Finding My Why: The Leap That Changed Everything
Father finds purpose through daughter's research, transforms failing city project.
07/06/2025
Father finds purpose through daughter's research, transforms failing city project.
Purpose Found: Your daughter becomes your why when work loses meaning.
Imagine standing at the edge of an airplane door, 13,000 feet in the air. The world below looks distant and blurred; your heart pounds, and your grip tightens around your parachute straps. You start questioning every decision that led you here. Why am I doing this? This is terrifying. I should be home with a book and a cup of coffee…
But then, you remember your why—the reason you committed to this in the first place. Despite the fear and second-guessing, you take a deep breath, trust your training, and step into the open air.
As I reflect on my career, taking on a high-risk, failing project felt like that moment.
The Unexpected Question That Changed Everything
At the time, I was managing the Project Management Office (PMO) for the City of Portland, fully engaged in my role. One day, during a check-in, my boss asked, “Have you ever jumped from a plane?”
I laughed and said, “No way!”
Then he hit me with the real question:
“How about leading the Portland Online Permitting System (POPS) program?”
My immediate reaction? Another NO.
POPS had failed multiple times. It was a political mess, plagued with delays and roadblocks. It had a reputation for being a project no one wanted to touch. Why would I leave my comfortable role to take on something this chaotic?
I started looking for excuses.
I called my mentor. He said, “Saby, if anyone can do it, you can.” That didn’t help, and I wasn’t convinced.
I talked to my wife, explaining the long hours, stress, and missed family moments this project would bring. She supported me wholeheartedly. But even that wasn’t enough to push me over the edge.
I still didn’t have my why.
Then, on Monday morning, I opened my email and found a message from my 10-year-old daughter.
She must have overheard my conversation at home and had done her research. She wrote:
“Daddy, if a project has failed multiple times and it’s a political mess, here are a few things you can do...”
That was it. That was my why.
My daughter was looking at me as a role model. If I backed away from a challenge, what lesson would that teach her? How could I ask her to be fearless if I wasn’t willing to do the same?
At that moment, I walked straight to my boss’s office and said, “I am accepting this project, and I am doing this for my daughter AND there is no power in this world that will stop me from making it successful.”
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Leading through the Chaos
Taking on POPS was stepping into the unknown. The project had been in the works since 2008, struggling through leadership changes, bureaucracy, and shifting priorities. Millions had been spent, yet little progress had been made.
When I stepped in, I quickly realized:
- People were waiting on decisions that no one was making.
- There was no clear roadmap—just endless discussions.
- Team morale was low, and trust in leadership was shaky.
I brought clarity to the project, worked with bureau leaders to align business and technology goals, and defined clear outcomes.
I also changed the narrative. Instead of dwelling on past failures, we focused on what we could control.
- We created a high-level Program Roadmap so everyone could see the vision.
- We filled skill and technology gaps by bringing in the right people.
- We prioritized agility over perfection, focusing on progress over process.
In July 2018, we had to stand before the Portland City Council and prove that POPS was finally on track. The pressure was intense. If we fail again, the project might be scrapped entirely.
We worked relentlessly, communicated transparently, and delivered on promises.
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"The two most important days in your life are the day you are born and the day you find out why."
- Mark Twain
Purpose Found: Your daughter becomes your why when work loses meaning.
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On February 10, 2020, after years of setbacks and uncertainty, we successfully launched Portland’s new online permitting system.
Lessons from the Jump
This experience reinforced a lesson I’ll never forget:
People lose their way when they don’t know their why.
If you’re facing a tough decision, ask yourself:
- What truly motivates you? You’ll give up when things get hard if you don’t have a compelling reason.
- Who is watching you? Your actions don’t just affect you—they inspire (or discourage) others.
- Are you willing to trust yourself? Sometimes, success is about taking the leap before you feel ready.
If you’re standing at the edge of a big decision, feeling fear creep in, remember:
- Find your why.
- Trust your skills.
- Step forward with confidence.
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Yes, you can provide text passages or key points from the book so that I can use them in the analysis. If this is not possible, then you can simply provide a
Yes, you can provide text passages
Yes, you can provide text passages
Yes, you can provide text passages
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