Did you really Want to Roll Back the Clock?
Why you did not act then but will you act now?
Woulda, Shoulda, and the Cost of Looking Back
Everyone wants yesterday’s price.
Not just in real estate, but in everything. They want Advanced Micro Devices at $3 in 2015, they want Microsoft Corporation at its public offering, and they want Seaside lots at 1987 pricing. What they are really asking for, though, is not the opportunity itself — they are asking for the outcome, stripped of the uncertainty that existed at the time.
That distinction matters, because the past only looks obvious after it has already worked.
Why the Past Feels So Certain
Behavioral economics addresses this directly through what psychologists Daniel Kahneman and Amos Tversky described as hindsight bias. In simple terms, it is the tendency to see events as having been predictable after they have already occurred. Once we know the outcome, we reconstruct the path as if it were inevitable.
Kahneman later summarized this tendency bluntly: people believe they “knew it all along,” even when they didn’t. The uncertainty, the conflicting signals, and the real possibility of failure all get edited out of memory.
That is exactly what happens with AMD. At $400 today, the move from $3 looks like a straight line. In reality, it was anything but. At $3, AMD was a distressed semiconductor company with legitimate questions about survival. The same distortion applies to Microsoft in the 1980s and to Seaside in its early years. None of these were obvious at the time.
The Seaside Example, Without Nostalgia
A buyer once said, “I wish I had bought in Seaside in the 80s or 90s.”
So we worked through the numbers, not to romanticize the past, but to compare decisions in their actual context.
In the more recent case, a property was acquired for $1,429,000, and redevelopment began in late 2017. The new construction cost another $1,429,000, bringing the total basis to approximately $2,858,000. The project was completed and sold in 2025 for $7,040,000. That outcome was not driven by luck or nostalgia; it was the result of acting decisively in a market that had already proven itself, with clear demand, established pricing, and a defined buyer pool.
Now compare that to the version people wish they had lived. A Seaside lot in 1987 might have cost $30,000, with construction around $125,000, for a total basis of roughly $155,000. Today, that same property might be worth $2,900,000.
On paper, the earlier entry looks superior. But that conclusion only exists because the ending is already known.
What People Remove From the Equation
The comparison is not about which number is higher. It is about what each buyer had to believe at the moment they acted.
In 1987, Seaside was not an established luxury market. It was a concept. There was no certainty of long-term demand, no proven resale structure, and no clear indication that it would become what it is today. That buyer accepted ambiguity and illiquidity in exchange for a low entry price.
By contrast, the 2017–2025 redevelopment operated in a fully formed market. Demand was visible. Pricing was transparent. The risk did not disappear, but it changed form. It became execution risk rather than existential risk.
Those are fundamentally different decisions, even if they occupy the same piece of land.
The Second Bias at Work
The other force influencing this thinking is regret aversion, a concept formalized by economist Graham Loomes and Robert Sugden. Their work describes how people make decisions in ways that minimize the potential for future regret rather than maximize expected value.
In practice, this shows up as fixation on missed opportunities. People replay the decision they didn’t make, not because it was clearly correct at the time, but because the outcome is now known. The emotional weight of “missing it” becomes larger than the reality of the risk that existed when the decision was available.
This is why the statement “I wish I had bought then” feels so compelling. It is less about the investment itself and more about avoiding the discomfort of having been on the sidelines.
The Quiet Part Most People Ignore
The same person who says they would have bought AMD at $3 rarely accounts for how they would have behaved afterward. They assume perfect conviction, perfect patience, and the ability to hold through volatility. More often, they would have sold early, reduced their position, or never committed meaningful capital in the first place.
The fantasy is not just about timing the entry. It assumes flawless behavior over time.
That assumption is almost never true.
Reality vs Realty
Both Seaside scenarios worked. One required vision in an unproven environment. The other required disciplined execution in a mature market. Neither was obvious when the decision had to be made.
What people actually want is something different. They want the return profile of early risk with the clarity of hindsight. Behavioral economics makes it clear why this happens, but it does not make it achievable.
The Only Question That Matters
The past is clean because it has already resolved. The present is uncomfortable because it hasn’t.
So the relevant question is not what should have been done in 1987 or 2015. It is what you are willing to do now, given incomplete information and real uncertainty.
Because ten years from now, today will look just as obvious as the past does now, and someone else will be saying they wish they had acted when the outcome was still unclear.
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