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    Home » Back in My Day — Why Boomers Don’t Get Gen Z’s Struggles: From Housing to Hustle, A Generational Gap
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    Back in My Day — Why Boomers Don’t Get Gen Z’s Struggles: From Housing to Hustle, A Generational Gap

    By Jeremy StapletonNovember 14, 2025Updated:November 14, 2025No Comments7 Mins Read
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    My dad still recounts how he used to race his bike through neighborhoods with just a wax paper-wrapped meal and an ambiguous pledge to “be home by dark.” When he narrates it, he leans back as though reliving a priceless highlight reel, and I can practically picture his old street as he talks about it. My teenage niece blinks politely in surprise when she hears the same scenario, wondering how anyone managed to get by without a phone, a navigation app, or a parent verifying their location every hour. That brief exchange between them reveals a generational divide that resembles discussions taking place at dinner tables all around the world, when a straightforward story turns into a subdued reminder that everything is shaped by circumstance.

    ItemDetails
    TopicBack in My Day — Why Boomers Don’t Get Gen Z’s Struggles
    Generations DiscussedBaby Boomers (1946–1964) and Generation Z (1997–2012)
    Key Tension PointsHousing costs, tuition burdens, wage stagnation, shifts in workplace culture, mental health pressures
    Influencing FactorsDigital saturation, changing labor markets, student debt, long-term financial uncertainty
    Communication DividePhone calls vs. messaging, hierarchy vs. flexibility, formal vs. adaptive communication
    Cultural Phrases“Back in my day,” “Pull yourself up,” “That’s not real work,” “Kids have it easy”
    Useful ReferencePew Research Center: https://www.pewresearch.org
    Practical InsightMore empathy, context-based advice, supportive policies, flexible workplace structures


    “Back in my day” conveys a tone that occasionally sounds educational, yet it frequently overlooks the structural distinctions that characterize younger experiences. Wages increased regularly, housing became more affordable, and career paths were surprisingly stable. For people who lived in those circumstances, the sense of regularity brought about by those benefits made sayings like “Just work hard and wait your turn” seem particularly obvious. That advise seems strangely removed from Gen Z’s everyday reality, as their college loans loom like dark shadows and their rent can devour half of their wage.


    This difference is often rooted in economic difficulties. Homes that used to only require a few years of savings now demand wages that are simply out of reach for many entry-level positions. Once paid for with part-time employment, tuition now balloons into decades of payments. A former professor recently informed me that she worked weekends at a bakery to pay for her entire degree; her students now balance internships, loans, and jobs that nevertheless still require full-time dedication. Comparing these circumstances makes the discrepancy incredibly resilient and unavoidable.


    The intriguing thing about Gen Z is that they are adaptable rather than pessimistic. They construct their own because they believe that conventional routes are brittle. I met a 22-year-old who is remarkably pragmatic about his work and makes more money editing short-form videos than he would in an entry-level media position. He is pursuing stability rather than stardom. Boomers’ dismissal of this as “not real work” is a harsh remark since it ignores the ability, tenacity, and inventiveness needed to make a living in new mediums. These digital endeavors are frequently very effective, very adaptable, and always changing to remain productive, much like a swarm of bees.


    The disparity is accentuated by workplace culture. Boomers frequently associate loyalty and long hours with identity, in part because those behaviors used to pay handsomely in the form of pensions and steady career development. Younger employes however, desire balance—not because they shun accountability, but rather because they have seen older family members make decades of sacrifice only to be faced with layoffs or precarious retirements. This change became particularly evident during the epidemic; millions of workers simultaneously experienced burnout, and younger employees concluded that personal well-being is a long-term survival strategy rather than a luxury.


    Another point of contention has been mental health. Because they were brought up to internalize stress, boomers may view candid discussions about worry or fatigue as excessive exposure. Because of public crises and continual digital input, Gen Z sees transparency as protective. They grew up with constant news alerts, viral videos of disasters, and emergency exercises. Their stress is cumulative rather than fictitious. Many clinicians claim that being exposed to material that was much less common to prior generations has significantly increased their psychological load. Recognizing this, however, is not about sympathy. It’s about realizing that resilience is multifaceted and changes with circumstances.


    More of this division is shaped by technology than either side fully acknowledges. Boomers remember analogue jobs from their early years, such as rotary phones, paper maps, lengthy payphone waits, and lengthy walks without an adult in sight. In contrast, Gen Z has lived in close proximity since early childhood. They may freeze when counting coins or reading traditional forms, yet they can debug apps with ease. Both weaknesses are merely the result of the available tools; neither is moral. I once observed my niece go through tutorial comments rather than the tutorial itself, and while it was funny, it also made me understand how information is digested differently these days. A feed-driven environment, not a library index, shapes her instincts.


    These inequalities are frequently widened by language. Phrases like “Because I said so” or “Kids have it easy” rarely have the desired effect. Gen Z hears judgment without context, while Boomers interpret them as a shorthand for tradition, discipline, or viewpoint. However, young adults occasionally overlook the fact that these terms were developed in contexts where lucidity was prioritized over compromise. It is simpler to have a discourse when older relatives offer these sayings without presenting them as absolutes. It calls for curiosity rather than defensiveness, much like translating idioms.


    Another layer is added by political involvement. Because they grew up in an era when silence was considered dangerous, Gen Z is outspoken—not because they like fighting. Concerns such as economic injustice, social justice, and climatic pressure are commonplace issues rather than theoretical discussions. Younger adults therefore frequently hear the phrase “Don’t bring your reality to the table” when someone says, “Don’t bring politics to the table.” It makes sense that the goal would be to maintain peace. However, quiet now comes at a greater cost, particularly to those who are formed by the ongoing evidence of interconnected catastrophes.


    Despite all of this conflict, there seems to be a particularly advantageous way forward. Empathy that recognizes context rather than ignores it is the first step. Boomers may provide valuable advice on patience, long-term planning, and resourcefulness—skills that are unquestionably useful in any time period. Instruction in adaptation, digital navigation, and mental health literacy—all of which are becoming more and more important in contemporary institutions—can be provided by Gen Z. Both generations would gain much from exchanging rather than guarding their abilities, which have been honed by necessity.


    Policies are also important; revised labor laws, student loan solutions, and housing improvements could reduce stresses that cannot be resolved by motivational speeches. Because young adults would not feel that they are being made to endure circumstances that were greatly diminished for previous generations, these structural supports would increase the effectiveness of intergenerational discourse.
    Most reassuringly, discussions are better when both parties exchange experiences without making them competitive. Lessons about confidence and independence can be learned from my father’s anecdote about riding a bike unattended. Lessons on prudence and emotional intelligence can be learned from my niece’s tale about overcoming online influences. These tales provide direction rather than complaints if they are viewed as parallel rather than hierarchical.


    Observing these interactions, I see the possibility of a softer generational tie based on the understanding that resilience takes different shapes in different eras. Gen Z learnt to understand enormous information without losing themselves, and Boomers learned to navigate uncertainty without continual information. Both are quite useful abilities, and when combined, they produce a viewpoint that is far more powerful than either one by itself.


    The discussion becomes uplifting rather than polarizing if we use “Back in my day” as an invitation rather than a closing sentence. Younger voices also respond with surprisingly generous insights if they feel like their opinions are truly heard. This collaborative mindset has the potential to bridge the generational gap and create a shared future in which knowing is not a luxury but a shared obligation, advice is given and solutions are found together.

    ‘Back in My Day’ — Why Boomers Don’t Get Gen Z’s Struggles
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    Jeremy Stapleton

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