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While browsing social media, you see that yet another acquaintance is engaged, your last supervisor now has an MBA, or your high school rival just bought a vacation home.
Even if you’re the only person you know who can run five miles or fix a computer, all your brain registers are the ways that you feel you’re falling short.
“A mix of things contribute to feeling pressured to achieve certain milestones by specific ages, such as societal norms, personal expectations, and economic influences,” said Jason Ickovitz, a licensed marriage and family therapist in Los Angeles. “Social media has also increased the illusion that we aren’t doing enough or are falling behind. While societal expectations can motivate us to achieve goals, they can also create stress and anxiety that lead us to make inauthentic choices.”
Maybe a reality check will help you tone down the negative self-talk. Let’s examine what milestones “everyone else” is reaching in areas that tend to impose pressure:
Each has their own promises and challenges, especially in the wake of the pandemic.
Educational attainment
Whether you’re trying to get into college, earn a post-grad degree, or complete a certificate program, meeting educational goals usually entails struggle. The pandemic was a particularly disruptive and shared challenge for students, yet everyone was affected differently and is moving forward at a different pace.
While the worst of it seems to be behind us, the recovery process is ongoing from pandemic-related educational setbacks, said Certified Educational Planner Laurie Kopp Weingarten. As president and chief educational consultant of One-Stop College Counseling in Marlboro, New Jersey, she has seen high school students showcase their resiliency and an impressive ability to pivot.
For most students, she said, working through difficult experiences like the pandemic “will serve them well in college and beyond, proving that they can adapt, overcome challenges, and thrive in uncertain times.”
That said, she’s also seen an intensification of mental health challenges, such as stress, anxiety, and burnout.
“I have some students who are pushing themselves too hard,” she said. “They look at what their peers are doing and strive to emulate them. We encourage students to challenge, but not overwhelm, themselves.”
This might mean, for example, moving from honors math to a regular class if a dedicated student is still struggling after working with tutors.
“Sometimes, you have to know when to make your life a bit easier and not worry that a college won’t accept you for making the best choices for yourself,” Weingarten said.
Whatever your educational goals, you’re more likely to succeed when you find an appropriate level of challenge. Set expectations based on your own needs, strengths, and weaknesses — not someone else’s.
Career progression
Maybe you’re working as a paralegal because you didn’t pass the bar, or maybe you’re getting passed over for promotions while your friends are becoming managers. Even though you enjoy your job, you worry that people will think of you differently because you don’t have an impressive title.
“I think a common misconception about career progression is that it follows a linear path — the assumption that the only way forward is up,” said human resources specialist Laura Addink, founder of Aerial HR, a fractional human resources company based in California. “In reality, lateral moves or even taking a step down into a new field can sometimes be the best option for long-term growth.”
That might feel especially true if you’re concerned about how artificial intelligence could impact your livelihood. Jobs you might never have imagined as a child, during college, or as a young professional are now some of the fastest growing. (Related: Why AI can’t replace your financial professional)
According to a 2025 LinkedIn study, these positions include workforce development managers, sustainability specialists, and, in first and second place, artificial intelligence engineers and consultants. In 2021, only one AI job made the list: the broad category of “artificial intelligence practitioners.” It placed 15th.
Another uncertainty: While the ability to work remotely has created new opportunities for independence, it’s also created a new reliance on technology platforms where one update, algorithm change, cyberattack, or new law can obliterate one’s livelihood overnight.
The pressure to adapt and learn new skills can feel overwhelming. In some cases, you can turn to your employer for support.
“Inquire with your HR department or manager about continuing education programs,” Addink said. “If the company doesn’t have a formal policy, take a proactive approach. Find a course or certification program you’d like to complete, and present that along with the business case for how it will benefit the company.”
Another option, especially if you get pushback on cost, is to propose a formal mentorship or succession planning opportunity for yourself within the company.
“These initiatives benefit employees by providing new skills and development opportunities, benefit managers by allowing them to share knowledge and gain fresh perspectives, and benefit the company by ensuring a strong succession plan,” Addink said.
Homeownership
If you’re struggling to become a homeowner — or haven’t even considered it because it seems unattainable — it’s probably not you. It’s the market.
