21 September, 2026 0 Comments

A Two-Fer: Housing Thoughts & Old School Square

September 21, 2026 By Leave a Comment

These sure are interesting times.

Recently, I  celebrated my 39th year as a resident of the Sunshine State.

Back in 1987, I was a kid fresh out of college seeking solace from the harsh winters I experienced going to school on Lake Ontario where it would sometimes snow in May.

Florida in the 1980s was affordable paradise.

I rented a two-bedroom apartment with a “Florida” room and tons of amenities for $600 a month. In 1988, when I bought my first home in Delray Beach, we spent $69,000 for a new townhouse off Barwick Road. That price included all the upgrades that were offered. Insurance was nominal (this was pre–Hurricane Andrew) auto insurance was less than half what I paid in New York, and there was no income tax.

Palm trees, warm breezes, year-round tennis and my childhood best friend living across the line in Broward made me a happy camper. I quickly fell in love with my new home.

After all, what’s not to like? (Heat, Humidity, Hurricanes—the three H’s –didn’t factor into my thinking at the time, Happy hour, Home fries at Poppie’s and Har-tru tennis courts did.)

But over time that affordability has eroded.

We’re not alone, but the situation in Boca-Delray is particularly acute especially when it comes to the cost of housing.

Insurance is no longer cheap. Auto insurance is very high, and the overall cost of living makes this a place where it’s hard to make ends meet unless you’ve been here a long time and already have a home, make a lot of money, have a lot of money, win the lottery or live on a friend’s couch.

Personally, I don’t know too many people who could afford to buy the house they are living in if they had it to buy it today.

Yet the notion of homeownership is a key to the American Dream.

As America marks its 250th birthday, perhaps it’s a good time to assess the state of the American Dream.

I think a corollary to homeownership is the power that Americans possess to create communities. Typically, that was made possible by the ability of Americans to tax themselves to fund local infrastructure and services.

According to a recent Wharton business school article: “After World War II, states legislated for, and localities implemented, master land-use plans that created an economic boom without rising home prices. We became a nation of homeowners as the homeownership rate went from less than half to two-thirds of American households. Although lagging other groups, a majority of minority households also became homeowners by the end of the 20th century. Nearly 90% of Americans achieved the American Dream of homeownership at some point in their lifetimes.”

That system allowed young people to become independent at a young age, typically starting their own households in their 20s or early 30s at the latest. Today, the median first-time home buyer is in their 40s, middle aged before they get their starter home.

Wow.

Just absorb that for a moment.

Since 2022, housing costs for new homes have more than doubled. In my neighborhood, they’ve quadrupled since we moved there in 2003.

Mortgage rates have gone from 3 percent to around 7 percent and rents have skyrocketed. Miami just passed New York City to become the most expensive big city to live in.

All this adds up to a very tough climate for people to live the dream. (Inflation, high health insurance rates, spiking food prices and expensive gas and electricity doesn’t help).

Economists are calling these factors the “Great Postponement” meaning young people are delaying key life decisions like marriage, having kids etc., because they just can’t get traction.

It’s interesting that housing and taxation are twin topics of concern these days, because they are linked.

Florida voters will decide in November whether to severely cut back on property taxes by increasing exemptions.

As a former elected official who worked on 7 budgets (which by law must be balanced, unlike our friends in Congress) I struggle with how this is all going to shake out especially since more than half of city budgets are devoted to police and fire services.

Yet, I understand the public’s need for relief. And I also understand that tax revenues, tied to rising property values, have made city budgets very large indeed.

Add a general lack of trust in government at all levels and it becomes a toxic stew.

Still, I think we should be careful what we wish for; and let’s be clear–this isn’t a tax cut, it’s a tax shift and we may end up paying more in assessments and fees because the need for public safety, roads, water, drainage etc. isn’t going away.

I noticed that the City of Delray Beach went on social media recently to thank taxpayers for the services they fund.

Cities are not supposed to advocate for ballot issues—but they are allowed to educate. I thought the post was interesting—but a strategic misstep. It just didn’t sound right, and it was met with a slew of comments complaining about spending and poor service delivery. Fair or unfair, it felt like the post invited a barrage of negativity.

Yes, government can always tighten its belt. Yes, services can always be improved. Government should be accountable for every dollar spent.

But that’s a different conversation from what I’m seeing. Granted, I’m not sure social media is a good gauge of public sentiment but there does seem to be a belief that either these services will magically pay for themselves or that we don’t need them.

On TV news, I keep seeing people saying that since their kids are no longer in school, they don’t want to pay school taxes. Well, don’t we have an obligation to invest in our future? Aren’t these kids our kids too? Don’t we owe them an education? Didn’t we help pay for your kids’ schooling?

The most disturbing thing I’m seeing is the lack of regard for home rule from our friends in Tallahassee. Since when does some legislator hundreds of miles from Delray or Boca know better than us how to run our cities?

Now if you don’t like the way your city is being led, run for office or vote for someone else who might do a better job but to cede control over your budget, land use decisions and other things seems to be fundamentally anti-Democratic.

One size usually doesn’t fit all. What works for West Palm Beach may not fly in Boca Raton. Cities and their stakeholders should have the right to create their own vision for what they want to be.

Regardless, we do have to tackle affordability, especially housing.

One out of three young adults ages 24-35 are living with their parents, according to the latest stats I could find — a return to the historic high point during the pandemic and earlier during the Great Depression.

The median age for a first marriage has risen by nearly a decade since the 1970s, and the average age for a first birth continues to increase. Just a generation ago, becoming a first-time parent after age 30 was viewed as unusual.  Today, it’s common.

So, what can we do?

Tools include zoning reforms, allowing accessory dwelling units, allowing higher density development (never easy politically) and hopefully lowering interest rates if economic conditions allow for it. Taming inflation would also help, also easier said than done despite the promises of politicians on both sides of the divide.

In the next few weeks, I will be speaking with some affordable housing experts about ways our philanthropy might get involved. I’ll let you know what I learned.

Meanwhile, buckle up. The next few months and years promise to be very interesting.

We need a national commitment to make sure our children can achieve the American Dream. A hand up, not a handout as they say.

Editor’s Note: And now for something different. I’ve rarely turned over this space to another voice, but when my friend former Commissioner Jim Chard asked if he could talk to you about the future of Old School Square, I said yes. On Tuesday, September 22, the Commission will be talking about the future of Old School Square. So this is certainly timely. Jim, take it away.

 

Restoring the Cultural Vibrancy Delray Once Had

By Jim Chard

Introduction

This study takes a deep dive into what has happened to Old School Square. It examines why the campus was shut down, what the citizens lost, and how we might possibly return to a vibrant cultural center at the heart of Delray.

