got some good years left. A lot can happen in ten years.

I'm grateful I had a mom who not only encouraged this kind of exploration, she reveled in it. Maybe that's why I'm thinking about those drives now. We're heading into very uncertain times, and I need memories like this to ground me.

My first political memories are of my mom cursing the TV during the Watergate hearings. I didn't understand what was going on, but I remember how I never heard her mutter such vitriol against anyone. She thought Nixon was evil incarnate, though she was far from a hateful person. I can't imagine what she'd think of Trump. But I have a feeling the righteous outrage would be on full display.

In a way, she prepared me for what's going on today. America has most assuredly become lost. And we're all going to need to find our way through it. I can still hear her voice, cheerful and steady, answering my anxious question: Are we lost yet? Not yet. Not yet. And then, when the time came: Yes. We're lost. Now let's find our way home.

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