Category: prompts
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The Extra Day: A Ten-Year Memory
What is one thing you want to remember in 10 years? For Rob, it’s not the holiday stress, but the phone call his 18-year-old son made to stay one more day. A reflection on the ‘Unexpected Win’ of being chosen, the end of custody arrangements, and the simple joy of…
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Of Training Wheels and Christmas Lights
We had set up her assisted living under the guise that she would have enough money to cover it as long as she needed. What we didn’t count on—and I know this sounds blunt—is her surviving as long as she has. Now, the training wheels are coming off. It’s time…
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Charity Starts at Home (And I’m Back in My Childhood One)
Living on a teacher’s salary in the 2026 economy means “charity starts at home.” Rob explores his favorite causes—from Habitat for Humanity to PBS—and how they fit into his 2026 Blueprint.
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The Muscle of Empathy
Is kindness a sign of weakness, or the ultimate display of strength? In “The Muscle of Empathy,” Rob explores why empathy isn’t just a feeling, but a skill that requires “heavy lifting.” From the political complexities of sovereignty in Venezuela to the legendary “strong enough to be gentle” philosophy of…
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Where Do We Go From Here? Five Years Since January 6.
Five years after the events of January 6, 2021, the ‘nightmare’ has expanded into new global territories. Reflecting on a year of unexpected shifts—from domestic politics to interventionism in Venezuela—I’m left with one haunting question: Where do we go from here?
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Bugs, Boundaries, and the Art of Not Being Invisible
What would you do if you found a hair in your food? From discovering bugs in his water to navigating the thin line between being a ‘Karen’ and being assertive, Rob reflects on the service industry, human decency, and the art of refusing to be invisible.
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No More Breadcrumbs
After 13 years and 850 consecutive days of writing, I’m drawing a line in the sand. From reclaiming fatherhood traditions to protecting my physical space, I’m implementing a “100% Policy.” No more settling, no more people-pleasing, and absolutely no more breadcrumbs.
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The Audacity of Staying Put (Or: 13 Years in the Middle)
In this milestone reflection on the “Rebuilding Rob” blog, I examine the 13-year evolution of my personal growth journey. Surpassing 850 days of daily posting, I share lessons on surviving divorce, the reality of single parenting, and why “holding on” is the ultimate strategy for 2026.
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The Mayor and the Machine – Is Kindness a Political Liability?
Can kindness and integrity survive the “political machine”? As New York City swears in Mayor Zoran Mamdani, I’m reflecting on the “Audacity of Potential,” my own history with political hope, and why I’m choosing cautious optimism over cynicism in 2026.
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Why I’d Pay Someone to Win the Lottery for Me
Can money buy happiness? Maybe not, but it can lease it. From the ‘decoy winner’ strategy to the reality of the lottery math, here is why I’d pay to stay invisible.
Rebuilding Rob 