Who Actually Had It Harder Financially: Baby Boomers or Millennials?
- 10 hours ago
- 4 min read
Housing costs, student loan debt, and the rising cost of living have millennials feeling the financial squeeze — but was it really easier for baby boomers? The Waymark Wealth team breaks it all down, from 18% mortgage rates in the '80s to $600K starter homes today.
Watch the latest Coffee with Waymark to hear both sides of the argument and decide for yourself: Which generation had it better?
Every generation thinks the next one has it easier.
And every generation thinks the one before them “just doesn’t get it.”
That debate came to life during a recent episode of Coffee with Waymark, where the team tackled a question that instantly sparked opinions:
Who had it harder financially — Baby Boomers or Millennials?
What made the conversation interesting wasn’t that anyone “won” the debate.
It’s that both sides made compelling points.
Brandon: Setting the Stage
Brandon opened the conversation by framing the debate between two generations:
Baby Boomers, born between 1946–1964
Millennials, born between 1981–1996
He positioned Brendan to argue from the Baby Boomer perspective and Hanifa to argue from the Millennial perspective.
And from there, things got interesting.
Brendan’s Perspective: “Boomers Had Challenges People Forget About”
Brendan argued that Millennials often focus heavily on housing costs and student loans while overlooking what Baby Boomers were dealing with financially decades ago.
His biggest point?
Interest rates.
In the late 1970s and early 1980s, mortgage rates climbed into the double digits — sometimes approaching 18–20%.
Yes, homes cost less in raw dollar terms.
But borrowing money was dramatically more expensive.
A lower home price paired with extremely high interest rates created monthly payments that were still incredibly difficult for many families to manage.
Brendan also pointed out the broader economic backdrop Boomers faced:
inflation
economic instability
geopolitical uncertainty
and difficult job markets
On student loans, Brendan acknowledged that Millennials carry significantly more debt than Boomers did.
But he also argued that people today have more educational choices available, including lower-cost state schools and alternative pathways.
Ultimately, Brendan’s argument came down to this:
Lifestyle and financial choices matter more than people want to admit.
Hanifa’s Perspective: “The Financial Landscape Changed”
Hanifa respectfully pushed back almost immediately.
Her argument centered around one major reality:
The cost of living has dramatically changed.
While she acknowledged that Boomers dealt with higher interest rates, she emphasized that home prices today are substantially higher relative to income.
Starter homes in many markets now regularly sit in the $500,000–$700,000 range, creating a major cash flow challenge for younger buyers trying to enter the market.
Hanifa also focused heavily on student debt and workforce competitiveness.
Her point was that today’s economy often demands more education, more credentials, and more specialization just to remain competitive professionally.
And while lower-cost educational options exist, she raised an important nuance:
Sometimes people pursue more expensive schools because of the long-term networking and career opportunities those institutions may provide.
Hanifa also challenged the common stereotype that Millennials are simply overspending or complaining.
Her argument: the cost of living has risen faster than income for many younger workers.
And for many people, that financial pressure feels very real.
Brendan’s Rebuttal: “Affordability Is Also About Lifestyle”
Brendan came back to one of the most debated parts of the conversation:
Lifestyle expectations.
He argued that affordability is partly driven by choices:
spending habits
travel
luxury consumption
and modern lifestyle expectations
That perspective tends to spark strong reactions online.
But it also raises a fair question:
How much of financial stress comes from economic conditions versus changing expectations around lifestyle and consumption?
The reality is probably somewhere in the middle.
Brandon’s Closing Take: “Both Sides Have Valid Points”
As the conversation wrapped up, Brandon summarized the debate perfectly:
There are real pros and cons on both sides.
Every generation faced legitimate financial challenges.
They were just different challenges.
Baby Boomers often dealt with:
crushing interest rates
inflation shocks
economic instability
Millennials often face:
higher housing prices
larger student debt burdens
delayed wealth-building
and rising costs across nearly every category of life
Comparing generations financially is difficult because they were solving different economic problems in different eras.
The Bigger Financial Lesson
Maybe the bigger takeaway here is this:
Financial planning is never about winning a generational argument.
It’s about understanding the financial reality you’re operating inside of today — and building a strategy around it.
Because whether you’re a Baby Boomer, Gen X, Millennial, or Gen Z…
The fundamentals still matter:
managing cash flow
avoiding unnecessary debt
investing consistently
and making intentional financial decisions
The economic environment changes.
Human behavior doesn’t as much.
One thing conversations like this remind us: most people are carrying more financial pressure than others realize.
That’s also why financial planning shouldn’t just be about spreadsheets, rates of return, or retirement projections.
Money decisions are emotional decisions.
They’re tied to stress, priorities, family, values, goals, and the life you actually want to build.
At Waymark Wealth Management, the focus is on helping people make financial decisions with clarity and intention — using behavioral finance principles to align financial planning with real life, not just numbers on a page.
Beyond the Numbers. Built Around You.
At Waymark Wealth, financial planning is designed to support your values, your vision, and your version of a meaningful life.
No matter what generation you’re part of.
Brendan is the Managing Director for Waymark Wealth Management. He has extensive experience in comprehensive wealth management. His focus includes retirement planning, behavioral finance, investment portfolio construction, education funding, insurance & risk management, taxes, charitable giving, and estate planning. Brendan has an ability to take clients' complex visions and distill them down to simple action plans, helping them move from where they are today to where they want to be tomorrow.
Securities and advisory services offered through LPL Financial, a registered investment advisor. Member FINRA/SIPC.
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Content in this material is for general information only and is not intended to provide specific advice or recommendations for any individual.
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