On the
Vagaries
of Optimism

If life had handed me lemons, I would have been grateful. Lemons are useful. You can make lemonade, squeeze them into tea, or arrange them attractively in a bowl and give visitors the impression that somebody in the house has a plan. What life handed me instead was chronic pain, several false starts, a collection of professional detours, and an optimism so unreliable that it should never have been trusted with machinery.

Yet it kept returning.

That is the vagary of optimism. It is not steady. It does not march into the room carrying a motivational poster. It wanders off when most needed, hides behind the furniture, and then reappears after the disaster asking whether we might try once more, perhaps this time after reading the instructions.

I used to think optimism meant believing the future would be kind. Science cured me of that. The universe makes no such promise. Stars exhaust their fuel. Bodies fail. Businesses collapse. Entropy, which has never needed a public-relations department, eventually sends an invoice.

And still, here we are: temporary creatures making plans.

The Prophetic Child Misses an Entrance Exam

I was the ninth child, with eight sisters before me; four children in the family did not survive. My arrival therefore acquired a significance I had done very little to earn. Somewhere in the background, The Who might as well have been playing “It’s a Boy.” I appeared less like an infant than a quarterly result the family had been waiting years to announce.

The prophetic child then went to the Doon School, whose reputation tended to enter a room several minutes before its students did. This should have been the opening movement of a triumphant life. Instead, I did not score well enough for the engineering college I wanted.

Prophecy, it turns out, has terrible follow-through.

I studied subjects chosen less from passion than from a desire to finish and fasten a degree to my name — proof, if nothing else, that the educational system had processed me and returned a receipt. I sank into depression. For a while I adopted the grave expression of a deep thinker, which was convenient because it discouraged people from asking whether I had any idea what I was doing.

I call this my nematode period. The adult C. elegans hermaphrodite has 302 neurons.^[2] I had considerably more, but the evidence was not always admissible.

My path then curved through Austria, where I acquired a hotel diploma that seemed permanently pasted to my forehead. It did not say future technologist or student of the universe. It said, more or less, this gentleman may know what to do if the breakfast buffet runs out of coffee. On my way out, I qualified for a job as a busboy on a cruise ship sailing from Miami. Nothing teaches a young man the vagaries of destiny quite like discovering that his grand intellectual future may involve clearing other people’s plates at sea.

There was no clean upward line. There was only movement — sideways at times, downward with surprising efficiency, but movement nevertheless.

The Lemon That Would Not Become Lemonade

At twenty-three, an injury established chronic pain as a permanent institution in my life. It still pierces behind my left eye. I did not speak much about it. I did not want my family to think their long-awaited son had arrived with a manufacturing defect, though by then the warranty had plainly expired.

Working with pain was hard. Money was often short. Expectations hung overhead with the ceremonial menace of the sword of Damocles. But pain also taught me something optimism alone never could: progress does not have to feel good to be real.

Years later, I built a business that succeeded long enough to make its collapse educationally expensive. I had started it on four credit cards in 1990 — a capital structure that, in retrospect, combined entrepreneurship with the suspense of a hostage negotiation. When it fell apart, the lawsuits arrived like buses: none for ages, then several together. Contracts vanished. Payroll developed moral objections to arithmetic. A printer once became stranded on an aircraft carrier, which is not a sentence business school prepares you to write.

I was frightened. I was broke. But I paid everyone I owed, down to the last penny. This was morally satisfying and financially inconvenient. I started again without investment capital, which meant that my business plan depended heavily on optimism continuing to report for duty.

But I never learned to treat a setback as a verdict. A setback meant that something I had attempted had not worked in that form, under those conditions, with that version of me. It was heavy, inconvenient and sometimes absurd. It was not the future.

The road was less a road than an abandoned construction zone: no signs, no useful detours, and someone moving the cones whenever I approached the correct bend. So I kept going. Obstacles without signage are not stop signs. They are missing instructions.

My Second Education

After forty, and after the business collapse, I returned to science. I did not return to earn the engineering degree I had missed. I returned because I wanted to understand why the world existed, how atoms came to be, why time travels in one direction, and whether the universe was any better organized than my own affairs.

Spoiler: it was not.

I read relativity, cosmology and physics with the anxious appetite of a man preparing for an examination no one had scheduled. Much of it resisted me. I repeatedly rammed my head against fundamentals that had long since escaped from my school days. The fundamentals remained unmoved. Eventually, however, I learned.

