A Flyer for the Prime Minister
A Flyer for the Prime Minister
August 5, 2025
Dublin
I’m rarely surprised these days—I’ve seen so much, experienced so much. But today in Dublin, after packet deliveries, I was shaken by what I saw on the streets.
The day began very well. At breakfast, Isabele led us in negotiating a “peace settlement.” First, for me: They can’t argue anymore in the car. For Isabele: When we’re not driving or delivering packets, we can go our separate ways—she needs quiet time. And for Lachlan, directed at me: No more changing plans.
Hopefully, this team reset sticks.
I did observe a pattern in Lachlan’s eating habits, though. He consumes a huge amount of cholesterol-laden food! In Belfast, it had been the full English breakfast: black pudding, fried potatoes, bacon, buttered toast. Here in Dublin, it’s become a full Irish breakfast. To keep the peace, I’ll refrain from giving a “healthy meal choices” lecture—at least for now.
As breakfast concluded, we reviewed our plan for the day: We would head out the door at 10:00 a.m. and make our way to the Department of Education, now open and in full operation after yesterday’s bank holiday. From there, we would continue to the National Council for Curriculum and Assessment (NCCA). Lachlan had identified this organization and deemed it vital for a packet delivery. The NCCA shapes education policy for the Republic of Ireland.
The first delivery went beautifully. The receptionist couldn’t have been lovelier. I told her what was in my packet and said I hoped it would reach Chief Executive Pengelly. She promised to get it to him straight away.
The second delivery? The opposite.
When we finally arrived at the NCCA’s new address after three separate people tried to help us find it, security refused to take my packet! The office, though listed, had not yet been officially occupied.
Lachlan, Isabele, and I were very frustrated at this point—angry, in fact, at the system and its rules. We walked back to the hotel, deciding we would ask them to mail the envelope on our behalf. The postal service, we hoped, might succeed where we had not.
After leaving the concierge desk, Isabele went for a walk in search of a bookstore. Lachlan began to chat with the hotel doorman. He makes friends wherever we go. People relax around him immediately.
Across the street, I noticed what looked like a massive government building—stone walls, iron gates. “What’s that?” I asked the doorman.
He smiled. “It’s the prime minister’s office.”
Lachlan and I looked at each other in disbelief. “Should we?” he asked.
“Yes!” I answered immediately.
I carry Overcoming Obstacles flyers with me everywhere I go. They’re colorful with student photos and words like “research based,” “award winning,” “free educator tools,” and “student life skills.” And “oolifeskills.org.” So off we went.
The security guard at the gate looked amused by our enthusiasm—Lachlan and I together tend to stand out. We believe deeply in what we’re doing, and it shows: big smiles, a lot of energy, and genuine respect for each other and everyone we meet.
Lachlan introduced me with pride, and I explained our work. The guard thanked us for what we are doing to help his country. I then held out an Overcoming Obstacles flyer and asked if he would help us get it onto the prime minister’s desk. His response lifted our spirits in ways I can’t describe: “I’ll make certain this flyer gets to the prime minister!”
For a moment, I imagined the flyer as something magical—lifting from his hands, moving through the hallways of that enormous government building, and landing softly on the prime minister’s desk.
We thanked our new friend and then headed to meet Isabele at the bookstore to share what had happened. That’s when reality came crashing in.
Only a few blocks from the prime minister’s building, we passed homeless encampments unlike anything we had seen anywhere in the world. The people we saw were young—young women, teenagers, even children. We had heard the phrase used here to describe homelessness: “sleeping rough.” Seeing it in person, it didn’t feel rough. It felt like abandonment. Where were the parents? Why wasn’t more being done to help these children? I thought about the airlines’ new phrase for turbulence: “rough air.” “Sleeping rough.” How could these children sleep at all on cold, dangerous streets?
We passed a row of boxes and tents. Everything was filthy, collapsing into itself. Lachlan lifted his phone to take a photo of a young woman sitting just outside her tent. Inside, we could see a small boy—we guessed her brother. Their belongings, the little they had, were piled around them. They looked exhausted, hungry, and painfully vulnerable.
As Lachlan raised his phone for the shot, a deep, gravelly voice came from the frail young woman: “No photos!”
I immediately reached up to lower Lachlan’s hand, but the photo had already been taken. I know he took it for me, because I’m documenting this trip. But I feel awful now. How dare we? I hate having my own photograph taken, even when I look my best. What right did we have to turn someone’s suffering into an image?
Later in the day, I accompanied Lachlan to a barber shop. He was giving Isabele a gift: shaving off his scraggly beard. Of course, he made fast friends with the barbers. Within minutes, he had them—and me—laughing with his jokes.
But tonight, alone in my room, I cannot stop thinking about those children on the streets of Dublin.
A person I care deeply about, Overcoming Obstacles board member Orayne Williams, experienced homelessness as a young man. Born in Jamaica, Orayne grew up in extreme poverty without electricity or running water. He endured abuse and instability, and later experienced homelessness after immigrating to the United States as a teenager. At one point, after police raids forced his family from their apartment building, they moved into a shelter.
He remembered nights when the atmosphere felt “thick with fear, pain, and uncertainty.” He described homelessness as the breaking up of families, the loss of safety, and the silent erosion of a person’s sense of worth.
Yet his story did not end there. Through mentorship and life skills education, Orayne rebuilt his life. He became a valedictorian, earned a master’s degree in social work, and now devotes himself to advocating for young people in need.
I know the magic isn’t in a flyer. It’s in the educators who bring life skills education to life for their students. Orayne experienced that kind of transformation. I hope Ireland’s children will, too.
Special Delivery from New York
August 7, 2025
Driving southwest from Dublin to Dingle
How can I put into words what it means to be heading back to Dingle? It’s the one place on Earth that John and I always talked about returning to. And now I’ll finally be there. For both of us.
Leaving the hotel this morning, Lachlan and Isabele were loaded down with their things while I rolled my duffel bag suitcase. I had to ask why they refused to use a porter when they’re available.
“I don’t trust anyone with my stuff!” Lachlan said.
Thinking about it now in the car, watching the precision with which he navigates and communicates, I get it. Sure, he doesn’t trust people with his stuff, but he’s also been conditioned to take care of himself.
About a half hour south of Dublin, we arrived at our scheduled morning stop: the town of Naas in County Kildare, home of the Education and Training Boards Ireland (ETBI). ETBI works with the Department of Education to support schools, training programs, and adult education services. As we pulled in, the shift in my thoughts from survival and self-reliance to the purpose of our journey felt abrupt but fitting. This was our final opportunity to put life skills education in front of a formal governing body in Ireland.
We found the address easily. Everything should have been open, but the front door was locked. I found a security box with a call button. After pressing it, I heard, “Who is it?” It sounded like something you’d hear at someone’s home in the United States. I don’t know if it was the cultural differences, the beautiful drive, or the excitement building inside me at the thought of finally reaching Dingle, but I became completely silly and answered, “I’m Jill. Special delivery from New York!
Maeve came to the door, a petite young woman with dark hair, blue eyes, and a lovely smile, and I thought I could smell coffee brewing. She told me the chief executive was away on summer holiday. I explained Overcoming Obstacles to her, and she assured me she would make certain he received the packet. Her office works with independently run ETBs throughout the country. If they decide to share our resource, this could be huge for the young people of Ireland.
We’re now heading south to Dingle.