  1. Once upon a time many years ago, Delray was a cultural center

The Crest Theater went dark on August 10th, 5 years ago. Not only the theater but many other cultural activities including an art school and concerts were terminated.   In a surprise move, the City Commission voted to terminate the contract with the Old School Square Center for the Arts without cause. And without a replacement strategy.

It is long past the time for the contentious groups to put down their pitch forks and implement a plan to return Delray to its position as a beacon of culture in South Florida.

This study will explore what we have lost as a community, reveal the roadblocks to returning to its former glory, and put forth a modest proposal to return the Old School Square campus in the center of Delray to its former glory.

Starting with a small group of visionaries in 1970s, the cultural center was built piece by piece over 30 years. By the early 2000s Delray had an active theater and lecture hall, a jewel of a museum, an amphitheater for concerts, a prestigious art school, and a lively community center in the Vintage Gym. The cultural campus at the center of Delray catalyzed the rebirth of downtown and energized civic renewal. With the exception of the Cornell art museum, none of the other cultural venues have approached their former prominence.

The campus was active 365 days per year, with some evenings offering activities in all the buildings and spaces.  Old School Square (OSS) at its height offered more than 3,000 activities per year.

 

Despite the termination of the OSS lease, the not-for-profit which founded and built Old School Square has not gone away. It is raising funds and offering grants all dedicated to teaching the value of arts and culture to our children including grants for school art supplies, scholarships for students, and the 6×6 art sale and show.

After all this time the key question is how to put Humpty Dumpty back together again. Where does the money come from? Who or what manages, schedules, recruits, and delivers all these activities.  Previously 75 to 80% of the annual costs were paid by the not- for-profit. Now the City (i.e., taxpayers) carries 100% of the cultural center expense: maintenance, programming, operations. Some of the costs are buried in the Parks and Public Works budgets, others consist of grants to the Downtown Development Agency. This strategy is not viable particularly with the current threat of a drastic reduction in property tax revenues.

The City owns the problem since they terminated the contract and repossessed the buildings. It’s past time for the City Commission to recognize its responsibilities and begin to rebuild what we once had.

  1. Cornucopia of Culture and Entertainment

This section is written to briefly mention a few of the activities we no longer have or are a shadow of their former selves. Old School Square was a magical place for events in the heart of the City – St Patrick’s Day, First Night, 100-foot Christmas Tree (including staffing) and Hannukah candles, and the Delray Affair. A few of the many examples are listed below:

  1. Speakers and Lecturers, some humorous, some musical, some thought provoking (Barbara Bush, Sandra Day O’Connor)
  2. Town Hall meetings educating all of us on issues that matter to Delray

(High Cost of Free Parking, Comprehensive plan)

  1. Extensive education programs for children and adults

Arts and culture were provided to public school children that were no longer available at school.

  1. Community gathering space, common ground to celebrate or to mourn

(student rally after mass shooting at Marjory Stoneman Douglas High School)

  1. Concerts in the Crest Theater and the Amphitheater

(Jimmy Buffet, Palm Beach Symphony Orchestra)

  1. Partnerships in the community

(Delray Art League, Orchid Show, first All America City award, Delray Beach Historical Society)

  1. Festivals found an inviting, affordable venue at Old School Square

(Roots Cultural Festival, open air art festivals, art of John Lennon and Yoko Ono))

  1. Education

(Full school – both day and night, National Water Color Society, League of Historic American Theaters)

  1. Lecture Series – nationally recognized figures spoke with Delray residents

General Alexander Haig– Sec of State, Bob Scha effer, Jane Russell

  1. Theater Productions

(Quest Black Theater group – Raisin in the Sun, Ain’t Misbehavin, Broadway’s Q Street)

  1. Cabaret Theater – patrons could gather at tables, enjoy a refreshing beverage and almost

reach out and touch the stars (Chita Rivera, Ann Hampton, Liz Calloway)

  1. Concerts at the Crest

(Jennifer Holiday, Lea Salonga)

  1. Minority Representation

(Preservation Hall Jazz Band, Tina Turner Review, Copeland Davis)

 

  1. Fund Raising and Programming Metrics

To give a sense of the activities available at OSS, here is the programming for a typical year

5 lectures per year

5 Broadway Cabarets (2 showings each)

10 mainstage shows

Art Exhibits 4- 6 per year

Field House (Vintage gym – 250 events

Art School – 25-30 teachers, 4000 students

16 free movies

10 free concerts

5 special events

5 comedies

Operations

Obviously such an encyclopedic schedule requires manpower and funding

Staff – 18 full time, 7-10 parttime

Volunteers 12 – 14 per Crest Theatre event, total of over 100

Members – 400 official members, donations exceeding $100k from Inner Circle

Annual ticket subscribers – 1,300

Total capital raised – $11 million to construct the campus

Economic Impact  (Source – Americans for the Arts) -$11- 15 million per year into the local economy

Fund Raising and Sources

National Endowment for the Arts

Grants – State Cultural Facilities and Historical Preservation

Elmore Family Fund, Lettie MacNeal Foundation, Laettner Fund, Cornell Family

Local donations and sponsorships from citizens and corporations

Florida State grants

Palm Beach County Tourist Development Council

Expense budget averaged $3 million per year

75% raised by OSSCTA, 25% from the City

  1. Call to Action

Four years ago the City Manager promised a “seamless transition with more and better cultural opportunities”. Obviously, that’s not the case…because we have lost so much. In August of 2022 the City held a charette to determine what residents and stakeholders wanted on the OSS campus.  The consensus was loud and clear, the participants wanted what they had previously.

 

As can be seen above, there are many moving parts to consider.  Several options have been attempted, including asking the Boca Museum to run OSS. Why should we ask another community to come in and run cultural programs in our town? A formal Request of Interest was posted nationally.  Although some entities expressed interest, no bids were received.

Meanwhile the Delray taxpayers are paying millions of dollars to put Humpty Dumpty back together again. However, no conversations are being held to solve this expensive problem – no plans for fund raising, programming or managing are being discussed.

With impending state legislation threatening a $21million revenue reduction and a change in Home Rule preventing investments in cultural affairs, it is hard to envision how the City can rebirth Old School Square. Meanwhile there is concern over deterioration of the 100-year-old buildings, especially the theater.

 

A Modest Strategy

The City should of course have great aspirations but minimize wishful thinking. We must recognize that at 350 seats, the Crest is a small theater with modest revenue. The average Broadway theater is 1500 seats and the Kravitz in West Palm is 2200, allowing more and higher priced tickets. Our expectations must be adjusted accordingly.

A smoothly operating cultural center must have a first-class management team, a governing entity like a board, a membership base, and a not-for-profit corporate structure with a strong local presence. This structure should not be imported from New York or Los Angeles (or Boca), and not be staffed or controlled by City Government.  Of course, we should look for a “Broadway angel” or bluebird financier but the likelihood of finding such is near zero.

