The 5,000 Mile Journey

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The HomelessByChoice Tour – Next Gen - I began the HomelessByChoice Tour on January 6th, 2025, in Los Angeles, California, with all the optimism in the world. “This is going to be a grand experience. A once-in-a-lifetime opportunity! I feel Like I need to do this” I said.

I’m going to be driving across the country a half a year journey, through 10+ states, to speak and inspire over 25,000 people, grow as a speaker, and hopefully provide a good life for my partner and I.

That’s what life is about, right?
Taking risks. Following passions. Chasing dreams.

If there’s one thing this six-month journey taught me, it’s that our life’s plan rarely goes how we imagine it in our heads. And anytime we take a risk, we better be willing to accept the losses that may come with it.

Because in the very first week of the tour, my relationship abruptly fell apart, my first keynote was all over the place, I had no leads, and  to top it off,  I was waking up to the cold creeping into my sleeping bag as I slept in the backseat of my Hyundai Kona.

Heartbroken, mind scattered, morale low, I began asking myself:

“What am I doing?”
“Why are you doing this?”
“You left everything to jump in a car and isolate yourself?”

On the outside, I wore a smile, this mask like I had it all figured out, like life was going exactly as planned.
But on the inside… man, I felt so defeated. Right out the gate, I was ready to throw the entire tour away.

Then I stopped and reminded myself:
If I’m going to be out here inspiring people to “not give up” and “keep pushing forward,” then I’ve got to walk the walk.

So that’s what I did. Not knowing what I was doing or where this journey was going to take me both physically or mentally.

Someone once told me, “What you focus on, multiplies.”

So during the long drives, I started focusing - intentionally, on improving myself. Putting in the work.

I would sit in silence, reflecting on my life and what I truly wanted. I would pray, cry, listen to eBooks, podcasts, and church sermons. I practiced my keynote speech, and in the downtime with host families who welcomed me in, I focused on my breath, read, and had real, honest life talks with those I considered elders.

(And if you’re wondering… yes, it was different staying with families you had just met.)

This rhythm, the stillness, made the journey a little bit easier.

Sure, I still questioned myself. But when I recognized those thoughts creeping in, I gently reminded myself to stay the path.
To trust that it would be worth it, even if I didn’t know what that “worth it” looked or felt like yet.

What truly helped me stay grounded were the students. The ones who opened up, confided in me, and shared how much my story inspired them.

When I wasn’t speaking in a new city, I’d find a local coffee shop to send out emails and call clients, trying to find new places and people to speak to.

I faced way more rejections than wins everyday to the point where I’d shut my laptop in frustration and just go for a walk.

My plan for how I wanted my life and this journey to unfold was out of my control, because life is unpredictable. My car broke down, clients canceled, new opportunities came, detours happened, family emergencies.

However this journey was still something special, not just because of the places it took me… but because of who it showed me.

The countless students who felt seen so they reached out and shared how inspired they were.
The people I had the honor of meeting who became an extension of family.
And the deeper relationship & connection I found with myself, personally and spiritually. 

This journey has taught me to believe that when we are faced with high emotions and uncertainty, we should embrace the feeling. It’s an opportunity to better understand ourselves and each other.

Let’s break the cycle of burying our emotions and pretending everything’s okay, that we know all the answers, while our minds continue to spiral. There’s power in vulnerability.

We can’t let fear and overthinking, make us believe the “I’m not (smart/strong/rich/etc) enough” or “I need to prove my worth, I hold no value unless I make X amount of money. This is so untrue!

We are already worthy.
We are already enough.

We are already worthy enough.

We are all on our own unique journey. 

We may have a plan for how we want life to unfold, but the truth is life is unpredictable.

We only do what we can… and leave the rest to God, the universe, or whatever we believe in.

So as I sit in this coffee shop in Gainesville, Florida on May 20th at 3:36pm, typing this out, it's bittersweet knowing this Friday marks the end of my speaking tour with over 25,000 lives reached! Reaching my goal!

But, If there's one truth I’ve come to embrace, it’s this… at some point, everyone should step away from the noise, detach from the comfort of routine, and spend intentional time in stillness (preferably in nature or solitude) not to escape or runaway from the world, but to meet themselves more honestly. This journey stripped me of every false layer I thought I needed and invited me to face the raw, unfiltered version of who I am. I’m no longer the same person who climbed into that car back in January. And maybe that’s the real victory, not in the metrics of the number of people reached, but in who I became while reaching them.