Throughout 2020 and 2021, ultralow 30-year mortgage rates — around 3 percent, according to Freddie Mac — made it inexpensive to borrow money to buy a home. But home prices increased by more than 50 percent from October 2019 through October 2024, according to the S&P CoreLogic Case-Shiller U.S. National Home Price Index.
At the same time, mortgage rates ballooned. And despite several cuts to the target federal funds rate by the Federal Reserve in 2024, mortgage rates have stayed stubbornly high: They haven’t dipped below 6 percent since September 2022.
New homes today cost more per square foot, and they’re almost 50 percent larger than they were 45 years ago. The median new house completed in 2023 was 2,233 square feet, according to the Census Bureau, and the median sale price was $428,600. In 1980, the median new house was 1,570 square feet and sold for $64,600, or $238,300 in 2023 inflation-adjusted dollars.
Real median household income was about $81,000 in 2023 and about $65,000 (in 2023 dollars) in 1980, per Census Bureau data. So, while income increased by about 25 percent, single-family home prices increased by about 80 percent, and square footage increased by about 42 percent.
While it’s easy to get down on yourself for not owning a home (yet), remember that external factors can make home ownership more challenging. And renting is sometimes a more sensible choice. Your homeowner friends might actually envy you for the flexibility and extra free time renting offers. (Learn more: How to make a down payment on a house: Do’s and don’ts)
Marriage and cohabitation
Back in the 1950s, it was common for women to marry at age 20 and men at age 23. As of 2024, the median age for getting married increased to 28 for women and 30 for men, according to the U.S. Census Bureau. Still, the median age when people first marry may feel meaningless when most of the people in your social circle are hitting that milestone and you haven’t.
If a client had questions about whether the time was right to seriously consider marriage, age would not be the determining factor, Ickovitz said. “To help them make a mindful choice, what we would explore is their emotional readiness, the strength of the relationship, and the intentions behind this decision.”
In 2023, 42 percent of U.S. adults aged 25 to 39 were living without a spouse or partner, according to Census Bureau data analyzed by the Pew Research Center. And 29 percent of adults aged 40 to 54 were unpartnered. (Related: 6 money questions to ask before moving in together)
It’s more common now than 30 years ago to be in good company if you’re single. In fact, nearly one in three single people aged 18 to 34 say they don’t want or aren’t sure if they want to get married. But you might be among the single people who are thinking, “I should have met someone by now.” This can be a frustrating and self-defeating headspace to dwell in.
“I always pay close attention when I hear the word ‘should,’” Ickovitz said. “It’s a trap that we all fall into. The word ‘should’ carries a sense of obligation or expectation from some external source. It can lead us down a path of feeling guilt, shame, or that we aren’t good enough.”
As the number of adults who have never been married continues to increase, it has become more socially acceptable to stay single. Whether you prefer being single or just haven’t found the right person yet, it can be comforting to know that you aren’t really the odd one out — even if your immediate surroundings seem to tell a different story. (Related: Estate planning for singles)
Embracing self-acceptance and cultivating resilience
While social media can be a platform for showcasing curated content highlighting an idealized life, it’s also become a platform for people to open up about their insecurities, perceived failures, and mental health.
Most people aren’t up for sharing their vulnerabilities so publicly, but doing so with a nonjudgmental friend, relative, or therapist can lead to reassurance that we’re not alone, and we’re probably being too hard on ourselves. Further, when we ask for help — whether from someone whose career we admire or a group of strangers online — people often step up to support us.
Another place you can turn to for help is a MassMutual financial professional. They will listen to your goals, help you formulate a financial strategy for achieving them, and support you with check-ins and adjustments as your life changes. (Related: How financial coaching adds value)
Even though life can be unpredictable, creating a plan and adjusting it as you go is still a tried-and-true way to get somewhere that might feel more comfortable, fulfilling, or secure than where you are now. And try to think of other people’s ideas of appropriate milestones as mere suggestions, not mandates.
Discover more from MassMutual…
Owning vs. renting: A guide for renters considering homeownership
Is borrowing money from your parents a good idea?
What to do when facing a sudden financial hardship or emergency
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