To relaunch a cultural center, the key ingredients are

  1. Management by a not-for-profit dedicated to art, culture and education.

The Arsht, Kravitz Center, Lincoln Center, and Palm Beach Dramaworks are all

501(c)3 not-for-profits.

  1. The plan should start small and build over a 5 -10 year period. An overly ambitious plan is likely to fail. We only have to look at Boca and its $50 million plan at Mizner Park to see the result of overweight plans.
  2. The not for profit has to be staffed and managed by theater and cultural professionals, ideally with a stake in Delray.
  3. A cultural center must reach out to multiple funding sources – grants, donations, tickets, sponsorships and memberships. It is unlikely that such an enterprise is ever going to make a profit; plans must recognize that cultural institutions rarely, if ever, make money.
  4. Involvement with Delray Beach government must be limited despite the fact that the City is the landlord of the buildings. The not-for-profit must have a long-term lease that doesn’t include a clause that permits termination without cause if donors and grants are to be a major component to the funding. And whatever the organization chosen; it should be considered a partner not a “tenant” as some City officials want to do.  That approach demeans the organization and makes it nearly impossible to recreate what we had…a thriving cultural center in the heart of Delray.

7.Leadership of the organization must redefine the cultural activities accounting for differences that have occurred since 2021in the current population, new competition, importance of home entertainment, and higher operating expenses (especially for talent).

 

 

Since it is going to take a long time and heavy lifting, we should start now. The City has many priorities but returning Old School Square to its former glory should be one of the top ones. A consultant’s proposal will be considered at City Commission on September 22. Let’s hope it incorporates most of the features listed above.

 

 

 

 

14 September, 2026 0 Comments

The Things We Don’t Know Are Important

September 14, 2026 By Leave a Comment

I recently came across a new book by retired Lt. Gen. Mark Hertling, If I Don’t Return: A Father’s Wartime Journal.

Hertling began writing the journal for his two young sons while serving in the Gulf War. He was given orders and the intelligence briefing was grim. His unit could lose 50 percent of its personnel. Can you imagine?

Hertling wasn’t sure he would come home. So he started writing down the things he wanted his sons to know if he didn’t.

That’s a pretty powerful premise.

Not a will. Not instructions about money or possessions.

A record of what a father believed mattered.

The book got me thinking about the things I would want to tell the people I love. What I would tell my children.

And the things I wish I had understood earlier.

Hertling’s lessons aren’t particularly complicated. Character matters. Trust matters. Family matters. Service matters. Be courageous. Admit your mistakes. Pay attention to the people around you. Don’t confuse success with a meaningful life.

But one idea hit me particularly hard:

Don’t spend so much time preparing for the future that you fail to live in the present.

That lesson got to me; I’ve spent a lot of my life looking ahead.

I would describe it as ambition. Drive. Restlessness.

And I’m proud of some of what that produced. I worked hard. I took risks. I built things. I went into business. I got into politics. I pursued opportunities. I cared deeply about doing things that mattered.

But there was a cost to all of it. Perhaps that’s inevitable but at the time I never did the math.

I never asked myself  whether it was worth it.

I was always thinking about what was next.

And sometimes “what’s next” became more important than “what’s now.”

I didn’t fully understand that until I thought about my children.

There was a year when I spent a concentrated amount of time with my daughter, Samantha.

She was little. My ex-wife’s job demanded crazy hours, so Samantha spent her days in childcare and I spent mine in a newsroom.

But the early evenings were ours.

I fed her dinner.

That’s the memory.

There were no profound conversations. She was too little for that.

She was just cute.

So was our enormous golden retriever, Magnum, who would sit nearby, waiting patiently for the inevitable scraps to fall from the high chair.

It became a ritual.

Samantha eating dinner.

Magnum waiting.

Me feeding her and trying to make her laugh.

Nothing particularly remarkable happening.

I even filmed some of it with an old-fashioned video camera.

I’m glad I did.

Because now, years later, I understand something I didn’t understand then.

That was the good stuff.

Not the important meeting.

Not the next opportunity.

Not the next campaign.

Not the next accomplishment.

Dinner.

A little girl being cute.

A giant golden retriever waiting for a scrap.

An ordinary evening.

I never had that same concentrated year with my son when he was little.

I went into business. It was a struggle. Then I got into politics, and politics was consuming.

There was always something that needed to be done.

Something important.

Something urgent.

Something next.

And then my son grew up.

You can’t slow it down.

That’s the part I wish somebody had explained to me.

You can work harder tomorrow.

You can take another opportunity.

You can start another business.

You can run another campaign.

You can accomplish another thing.

But you can’t ask your child to be eight again.

You can’t go back and have the Tuesday night you missed because you were chasing something that seemed so important at the time.

That’s not an argument against ambition.

I don’t regret being ambitious.

It served me well. Ambition helped shape my life. Some of the things I’m proudest of probably wouldn’t have happened without it.

But I wish I had understood earlier that ambition and contentment aren’t opposites.

You can want more from your life and still appreciate the life you have.

You can be ambitious about tomorrow without being impatient with today.

That’s something I didn’t always know how to do.

Hertling’s book has me thinking about another of his ideas: that legacy isn’t simply what you accomplish or leave behind. It’s what you leave in other people.

I’ve spent a fair amount of my life thinking about what I would leave behind.

Maybe I should have spent more time thinking about what I was leaving in people.

The kindness.

The conversations.

The example.

The memories.

The dinners.

The ordinary Tuesdays.

Those things don’t show up on a résumé.

They don’t win awards.

Nobody gives you recognition for them.

And maybe that’s the irony.

I spent years chasing recognition.

What I really wanted, I think, was to know that I mattered.

But the older I get, the less interested I am in being recognized and the more interested I am in being remembered by the people who actually matter.

Not for the titles.

Not for the accomplishments.

Not for the things that seemed so urgent at the time.

Maybe just for being there.

For the dinners.

For the laughter.

For the ordinary moments that didn’t seem like much when they were happening.

Because those moments were happening to us only once.

And you can’t slow it down.

You can’t get them back.

So maybe that’s the lesson I’m taking from Hertling—and from my own life:

Don’t stop reaching for what’s next.

Just remember to look at what’s in front of you while you’re doing it.

Because someday, what’s in front of you will be behind you.

And you’ll realize it was the thing you should have been paying attention to all along.

7 September, 2026 0 Comments

Summer Winds

September 7, 2026 By Leave a Comment

A picture perfect late summer day  Portland, Maine.

For the first 22 years of my life summer was my favorite season.

