Retirement Social Security

Kevin O’Leary Says Relying on Social Security Is a Big Mistake - Here’s Why

Counting on Social Security as your main income can put your retirement at risk.

By David Maina

Edited by Laura Hohenstein

Updated Nov. 21, 2025

Kevin O'Leary isn't known for soft opinions, and his stance on Social Security is no exception.

He warns that treating Social Security like a full paycheck is one of the fastest ways to fall short in retirement. In his view, Social Security should steady your income, not shoulder your entire financial future.

Below, we break down O'Leary's perspective, why he stresses these risks, and how his advice can help you avoid money mistakes as you plan for the years ahead.

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Social Security was never meant to fully fund your retirement

As of 2025, the average retired worker's Social Security benefit is about $2,008 per month, or roughly $24,000 a year. Even if that sounds substantial at first, it falls well short of what most people need to sustain a typical retirement lifestyle.

In fact, the Social Security Administration (SSA) estimates that benefits are designed to replace about 40% of the average worker's pre-retirement earnings. By contrast, many financial planners suggest most retirees need 70% of their former income to keep a similar standard of living.

Kevin O'Leary is direct about what that gap means in practice. As he puts it, "That check was never designed to fully support retirees," and relying on it alone can lead to what he calls a "poverty-level retirement."

If you want financial comfort rather than just getting by in retirement, you may need other sources of support, like savings, investments, or workplace retirement plans.

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Retiring too early can trap you in Social Security dependence

A second theme of Kevin O'Leary's message is timing. He pushes back against the idea of retiring just because you have hit a milestone birthday.

As he puts it, "Don't retire until you can afford it. Throw out your plan for freedom at 55 or even 65 … If you have debt, you need your job, so you have to do everything in your power to keep it."

His warning ties directly to how Social Security calculates your benefit. It's based on your 35 highest-earning years. If you leave the workforce too early, you may lock in more low-earning years or even zeros in that formula.

Claiming before your full retirement age can also cut your monthly check permanently, while delaying can boost it.

In short, O'Leary argues that a few extra years on the job can make a big difference, as it can help you:

Pay down debt
Save and invest more
Replace low-earning years with higher-earning ones, which can raise your benefit

The earlier you exit, the more likely it is that Social Security becomes your main source of income, and not the supplemental one it was designed to be.

Retirement can be cheaper than you think

O'Leary also urges people to rethink what retirement actually costs. Many workers often assume they'll need to match their current lifestyle down to every dinner out and monthly subscription.

He pushes back on that fear. "First of all, you need less than you'd imagine, and panicking helps nothing," he says.

For many retirees, several major costs drop at once because commuting, work clothes, daily job-related expenses, and even many family-related costs often disappear. These changes mean your baseline cost of living may be lower than you expect.

O'Leary puts it plainly: "If you're healthy and happy, being old is cheap." A simple, intentional lifestyle can stretch your money farther than you think.

Start trimming expenses before you retire and see what you miss and what you don't. That simple shift can help you understand your real needs and give you a clearer picture of how far your income can go.

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Build independent wealth so Social Security becomes a bonus

Kevin O'Leary also stresses one idea: control what you can. You cannot change future COLAs or solve the politics around Social Security. But you can decide how much you save, how you spend, and whether you invest steadily over time.

As he says: "Start your journey toward financial freedom today by taking three steps: spend less, save more, invest the rest."

The framework is simple, but the discipline behind it is what separates people who treat Social Security as a supplement from those who depend on it just to get by.

For growth, he points to the stock market. A diversified portfolio can move up and down in the short term. Over decades, though, it has rewarded people who stay consistent. Even small weekly deposits can compound into serious wealth if you keep at it year after year.

The more assets you build outside Social Security, the less pressure you put on your monthly benefit to cover housing, healthcare, and the rest of your expenses.

Bottom line

Kevin O'Leary's view on Social Security is blunt, but it's not alarmist. The program was never designed to replace a full paycheck, undo years of limited savings, or fund the lifestyle many people imagine for a stress-free retirement.

That reality puts the responsibility back on you. It may mean staying in the workforce a little longer, cutting back now, or saving and investing more consistently.

In the end, your retirement rests on the assets you accumulate and the decisions you make, with Social Security serving as a helpful supplement.

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