John Masters, Author at Deep Something

Can You Be a Stoic and a Political Activist?

September 26, 2026 B. John 53 Views 0 Comments civic responsibility, justice, Political Activism, common good, Political Division, Democracy, Stoicism

This entry is in the series 2026 Elections

This entry is in the series Journey Through Stoicism

Can you be a Stoic and still be politically active? I think the answer is not only yes, but that Stoicism gives us a better way to do it. The ancient Stoics did not confuse acceptance with surrender. They accepted what could not be changed, while challenging injustice when action was still possible.

That question feels especially urgent now. We are living in a time when division itself has become a political tool. Culture war fights can dominate attention while people are still struggling with housing, health care, violence, war, and the basic question of whether government can still solve real problems. Anger may be useful in campaigns. It is rarely enough to build a decent society.

Stoicism asks something harder of us. Stay engaged without becoming consumed. Think clearly when others are trying to provoke you. Act with courage when something is wrong. Keep justice at the center. And remember that the people on the other side of a political argument are still part of the same community.

Politics, at its best, is what we choose to do together. This essay asks what Stoicism can teach us about showing up for that shared life, especially when the temptation is to give up, tune out, or shout louder.

Politics Election Economy Featured Places Tampa

Cool Classrooms and Common Sense: Why Hillsborough Must Renew the Half-Penny Promise

September 23, 2026 B. John 70 Views 0 Comments citizen oversight, Hillsborough school sales tax, half-penny renewal, public school funding, school maintenance, HVAC repairs, classroom investment

This entry is in the series 2026 Elections

This entry is in the series Education

This entry is in the series Florida Amendments and Referenda-2026

Florida summer heat is not theoretical. It is a relentless physical reality. Anyone who expects children to concentrate on algebra or reading in an eighty-eight-degree classroom with a dead air conditioner and water dripping into plastic buckets has never spent an afternoon inside an aging Florida school building. You cannot build academic excellence when students and teachers are simply trying to survive the humidity.

Hillsborough Referendum 3 asks voters to renew the half-cent sales tax for another ten years to pay for air conditioning, roof repairs, and security at schools. Opponents talk about tax fatigue, but this is not a new tax. It keeps the same rate as in 2018. If it ends, your grocery bill will not go down, but school maintenance will lose $120 million a year.

The results speak for themselves. Since 2018, the Half-Penny Promise has funded over 750 projects, including air conditioning upgrades at 177 schools, all overseen by an independent Citizen Oversight Committee. Tourists pay about a quarter of the cost, and over $716 million has gone to local contractors and workers in Hillsborough County.

While the state Capitol stays busy manufacturing political culture wars and diverting public funds into private vouchers, local communities must take care of their own. Read the complete breakdown on why renewing this capital surtax is an investment in our kids, our local workforce, and our neighborhood schools.

Featured Places Tampa Politics Election Legislature

Trading Four Votes for One: The Cynical Math Behind Hillsborough’s Commission Power Grab

September 23, 2026 B. John 74 Views 0 Comments local control, Charter Referendum 2, single-member districts, county governance, at-large seats, voter representation, Hillsborough County Commission

This entry is in the series Florida Amendments and Referenda-2026

This entry is in the series 2026 Elections

If someone came to your door and offered to trade four hundred-dollar bills for a ten-dollar bill, you would quickly close the door and check your security cameras. That is exactly the kind of deal behind Hillsborough County Charter Referendum 2, a Tallahassee plan that would undo forty years of balanced local government.

For forty years, Hillsborough has used a mix of four district commissioners and three countywide at-large commissioners. This lets every voter choose four out of seven seats, giving people a say in the majority. Referendum 2 would end this system by expanding the board to nine and removing all at-large seats.

Think about what this means for your representation. You would go from voting for four commissioners to just one. You would not be able to vote for or against the other eight, even though they decide on taxes, infrastructure, and big development projects. Single-member districts encourage commissioners to trade favors for their own areas and ignore countywide needs like Port Tampa Bay and regional transit.

Tallahassee politicians love to lecture local communities about neighborhood control while quietly shrinking our democratic leverage from afar. Read the full commentary to see why trading away four seats for one is a bad trade for Hillsborough taxpayers, and why we must vote No on Charter Referendum 2.

Legislature Society Education Featured Places Tampa Politics

The Ballot-Box Bureaucrat: Why Electing Hillsborough’s Superintendent Is Bad for Business and Worse for Classrooms

September 23, 2026September 23, 2026 B. John 97 Views 0 Comments elected superintendent, Public Education, Hillsborough School Board, Local Governance, Tallahassee preemption, school referendum, Michael Owen

This entry is in the series Florida Amendments and Referenda-2026

This entry is in the series 2026 Elections

This entry is in the series Education

Imagine Tampa General Hospital announcing that it will now select its President and CEO through a countywide partisan primary. Picture candidates debating surgical protocols on debate stages, taking a full year off to solicit campaign checks from medical supply reps, and catering to partisan party bosses instead of patient care. No board of trustees would tolerate it, and no major health system would survive it. Yet that is the exact circus Tallahassee politicians want to bring to Hillsborough County Public Schools, the single largest employer in our community.

