John Masters, Author at Deep Something

The Promise and the Pain of 250 Years

July 2, 2026July 2, 2026 B. John 86 Views 0 Comments John Lewis, Fourth of July, Constitution, American Democracy, Declaration of Independence, American History, Civil Rights, More Perfect Union, Patriotism

For many Americans, the Fourth of July is a celebration filled with fireworks, flags, and patriotic pride. But as our nation marks the 250th anniversary of the Declaration of Independence, I find myself looking back to the optimism of the 1976 Bicentennial and wondering what became of the country I believed we were becoming. This is not a rejection of America, but a lament for a promise that feels increasingly out of reach.

The Declaration was never meant to be proof that America had achieved liberty and equality. It was an invitation for every generation to continue the work of building a more perfect Union. As constitutional norms erode and our politics become more divided, I struggle to celebrate, but I also remember John Lewis’ reminder never to surrender to despair. Patriotism, perhaps, is not blind celebration, but the willingness to keep defending the ideals that first gave birth to this nation.

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Is Karen Gonzalez-Pittman Representing South Tampa or Tallahassee?

June 29, 2026 B. John 124 Views 0 Comments school boards, wage recovery, South Tampa, Karen Gonzalez Pittman, Home Rule, local control, Tallahassee preemption, housing policy, infill redevelopment

This entry is in the series 2026 Elections

Karen Gonzalez-Pittman represents South Tampa, but her voting record raises a fair question: is she representing this community, or carrying Tallahassee’s agenda back home? Again and again, she has voted for bills that take decision-making power away from local governments, local school boards, and local voters.

From housing and tenant protections to infill redevelopment, school policy, civilian oversight, and local employment standards, Gonzalez-Pittman has sided with state preemption over home rule. For South Tampa, where traffic, flooding, housing pressure, schools, and neighborhood character are intensely local concerns, that record deserves much closer scrutiny.

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Josie Tomkow’s Record Shows Tallahassee Comes First

June 26, 2026June 26, 2026 B. John 163 Views 0 Comments Senate District 14, Hillsborough County, Josie Tomkow, Brian Nathan, Home Rule, local control, Tallahassee preemption, Public Schools, South Tampa

This entry is in the series Florida Legislature

This entry is in the series 2026 Elections

Florida Republicans love to talk about freedom, but their voting records often tell a very different story. Over and over again, Tallahassee politicians have voted to take decision-making power away from local communities, local governments, and local school boards. Josie Tomkow’s record in the Florida House is a clear example.

Tomkow is now running again against Brian Nathan in Senate District 14, asking Tampa-area voters to send her back to Tallahassee. But when she served in the House representing Polk County, she repeatedly voted for state preemption over local control, including on housing, zoning, infill redevelopment, civilian oversight, and public schools.

That matters here. Tampa and Hillsborough County deserve representation rooted in this community, not another vote for Tallahassee control. The question for voters is simple: if Tomkow voted this way in the House, why should anyone expect her to vote differently in the Senate?

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Tallahassee Keeps Telling Local Communities to Sit Down

June 23, 2026 B. John 193 Views 1 Comment zoning, Home Rule, Preemption, local democracy, Hillsborough County, worker protections, Florida Legislature, heat safety, Tallahassee

This entry is in the series 2026 Elections

This entry is in the series Florida Legislature

There is a word in Florida politics that sounds dry enough to cure insomnia but is quietly reshaping life in our communities: preemption.

Preemption is what happens when Tallahassee tells local governments they are not allowed to solve local problems. In recent years, the Legislature has used it to block local worker protections, weaken local control over zoning and development, and shift more decisions away from the people who actually live with the consequences.

My latest article examines this growing pattern, including Florida’s ban on local heat protections for outdoor workers, recent development bills that override local planning, and the legislators who keep voting to shift power away from communities and into the state’s hands. This is not just a procedural fight. It is about whether local democracy still means anything when powerful interests want it out of the way.