I had become an autodidact before I knew there was a respectable word for it. Human beings have always depended on knowledge distributed across other people — accumulated, revised and passed through generations. Researchers call this cumulative cultural evolution: no one of us invents the world from scratch; we inherit a vast, social store of solutions and add our uncertain piece to it.^[1] Our oldest technology may not have been the stone tool. It may have been the story that taught someone else how not to use it.

While trying to understand the universe, I founded FedMine, a company built around federal spending data. I had no programming experience, so naturally I decided to build a data company. I created a database before properly understanding what a database was. This sounds bold only if one omits the many hours during which it was merely confused. I treated ignorance as an implementation detail, asked questions, distrusted the first answers, and asked again.

In 2021, I sold FedMine to GovSpend, a portfolio company of Thompson Street Capital Partners and Endicott Growth Equity Partners.^[5] Endicott’s information-services effort had been built in part by former leaders of SNL Financial and S&P Global Market Intelligence — people professionally qualified to recognize a data business when they saw one. Their portfolio company bought the one I had built with no outside capital and no programming experience. I mention this not to polish a trophy, but because an essay about optimism that stops before optimism works would be suspiciously committed to irony.

Somewhere in that process, optimism changed shape. It stopped being a feeling and became a method: curiosity, iteration, humility, humor. Fall. Examine the ground. Get up with slightly better information.

The Silicon Optimist

All of this has prepared me, improbably, for the present moment. Biological humans — emotional, contradictory, intermittently intelligent — have built systems that can mimic language, anticipate needs, extend human reasoning, and hallucinate with the poker-faced confidence of a politician who has misplaced both the facts and the expression required to acknowledge it.

Artificial intelligence is made from mathematics running on machines fashioned, ultimately, from ordinary matter. Sand learned statistics; statistics learned syntax; syntax began offering career advice. If that does not strike you as funny, terrifying and magnificent at the same time, I recommend checking whether your optimism has wandered behind the furniture again.

The easy positions are that AI will save us or destroy us. Both relieve us of responsibility. Salvation asks us to wait for the machine. Doom asks us to surrender to it. Disciplined optimism asks more: use the systems, test them, argue with them, give them clear purposes, measure their failures, and build safeguards before convenience makes scrutiny feel old-fashioned.

That is not merely a philosophical preference. The National Institute of Standards and Technology describes trustworthy AI in practical terms: systems should be valid, reliable, safe, secure, resilient, accountable, transparent and fair, with harmful bias managed.^[3] Its risk framework is organized around four verbs — govern, map, measure, manage — which sound less stirring than “the machines will save us,” but have the advantage of being useful.^[4]

AI is still brilliant at some things and embarrassingly bad at others. That will change. Our task is not to worship statistical minds or to mock their current mistakes. It is to teach, test and use them without outsourcing judgment. If we do this well, they may help remove drudgery, extend discovery and take on work too dangerous for human bodies. If we do it badly, they will reproduce our worst habits at a speed and scale our wetware never managed.

No Guarantees

My optimism is not based on the belief that the universe is benevolent. Quite the opposite. Once you understand that existence is not guaranteed by divine plan or cosmic necessity, you stop waiting for the universe to make sense of itself on your behalf. You start paying attention. You start moving.

Meaning does not arrive from outside with assembly instructions. We assign it while we are here. That makes meaning fragile, but not false. Music is temporary too. So is laughter. So is the moment when a difficult idea finally becomes clear. Their impermanence is part of their value.

This is why I remain stubbornly optimistic: not because I expect kindness from the future, but because I have seen iteration, humility and humor turn failure into progress. Keep curiosity close. Treat failure as information, not identity. Build systems that fail safely. Do not confuse hope with evidence, or evidence with destiny.

Writing History’s Future is my attempt to make sense of that journey — from a prophetic child who missed his engineering college, to a hotel graduate with cosmic questions, to a businessman who discovered that collapse is a very thorough teacher, to an autodidact trying to understand the new intelligence we have made from sand.

I do not know whether humanity will use artificial intelligence wisely. Nobody does. Optimism does not require me to claim otherwise.

It requires only that I refuse to mistake uncertainty for permission to do nothing.

After spending decades trying to understand my own life, I turned to the universe. It was not better organized. But it was still here.