Proponents dress up the proposal in the language of parental rights and democratic empowerment. But under the current model, the superintendent answers to an elected, seven-member School Board every single day. If the superintendent mishandles district finances, botches bus routes, or mismanages schools, the board can act immediately. Under an elected system, that daily accountability vanishes. The School Board loses its supervisory power, leaving a single partisan politician in charge of a $4 billion budget and 220,000 students, answerable to voters only once every four years.

An even bigger problem is the smaller pool of candidates. Instead of searching the country for experienced school leaders, we would be limited to local registered voters. The best-performing states treat school administration as a professional job, while the only two states that still elect superintendents are not among the top performers.

Injecting culture-war primaries and campaign fundraising into our school system’s executive suite is a disaster waiting to happen. Read the full analysis on why turning school administration into a political prize hurts our students, undermines teachers, and destabilizes our local schools.

Economy Featured Politics Legislature

The Free Lunch Mirage: How Florida Amendment 3 Squeezes Renters and Municipalities

September 22, 2026 B. John 115 Views 0 Comments tax shift, Florida Amendment 3, homestead exemption, local government funding, Property Taxes, first responders, renter costs

This entry is in the series Florida Amendments and Referenda-2026

This entry is in the series 2026 Elections

Every politician knows that promising a giant tax cut is an easy way to win an applause line. Florida Amendment 3 dangles that exact bait, promising homeowners an expanded homestead exemption and tighter assessment caps. It sounds like an effortless win until you calculate what actually pays for the fire rescue station down the street.

State analysts project this measure will strip over $8 billion from local budgets across Florida in a single year. That is not trimming bureaucratic fat; it is a fiscal sledgehammer aimed directly at 911 dispatchers, sheriff’s deputies, paramedics, and neighborhood road repairs. When both the Florida Sheriffs Association and statewide firefighter unions sound the alarm, voters need to look past the political marketing.

Because essential emergency services cannot simply be shut down, local communities will be forced to raise utility fees and regressive sales taxes to survive. That leaves working families, retirees on fixed incomes, and renters footing the bill for a tax break they will never see. Read the full analysis on why defunding your local first responders is too high a price to pay for a campaign slogan.

Featured Politics Legislature

Corporate Welfare in Overalls: The Rural Shell Game of Florida Amendment 2

September 22, 2026September 22, 2026 B. John 112 Views 0 Comments agricultural tax exemption, corporate agribusiness, Hillsborough County, tax shift, Property Taxes, Florida Amendment 2, Home Rule

This entry is in the series Florida Amendments and Referenda-2026

This entry is in the series 2026 Elections

The television commercials for Florida Amendment 2 are almost entirely self-written. All you have to do is play the acoustic guitar, show the video of a dusty tractor, and then tell the heartwarming tale of a fourth-generation family farmer who is struggling. Although the story is touching, the sentimental presentation covers up a costly performance by the corporation.

Florida businesses currently have a standard exemption of $25,000 for tangible personal property, which covers a significant portion of the equipment needed by genuine small-scale growers. The main benefit of Amendment 2, however, goes to industrial agribusiness syndicates, huge commercial packing houses, and luxury agritourism event venues that operate fleets of machinery costing six figures.

When Tallahassee eliminates equipment taxes on commercial agricultural land, those multi-ton transport trucks do not stop chewing up county roads. The bill simply shifts. County commissions are left to either gut local services or force residential homeowners to make up the difference. Read the full breakdown of how Amendment 2 puts corporate welfare in overalls and leaves local taxpayers holding the tab.

Featured Politics Election Legislature

Rainy Days and Blue Tarps: Why Hoarding Billions in Tallahassee Won’t Protect Hillsborough

September 22, 2026September 22, 2026 B. John 97 Views 0 Comments Budget Stabilization Fund, rainy day fund, Hillsborough County, state budget, Tallahassee preemption, Florida Amendment 1

This entry is in the series 2026 Elections

This entry is in the series Florida Amendments and Referenda-2026

Tallahassee politicians often present Florida Amendment 1 as basic common sense. After all, who would argue with saving for a rainy day? But there’s a big difference between keeping an umbrella handy and locking away billions while your ceiling is falling in.

If you drive through Hillsborough County, you’ll see blue tarps still on roofs from storms years ago. Homeowners are struggling with high insurance costs, classrooms have broken air conditioners, and stormwater ditches need repairs. Yet Amendment 1 would require up to $750 million a year to be set aside in Tallahassee until the fund reaches 25 percent of general revenue.