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The Decision Was Mine-The Outcome Was Not

June 18, 2026 B. John 180 Views 1 Comment Dichotomy of Control, wisdom, regret, decision-making, uncertainty, job loss, self-respect, Stoicism, Resilience

This entry is in the series Journey Through Stoicism

Lately, life has been asking for more decisions than usual. Not small ones, but the kind that seem to carry a future inside them. Work. Money. Health insurance. A parent’s care. A funeral. An estate. What to keep. What to let go. What to protect. What to release. In this season, I have learned that decision-making is not only a matter of logic. It also carries emotional weight, especially when the outcome remains uncertain.

In this essay, I reflect on a difficult job-search decision that still brings occasional regret, and how Stoic philosophy helps me think about it more clearly. The Stoics remind us that we can control the care, judgment, and integrity we bring to a decision. We cannot control the outcome. That distinction does not eliminate uncertainty, but it does offer a kind of mercy. Sometimes the best we can do is choose honestly from the place where we stand, then release what was never fully ours to command.

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What We Choose Together

June 12, 2026June 12, 2026 B. John 378 Views 0 Comments Citizenship, The New Colossus, public life, Stoicism, government, justice, Civic Engagement, common good, Faith250

This entry is in the series Journey Through Stoicism

Politics can make otherwise reasonable people turn strange. It can harden conversations, flatten human beings into talking points, and tempt us into anger, contempt, or despair. But avoiding public life entirely is also a moral choice. If government is, as Barney Frank once said, “the things we choose to do together,” then citizenship is one of the places where our values become visible.

This essay reflects on a recent Citizen Engagement training at Hyde Park United Methodist, the beginning of the Faith250 series, and Emma Lazarus’s “The New Colossus” as a way into a larger question: what does a Stoic owe to public life? The answer is not withdrawal. It is disciplined participation, rooted in justice, guided by wisdom, restrained by temperance, and sustained by courage.

The Stoic citizen does not control the whole outcome. But we can still show up with clarity. We can still speak truth without surrendering to hatred. We can still widen the circle, lift a lamp, and choose together as wisely and justly as we can.

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When Principle Gets Called Partisan

June 11, 2026June 12, 2026 B. John 229 Views 0 Comments civic responsibility, partisanship, political bias, motivated reasoning, Democracy, confirmation bias, public discourse, moral principles, Civic Engagement

After a civic engagement event I helped organize, a woman approached me with a question that stayed with me. She wondered what a similar event held by “the other side” might look like. Would they just sit around saying ugly things about “us”? When I explained that our event was designed to be nonpartisan, focused only on helping people engage with public officials on whatever issue mattered to them, she looked at me and said, “Well, I’m here to tell you this was definitely partisan.”

That moment got me thinking about the difference between being partisan and being principled. We often call something partisan because it actually promotes a party, candidate, or ideology. But sometimes we use the word because something made us uncomfortable, challenged our assumptions, or touched a moral concern we have already sorted into a political box.

This essay explores how bias shapes what we hear, why two people can sit in the same room and experience almost different events, and why civic responsibility itself has started to feel suspicious in our divided culture. Democracy cannot survive if every effort to help people use their voice gets treated as a political threat.

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The Tuition of Regret

June 2, 2026 B. John 217 Views 0 Comments personal growth, wisdom, regret, last great days, Memento Mori, Friendship, Stoicism, Resilience, Reflection

This entry is in the series Journey Through Stoicism

Most of us have regrets, whether we admit them or not. A word spoken too sharply. A kindness withheld. A friendship allowed to drift. A warning sign ignored until it was too late. We may like the idea of living with “no regrets,” but that has always struck me as too clean. If we have lived fully, loved deeply, failed honestly, or hurt someone along the way, regret eventually finds us.

In this essay, I explore regret through the lens of Stoicism, Daniel Pink’s work on The Power of Regret, and my own recent life. I have come to think of regret as life’s tuition. Nobody wants to pay it. Sometimes it is painfully expensive. But if we refuse to learn the lesson, we pay the tuition and never receive the education.

