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TAMPA BAY • FEBRUARY 23-24 2026

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Life Lessons from the Homeless Girl

I don’t get to Manhattan often enough, but I love it when I do. The rush of the city, people everywhere, cars honking, food on every corner, and the “live-and-let-live” attitude. New York is welcoming and dismissive all at once.

It was a cold April afternoon, the sky was clear blue and the buzz of the city enticed me outdoors. Walking across the intersection at 2nd Avenue, I saw a young woman sitting on a suitcase with the telltale cardboard sign indicating that she was among the city’s 60,000 homeless people. I felt the uncomfortable pang of empathy and concern in my heart and looked back to read her sign. “If you can’t donate – gratitude, kindness and well-wishes are free!” My heart opened as I read such a beautiful sentiment and see such a beautiful young girl sitting, homeless and alone. But I kept walking.

For the rest of my walk past the Avenue of the Americas, past Park Ave, Lexington Avenue, and into Times Square I was totally preoccupied with the young gal. Why hadn’t I stopped? Why didn’t I give her money? What is it about homeless people that have us look the other way?

The frigid air and my distressed emotions ushered me back to find the young girl on 2nd Avenue. I’m staying in a $250 a night hotel, I thought, the least I can do is give this girl some money.

My steps hastened and as I approached the corner, there she sat, cardboard sign on her lap and paper cup in front of her. Our eyes met and she cast a simple, warm smile my way. “I like your sign,” I said. And thus began our exchange in which I witnessed these five life lessons from the homeless girl on the corner of 42nd and 2nd.

  1. Take Full Responsibility For Your Circumstances.

As if it was any of my business, I looked at the gal sitting on her suitcase and with compassionate concern, I asked, “What happened?”

Intuitively understanding that I meant, “How the hell did you end up on the streets?” she responded with clarity and no remorse, “Just a couple months ago I was doing fine in Florida, making $1000 a week, but my mother got sick here in NY, so I came home. It didn’t go so well between us, we had a fight and she threw me out. There’s a lot of baggage between us.”

She could have just as easily thrown her mother under the bus and said, “I left a good job in Florida to come home and help when my mother was sick and she ended up throwing me out!” But she didn’t do that. She didn’t blame her mom. She simply said what was so. “We have baggage. She’s sick (her intonation led me to believe she was referring to emotional and mental illness more than physical) and she threw me out.” No drama, just the facts. Which led to the next lesson…

  1. Ask for Help

She wasn’t too proud to ask for help. Looking at me straight-faced, she said, “I’ve never been down this low before and I don’t plan on being here again, but for now, there are good people everywhere who are willing to help. I just have to ask.” How true. The vast majority of people are more caring than hurtful, wanting to help more than cause harm. You get what you see and she saw good people everywhere. Because of this, so she was able to….

  1. Maintain Optimism

Despite how low this gal had found herself; sleeping in Bryant Park, washing up in public restrooms, asking strangers for money on the street, she was incredibly optimistic about her future. “I will be back on my feet again soon when I get back to Florida where things are less expensive. I can get my job back down there. They liked me and were sad that I left. I just have to get back there.” When I asked how she was going to do that, she did not hesitate for a moment, because she knows it is important to…

  1. Have a Plan

Her reply was quick and determined. “I just need to get $250 for a bus ticket to get back down there. It’s cheaper to fly, only $78 for one-way airfare, but I don’t have any ID.” It didn’t occur to me to ask her why not, or if it wouldn’t be cheaper to get ID than save up $250 for the bus. But she was clear. She was going to have the $250 within a couple of weeks and head back down to Florida where she had friends to stay with and a job she was sure she could reclaim. And therefore, she knew to…

  1. Be grateful

Perhaps the most striking quality about this young gal was her upbeat optimism. As we chatted, a few folks dropped coins or bills into her paper cup and she would respond as if she had just won the lottery. “Thank you! You are so kind! God bless you!” she would exclaim with enthusiasm and sincerity.

I walked away feeling like a better person for having chatted with her. Half a block away, the delicious aroma of New York City pizza wafted around me. I walked in and ordered 2 large slices and walked back to my sage on the street. She saw me coming, pizza boxes in hand, and her face lit up once again. “It’s just cheese pizza,” I said. “It’s not much,” feeling insufficient in my sparse offering. In her continued gracious humility, she gratefully exclaimed, “No, it is a lot! It’s so much. I was just sitting here getting hungry and wondering what I would do, and then you came along.”

Maybe there is something to these lessons, after all. When we live with willingness, humility, gratitude, and optimism and have a plan to follow, maybe, just maybe, good things find their way to us more easily.

If you enjoyed reading this, might also enjoy my simple, beautiful e-book: 59 Life Hacks for an Amazing Life.

Jackie Woodside
Jackie Woodsidehttps://jackiewoodside.com/
Jackie Woodside is a bestselling author, TEDx speaker, coach, and trainer. She is the founder of the Curriculum for Conscious Living and the Conscious Living Summit, and trains coaches around the world to deliver this life-changing work. Jackie is a certified professional coach and licensed psychotherapist with 30 years of experience in both fields. She has authored three best-selling books and 25 training curriculums. Her books are; Calming the Chaos: A Soulful Guide to Managing Your Energy Rather than Your Time; Time for a Change: Essential Skills for Managing the Inevitable, and; Money Vibe: Your Financial Freedom Formula Whether You Have Money or Not. Inc. Magazine selected “Calming the Chaos” as one of their top ten motivational books. Jackie leads spiritual retreats, offers professional development training and keynote speeches around the country.

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3 CONVERSATIONS

  1. Thanks Jackie! Yes, enjoyed reading this thoughtful reflection on the girl you met who knew what she wanted and lived with appreciation and action. Thanks for your life hack book – downloaded and read it before returning to comment here.

    Brilliant reflection. And great book for putting more Amazing into life.

    blessings,
    Cynthia

RECIPIENT OF THE 2024 "MOST COMPREHENSIVE LIFE & CULTURE MULTIMEDIA DIGEST" AWARD

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