Florida already has a fully funded emergency reserve at 10 percent. Forcing billions more into storage isn’t smart budgeting; it’s a way to cut local spending now so politicians can brag about a big balance later. Read the full essay to see why we should fix our roofs before Tallahassee builds another vault.

Society Education Crack Pots Featured Places Tampa Politics

Brittany Lyssy’s School-Board Training Network Deserves a Closer Look

September 21, 2026 B. John 146 Views 0 Comments school board politics, Hillsborough County Schools, Moms For Liberty, Bridget Ziegler, Brittany Lyssy, Leadership Institute, Hillsdale College

This entry is in the series 2026 Elections

This entry is in the series Education

Brittany Lyssy cites her work with the Leadership Institute’s School Board Leaders Program as part of her education-policy experience. A closer look at that program shows a national conservative network built around recruiting, training, and supporting school-board candidates, with direct connections to Moms for Liberty and to policy resources from Hillsdale College and the Heritage Foundation.

One connection deserves particular attention. Bridget Ziegler, an early figure in Moms for Liberty, served in leadership of the same Leadership Institute school-board program where Lyssy worked on communications, policy analysis, ethics, and governance. Public records do not show that Lyssy belonged to Moms for Liberty or adopted every position promoted within that network, but the institutional ties are clear enough to warrant scrutiny.

The larger question is what parts of that philosophy Lyssy would bring to Hillsborough. The full article follows the connections among the Leadership Institute, Moms for Liberty, Hillsdale, Ziegler, and Lyssy’s own policy background, then asks what voters should examine before deciding how much those ties matter.

Featured Places Tampa Politics Legislature Society Crack Pots

Josie Tomkow Discovers Homeowner Rights

September 21, 2026 B. John 95 Views 0 Comments Senate District 14, Josie Tomkow, campaign contributions, homeowners insurance, attorney fees, Florida insurance reform, Homeowner Claims Bill of Rights

This entry is in the series 2026 Elections

Josie Tomkow says she wants to create a Homeowner Claims Bill of Rights and make sure insurance claims are fully paid. This sounds reassuring, especially in a state where rising premiums and storm losses have made things tough for homeowners. There is just one awkward detail: Florida already has a Homeowner Claims Bill of Rights. Even more, Tomkow spent years voting for laws that made it harder and more expensive for policyholders to challenge insurers when claims were denied or underpaid.

Campaign records also show ongoing support for Tomkow from insurance companies, industry groups, civil-justice organizations, and a former Florida Insurance Commissioner who now works in insurance advisory.

So is this a real change of heart, or just a shift for campaign season? Her voting record, contribution history, and new promises make it worth taking a closer look.

Featured Politics Election Legislature

Whose Voice in the Committee Room? Michael Owen, Insurance Cash, and the Squeeze on District 70

September 20, 2026September 20, 2026 B. John 99 Views 0 Comments Michael Owen, HB 4027, HB 4029, Hillsborough County, Property Insurance, Campaign Finance

This entry is in the series 2026 Elections

Michael Owen sits where Florida’s property insurance laws are shaped: the House Insurance & Banking Subcommittee. His campaign finance reports also show substantial support from insurance companies, insurance political committees, agents’ groups, and lobbyists. The article examines that money alongside the choices he has made in office.

Owen has shown no shortage of legislative ambition when Hillsborough County government is involved. He sponsored HB 4027, which puts an elected school superintendent before Hillsborough voters, and HB 4029, which would substantially restructure the County Commission. Both measures passed the Legislature and require local voter approval.

That leaves a harder question. With homeowners still confronting steep insurance bills, what has Owen used his seat on Insurance & Banking to do for them? The campaign money does not answer that question by itself, but it makes his legislative record worth examining closely.

This article follows the money, looks at where Owen has chosen to spend his political capital, and asks what those priorities tell District 70 voters about whose concerns are getting attention in Tallahassee.

Featured Stoicism

Wisdom: Whittling Away at Uncertainty

September 20, 2026September 20, 2026 B. John 113 Views 0 Comments self-knowledge, experience, Stoicism, Reflection, wisdom, decision-making, uncertainty, judgment

This entry is in the series Journey Through Stoicism

This entry is in the series The Stoic Virtues

How do we know when we are wise?

I have been thinking about that question because wisdom may be the hardest Stoic virtue to define. Courage, justice, and temperance all give us something concrete to work with. Wisdom feels different. We rarely have all the information we want, yet life still requires us to decide, act, adjust, and sometimes admit we were wrong.

In Whittling Away at Uncertainty, I look at some decisions I would make differently today, a new job I am about to begin, and what experience has taught me about research, judgment, and knowing when enough information is enough. Wisdom may not be about certainty. It could be learning how to make the best decision we can, then having the courage to begin.

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