Another commonly held belief seems to be that older generations are somehow tougher than younger ones. That life was harder for them and people have gotten progressively more comfortable.

I beg to differ.

Although the tremendous sacrifices and bravery of the so-called “Greatest Generation” can never be overestimated (they literally risked everything to defeat the Nazis), I would argue that non-marginalized groups in the following generation (my parents cohort) have had it pretty good. Many went from lower class (aka poor) to highly comfortable and secure in a single lifetime. And although we benefited from our parents’ prosperity, the following generation (mine) has had it harder in many ways. And our kids are going to have it even harder.

Not to be a Debbie Downer, but there are reasons the birthrate is historically low in 2025. We all know millennials who are choosing not to have children (or GenXers & Boomers who are sad that they will never be grandparents).

I asked ChatGPT to compare the lives of someone born in the mid 1930s, mid 1960s, and mid 1990s.

Facts:

1. Income & Jobs

Born mid-1930s (entered workforce ~1950s): Median household income in 1955: ~$5,000 (≈ $58,000 in today’s dollars). A single income (often the father’s) could support a family, home, and college savings. Job security was higher; pensions were common. Born mid-1960s (entered workforce ~1980s): Median household income in 1985: ~$23,600 (≈ $66,000 today). Both parents often worked, but wages grew more slowly compared to the cost of living. 401(k)s replaced pensions, shifting retirement risk to individuals. Born mid-1990s (entered workforce ~2015–2020): Median household income in 2019: ~$68,700. In real terms, wages for young workers have stagnated since the 1970s, while housing, education, and healthcare rose sharply. Gig economy and contract jobs more common, less stability/benefits.

2. Cost of College (Public University, In-State Tuition)

1930s cohort (college in 1950s): $200/year tuition ($2,400 today). College was affordable even with part-time work; no significant debt. 1960s cohort (college in 1980s): $1,500/year tuition ($4,000–$5,000 today). Still affordable with summer jobs; modest debt possible. 1990s cohort (college in 2010s): ~$10,000/year tuition (public); $35,000–$50,000/year (private). Widespread reliance on loans; average borrower debt: $30,000+.

3. Healthcare Costs

1930s cohort: Out-of-pocket affordable; many employers covered full family insurance. Doctor visits and hospital stays far cheaper relative to income. 1960s cohort: Insurance became tied to employment. Costs rose, but still manageable. Deductibles/co-pays introduced. 1990s cohort: Healthcare costs skyrocketed (family premiums ~$24,000/year by 2025, often split with employer). Medical debt is a leading cause of bankruptcy.

4. Cost of Raising a Child (to age 18, middle-class family), not including college

1930s cohort (raising kids in 1960s): ~$25,000 total (≈ $240,000 today). 1960s cohort (raising kids in 1990s): ~$150,000 (≈ $280,000 today). 1990s cohort (raising kids in 2020s): ~$310,000. Housing, childcare, healthcare, and college costs exploded. Childcare alone can rival college tuition.

5. Retirement

1930s cohort: Retired with pensions, Social Security, mortgage-free home. Comfortable retirement was realistic for average workers. 1960s cohort: Retirement savings depended on 401(k)s and IRAs; investment risk shifted to individuals. Some still had pensions, but they were fading. 1990s cohort: Retirement is much more uncertain. Pensions rare; Social Security’s future questioned. Rising housing and healthcare costs make saving harder. Many expect to work past 65.

A final note: When my friend Carla was dying in 2022 at age 57 from brain cancer, she commented that at least she wasn’t going to have to worry about paying bills anymore. She felt that one upside of an early death would be a release from financial concerns. Carla had an advanced degree in nursing and worked (very hard) as a hospice medical director. She was married with two adult children that she’d been able to send to college.

And I’m sure she walked to school in the snow plenty of times.