2025 In Review

That tower again, it’s watching me

Waiting for Moses to descend the mountain with his commandments

Allons! the inducements shall be greater,

We will sail pathless and wild seas,

We will go where winds blow, waves dash, and the Yankee clipper speeds by under full sail.

—Walt Whitman, Song of the Open Road

 

 

Ah, warm water

Old men ought to be explorers

Here or there does not matter

 

We must be still and still moving

Into another intensity

For a further union, a deeper communion

Through the dark cold and the empty desolation,

The wave cry, the wind cry, the vast waters

Of the petrel and the porpoise. In my end is my beginning.

—TS Eliot, East Coker

 

 

A neighbor visits in San Diego

Last Year

When I last wrote about us (December, 2024), I was living in San Diego, California with my wife Misa. Our son Max was in college at Embry Riddle Aeronautical University in Prescott, Arizona. I was not working, after being laid off from Big Financial Company, where I worked for twenty-five years. 

We Moved

Misa and I live in San Francisco, California. 

 

Max, pre-graduation

Max graduated

In summer, Max lived in Los Angeles and worked for United Airlines at LA International Airport. He graduated from Embry-Riddle, Magna Cum Laude, on December 13. He will begin work for an airline in Las Vegas, Nevada, in January, 2026. 

 

Us and San Francisco

Regular readers can't be surprised that we moved back to San Francisco. Or maybe you are. 

Why did we do it?

The short answer: We are insane. 

We are literally insane. 

Longer answer: We felt the city pulling us back. Armistead Maupin wrote about his character, Michael Tolliver's decision to stay here, during the worst days of the AIDS epidemic.

To get away from the tragedy—and the talk—some of his friends had moved to places like Phoenix and Charlottesville, but Michael couldn’t see the point of it. The worst of times in San Francisco was still better than the best of times anywhere else. There was beauty here and conspicuous bravery and civilized straight people who were doing their best to help. It was also his home, when all was said and done. He loved this place with a deep and unreasoning passion; the choice was no longer his. —Armistead Maupin, Significant Others

 

Land’s End, red socks, 1987

From my first contact with the city life was different here. People liked me better. I don't know why. Misa says I look happier here and that's attractive. I can do things that are impossible for me elsewhere. It's exactly like falling in love with an extraordinarily beautiful person, who lifts you off your feet. In return, she takes over your life and you must obey her. Like Michael Tolliver, you give up your power of choice. From then on, you are at her mercy, and she has little mercy. She takes all your money, and she ruins other places for you. You can go shopping for houses, but she decides which one you'll live in. That is what happened to us. 

At what price?

While we were house hunting, I had occasion to remember this story.

In 1988, a big, blonde real estate developer in New York purchased The Plaza Hotel on Central Park South. He took out a full-page ad in the New York Times, wherein he wrote, 

For the first time in my life, I have knowingly made a deal which was not economic—for I can never justify the price I paid, no matter how successful The Plaza becomes. 

Like Donald’s decision to buy the hotel, our return to the city cannot be justified economically, only with a guilty grin and, “the heart wants what it wants.”

 

So we are back, living on a steep hill overlooking Golden Gate Park. We did it for love. The city has many problems, and it can be quite annoying, but it's home for us. 

 

Special thanks to Pam and Doug Barry, Daniel, Erika and Ezri Duke, Christian Wignall and Ling Khong, who hosted us during our transition. We moved at the end of March. A lot of stuff went wrong, but we were patient with each other and 'cautiously optimistic.’ 

The old Nob Hill Gang: Andy Stevko and Dale Forest

 

In summer, we had a party for new and old neighbors, allowing us to reunite with many old friends. 

Both of us began looking for jobs, right away. Misa was not successful, and for a long time, neither was I. In September, I received a contract position in information security. Special thanks to Matt Gonko and Tony Stevens. They talked me up, and without them I would still be unemployed. I work near Fisherman’s Wharf.

Fog attacks the lowlands, where we lived before 2012
It’s nice to be higher, like flying above the fog in an airplane

Life on our little mountain
I have lived in the Richmond District, Nob Hill and the Outer Parkside (Ocean Beach) neighborhoods. The new house is near the geographic center of our square city, just west of Twin Peaks. We are directly south of the museums in Golden Gate Park and that famous Bridge. The neighborhood is everything we could hope for, quiet at night but near everything we need. Public transportation improved markedly since we left in 2012, and we are well-served in all directions.

The eternal picture

Yes, incredibly, still working. You can see the current state here, scroll all the way down. You know by now, I’m in no hurry to finish, but I actually paint as much as I can. Honestly, I do. One thing all our 2025 changes have in common is that they killed painting time.

