The Best and Worst Years of Our 20s

POPSUGAR editors describe the ups and downs of being 20-something.
Publish date:
June 5, 2014
relationships, growing up, college, school, mistakes, nostalgia, dream jobs, 20s, popsugar

Your 20s are a period of growth with definite ups and downs. In an article from POPSUGAR, their editors share their best and worst experiences from that time in their lives.

Being a 20-something woman isn't easy. It's an ever-changing transitional period that often includes college and a lot of firsts — be they in our professional lives or relationships. There are first jobs, first serious relationships, first marriages, first children, and first homes. We're at a time in our lives where we're figuring out who we are as adults and what we want to be. As I approach the big 3-0 myself, I reached out to fellow POPSUGAR editors about the struggles and triumphs of their 20s. These women have shared their best and worst years in their 20s along with some life lessons sure to encourage any other 20-somethings making their way. Read their thoughts below, and share your own highs and lows from your 20s in the comments!


Worst: "I was at a strange stage in college and I was so undecided about what I wanted to do in life — I wish I could have just told myself everything would turn out better than I imagined!"

Worst: "I thought I was much older, wiser, and sophisticated than looking back I actually was. Just because you're 20, doesn't mean you have the life experiences of your 20s!"

Best and worst: "At 20, I studied abroad and traveled the world, feeling like an adult for the first time and collecting some of my most special, unforgettable memories. That year also carried my first true, once-in-a-lifetime heartbreak — the kind that leaves you raw and gutted and open. The vulnerability left me fearless, too, and months later, at the end of 20, I met my now-husband."


Worst: "I have to say, for the most part, I really loved my 20s, but that's a cop-out answer, so I'll go with 21. The uncertainty of graduating and not knowing what lies ahead in the 'real life' department is at once thrilling and terrifying."

Worst: "My 21st was easily the worst. It was my senior year of college and I had no clue what was going to happen to me come May. I was also dealing with a semicrazy ex, so that made it hard to enjoy what was supposed to be the 'best year of my life.' I was beyond happy to blow out the candles on my 22nd birthday cake."


Best: "I moved from California to Seattle to be with my boyfriend the year I turned 22. It was kind of a risk since we had only been officially dating for a month before he left, but the move ended up being totally worth it — we've been together 10 years, married almost four, welcomed our son in February, and have a lifetime of incredible memories of 'our' city."

Worst: "I had just graduated college in Florida and had to move back home to Ohio for several months. It kinda sucked moving back in with my parents after being on my own. I also wasn't working, so I never had money, and most of my friends were still in school. It was super lame and boring."

Worst: "I was very much in that in-between stage after college: back home living with the parents, in a long-distance relationship with the college boyfriend I wasn't quite sure about anymore, and getting rejected from what felt like a million different jobs. I had no idea what I wanted to do with my life or who I wanted to spend it with. In a word, I was lost."

Worst: "I started law school right after turning 22, and after a year of tough exams and often mind-numbing internships, I decided to take a leave of absence. It was the toughest decision I ever made, since I had worked so hard to get there and had actually done well in my first year. Still, I knew I just had to find a career that was more fulfilling to me. I had some challenging days when I was trying to figure out what to do next and depended on my friends and family a lot to help me stay positive."

Worst: "I lived in Los Angeles, Amsterdam, New York City, and San Francisco all in one year. Though one could romanticize traveling and living around the world, it was really tough financially, socially, physically, and emotionally. I had four different jobs, attended culinary school on top of working, led a turbulent dating life, struggled to make friends or even have time outside of work for them, and felt as exhausted as a 90-year-old all the time."


Best: "The year I was 23 was probably my favorite, because it was my first whole year I lived in California, and my friends and I were driving down to LA from San Francisco pretty often to go to shows and clubs on the Sunset Strip and check out movie sets, and we just went to all kinds of events all over the state."

Best: "I ended a relationship and, after much deliberation, moved to a new city for a fresh start. I landed my dream job within three weeks of moving. I made a ton of new friends who were warm, welcoming, and eventually became my family away from home. It felt like all the pieces fell into place at the same time, which justified the tough decision to move away. It really changed the game for my 20s, though, so I'm so glad I took the risk."


Worst: "One of my best friends passed away, and I quit my job, broke up with my long-term boyfriend, and moved back across the country to California. It was a difficult year of tough (but for the most part necessary) changes."

Worst: "The college afterglow that made me feel like life would be a nonstop parade of endless possibilities and fun had dimmed a little bit and real-life responsibilities started to weigh on me a bit more. I'd put in a couple of years in an entry-level position in my career path but was itching for more responsibility, respect, and better pay. I felt like I'd taken on all of the markers of adulthood — paying my own rent! holding down a 'real' job! maintaining a fulfilling romantic relationship! — without really reaping the rewards of grownup-hood."

Worst: "We had recently moved across the country to SF, where I knew no one except my husband. I felt so far from my family and friends. I got a job at a really wonderful company but I was doing something I knew I didn't want to do long term. It was a grind, and although I loved most of the people I worked with, I cannot say the same about my bosses. It was still a great learning experience, but being homesick and feeling like I was missing out from a lot of postcollege life with my good friends was a hard adjustment for me while my husband was working supercrazy hours and I was left home with our dog and some earthquakes that made me want to run back to the East Coast as fast as I could."

