Starting Out: Was I Insane?

Jo Landolfo
Jan 17
2 min read

It looked like this—head down, hands together, wondering if I’d lost my mind… and choosing the road anyway.

I didn’t feel brave when I started out. I felt suspicious of myself.

I kept thinking, what will people think? Will they think I’m crazy? Will they think I failed at life? Will they whisper, “She’s basically homeless now,” just using nicer words like free spirit or traveler?

I didn’t feel like some bold explorer. I felt like someone who just stepped off the map and hoped the ground would still be there.

I remember lying awake some nights wondering if I had completely lost my mind. I had no script to follow anymore. No familiar markers of what “success” was supposed to look like. No one handing me approval.

Just me. My choice. And a road I had never walked before.

Fear showed up dressed like logic. It said, you’re being irresponsible. It said, you’re too old for this. It said, what if you can’t make it work?

And underneath all that noise was a quieter voice asking a different question: What if you can?

Starting out didn’t feel like freedom. It felt like standing on the edge of a cliff, trying to decide if the wind was going to hold me—or knock me down.

But something in me knew this wasn’t running away. It was running toward.

Toward space to breathe. Toward a life that felt like mine again. Toward choosing instead of being assigned.

I had to redefine words. Homeless meant lost. What I was choosing was movement. Choice. Belonging to myself.

The road didn’t promise comfort. It didn’t promise safety. It didn’t promise applause.

But it promised honesty.

Every mile taught me something—about fear, about strength, about how much I could carry and how much I could let go of. Some days were beautiful. Some days were lonely. Some days were hard enough to make me question everything all over again.

And still, I kept going.

Because I wasn’t chasing perfection. I was choosing my road. My life.

Good days, bad days, breakdowns, breakthroughs—whatever the road threw at me, I would survive it. And more than that, I would grow from it.

I wasn’t just traveling. I was building a life out of moments. Memories layered one mile at a time.

And somewhere along the way, without fanfare or fireworks, I realized:

I wasn’t insane. I was alive.

I was on an adventure that would shape me until my last breath—And for the first time, I wasn’t asking permission to live it.