On the positive side, I’m back living in my picture. Every time I take the streetcar to my office, I see the buildings down town and at Pier 39. I paint a tiny dot on the Embarcadero, and that’s me. 

This year, the main campaign was to put more boats in the water. This helps  the plane of water look right. I made more than one hundred paper dolls of boats and taped them to the canvases, and now I’m painting in the winners. “For many are called, but few are chosen,” which is one of the more depressing truths Jesus shared with us. 

My portrait of Carol, 1990s

In memory

Carol Simonszky Ragle 1941 - 2025

Carol was an accomplished artist, married to another accomplished artist, Roy Ragle. 

Carol’s fashion illustration, 1970s

I met the couple in 1989, at my Open Studio event. At that time, we lived a few blocks away from each other in the Richmond District. Roy and Carol were wonderful friends, always encouraging. They believed in me, and I am forever grateful. Roy died in 2014, and in the intervening years, Carol enjoyed looking out at her view of Golden Gate Park and studying astrology. Her apartment was a comfortable library, and I spent many pleasant hours there. Carol went completely deaf, yet we still understood each other, and took comfort from our presence together.

Carol’s portrait drawings, 1990s

We exchanged many pictures, and they put mine in places of honor, about their fireplace. The foil heads were life masks and skull masks Roy made.

My portrait of Carol and Roy, 1990s

2005, Roy’s work premiers at the Oakland Museum
Misa prevents little Max from destroying the glassware

In Conclusion

I’m spent. What happened to you in 2025? Please share. I hope you went after what your heart wanted.

Concentration Is Power: From Renaissance Portraits to Risk Management

In war, concentrate your forces.

In work, concentrate your information.

In my recent work, I’ve been reflecting on how organizations handle complexity—and how simplicity often hides in plain sight. 

A long time ago, I began keeping a Commonplace Book. This is a simple collection of quotes and thoughts from my reading. I read novels, poetry, history, science, every subject imaginable, and took stuff from each. As I kept up the practice, this collection blossomed—perhaps “bloated”—to more than 1.1 million words. This rather large body of information is not organized, in any meaningful way. It’s set down in chronological order, according to when I read it. You might think this disorganization would make it fairly useless, a big landfill of typing, but you’d be wrong. It’s unbelievably useful. 

To illustrate how concentrated information can unlock insight, let’s take a detour to the Renaissance. Let’s ask, “Why is the Mona Lisa smiling?” 

I think there is a real, true answer to this question, not just idle conjecture. I read about it somewhere, a long time ago. I mean a really long time ago, when some of you were not yet on the planet. Where did I see it?

Answer in two seconds.

Leonardo undertook to execute, for Francesco del Giocondo, the portrait of Mona Lisa, his wife; and after toiling over it for four years, he left it unfinished; and the work is now in the collection of King Francis of France, at Fontainebleau.

Mona Lisa being very beautiful, he always employed, while he was painting her portrait, persons to play or sing, and jesters, who might make her remain merry, in order to take away that melancholy which painters are often wont to give to the portraits that they paint. And in this work of Leonardo's there was a smile so pleasing, that it was a thing more divine than human to behold; and it was held to be something marvellous, since the reality was not more alive. — Giorgio Vasari, The Lives of the Artists

Why was this record of my long-ago reading experience found so quickly? 

Because all my notes are in one place. 

When all necessary information is in one place, it’s easy to find answers. It’s easy compare and contrast. It’s easy to recognize patterns in the information. It’s easy to see how the different components relate to one another, how they support—or defeat—the larger purpose. It’s easy to know if an action is consistent with a company’s risk appetite. All this can be done without laborious catalogues, tables of contents or indexes.

Why do I bring this up?

In business, a body of information often disintegrates, when it should concentrate. “Experts” claim their territory, and their first step is to insist that “this” cannot live alongside “that.” I once worked on a set of policies (lists of ‘shoulds’ and ‘should nots’) and its accompanying set of procedures (here’s how we do the shoulds and avoid the should nots). The policies and the procedures were kept in separate libraries, at separate intranet locations. Our company expected employees to know this, and to ricochet between the two. 

 

Several times I asked, “If we want people to carry out the policies using the approved procedures, would that be more likely to happen if they could find both together?”

No one else asked this question, and no one agreed. No problem; I’m comfortable being Mr. Weirdo. When the two libraries were consolidated years later, I suggested we put the polices and procedures in one document. That was the stupidest idea my coworkers ever heard. Instead, they made three separate entries in the remaining library, covering our policy area.

When systems resist clarity, create your own. 

We can’t reorder the world, but we can reorder our copy of it. Accepting my failure to persuade, I thought about my job and asked myself, “What can I do to make this easier?” I would be asked about these policies and how to implement them, nearly every day. I went to the library, copied all three reference documents, and pasted them into one. When I got a question about mobile devices, I clicked on my document, typed in “mobile” and threw the appropriate language back. This one favor saved me many hours, hunting for answers. 