Then I moved to Florida.
Now winter is my favorite time of year. Very few things in this world beat winters in South Florida. Cool breezes, bright sunshine, few gray days. And oh, those palm trees. They are not only aesthetically pleasing, they make a statement: welcome to paradise.
Still, my relationship with summer became complicated when I moved to Florida in July 1987.
When I lived in New York, I got used to hibernating during the winter months.
Summer was what I lived for: no school, no alarm clocks, days spent with my friends playing tennis and one wall racquetball, days at the beach with a boom box and nights spent under street lamps with neighborhood kids just passing time and goofing off. Shorts and t-shirts, summer songs, summer romance and muscle cars. (I had a friend who thought an AMC Pacer was a muscle car. It wasn’t. )
Ahh…summer.
But when I moved to Florida, things flipped. Summer was when I hibernated. Winter is when we rediscovered the outdoors.
It took a few years to get used to this new paradigm.
This summer, I made it a point to sneak away to Maine where I rediscovered my love of summer.
It’s been a busy season of life. My work at the Carl Angus DeSantis Foundation ramped up just as my playwriting took off with my first Off Broadway production. Now I say that as if there may be more coming. Who knows, but a guy can dream right?
Anyway, it’s been busy and I felt a need to reset, to step away, spend time with family and recharge.
Step away is a relative term. Truth is, I never stepped away.
I remain connected to the office, my email, my zoom calls, my office computer and all the rest. But merely changing where I took those calls and answered my emails did me a world of good.
I’m fortunate to have a supportive team at the office who made this possible. There is nothing like working with a team that makes you feel seen and appreciated. I’m a very lucky guy. The team I work with is stocked with intelligent people with big hearts. That’s not only an advantage for our work in philanthropy but it has filled my heart as well.
I believe that we do our best work when we make room for people to bring their whole selves to the job.
That means we listen closely to their insights and recognize that they are also people with children, elderly parents who need them, outside interests that make them who they are and individuals who need a change of scenery here and there.
Anyway, coming to Maine in August allowed me  to open the windows and shut off the air conditioning. It enabled me to take long walks in the woods, to explore the rocky coast and soak up the charm of small New England towns.
As a result, I fell back in love with summer, spent precious time with my dad and his significant other, enjoyed a long weekend with my sister and spent quality time with my amazing wife.
I wrote a little. Less than I thought I would and less than I hoped.
As mentioned, I stayed connected to the office and our grantees but I ditched the alarm clock, listened to music, read and spent time outside just breathing.
I’m fortunate to be able to do this.
I know others can’t. But if you can, please consider it.
And if you can’t, maybe there are small things you can do to recharge and renew.
Music, a walk, a good book. Nothing radical necessary . Life is rich. It’s also fragile and finite. Make the most of the quality time remaining.
31 August, 2026 6 6 Comments

Summer Songs Linger On

August 31, 2026 By 6 Comments

Boston’s debut album conceived and recorded in a basement.

I’m an avid listener of “Behind the Song” a podcast devoted to the fascinating back stories behind some of the greatest songs ever written.

I never miss an episode.
The host, Janda, is a Chicago radio personality who really knows her stuff. She also happens to have the best radio voice I’ve ever heard. Check it out to see what I mean.
Anyway, a recent episode focused on the year 1976. Turns out the bicentennial was a landmark year in music as well as a special time in American history.
I was 12 years old that year. And I remember the tall ships coming to New York, flag bunting everywhere and a sense of unity and patriotism.
We were post Watergate, post Vietnam, post energy crisis and dealing with inflation and what Jimmy Carter referred to as malaise.  But I don’t remember that as much as I remember the pageantry and the good feelings behind a landmark anniversary.
I also remember the music.
And the podcast brought it all into sharp relief.
Amazingly, the music released 50 years ago still resonates with me now that I am approaching my Social Security years.
What is about music that endures?
After all, I’m not into much that I liked when I was 12. Sports, for sure. Dogs, definitely. But I’m no longer reading what I read back then: Mad Magazine, the Chronicles of Narnia, Encyclopedia Brown. I’m not watching Laverne & Shirley or the Six Million Dollar Man and I’m not longing to buy a pitch back, the ultimate piece of sports equipment back in the day.
I’m also not playing Boggle or marveling at my friend’s Stretch Armstrong toy. Do you remember Stretch? He was the hit of ‘76, a latex action figure filled with corn syrup that could stretch up to four feet.
Nope, Stretch is no longer compelling.
But Boston’s debut album, Bob Seger’s “Night Moves” and Tom Petty’s first album are still on my playlists.
Songs in the Key of Life by Stevie Wonder, Hotel California by The Eagles, Frampton Comes Alive and Aerosmith’s Rocks—all released in 1976 and all still in heavy rotation. If you were there, you  can’t forget those songs.
What is it about music? Why do these songs linger?
 I have a theory.
Music attaches itself to our memories. We associate certain songs with eras of our life and moments in our culture.
So Boston’s “More Than A Feeling” with its soaring vocals and big guitars just  fits the bicentennial feeling.
And Hotel California fits the ennui of the post Watergate era.
Back then, I remember the adults in my life lamenting the scandal in Washington. But viewed in hindsight, Watergate showed the power of accountability and the importance of a free press.
Senators from the president’s own party held him to account and ushered him out. Woodward and Bernstein, backed by a legendary editor Ben Bradlee and a brave publisher Katharine Graham wrote stories that outraged Americans and inspired a generation of journalists to follow their lead.
A dozen years later, I was one of those reporters motivated by All The President’s Men.
Today, we have a scandal every day. We forget last week’s outrages and we never  hold a member of our team accountable. We just plow through. We just double down.
There are no shared facts, one side’s outrage is celebrated if it manages to annoy our enemies.
As for the press, we no longer trust the Fourth Estate. A scenario I find sad, dangerous and unsettling.
But the music endures. It rises above the rancor and division.
We can agree on Bob Seger’s brand of Midwest genius. How he captures  the excitement and drama of young love.
Night Moves—trying to lose those awkward teenage blues. That’s specific and universal. We all had those blues. All of us  remember them.
1976 was also the year of “American Girl”. The opening lines just nail it.
“Well, she was an American girl
Raised on promises
She couldn’t help thinkin’ that there
Was a little more to life
Somewhere else
After all it was a great big world
With lots of places to run to”
Yes!
Universal themes. The smallest lens. That’s the power of music. The words, the riffs, they are timeless and enduring.
Thank goodness.

