11 Things Boomers Thought Would Make Them Happy But Actually Didn't

Happiness isn't about what society expects of you.

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Each generation believes they've unlocked the secret to happiness, whether it's by acquiring the latest gadgets, landing the highest-paying job, or indulging in the most luxurious vacations. Boomers, in particular, had a set of expectations about what would lead to fulfillment, driven by societal pressures and cultural ideals of the time.

But there were many things boomers thought would make them happy but actually didn't. They swore that certain things in life would be accomplishments that would launch them into a successful life; however, they unfortunately discovered it was quite the opposite. In fact, for some, it led to disillusionment as they realized that happiness wasn't as simple as checking off boxes on a societal checklist.

Here are 11 things boomers thought would make them happy but actually didn't

1. Owning a big house

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In their 20s and 30s, many boomers equated having a big house with a suburban dream. They reasoned that they would be able to fit their growing families and pets, while showing off their wealth in the form of a home.

However, owning a huge home is one of the things boomers thought would make them happy but actually didn't. For one, having a big house often leads to stress due to upkeep and financial strain rather than the joy many people anticipate from having a bigger living space.

Other than expenses and maintenance, bigger homes allow the opportunity for clutter to accumulate, creating a constant feeling of being overwhelmed with chores and responsibilities. Boomers failed to realize that they may actually be happier living in a one story, single bedroom house than they ever were living in a mansion.

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2. Climbing the corporate ladder

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The pressure to climb the corporate ladder to reach career fulfillment and financial success has existed for many generations, and boomers are no exception. Many believe that scoring higher positions at work will bring them lasting satisfaction.

But constantly focusing on work often leads to burnout, exhaustion, and more time away from the hobbies that bring true fulfillment. In fact, a recent survey from Gallup found that corporate workers are unhappy, with 31% of U.S. employees feeling engaged while just 18% are extremely satisfied with their jobs, a new low in the last decade.

The long hours, constant pressure to succeed, and isolation from personal life are often overshadowed by any sense of achievement.

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3. Material wealth

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While financial success and owning luxurious material items can bring a person temporary satisfaction, many boomers learned that money alone doesn't provide lasting happiness or a sense of purpose, despite believing it would.

The initial joy of buying that new designer purse, spending extra for the latest trend, or splurging on an expensive vacation is often short-lived, as the novelty fades and the focus shifts to the next desired item. The next item comes along, and the cycle repeats.

Happiness is more closely tied to emotional well-being, self-worth, and sense of purpose. Material wealth does not address any of these emotional needs, making material wealth one of the things boomers thought would make them happy but actually didn't.

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4. Expensive cars

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Luxury and overly expensive vehicles are often tied to status and success. However, having a flashy car likely won't lead to long-term happiness and fulfillment. While the allure of owning an expensive car is strong, the reality of it is higher costs, maintenance hassles, and rapid depreciation that drops the value of the vehicle.

Most boomers would much prefer an affordable car that they know will keep them safe, rather than one that will have people oohing and ahhing as they drive it down their neighborhood streets. And though an expensive car may have brought some clout decades ago, in the current economic climate, it's just for showing off.

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5. Big weddings

newlywed couple at their big wedding Oleksandr Schevchuk | Shutterstock

The societal expectation that once you are engaged, you must have a luxurious wedding has existed since boomers were young. Weddings were seen as a pinnacle of happiness, and while it certainly can be for some couples, many find that the long-term happiness of the marriage had to do with compatibility and effort, not the wedding day itself.

For many boomers, even though planning and throwing a big wedding was more of a headache than anything else, and one that often left them financially drained, it was likely what was expected of them. According to Zola, a website for couples planning their wedding, the average wedding cost in 2024 was $33,000, a much larger sum compared to weddings from decades ago.

Most couples could spend that same amount of money in a few years' time on the things that will last them longer, like putting it toward the down payment of their first home or using it to spend time traveling together. Even if the memory of the wedding day may be something couples enjoy looking back on, for many of them it is not worth the chaos and financial strain.

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6. Retirement at 65

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Many boomers have the idea that once they retire at age 65, their worries will come to an end and they will spend the rest of their days traveling the world. However, for some, retirement comes with a loss of purpose. For decades, a job gives people a set routine. Retirement strips them of this structure, leaving many people uncertain of how to fill their time.

Almost 1 in 3 retirees say they feel depressed, a rate higher than that of the adult population overall, according to a WebMD survey. Other retirees may still experience financial hardship if they never set up a retirement fund, and may even have to go back to working part time well into their 80s to make ends meet.

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7. Grandkids

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Many boomers constantly ask their adult children when they plan on giving them grandkids, with the assumption that being grandparents will invigorate some energy back into their lives and give them a source of entertainment.

However, some of them discover that being grandparents means having to parent all over again, especially if their kids constantly rely on them for childcare, making it another of the things boomers thought would make them happy but actually didn't.

Some boomers don't have the same liveliness they had when they were parents themselves, meaning it becomes difficult to keep up with their grandkids. They may find themselves more exhausted and frustrated than happy when they are with them.

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8. Having the 'right' job

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Many boomers believe that having the perfect job that will bring them financial comfort, flexibility and passion for their work is the key to happiness. However, many of them soon realize that fulfillment is more about work-life balance and a meaningful relationship with a job title.

Even having a job you enjoy won't eliminate burnout and exhaustion. A recent survey from Accountemps found that 74% of employees are tired on the job, no matter how much they love it. And while boomers tend to have a very strong work ethic, the reality is that no job will be the perfect or right job that is free of struggles.

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9. Buying the latest gadgets

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Even if boomers thought that upgrading to the newest tech or gadgets would bring them happiness, it only often leads to a neverending cycle of consumerism without any lasting sense of satisfaction.

When you first get a new gadget, it's exciting, but soon you become accustomed to it. The novelty wears off, and what was once thrilling becomes just another part of your daily routine, craving the next upgrade. Not to mention the confusion many boomers experience when trying to set up their latest gadgets that give them far more stress than happiness.

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10. Luxury vacations

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While many boomers believe that high-end vacations at the most expensive resorts will bring them joy and relaxation, planning and paying for the vacation is not so relaxing. Once you get the bill for plane tickets, transportation fees, hotel expenses and restaurant reservations, the vacation may seem anything but a fun little getaway to recharge.

In fact, you may feel just as stressed planning and being on vacation as you do at work. While the cost of vacations all depends on the location and duration of the trip, according to Budget Your Trip, "The average cost of a one-week vacation in the U.S. is $1,991, but it could be as little as $739 or as much as $5,728. If you're traveling as a couple, the average vacation cost for two people is $3,982."

In the 1980s, the cost of a vacation was actually affordable, but now, unfortunately, vacations can be more of a financial stressor than a relaxing getaway.

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11. Achieving the American Dream

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While the American Dream is something older generations were likely taught was the ultimate goal, it really just ended up being one of the things boomers thought would make them happy but actually didn't.

The American Dream is made out to be a life that consists of marriage, kids, a career, and a home. While it is advertised as the perfect life, boomers may not be fulfilled even when they have all of these things. Some of them feel as if they are trapped in a very regimented mold that didn't lead to the happiness they expected, never realizing that it is okay to want things beyond these ideals.

The true American Dream is fulfilling yourself with whatever brings you genuine happiness, whether it be leaving a dead-end job, ending a toxic marriage, or deciding to have pets instead of children.

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Megan Quinn is a staff writer with a bachelor's degree in English and a minor in Creative Writing. She covers news and lifestyle topics that focus on justice in the workplace, personal relationships, parenting debates, and the human experience.

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