Card Counting for Retirement: Stack the Deck in Your Favor

What does a blackjack strategy have to do with securing your retirement? More than you might think, according to financial advisor Dana Anspach, CEO of Sensible Money, who has pioneered a systematic approach to retirement planning inspired by the card counting techniques made famous by MIT students in the book Bringing Down the House and the movie 21.

The premise is simple but powerful: just as successful card counters don’t win every hand but tilt the odds in their favor through consistent methodology, retirees can dramatically improve their financial outcomes by applying a disciplined, analytical framework to every major decision they face.

The Problem with One-Off Decisions

Most people approach retirement planning haphazardly, Anspach explains. They read an article about Social Security and make that decision one way. They hear that annuities are bad and dismiss them entirely. They react to market headlines and move to cash before an election.

“Those are all one-off decisions,” Anspach says. “They’re playing each hand on its own versus a methodology that would look at each decision in a framework and say, ‘How do I make this decision in a way that tilts the odds to my favor?'”

This scattered approach means missing opportunities to compound good decisions—similar to a card counter who only counts cards on some hands but not others. The strategy only works when applied consistently.

The 60% Rule: Finding Your Edge

“Sixty percent of the time, in many cases 70, 80, 90% of the time, this decision is going to work in your favor. But sometimes we get so emotionally caught up in the ‘but that 1% of the time’ or ‘that 5% of the time.’ And we’re like, yeah, but that is not the likely outcome.”

Unlike a casino where the house edge might be just 52%, Anspach aims for decisions that work in clients’ favor at least 60% of the time—and often much higher. The key is basing choices on the most probable outcomes rather than emotional worst-case scenarios.

How the Card Counting Method Works for Major Decisions

Social Security claiming strategy serves as a prime example. Rather than relying on rules of thumb, Anspach’s firm uses a mathematical model that factors in:

Customized life expectancy (educated, higher-income earners typically live longer than average)

Marital status

Tax situation and Roth conversion opportunities

Discount rates based on reasonable portfolio returns

A metric called “fundedness” that measures overall financial health

The analysis determines whether claiming at 62, full retirement age, or 70 will likely leave more money available over a lifetime—or translate that into higher sustainable spending from day one.

Not All Cards Are Weighted Equally

The importance of each decision varies dramatically based on personal circumstances. For a household with $10 million in assets, Social Security’s present value of around $1 million may not significantly impact their overall plan. But for someone with $500,000 in savings, that same Social Security decision becomes crucial—a major card that can stack the deck considerably in their favor.

For wealthier individuals, investment methodology and avoiding headline-driven decisions carry more weight. For those with less than $1 million, timing Social Security, considering reverse mortgages or annuities, and deciding when to retire become the heavily weighted cards.

When Small Decisions Compound

During the low-interest-rate environment through 2021, where cash sat didn’t matter much. But when rates rose in 2022, Anspach’s team actively encouraged clients to move idle cash into higher-yielding accounts.

$100,000 earning 4% versus 0% generates $4,000 annually—a difference that might seem minor to some households. But when these “minor” optimizations stack up across multiple decisions year after year, they can mean tens of thousands of dollars over retirement.

“If you do that with all of these minor decisions—’that’s just a couple hundred dollars’ or ‘that won’t really matter’—well, all of those add up,” Anspach notes.

The Discipline Factor: Method Is Everything

Like the MIT blackjack team whose professor demanded perfect adherence to their counting system, successful retirement planning requires unwavering consistency. Anspach’s firm maintains a standardized framework applied to every client, creating a reliable measuring process for evaluating decisions.

This doesn’t mean ignoring human factors. Sometimes emotional peace of mind justifies decisions that don’t optimize the numbers—like clients who paid off a 2.75% mortgage despite being able to earn more by investing those funds. The key is making these emotional choices consciously, understanding their financial impact rather than defaulting to them repeatedly.