24 August, 2026 6 6 Comments

Don”t Plant Your Bad Days

August 24, 2026 By 6 Comments

“Don’t plant your bad days. They grow into weeks. The weeks grow into months. Before you know it, you got yourself a bad year. Take it from me – choke those little bad days. Choke ’em down to nothing.”
~ Tom Waits
I’ve been listening to The Beatles song “When I’m 64” since I was 8 years old.
Back then, 64 seemed a million miles away. Heck, even my Bar Mitzvah seemed way off in the distance.
Childhood is a time of endless summers, long stretches between Christmas break and Spring Break and dreams of what you’ll be when you grow up.
My friends and I would sit in our rooms or shoot hoops in our driveways talking about becoming lawyers, doctors, center fielders and pro tennis players. The possibilities were endless even if the probabilities weren’t.
After all, there are not too many center fielders who can’t hit a curveball.
When the Fab Four sang about whether they would still be needed when they were 64, they were decades from that time of life. Today, the two surviving Beatles are in their 80s and the two late Beatles never made it to 60, never mind 64.
The protagonist of their timeless song was portrayed as doddering, wondering whether they would still be worthy of a valentine or a bottle of wine.
I’m going to be 62 this week. Fortunately , I don’t have those concerns. I’ve been lucky in love and I’m pretty sure if I asked nicely, my wife would join me with a glass of wine, if not a bottle.
The 60s are an interesting decade. In many ways I feel at the top of my game. I can draw on forty plus years of career experience and that’s been helpful as I’ve reinvented myself yet again this time as a philanthropy exec/playwright. That’s quite an interesting combo if I say so myself.
At 62, I feel I’m still evolving, still learning and still discovering the joy of new experiences.
And yet, I can feel age creeping up. I feel good, but there are days when I have aches and pains and my energy level and desire to run around has significantly diminished.
Instead, at the end of a hard day at work, I dream of my easy chair and playing with my two dogs. My idea of an exciting Saturday night is a quiet early dinner and Netflix.
But I still have aspirations; for the foundation I co-lead and for my playwriting which has been a joyous and collaborative experience. Both were complete surprises proof that as you age can discover, grow, learn and hopefully make a difference.
After a dozen years in business post Delray politics, philanthropy has enabled me to return to community work in a different and much less stressful way. I didn’t see any of it coming.
Six years ago, I struggled to survive a vicious bout with Covid. While I never stopped fighting, I remember feeling for the first time in my life that I may not survive. Isolated from loved ones, I had lots of time to think about my life.
What did it add up to? Did I do my best? Was I good to people? Did I contribute? Was I a good dad, son, husband, brother, friend etc?
As the virus attacked my lungs, those thoughts gave way to mere survival. Just keep breathing I thought. One gasp at a time.
When Covid finally let me go, I went back to the deep thoughts. Many patients I went in with at the time did not come out. Why did I make it?
I suffered what my friend the late Delray police officer Skip Brown called “survivor’s guilt “ and what a counselor told me was PTSD, common for people who spend extended time in the ICU.
I was thrilled to be home with my family. But something felt off, it’s hard to describe.
Gradually, the fog lifted and my strength returned with the help of physical therapy and my own desire to heal.
I resolved at the time to make whatever quality time I have left matter.
In the subsequent years, I’ve taken Tom Waits’ advice. I do not “plant “ bad days. And I have them.
I have a restless mind, it’s hard for me to shut off completely. I’m also a terrible sleeper. So when I wake up in the wee hours my mind will often engage.
And most times it wanders to my worries. I know I am not alone. I try and feel what I’m feeling but I don’t let myself stay in those dark places. Like most people my age, I have the usual share of stressors—aging relatives and friends, health conditions in my circle that scare me and the usual concerns about my kids, our country and our world.
I know I am not alone. And that’s why I share my thoughts in this space. When I had Covid, when I was able to,  I shared my experience on social media. It helped connect me to my community. That community healed me. I was also hoping to educate those willing to listen.
It wasn’t political. It was testimony.
Since then, I have lost many important people in my life.
Close friends gone to soon from cancer, Alzheimer’s and heart disease.
A woman I loved like a second mom, civic heroes and mentors and a man who changed my life and entrusted me to help lead his philanthropy so that his generosity and kindness could benefit people for generations to come.
These losses sting. You never quite get over them and honestly I don’t want to.
Because I’ve learned that death ends a life but it does not end a relationship and these wonderful people will continue  to shape and guide me for the rest of my days.
As I grow older, there are sure to be other losses. I dread that unavoidable part of life.
But love and loss focus me. I’m still open for growth and experiences. Still open to loving and learning and more appreciative of the good things in life than ever.
The love of a good woman.
The comfort that we’ve raised good kids.
The warm embrace of a family.
The joy of friends old and new.
The adoring gaze of my two adorable dogs.
I love Florida winters and the Maine coast.
When I type End Of Play, I feel a sense of accomplishment. When we call a grantee with good news it’s a thrill I can’t describe. There’s nothing like saying we believe in you, here’s some resources to bring some good into a world that needs it desperately.
And when I find that easy chair at the end of the day it feels like home.
17 August, 2026 0 Comments

Remembering Tommy John

August 17, 2026 By Leave a Comment

 

 

 

 

Tommy John said goodbye to his fans recently.
The legendary pitcher issued a statement through the New York Yankees thanking fans for their support through the years. It was a touching statement from a class act.
Yesterday, August 15, we learned that he passed. He was 83.
To baseball fans of a certain era, the name
Tommy John conjures up memories of a terrific sinker ball pitcher who could be counted on to eat innings and win big games.
I was a big fan. John played on my favorite teams during a golden era in the 70s. Reggie, Thurman, Bucky, Sweet Lou, Sparky, Goose and Louisiana Lightning. Those were some special years.
They called it the Bronx Zoo, but Tommy John always seemed above the drama of Billy Martin and George Steinbrenner. He just took the ball every five days and did his job getting hitters to hit ground ball after ground ball.
In the early 70s, Tommy John would have a pioneering surgery on his arm that saved his career. The procedure,
performed by the legendary Dr. Frank Jobe, would be named after Tommy  and would be used to save the careers of countless other pitchers at every level of the game.
John became the first major leaguer to come back after tearing his ulnar collateral ligament. An astonishing 35 percent of MLB pitchers have had the surgery at some point in their careers.
But Tommy John was more than a surgical procedure to his fans.
He was a workhouse who got by on savvy and movement because his injury robbed him of velocity.
Watching him pitch was akin to observing an artist at work. He would change speeds, paint the corners of the plate and more likely than not he would induce hitters into hitting an easy ground ball out.
Yes, power pitchers are exciting.  But there’s room for people like Tommy John. They are fun to watch.
He pitched 26 seasons in the majors finally hanging up his cleats at the ripe old age of 46. Only Nolan Ryan pitched more years.
After his career ended, he went into broadcasting, coached a bit and also ran a nonprofit dedicated to suicide prevention.
A New York Times profile called him a good natured family man.
That’s pretty good isn’t it? A good life. Tommy John lives in Bradenton, Florida. I read that he stopped watching baseball in 2019 because he no longer recognized the game he spent a good part of his life playing.
Tommy John was from another era. A good era.
I love 70s and 80s baseball. It was a fun time to be a baseball fan. I still think the game is wonderful and I admire the athletes and marvel at what they can do. But things have changed.
Throwing 100 miles per hour is common these days.
It’s impressive (although it tears those ligaments with regularity) but I miss the days when Tommy John and Luis Tiant and Jerry Koosman took the mound and worked their magic through guile. They were pitchers, not throwers and they were special.
Very special.
It’s not easy seeing your childhood heroes age. In your mind’s eye they remain forever young. Only they are not. And neither are we.
Thanks Tommy John. You are a class act. Goodbye and thanks for the memories. I hope there’s a field of dreams on the other side of this life and that we’ll see you throw that sinker again.

