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Retirement used to come with benefits that made life easier. Boomers had lower college costs, reliable pensions, and better healthcare coverage. Younger workers are finding some of those advantages aren’t there anymore, making it harder to feel secure about the future.

Almost-Free College

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Boomers entered the workforce when higher education cost a fraction of what today’s students face. Public college tuition used to be heavily subsidized, and many graduated without crippling debt. That allowed them to invest in homes, retirement accounts, or other financial opportunities much earlier.

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Now, students graduate with six-figure debt, delaying wealth-building for years. That makes a huge difference when time is your most valuable asset.

Defined-Benefit Pensions

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Traditional pensions—where you got a guaranteed paycheck for life—were a mainstay for Boomers. Employers used to fund these plans and take investment risk off your hands. Many younger workers today have 401(k) accounts that shift risks to them and offer no guarantee of income.

Those pensions provided security and predictability that’s almost vanished now. Without them, retirement feels far more uncertain.

Employer Healthcare Coverage into Retirement

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Many Boomers enjoyed healthcare continuation after retiring—thanks to plans that covered medical costs in retirement. That kind of employer-supported healthcare helped shield them from skyrocketing medical bills.

Today, few employers offer retiree health plans, leaving most to rely on Medicare—and its gaps. The financial safety net Boomers had is nearly gone for incoming retirees.

Generous Social Security

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Social Security once offered a more robust replacement of your working income. Automatic cost-of-living adjustments (COLAs) were built in from the start—something younger workers face uncertainty about today.

Though Social Security still exists, benefits now don’t go as far when healthcare and housing costs have climbed so much faster. The system’s strain makes it less dependable for future generations.

Affordable Housing Boom

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Boomers graduated into housing markets where you could buy a home on a single income—and property values rose steadily. Housing appreciation helped many lock in low costs and build home equity.

Today’s buyers face unaffordable prices and tighter mortgage terms, making homeownership harder to reach. That shift removes a key source of security that Boomers enjoyed.

Stable Job Trajectories

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Many Boomers enjoyed stable 30- or 40-year careers with one or two employers, with gradual raises and built-in retirement arrays. That stability made it easier to predict income growth and plan retirement.

Today, job hopping and gig work are common, and tiny raises don’t keep pace with inflation. That instability undermines long-term planning.

Lower Student Loan Burden

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Boomers paid far less for college—even those who borrowed did so at low interest rates and easy terms. Paying off college debt usually didn’t mean putting retirement on pause. Now, student loan debt can easily eat into your 20s and 30s, and in some cases into retirement, leaving less room for saving. That delay in wealth accumulation hurts long-term security.

Lower Healthcare Cost Expectations

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Beyond Medicare, lifetime healthcare costs were lower for Boomers when they retired. Prescription drugs, dental, and vision were more affordable or even covered through employer plans. Baby Boomers could often count on savings lasting through rising costs in older age. With medical inflation now far outpacing COLAs, today’s retirees face shrinking wallets and stagnant benefits.

Fewer High Cost Living Expenses

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Boomers retired when essentials like utilities, childcare, and transportation cost relatively less compared to their incomes. That left more disposable income available for saving or discretionary spending.

Today’s retirees juggle much higher real costs, often without the buffer to absorb them. Peak spending years now collide more painfully with retirement needs.

Tax Advantages on IRAs and 401(k)s

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Boomers reaped benefits from favorable tax rules on retirement accounts for decades as they built their balances. They could tap tax-advantaged growth and take withdrawals strategically. Though tax-deferred accounts still exist, rising tax rates and proposed changes threaten future flexibility. That makes present-day planning more complex and uncertain.

Stable Social Support Systems

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Boomers retired into a world where Social Security, Medicare, and aid programs were well-funded and reliable. These programs helped cushion income gaps or unforeseen expenses. Today, funding strains and proposals to cut or restrict benefits mean future retirees may not have the social safety net they expect. Boomers grew up with more predictable government support.

Political Attention to Older Voters

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Boomers have long held strong voting power, so politicians catered to their needs—prioritizing policies that protect Medicare and Social Security. That political clout preserved key benefits that saved their retirement.

As demographics shift and political focus changes, younger generations risk being deprioritized. That shift could leave future retirees advocating just to maintain what Boomers had.

Retired and Restless? These 11 Jobs Are Perfect for You

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Retirement doesn’t have to mean the end of work; it can mark the beginning of doing something meaningful, flexible, and enjoyable. Many retirees choose to take on new roles to supplement income, stay engaged, or explore passions they didn’t have time for earlier. Here are 11 rewarding job opportunities perfect for retirees with diverse interests and skills. Retired and Restless? These 11 Jobs Are Perfect for You