Best: "This year — my 24th — has been very good to me. I finally landed my dream job (a week after my birthday, no less), found an amazing group of friends, completed my first (of hopefully many) half marathons, and modeled swimsuits for a magazine. But mostly I feel like I'm starting to become the person I've always wanted to be — independent, strong, and smart."


Worst: "Age 25 felt like a weird limbo between adolescence and adulthood. I remember going 'home' to my mom's house and just feeling out of sorts. I looked good, but I lacked confidence. I loved my job, but I still felt inexperienced. I was also in a relationship that went on at least a year too long, which I think is a mistake we often make in our 20s."

Best: "As much as getting older is weird and kind of sucks, you do get more comfortable in your own skin."

Best: "I finished grad school, got my job at POPSUGAR, and traveled to three different countries. When I was turning 26 and looking back on that year, it hit me how lucky I was. I'll never forget feeling so thankful for all the great things in my life."

Worst: "I moved away from my long-term boyfriend and we did the long-distance thing before breaking up, which was devastating. I had a great job, but I had to move back in with my parents for three months with a two-plus-hour commute (each way), which meant no social life. Then I ended up moving into an apartment with an insane roommate and her insane boyfriend for the remainder of the year."

Best and worst: "First, I got called that I got a job as a fashion editor at Time Out New York an hour before my birthday happy hour! Then, later that year, I totally had a quarter-life crisis. I went out all of the time in NYC and Fire Island during the Summer, and I took more fashion and beauty risks (like cutting bangs and wearing red lipstick). Even though it was the most fun year, it was also a difficult one. I broke up with my boyfriend of three years at the time and had to find myself. I had to grow and grow up. But I am thankful that I went through it all."

Best: "My now-husband proposed to me on my 25th birthday, and the entire year felt like one big celebration."


Worst: "My grandmother died when I was 26. She had been diagnosed with myelodysplastic syndrome several years prior and seemed to be managing it pretty well, but a string of illnesses really took their toll on her. She went in to see her doctor about what she thought was the flu on a Saturday morning and passed away two days later. This loss really sent my family into a tailspin since she was our compass. Six years later I still can't think about her without crying."

Best: "Now, at 26. I finally feel like I've grasped adulthood, financial independence (and responsibility), living alone, being in a healthy, happy relationship, and maintaining a work/life balance."

Best: "I got engaged and married at 26, so it was a memorable, beautiful year bursting with love and encouragement from my friends and family, and of course, my husband. Plus, I had an unexpected promotion at POPSUGAR and loved every minute of my new role in the company and was finally making a home in San Francisco. For the first time I felt like I was where I should be, alongside the person I should be with, and it was bliss."


Best: "I had been living in New York for four years, at a great job for about the same length, and had a wonderful group of friends surrounding me. Basically, I had experienced enough of my 20s to know who I was, but still had enough ahead of me to not be panicking about 30 . . . yet."


Best: "I was very blessed at 28. I got married, traveled to some of my favorite places in the world, and spent a lot of time with my family. At work, I got a lot of fun opportunities and felt confident about my career path. It always seemed like there was something to look forward to! If I could do one year on repeat, it would probably be that one."

Best: "This is really when I began to understand and appreciate who I was. I had the face and body of a 28-year-old, but more important, I was comfortable in my own skin. I had a job I loved (POPSUGAR) and was good at. I had an awesome rebound relationship — which I knew wasn't going anywhere but which was really fun — before embarking on the relationship with the man I'd eventually marry. Sure, we're divorced now, but I'm where I am today because I felt so comfortable with myself before we got together."


Best: "The last nine years have been less than great overall, so for the final year of my 20s, I've committed to relaxing more, worrying less, and doing the things I love with the people I love. Plus, I can't wait to turn 30. I still have nine more months so hopefully I didn't just jinx it!"

Best: "I had a pretty off-the-charts 29. I took two of the most memorable trips of my life. I started writing more and publishing short stories, which was something I'd been 'meaning to do' for years. I got serious about whipping my finances into shape, which took a huge, stressful weight off my shoulders. And I had one of my best career years to date, launching my own project that brought me a lot of personal fulfillment. That year, I also felt like some intangible something clicked into place that allowed me to enjoy myself more, worry less, and be more confidently myself."

Best: "I had started writing POPSUGAR a few months before I was 29, and it was taking off. I was so inspired and thrilled with being creative and being able to balance a freelance job to pay the bills as well as writing POPSUGAR on the side. I had made San Francisco my home and was proud and thankful to be living in such a fabulous city full of new, amazing friends. I felt so confident with who I was and who I was about to become as this was the year I had always wanted to start a family and I had Katie that June. So by 29 I was fortunate enough to create my dream job, launch a company, and have my first daughter. I didn't think life could get any better (it does — welcome to my 30s)!"

Check out more great stories from POPSUGAR:

A Guide to Dating Dudes in Their 20s vs. 30s

10 Reasons Why Marriage Isn't For Everyone

9 Things You Should Know About Being a 29-Year-Old Virgin