The Stoics did not ask us to deny regret or drown in it. They asked us to examine it, learn from it, make amends where we can, and then lay it down. Regret is not meant to become a permanent home. It is a classroom. The lesson may be to call the friend, offer the apology, act sooner, speak more gently, or create new great days while we still can.

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Viktor Frankl: The Last Human Freedom

May 23, 2026May 23, 2026 B. John 3344 Views 0 Comments Man’s Search for Meaning, Meaning and Purpose, Stoicism, Grief and Loss, Mental Resilience, Resilience, personal growth, Viktor Frankl, philosophy of life

This entry is in the series The Stoics

This entry is in the series Journey Through Stoicism

There are seasons in life when the question is no longer whether things are difficult. The difficulty is already there. A parent dies. A career changes unexpectedly. A familiar version of life begins slipping away, and suddenly the future feels less certain than it once did. In those moments, we are left asking a quieter and more important question: What now?

In this essay, I reflect on Viktor Frankl, a Holocaust survivor, psychiatrist, and author of Man’s Search for Meaning. Through Frankl’s life and philosophy, and through some deeply personal experiences of grief, transition, and rebuilding, I explore the idea that meaning is not something we discover once and hold forever. It is something we continue choosing, step by step, even when life feels unsettled. Read more.

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Hillsborough School Board District 2: The Choice Between Proven Dedication and Outside Ambition

May 13, 2026May 13, 2026 B. John 742 Views 0 Comments Hillsborough School Board, District 2, Chris Taylor, Brittany Lyssy, Campaign Finance, Local Governance, Tallahassee Influence, Education Leadership, Public Education

Is a seat on our local school board up for grabs by the highest out-of-county bidder? For months, the District 2 race was a focused contest between candidates with deep, functional ties to our classroom, including professionals like veteran educator Chris Taylor, who has spent years in the trenches of our district. Chris understands student achievement because he has managed it from the front lines, and his commitment is rooted in the actual lives of the students he has taught and the teachers he has led. His vision is focused on stability, inclusivity, and the professional integrity our schools need to thrive.

In sharp contrast, the late entry of attorney Brittany Lyssy introduces a jarring shift toward outside influence and corporate-backed interests. While Chris Taylor’s support is local and organic, an analysis of Lyssy’s campaign finance reports reveals that nearly 45% of her total donations—excluding personal loans—flow from outside Hillsborough County. Backed by Tallahassee-based PACs and out-of-county law firms, her candidacy suggests an agenda more beholden to a state-level political machine than to our community. Hillsborough deserves a board member whose only “client” is the child in the classroom, not a strategist using our schools as a policy laboratory.

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The Tale of Two Doctors

May 4, 2026May 6, 2026 B. John 714 Views 1 Comment Affordable Housing, Accountability, Social Safety Net, 2026 Election, Healthcare Policy, Hillsborough County Commission, Local Government, Donna Cameron-Cepeda, Dr. Neil Manimala

This entry is in the series 2026 Elections

In a political era where labels are often used as shields, few examples are as stark as the “Dr.” honorific Donna Cameron-Cepeda wears to project authority over Hillsborough County’s $12 billion budget. While she cites her background as a financial analyst for a global corporation, her actual policy record reveals a troubling pattern of “pulling up the ladder” behind her. Having once relied on the very social safety nets and affordable housing she now votes to dismantle, her leadership has become a case study in the disconnect between personal history and public consequence.

The upcoming election presents a rare, high-contrast choice as Dr. Neil Manimala, a board-certified physician, enters the race with a platform centered on “healing” the damage done by recent regressive shifts. While Cameron-Cepeda’s tenure has been defined by culture-war distractions and the defunding of vital community nonprofits, Manimala represents a return to verified, professional competence. With even members of her own party filing to challenge her, the message is clear: Hillsborough is ready for a leader who values evidence over ideology and people over performance.

To understand the full scope of this “Doctor vs. Doctor” showdown and why this race has become a focal point for the future of our county, read the full analysis.

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