Feeling 'behind' on life’s milestones? You’re not alone

Amy Fontinelle

By Amy Fontinelle
Amy Fontinelle is a personal finance writer focusing on budgeting, credit cards, mortgages, real estate, investing, and other topics.
Posted on Mar 8, 2022

Many of us get constant messages that we’re supposed to achieve certain milestones by certain times in our lives: Graduate from college by age 22, maybe 23. Immediately get a foot in the door at a promising company, even if it means doing grunt work for a year — or pursue an advanced degree. No matter how demanding school and work have been, we’re supposed to find our one true love and marry them no later than 30. Buy a house, or at least a condo. Start having kids no later than 35.

The uncomfortable truth is that many of us feel shame, regret, or anger when we don’t meet traditional milestones. The good news is that better technology, an increased openness to new ways of living our lives, and the societal trauma of the pandemic have caused many of us to reevaluate the old milestones and push back against the idea that there’s one right way to do things.

Here’s what can be gleaned about recent trends and the pandemic’s effects on: 

Educations disrupted

The COVID-19 pandemic has fractured the traditional high school and college experience for young adults worldwide, but it will be years before we can assess the long-term earnings effects of this disruption. However, we’re already seeing how completing part of college or high school virtually instead of in person has been problematic for students.

“Students lost 1.25 years of maturing and learning to self-advocate,” said Certified Educational Planner Laurie Kopp Weingarten, president and chief educational consultant of One-Stop College Counseling in Marlboro, New Jersey.

“The current high school seniors have only had one full normal year of high school, which was in ninth grade, a long time ago,” she said.

“I’ve spoken to many college admissions officers who are reporting that current freshmen seem to be struggling more academically — they didn’t complete the course curriculum during the pandemic — and emotionally. Mental health visits have increased significantly at the colleges I’ve spoken with.”

Weingarten said the college-bound high schoolers she counsels complained of exhaustion and seemed stuck in 2021, unable sometimes to complete their homework or write their college essays.

“I’ve never seen so many students suffering from anxiety and depression,” Weingarten said.

“And during the fall semester, I had an unprecedented number of students drop down a level, from AP/honors to a regular academic class, or even withdraw from the course completely,” she added. “Teens are definitely finding these last few years to be more difficult than previously, and it’s going to take a while to get back to normal.” 

On the positive side, opportunities to earn a degree online have expanded substantially, as have enrollment in distance learning and opportunities to earn a degree at a lower cost. Students who are introverted, experience social challenges, learn differently, or were regularly sleep deprived when they attended class in person have gained ground. Increased options for how, when, and where students learn and what they can study may put educational milestones in closer reach for more students than ever before. (Related: The costs of doing a college transfer — and how to limit them)

Earning potential

Earning a college degree remains one of the best ways to boost your financial security. That’s true even if you must borrow, as long as you use student loans wisely. However, graduating from college has also become less of a privilege and more of a requirement.

Adults with only a high school diploma or some college now have lower annual earnings than previous generations did at their age; it’s only the college educated whose earnings have increased over time, according to a 2018 Pew Research Center analysis. A household headed by two adults with college degrees will have more than double the annual income of a household headed by two adults with only high school diplomas.

The pandemic showed us that jobs that don’t require college degrees don’t just pay less. They’re also often less stable and higher risk. Retail and service workers faced exposure to the novel coronavirus at work and lost jobs due to stay-at-home orders, while white-collar office workers kept their jobs and transitioned to remote work.

College retention and graduation rates may drop in the short term because of the pandemic, and they were already far lower than many people may realize: the four-year graduation rate was 45 percent, and the six-year graduation rate was 63 percent. 

The good news is that colleges may be looking to support students better — including those who took a break or dropped out and want to return — and improve these rates without lowering their standards. In addition, students who have had more time to self-reflect may feel clearer about their goals regarding choice of major, plans to attend graduate school, and career decisions.


The pandemic has had both good and bad effects on people’s usual career milestones. When companies and government agencies shut down in-person operations, some college students couldn’t complete their internship and missed what is often a crucial first step on the career ladder. Recent graduates just starting full-time careers may have kept their jobs, but lost opportunities to build relationships and find mentors.

Even people who were well-established in their roles may feel they’ve lost ground.

“Some people were forced to quit their jobs or leave the careers that they had worked so hard to get because they needed to manage child care or other family obligations,” said Deanna Baumgardner, owner and human resources consultant for Employers Advantage, a company that provides HR services to small businesses. “They may go back to their career path at some point, but more than likely they will have to take a couple of steps back in order to get back on the career track that they had mapped out.”

Others have taken a bad situation and quickly turned it around. (Related: Retooling your career amid COVID-19)

“We saw people who may have been laid off or furloughed through the pandemic and took that as an opportunity to grab hold of their career dreams and move them along,” Baumgardner said. “Whether it’s starting a business, going back to school, or changing industries and career paths altogether, I definitely think a lot of people reevaluated their career paths and have shifted either out of necessity or out of a change in perspective.”