10 August, 2026 2 2 Comments

Where Have All The Stories Gone?

August 10, 2026 By 2 Comments

Is it me, or is there nothing on TV these days?
Yeah, yeah I know I should be reading, writing or learning to play Mah Jong like half the planet seems to be doing.
Truth is, I am reading and writing but I’m also eager to lose myself in a good movie or streaming series.

I have the usual array of pricey services: Netflix, Apple TV, HBO, Prime. Something happened to my Hulu account. I don’t know what. I’ve  given up on trying to get it back.

Regardless, I can’t find anything to watch. I don’t want to be terrorized, I don’t want a documentary about a serial killer and I don’t much care for the endless array of derivative stories that mine the Super Hero canon.

Nothing wrong with them,  but I just want to lose myself in a story, a romantic comedy or a well written drama.
There was a time, a few years back, when I had the opposite problem. Too many things to watch, not enough time. I think they called that era “Peak TV”. They may as well call this era Bleak TV.
Anyway, I found a station called Tubi, that has old shows and old movies.

So I decided to dive back into some old favorites to see if they held up.

I started with Neil Simon’s “Goodbye Girl” and “Chapter Two” both starring Simon’s ex-wife Marsha Mason.
Marsha was great. The movies were OK. The Goodbye Girl held up better,  but Chapter Two was lacking something. I can’t quite name it.

Then I tried “State and Main” by acclaimed playwright David Mamet, a terrific writer not such a terrific guy. Mamet has become irascible as he’s aged. I suppose that’s understandable. But State and Main didn’t hold up. Only two characters to root for out of a large cast of creeps.  It just wasn’t enough.

Wanting to feel better, I spent a rainy evening watching Dudley Moore in Romantic Comedy. It was…not very good.
Then I turned to “Love and Death” with one of my favorites Diane Keaton. Yes, I know it’s a Woody Allen film and it’s not politically correct to watch but I was feeling nostalgic. Love and Death held some sentimental value for me. It was the movie I took my first ever date to see at the Smith Haven Mall in Lake Grove Long Island in 1975.

I was in 6th grade, the new kid in school and a very nice young woman named Sue took pity on me. We went to the movies with her older sister and her boyfriend who drove. Sue and I sat in the back seat and watched them kiss at every red light.

That behavior continued throughout the whole movie. They didn’t see a single frame. I sat in my seat frozen, staring straight ahead as Sue waited for me to hold her hand, or put my arm around her. I couldn’t.

I arranged for a friend to meet me at the theatre. I made several excuses to leave the movie and seek advice from my friend in the lobby. He had no wisdom to offer.
Just some raisinettes. To this day, on the rare occasion when I go to the movies, I always try to buy those chocolate covered raisins—a genius invention that all these years later I still find irresistible.
But I digress.

Love and Death was unwatchable. Diane Keaton was magical.
Still, optimistic I turned to an old favorite “No Way Out” an early Kevin Costner vehicle that also stars one of my favorite actors Gene Hackman.
I remember this film as being extraordinary. My memory was… wrong.
It felt very 80s, complete with annoying synthesizer music and some serious holes in the plot.
Sigh.
I give up. For now.

I haven’t lost my faith in old movies. But I think I have to be a little bit more discerning. “The Godfather”, “Unforgiven”, “All The Presidents Men,” “Butch Cassidy & The Sundance Kid,”  “American Graffiti”,  and “Good Will Hunting” hold up well.

Still, while I love those movies I long to be swept away by something new.
A modern day “When Harry Met Sally” or a new buddy movie with stars that gel like Newman and Redford.
That would be something.
Come on Netflix. Come on HBO. You can do it.
Meanwhile, any suggestions?

3 August, 2026 16 16 Comments

Say My Name

August 3, 2026 By 16 Comments

So I premiered a play Off Broadway recently.

That’s a sentence I never thought I’d write.

Excuse me for a moment… I did it! Sorry, thanks for the indulgence, I’ll try and behave from here on out.

 

Say My Name opened at the AMT Theater as part of the 10th Annual Broadway Bound Theatre Festival, and I’m still trying to process everything I felt that week. I don’t think I’ll ever forget those three performances.

 

A Play That Wouldn’t Let Me Go

 

I wrote Say My Name about a year ago, and it’s gone through more drafts than I can count. It began as a ten-minute play called Press Conference, which won a few contests along the way and is still licensed in that form by Tiny Scripted, a distribution company.

This was a story I couldn’t quite let go of. The characters kept talking after the curtain came down on the 10-minute version, so I expanded it into a full-length play and brought it to Working Title Playwrights in Atlanta for development.

 

That process reminded me of something I believe more every year: writing may begin alone, but good writing rarely stays that way. A good play requires collaboration; people who help you wrestle with the work, talented artists who help you bring it from the page to the stage.

Throughout the process, I’d send pages written on my phone or in my mancave at home.  My collaborators, first in Atlanta, later in New York City, asked hard questions. I’d process the comments and then rewrite. Then we’d do it all over again. It’s the kind of collaboration that keeps a writer honest, and it’s why I seek out thoughtful partners whenever I can. Writing is solitary work. It doesn’t have to be lonely.

 

A great dramaturg knows when to challenge you and when to step aside. He or she pushes you toward a better version of your play without ever forgetting that it still belongs to you.

 

But once a playwright hands over a script, something remarkable happens.

 

It stops being my play.

 

It becomes our play.

 

That may be my favorite part of theater. That’s when the fun begins.

 

Words that lived for months inside one person’s imagination suddenly belong to actors, designers, directors, stage managers, technicians, and eventually an audience. Every one of them finds something you never knew was there.

Say My Name tells the story of a 15-year-old boy who was shot and killed outside a school dance. I wrote the play to honor the memory of Jerrod Miller, a 16-year-old who was shot by a rookie police officer in 2005 outside the Delray Full Service Center. I was mayor at the time.

