Beyond Resilience: Building an Antifragile Retirement

The first day of school is supposed to be exciting: new backpack, fresh pencils, a classroom full of possibilities. For my six-year-old, this year looked different. The night before school started, he fell off a zipline at his back-to-school picnic. Instead of bounding into the classroom, he trudged in with a bright yellow cast.

He was devastated. And I can’t blame him. Having a cast is frustrating: It itches, it slows you down, and for a kid, it feels like the fun has been put on hold. At dinner, we talked about how sometimes life hands us things that aren’t flexible. But, unlike his cast, our minds can be. If we practice flexible thinking, we can still make the most of a challenging situation.

That conversation got me thinking about retirement.

Retirement Requires Flexibility

If there’s one thing I’ve learned working with families in retirement, it’s this: life rarely unfolds according to the spreadsheet. Markets move, health changes, families grow, opportunities arise. Some surprises are wonderful, others are extremely difficult.

The families who thrive are the ones who can adapt. Flexibility in retirement doesn’t mean giving up control. It means creating a plan that can bend without breaking. It’s about leaving room for change, so that when life doesn’t go according to plan, you still have choices.

This idea lines up beautifully with the work of Nassim Nicholas Taleb, whose book Antifragile explores how certain systems don’t just survive stress but actually grow stronger from it.

Fragile, Robust, and Antifragile

Taleb’s central framework is a “Triad” that categorizes systems based on how they respond to stress and uncertainty:

• Fragile: These break under pressure. A wine glass dropped on tile, or a retirement plan that only works if the market follows a straight line up and to the right. Fragile systems crave stability, but when the inevitable shock arrives, they shatter.

• Robust: These withstand stress and remain unchanged. Like a concrete wall in a storm, a robust retirement plan resists market swings but doesn’t necessarily improve from them.

• Antifragile: These thrive on volatility and stress. Muscles grow stronger when you exercise them, bones strengthen under weight, and biological evolution flourishes through random shocks. Antifragile systems need stress to adapt and improve.

Taleb comes from a background in options trading, where antifragility can be engineered and profited from through complex strategies. Most of us don’t have the time, expertise, or interest to approach investing that way. But the principles he lays out have much broader application. In fact, they offer a helpful lens for building retirement plans and portfolios that are more resilient, adaptable, and even strengthened by uncertainty.

Five Antifragile Principles for Retirement

Here are some of Taleb’s central themes and how they can shape your financial life in retirement.

1. The Barbell Strategy

Taleb’s “barbell” approach involves putting the majority of resources in extremely safe, low-risk assets, while placing a small portion in very risky, high-upside opportunities. The middle ground—moderate risk taken across the board—tends to be the most fragile.

For retirees, this principle translates to balance. Most of your portfolio should protect your ability to cover living expenses and weather market downturns. At the same time, you can (and should) allocate a meaningful portion to growth-oriented investments that allow you to participate in upside when markets surprise to the positive. This way, you protect your downside while profiting from longer-term growth.

2. Via Negativa: Subtraction Over Addition

Taleb emphasizes that often the best way to improve a system isn’t to add more complexity but to remove what’s harmful. In medicine, stopping smoking has saved more lives than inventing new treatments.

In retirement planning, subtraction matters too. Avoiding unnecessary investment costs, reducing debt, and steering clear of overly complicated financial products are all forms of “via negativa.”

3. Optionality: Keeping Your Choices Open

Optionality is the idea of creating situations with limited downside but potentially unlimited upside. It’s about having choices when the future is uncertain.

In retirement, optionality can mean keeping cash reserves so you’re not forced to sell investments in a downturn. It might mean designing a spending plan with flexibility, so you can adjust when markets are rough. Optionality also comes from life choices—having the ability to downsize, take on part-time work, or protect against asymmetric risks through insurance.

The more options you have, the less fragile you become.

4. Skin in the Game

Taleb argues that decision-makers should share in the risks of their choices. Those who make decisions for others without bearing the consequences, what he calls “fragilistas”, tend to create fragile systems. They are often overconfident in their models, theories, or ability to predict outcomes. In short, fragilistas are people who think they’re reducing risk and disorder, but by attempting to smooth out or intervene in complex systems, they actually magnify hidden fragility.

For retirees, this means owning your plan. You can (and should) work with advisors, but you want to ensure incentives are aligned and that the strategies you adopt are ones you believe in. For me, as an advisor, it means only recommending approaches that I’m comfortable using myself or for my own parents.

5. Don’t Suppress Volatility

One of Taleb’s strongest critiques is of systems that try to eliminate volatility. When more minor stressors are smoothed away, bigger problems build up in the background. It’s like suppressing every minor fire in a forest until one day a massive blaze wipes everything out.

In investing, this plays out when we try to over-intervene, chase stability, or over-optimize. The reality is: markets go up and down. Small fluctuations are not a problem—they’re the system’s way of staying healthy. Trying to suppress them usually makes things more fragile.

The Takeaway

My son’s cast may be rigid and inflexible, but he’s learning to adapt. When it comes off, his arm and his mind will be stronger for the experience.

Shocks, uncertainty, and even setbacks are part of the journey. You can’t control every variable, but you can design a plan that doesn’t just survive stress—it adapts and even improves from it. Flexibility and antifragility give you choices, confidence, and freedom.