Many people had the opportunity to work remotely for the first time and learned that it gave them the work-life balance they’d been craving — or obliterated the boundaries between work and personal time. Both outcomes helped inform how people wanted to proceed. 

“I think that the pandemic has redefined career milestones for a lot of people, and it isn’t all about climbing the corporate ladder anymore,” Baumgardner said. “That will have a long-term effect on what people see as success for themselves and their careers, and how companies operate. Career milestones will look more like balance, flexibility, and doing fulfilling and rewarding work.”


The St. Louis Federal Reserve has tracked U.S. homeownership rates since 1965. Then, the rate of households that were owner-occupied was about 63 percent. It reached almost 66 percent in 1979, nearly fell back to 63 percent in 1985, peaked at 69 percent in 2004, and fell back to 63 percent by 2016. We can see from more than 55 years of data that about a third of households are occupied by renters at any given time, which puts you in excellent company, at least on a national scale, if you rent.

Low mortgage rates during the pandemic have made it inexpensive to borrow money to buy a home, but home prices have soared, compounding an increase in home prices that began long before the pandemic.

Today’s new homes are larger than ever. The median new house sold in 2020 was 2,333 square feet, according to the Census Bureau, and the median sale price was $336,900. Forty years earlier, in 1980, the median new house was 1,570 square feet and the median sale price was $64,600, or $194,978 in 2020 dollars. New homes cost about $124 per square foot in 1980 and about $144 per square foot today. (Related: Buying a home together while unmarried has challenges)

Of course, younger workers aren’t all trying to buy new homes, and mortgage rates, inflation, and wages were different in 1980. But one reason people may be struggling to meet that milestone of buying a first home is that not only do new homes cost more per square foot, but also they’re also almost 50 percent larger.

Now for some trends that could put a first home in reach for many who hope to achieve this milestone. Builders started construction on more homes in 2021 than in 2020, and more homes in 2020 than in 2019, despite labor and materials shortages. In addition, now that more employers allow their employees to work 100 percent remotely, more opportunities exist to move from high-cost housing markets to lower-cost ones. 

That doesn’t mean every renter in California wants to move to Kansas: relationships, weather, and lifestyle matter, too. It’s also not a totally positive trend: prices have increased in many outlying areas, making them less affordable for existing renters and future newcomers. (Learn more: How to put together a house down payment)


Americans’ median age when they first marry has been rising since the 1950s. Women used to marry at age 20 and men at 23. However, as of 2021, women were marrying after turning 28 and men were marrying after turning 30, according to the U.S. Census Bureau. Still, medians don’t mean much when everyone around you seems to be getting married (or staying single) and you’re the outlier. (Indeed, people can sometimes be stigmatized for marrying “too young.”)

“When we don’t achieve certain milestones by the time we think we should, we are often hard on ourselves and talk to ourselves with the shoulda, coulda, woulda’s,” said Rebecca Hendrix, a licensed marriage and family therapist in New York City. “But we have to remember that these are timelines that we set without taking into consideration things that are beyond our control.”

In 2019, 38 percent of adults ages 25 to 54 were living without a spouse or partner, compared with 29 percent in 1990, according to The Pew Research Center. Even adults ages 40 to 54 were more likely to be unpartnered. This means that those of us whose domestic lives are not what we may have envisioned when we were younger are in good company.

Unfortunately, single adults also tend to be worse off than their married or cohabitating friends and family, with less education, lower earnings, and worse health. Also, COVID-19 reduced opportunities to meet people and increased the health risks of dating, likely pushing back timelines for many people wanting to find a long-term partner. It postponed weddings and increased anxieties for those looking to have children and start families. It ended relationships between people who found out their partners weren’t up for supporting them during the worst of times. (Related: Money questions before cohabitation)

However, the news isn’t all bad: The increased popularity of video calls and flexibility to work remotely have made it easier for people who don’t live near each other to contemplate a future together. Also, pandemic-induced soul-searching helped many of us refine our ideas about what’s most important in a long-term relationship.

Rethinking milestones

The pandemic has helped some people realize that things are beyond their control, accept what is happening, and be more flexible about their goals, Hendrix said.

Think about life’s traditional milestones as guidelines — not deadlines. You’re free to rearrange or omit them as you see fit to create your own fulfilling path.

Discover more from MassMutual…

How to make a financial plan for your family

Buying your first home

Younger moms vs. older moms: The financial implications


The information provided is not written or intended as specific tax or legal advice. MassMutual, its employees and representatives are not authorized to give tax or legal advice. You are encouraged to seek advice from your own tax or legal counsel. Opinions expressed by those interviewed are their own and do not necessarily represent the views of MassMutual.