The tragedy left a hole in my heart and the hearts of many, many others. The loss has also been largely forgotten by many, something that didn’t sit right with me. I wanted to write something that forces audiences to stop and consider the names that scroll by on TV screens when violence occurs. It is not Jerrod’s story per se, but it is a composite of too many young lives lost in this country.

I sent it in for consideration to the Broadway Bound Theatre Festival, a prestigious event that celebrated its 10th year in 2026. It was chosen and I was thrilled to lead off the festival which runs through August at the AMT Theatre in the heart of the NY’s theatre district.

I was fortunate to work with visionary Director Reena Dutt who saw things in the script that I hadn’t seen myself. Every conversation we had, every adjustment she suggested, every staging choice she made ultimately strengthened the play. It’s a rare gift to trust someone so completely with something so personal.

 

Working mostly from Florida, I leaned heavily on our extraordinary stage manager, Lauren Linsey, who somehow managed to make the distance disappear with grace, kindness, and remarkable organization.

Then there was the cast.

Watching actors breathe life into characters who had existed only in my head for more than a year was one of the great privileges of my life.

 

Acclaimed stage and screen actor Tim Redmond brought intelligence and warmth that audiences immediately embraced. Eric Ruffin told me he had read the script more than a hundred times and every ounce of that commitment showed in a performance filled with quiet gravity and extraordinary compassion. Veteran actor Guiesseppe Jones gave Reverend Clayton exactly the presence I had imagined when I first wrote him.

 

Jennifer Laine Williams did something I’ll never forget. Audience members told us afterward they had expected to dislike her character. Instead, they found themselves understanding her—perhaps even rooting for her. There may be no greater compliment an actor can receive than making people reconsider their own assumptions.

 

Imani Jones brought enormous tenderness to her role, often leaving audiences in tears. Craig Cartwright embraced one of the play’s most difficult characters with remarkable courage. Richard Yarrell III’s voice, by more than one account, was simply heavenly. And Amanda Bailey captured my heart on our very first Zoom encounter, became exactly the spiritual heartbeat I had imagined for the ancestors guiding Eric’s character Marcus. Her voice alongside Richard’s created moments I’ll never forget.

Actors are remarkable people. Impossibly dedicated, smart and passionate, they can make even a newbie like me look good.

 

The Hours Nobody Sees

 

People see opening night.

They don’t see the months that come before it.

For me, rehearsals began after my workday ended; night after night from seven until eleven, weekends included. Most of my work happened over Zoom before I finally joined everyone in New York for final rehearsals and tech. I was so happy to be with these people, even for a few hectic days. I savored every moment. It still feels like a dream.

There is something wonderfully surreal about the creative process. One evening you’re discussing where a scene should go and rewriting a speech alone at your desk. A few months later you’re watching an actor deliver those same words to a silent theater full of strangers, and they’re wiping away tears.

When the house lights dimmed on opening night, I realized there was nothing left for me to do.

For months I had rewritten scenes, questioned every choice, and obsessed over every page. Suddenly the play belonged to the people onstage—and to the audience sitting in the dark. For the first time since typing “END OF PLAY,” I was simply another audience member.

 

What You’re Actually Chasing

 

People sometimes think theater artists chase applause.

Applause is wonderful.

But that’s not really what we’re after.

When a play truly works, you can feel something move through the room. You hear people laughing or crying together. You feel something that can’t be described, energy, emotion, connection to a story. Then the lights come up, and nobody rushes for the exits. They linger in their seats. They gather in the lobby. They continued conversations they weren’t having two hours earlier on the sidewalk with the actors and each other.

That’s exactly what I hoped this play would do.

The cast got a standing ovation which they richly deserved for immersing themselves in their roles and telling a story that is important. The tears, and the generous applause were deeply moving, but the moments I’ll remember most happened afterward. I collected dozens of audience comment cards over those three performances. Nearly every single one praised the extraordinary work of the cast, the direction, and the production itself. More importantly, people wanted to keep talking. They debated. They reflected. They asked questions.

That was always the goal.

To help people feel something.

To help people think and remember.

And maybe, just maybe, to help them talk to one another again.

 

Full Circle

 

What made the experience even more meaningful was looking out into the audience and seeing people who had been part of this journey long before opening night.

Friends traveled from far and wide to support me.  A wonderful group from Delray Beach made the trip north as well, a reminder that while this play opened in Manhattan, it carries a great deal of Florida with it.

More people than I can count have told me they hope this story finds a larger audience.

I hope it does too.

If it does, I hope this same creative family is standing beside me again. I can’t imagine a better group of artists, or a more compassionate group of human beings, to continue telling this story.

At its heart, Say My Name asks us to do something both simple and impossibly difficult: to truly see one another, to love one another, and to remember our shared responsibility to serve and protect each other.

Reflections

Ten years of the Broadway Bound Theatre Festival.

And somehow I had the privilege of opening its tenth season.

I still catch myself saying it out loud every now and then, just to make sure it’s real.

I premiered a play Off Broadway.

That’s still a sentence I never thought I’d get to write.

I hope this story inspires you to try something you never thought possible.

 

27 July, 2026 2 2 Comments

Faith Not Hope

July 27, 2026 By 2 Comments

 

