Squire | Generational Retirement Trends

By Nathan Larsen, Partner at Squire

Generational Retirement Trends: Millennials vs. Boomers

Retirement savings is a critical concern across generations, yet many Americans lack sufficient funds for their golden years. According to a 2024 national Transamerica survey, over a quarter of baby boomers (born roughly 1946–1964) have no retirement savings at all and more than half of boomers are actually expected to run short of money during retirement. Millennials (born roughly 1981–1996) face their own challenges as only about half of millennials even have a retirement account such as a 401k or IRA, and their median retirement savings, around $50,000, lags far behind that of boomers, which is around $194,000. These numbers show both generations have work to do in preparing for retirement. Boomers and millennials are often pitted against each other in financial debates, with stereotypes of extravagant millennials or underprepared boomers, but the truth is each generation has its own unique strengths and weaknesses in retirement planning. Instead of competing, there’s a lot they can learn from each other to improve their financial futures.

Advantages and Disadvantages

Each generation’s retirement outlook comes with its own advantages and disadvantages. Baby Boomers are at or nearing retirement now, often with decades of work and savings (hopefully) behind them. Millennials are further from retirement, giving them time to adapt but are also facing different economic realities. Below, we break down the retirement landscape for boomers and millennials, what’s working in their favor and what obstacles they must overcome.

Retirement for Boomers

Advantages

• Accumulated Wealth and Assets: Many boomers have had a lifetime to build up assets. As a group they hold a significant share of America’s household wealth. They benefited from decades of rising real estate values and stock market growth. Many own homes, often paid off, that have appreciated significantly. This accumulated wealth and home equity can be a strong foundation for funding retirement.

• Social Security Benefits: Boomers can generally count on receiving full Social Security benefits, which provide a stable income floor in retirement. Many expect Social Security to be their primary source of retirement income. Unlike millennials who worry whether Social Security will exist for them, most boomers are already eligible or soon will be, and they’re less likely to face benefit cuts.

• Favorable Tax Rules for Seniors: Older Americans enjoy certain tax advantages that can help with retirement savings. Once over age 50, boomers can make “catch-up” contributions to 401k’s and IRA’s, allowing them to boost their savings in their 50s. Retirees also get higher standard deductions after age 65, and some income may be tax-advantaged.

• Experienced Strong Economies: Many boomers entered the workforce in an era of rising middle-class prosperity and lower relative costs for college and housing, making it easier to save and invest earlier in their careers.

Challenges

• Rising Healthcare Costs: Longer lifespans and medical inflation mean boomers face soaring healthcare expenses in retirement. Medicare helps, but it doesn’t cover everything, so costs for prescriptions, supplemental insurance and long-term care can quickly eat into savings.

• Declining Pensions: Boomers were the transitional generation from guaranteed pensions to 401k’s. This shift left some unprepared and suddenly responsible for their own retirement investing without much guidance.

• Longer Lifespans: Retirees in their mid-60’s today could live 20–30 more years, increasing the risk of outliving their savings. Managing withdrawals carefully so savings last is a key challenge.

• Insufficient Savings (Retirement Planning Mistakes): Not all boomers saved enough. Many now regret not saving more or starting earlier, a classic case of retirement planning boomer mistakes, leaving a large portion of this generation financially vulnerable.

• Inflation and Economic Shocks: Events like the Great Recession and recent inflation have eroded purchasing power and, for some, reduced portfolio values at critical times.

Retirement for Millennials

Advantages

• More Time for Compound Growth: The greatest advantage millennials have is time. Starting early allows compound interest to work for decades, which is why it’s vital to emphasize when to start saving for retirement. Millennials increasingly understand why it is important to invest for retirement as early as possible.

• Greater Financial Literacy & Tech Savvy: Millennials leverage budgeting apps, robo-advisors and online resources to manage money, invest and automate good habits.

• Multiple Income Streams (Side Hustles): Many millennials maintain side gigs to supplement income, pay down debt faster and invest more consistently.

• Higher Education and Earning Potential: According to Brookings, millennials are the most educated generation, which can translate into higher lifetime earnings and greater capacity to save over time.

• Comfort with Diversified Investing: Younger investors often use low-cost index funds, target-date funds and diversified portfolios and are open to new platforms that lower barriers to investing.

Challenges

• Shift from Pensions to Self-Funding: When compared with boomers, millennials are much more likely to have no pension income in retirement. The burden of saving often rests on them through 401k’s/IRAs, and not all have access to employer plans.

• Heavy Student Loan Debt: Larger student debts have delayed milestones and diverted dollars away from early retirement savings.

• Skyrocketing Housing Costs: Lower homeownership rates and higher rents/mortgages reduce capacity to save and build equity early in life.

• Economic Instability and Recessions: Starting careers during the Great Recession and disruptions like the 2020 pandemic and inflation created a rocky start to wealth-building.

Learning From Each Other

Despite differences, both generations share the same goal: a comfortable, secure retirement. Rather than “Boomers vs. Millennials,” it’s more productive to see what each generation can teach the other.

What Boomers Can Learn From Millennials

• Embrace Technology for Finance: Use budgeting apps, automation and low-cost investing platforms to simplify and optimize money management.

• Adaptability and Flexibility: Consider phased retirement, part-time consulting or new skills to stay engaged and supplement income if needed.

• Continuous Learning: Keep up with financial, tax and tech changes. A lifelong learning mindset helps avoid scams, reduce costs and seize opportunities.

What Millennials Can Learn From Boomers

• “Start Early”: The single biggest advantage is time. Start saving and investing with your first paycheck. Make retirement contributions a non-negotiable bill.

• Have a Long-Term Plan (and Get Advice): A written plan and periodic guidance can prevent costly mistakes and keep you on track toward your goals.

• Avoid Excessive Debt, Live Within Means: Prioritize paying off high-interest debt, be cautious with big purchases and aim to be debt-free by retirement.

• Patience and Long-Term Perspective: Stick with diversified, long-term investing through market ups and downs. Slow and steady wins the race.

Professional Retirement Planning Services

“Whether you’re 25 or 65, the best time to get intentional about retirement is now,” said Nathan Larsen, partner at Squire. “Our team pairs tax-smart strategy with practical steps you can act on today—building confidence that lasts.”

Squire’s advisors specialize in personalized retirement planning and will identify your resources, determine your goals and design a tax-efficient strategy for the retirement that’s right for you. For younger clients, that might mean disciplined saving plans, smart investment choices and milestone mapping (home purchase, family planning and education funding). In addition, Squire offers access to Flourish Cash, an invitation-only cash account that provides interest rates up to 10× the national savings account average and FDIC insurance coverage up to 12× what a single bank can offer. With no minimums, seamless transfers, and waived administrative fees for Squire clients, it’s an effective tool for maintaining short-term liquidity—whether building an emergency fund or setting aside money for near-term goals. For those closer to retirement, we help with catch-up contributions, Social Security timing, 401k/IRA rollovers and building a sustainable income plan so you don’t outlive your assets. We also cover long-term care, insurance reviews and estate planning. Most importantly, we pair technical expertise with a human touch, answering questions, implementing the plan and adjusting as life evolves.

Bottom line: Start early, invest wisely, be adaptable and lean on professional guidance when you need it. To learn more, connect with Squire’s retirement planning team or set up a complimentary consultation, visit www.squire.com.