You wouldn’t go into battle with half your ammunition hidden in eight places. Put everything you need to know in one place, and you may be surprised at how simple the work becomes.

Testing Is Not Optional: Why Constant Vigilance Drives Long-Term Business Success

People usually fail when they are on the verge of success. 

So give as much care to the end as to the beginning;

Then there will be no failure. —Lao Tzu, Tao Te Ching, translated by Gia-Fu Feng and Jane English

[In computer simulation games] The good participants differed from the bad ones . . . in how often they tested their hypotheses. The bad participants failed to do this. For them, to propose a hypothesis was to understand reality; testing that hypothesis was unnecessary. Instead of generating hypotheses, they generated "truths." —Dietrich Dörner, The Logic of Failure: why things go wrong and what we can do to make them right

We often dream of that one world-changing idea—the product with our name on it, immortalized. But that fantasy plays out like a romantic comedy: the couple meets, kisses once, and the screen fades to gold. That’s not the real ballgame. What happens after the great idea dawns is what truly matters. The actions you take—or avoid—once the system is built ultimately determine your success. 

Here’s the uncomfortable truth: we’re wired to conserve effort. Our own plans always make perfect sense to us, so we don’t want to test them. We love thinking about how other people can benefit us, but if asked to think about how we can benefit others, our focus narrows. Our enthusiasm quickly flags, if it doesn’t die altogether. I’ve seen this play out in business settings. Instead of putting the customer first, we run away from helping the customer. 

I recently spoke with a developer, who was launching an app designed to simplify product purchases—a promising idea to boost sales. I asked, “Who’s going to test this every day, indefinitely?” He didn’t understand the question. I explained: networks, operating systems, and integrations will constantly change. What works today will break tomorrow. If you’re testing regularly, you’ll catch it. If not, frustrated users will quietly delete the app and move on.

Stated that way, it’s hard to argue against constant testing with real-life users, but there’s a big problem: No one wants to do this. No one wants to pay for this. We want to launch a website, an app, or an AI chatbot—then walk away and expect it to serve customers flawlessly while we nap.

The companies who overcome this natural lethargy will attract more customers than those who “let it ride.” Will anyone at the failing company notice? Probably not. By the time those lost customers are counted—by the time they show up on someone’s Metrics Dashboard—nothing will bring them back. Here’s how that happens.

I once opened a tax-advantaged college savings account for my son. I thought my regular bank, Company 1 could set me up, and they did. A week later, I logged into Company 1’s site and couldn’t find the account. The representative explained that it was actually managed by a partner—Company 2—and that I’d need to use their platform.

“But I bought it from you. Don’t you want to be my go-to bank?”

“That would be great,” he said, “but it’s not set up that way.”

“Is anyone working on this?”

“Not that I know of.”

The story doesn’t end there. As I was forced to log in and do business directly with Company 2 each week, I noticed something. Company 2 did everything better than Company 1. Their interest rate on savings was much higher and they answered the phone quicker. Today, all my paper assets are managed at Company 2, zero at Company 1. Company 1 lost me—not because of one missing feature, but because they stopped at the sale instead of thinking about the experience.

Right now, I’m looking for work, and I submit applications via online forms. Many of them fail to save or submit properly. Either no one is testing them, or their testing is insufficient. And there’s no technical support—just silence.

What kind of candidate gives up and moves on? The high-value one. The candidate with multiple offers. The one who could have made a transformational difference. They disappear—quietly, permanently. Metrics don’t always tell this part of the story. When we consider and include the quality of opportunities lost, that annoying, expensive testing becomes imperative. 

Some business goals—such as hiring only the best people—will not happen without it. 

For a further distinction, security engineering expert Ross Anderson offers a valuable insight into collaborative testing and design thinking:

Requirements engineering, like software testing, is susceptible to a useful degree of parallelization. So if your target system is something novel, then instead of paying a single consultant to think about it for twenty days, consider getting fifteen people with diverse backgrounds to think about it for a day each. Have brainstorming sessions with a variety of staff, from your client company, its suppliers, and industry bodies. 

But beware—people will naturally think of the problems that might make their own lives difficult, and will care less about things that inconvenience others. We learned this the hard way at our university where a number of administrative systems were overseen by project boards made up largely of staff from administrative departments. This was simply because the professors were too busy doing research and teaching to bother. We ended up with systems that are convenient for a small number of administrators, and inconvenient for a much larger number of professors. — Ross Anderson, Security Engineering, Second Edition

Businesses who take testing seriously don’t just avoid failures—they unlock growth others never see. If you're looking to build that kind of resilience, I’d love to help.