I wasn’t expecting anything from the podcast.
I rarely do.  It was background noise  — something to fill the drive, maybe I could learn a thing or two.
And then Brian Quint said something that made me reach for the volume knob.
He runs a theater company in Canada called Nightswimming. Cool name. I’m thinking it may be named after one of my favorite REM songs. Quint never said.
But he did say he runs a theater of faith, not hope. He didn’t elaborate much, at least not right away. He didn’t need to. The distinction landed before the explanation did.
I’ve been turning it over ever since. I’m not sure why. These kinds of things have been happening to me lately. In a world of noise, I get signal. For just a moment.
I think the word hope was what landed for me.
Hope, I think, is what most of us run on. It’s the fuel of the aspiring playwright, the unfunded foundation initiative, the relationship that needs one more good year to find its footing. Hope is useful. It gets you out of bed. But there’s a fragility to it — hope depends on something coming through. Someone returning that email. Someone saying yes.
Hope is, at its core, a negotiation with the future.
Faith is something else. Faith doesn’t wait for the outcome to justify the act. Faith doesn’t need someone else to say yes.
It says: this is worth doing because I am doing it. Not because of what it might become. Not because someone decides to take a risk on your idea.  The doing is the arrival. The doing is the point.
I think I’ve spent most of my life working from hope when I thought I was working from faith. The difference turns out to matter.
I write. A lot. Plays, essays, a stray poem. I have screenplays in a drawer, book ideas in folders. I love writing. Even though it’s hard. Even though, at times, it has broken my heart.
These days I’m writing plays.
I have for three years now, with a seriousness that crept up on me slowly and then all at once. Most of them have not been produced. Some have had readings. A few have found small stages. One just got produced  Off Broadway, which still surprises me when I say it out loud.
But here’s what I know: I wrote them anyway. All of them. Not because I had a production lined up or an agent waiting or a theater that believed in me. I wrote them because not writing them felt like a kind of dishonesty. Like I was withholding something I owed — to the work, to myself, maybe to the people the plays were secretly about or the ones I long to touch with a story that may have  meaning.
That’s not hope. Hope would have quit by now. Hope would have done the math. Hope would have figured out that it is hard to make it. I started kind of late, I’m learning on the job. I have
a lot of ground to make up and a finite amount of fuel in the tank.
Yes, hope would have thrown in the towel. But I haven’t. And I won’t.
That’s faith.
I co-lead  a foundation. We try to put resources into communities and institutions and ideas that we believe can matter. A lot of that investment lands in uncertain soil. You make the gift, you trust the people, you let go. In many cases, you don’t get to know how it turns out, not really, not on any timeline that satisfies the part of you that wants proof. Philanthropy, done honestly, is an act of faith dressed up in spreadsheets.
When we started our philanthropic journey we made a pilgrimage to see David Odahowski. He runs the Edythe Bush Foundation in Winter Park.
Dave has been called the “Dean of Florida philanthropy “ a title he has earned.
We were the rookies coming to see the veteran. The first thing Mr. Odahowski said to us was that we would never solve any of the issues we were seeking to impact.
That diagnosis, struck me. I had hope we might solve a problem or two.
But I understand what he was saying. The message was delivered with care through the lens of experience.
But the more I sit with it (and it has been a year) the more faith I have that we will make an impact. We will change lives. We will help people and communities.
 We make a daily choice to keep showing up for the things and people we’ve  decided are worth showing up for don’t we?
Brian Quint probably wasn’t talking about any of that on that podcast. He was talking about theater. But faith, once you start pulling on it, doesn’t stay put. It led me down so many paths. Paths I happily walk.
I don’t know much about Nightswimming. Is it named after my favorite REM song?
 I looked them up after the podcast ended. A small company. Developmental work. The kind of theater that exists in the margins of the industry, which is often where the most honest work gets done. What struck me wasn’t their catalog. It was that they had named their posture. They had decided, out loud, what kind of company they were going to be — not in terms of genre or aesthetic, but in terms of orientation. Faith, not hope.
That takes courage. Hope is easier to defend. Hope sounds reasonable. Hope has a plan.
Faith sounds reckless until you realize it’s the only thing that was ever actually holding you up.
I’m not ready to abandon hope entirely. I don’t think that’s what Quint was suggesting either. But I want to be more honest about which one I’m operating from on any given day. Hope can masquerade as faith for a long time before you notice the difference. Hope says I’ll keep going as long as there’s a chance. Faith says I’ll keep going.
Full stop.
I write. At the foundation we give.
I’m someone who has chosen, over and over, to bet on people and places and ideas that don’t come with guarantees. I think I’ve been a person of faith longer than I’ve had the word for it.
Thank you, Brian Quint. I wasn’t expecting anything from that podcast.
Turns out I should have had more faith.
20 July, 2026 2 2 Comments

In Defense of Getting Lost

July 20, 2026 By 2 Comments

In my office there’s a drawer full of dead ends.
Half-finished plays. Scenes that seemed brilliant at midnight and embarrassing at breakfast. Openings for columns that never found their second paragraph. A few big civic ideas that got as far as a legal pad and no further. For years I thought of that drawer as a graveyard — evidence of all the times I set out for somewhere and didn’t arrive.
I’ve come to believe I had it exactly backwards.
Here’s the thought by author Seth Godin I want to put in front of you, and I’d suggest reading it twice: Don’t curse the dead ends and the failures. They’re the key element of the work you’re doing. We find our way by getting lost. Anything other than that is called reading a map.
Kindly sit with that last line. It’s doing some heavy lifting. Because a map, when you think about it, is just a record of where somebody else already went. Maps are wonderful things — I don’t want to romanticize being lost on a highway late at night — but a map can only take you to places that exist. If the thing you’re after doesn’t exist yet — a play nobody has written, a story nobody has told, a version of a town nobody has built — then there is no map. There can’t be. The territory hasn’t been surveyed because you’re the one being sent to survey it.
Which means the wrong turns aren’t the interruption of the work. They are the work.
I learned this first as a writer. Every playwright knows the experience of following a scene confidently for ten pages before realizing it’s a cul-de-sac — the characters have nowhere to go, the energy has drained out, you took the wrong exit three pages back. The temptation is to treat those pages as waste. But they’re not waste. They’re reconnaissance. You now know something about your play that you could not have known any other way: you know where it doesn’tgo. And nine times out of ten, somewhere in that dead-end scene is a single line, a gesture, an image — the thing you were actually digging for, buried in ground you’d never have turned over if you’d stayed on the path. The failed scene isn’t the opposite of the finished play. It’s the tuition.
I learned it again in public life. Cities are the ultimate argument against map-reading. Every town has a shelf of master plans, and every honest person who has served in local government will tell you the same thing: the plans that worked were the ones that left room to get lost. You try a pilot program and it flops — but the flop teaches you what the neighborhood actually wants, which is never quite what the consultants’ map said it wanted. You back a project that dies in a 3–2 vote, and two years later the fight it started produces something better than the original idea. The failures weren’t detours from the town’s progress. They were how the town found out who it was.
The trouble is, we live in an age that has declared war on being lost. GPS reroutes us before we even feel the wrongness of a turn. Algorithms serve us more of what we already liked. Career advice comes bulleted and optimized: five steps, proven path, guaranteed arrival. We have built a civilization of maps, and we wonder why so much of what it produces feels like a place we’ve already been.
Meanwhile, everything genuinely new — every original book , every real reinvention, every town that became more than a strip of chain stores — came from somebody willing to wander off the surveyed grid and burn some daylight in the weeds.
I want to be careful here, because there’s a cheap version of this idea and I’m not selling it. “Fail fast” makes failure sound painless, and it isn’t. The dead ends cost real things: months, money, confidence, sometimes relationships. Getting lost is frightening precisely because it’s real — because for a stretch you genuinely do not know where you are, and no one can tell you. I’ve had those stretches. I’ve hated them. Every one of them, without exception, is where the work changed.
So here’s the question I keep coming back to, and I’ll leave it with you rather than answer it: when was the last time you let yourself get lost — genuinely lost, no map, no reroute — in anything that mattered to you?
If the answer is “a while,” the drawer full of dead ends is waiting. Mine is right here. I used to think it was a graveyard.
Turns out it’s a trailhead.
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