“Who Knows What Is Right? What Is Wrong?”: 3 Women’s Unique Paths to Happiness

SK-II beauty man repeller

In partnership with SK-II.

My Godmother Sally has one rule: Whenever you get into her VW Bug (red, always red, like her head of gigantic curls), you have to sing “Mustang Sally.” You can take the lead, you can do backup vocals, whatever you want, but you must sing.

Growing up, Sally expanded my worldview. She took me to the theater and to cool restaurants; she had a cool job at American Girl Magazine at a time in my life when it was very impressive to have a connection at American Girl Magazine. She wasn’t like anyone else I knew. I don’t think I noticed she wasn’t married until she actually got married at the age of 41. Maybe because my mom had a lot of friends who were unmarried in their 40s: Her friend Barb who threw amazing parties, her friend Jackie who traveled alone and took flamenco lessons, my Auntie Gloria who was glamorous and sharp and gave me $2 bills whenever I saw her. My childhood was shaped by these women who did interesting things and lived fascinating lives and were the types of friends who became family.

When I was 27 and decided to upend my life—with a move to New York, a new degree, a new career, and so much money down the drain—I felt like I was starting over at a time others were settling down. And if it weren’t for my godmother, my auntie, and the rest of my mom’s friends, I think I would have been consumed with anxiety about the choices I was making. But for the first time, it finally felt like I was living the right life.

There are so many stories about how young couples met, dated, and married, but few about the makings of interesting unmarried women; the ones who marry and divorce, date and never marry, stay single and marry late, or none of the above. Together with Katie Couric SK-II has set out to change the conversation around love, marriage, and expectations with its Change Destiny campaign and their new series “Timelines” which documents four women around the world who are challenging societal notions of the “right” time to get married and defining their own timelines instead.

In the spirit of the campaign, I spoke with three women, each with unique and interesting stories, who took unconventional approaches to traditional timelines. We spoke about the ups and downs, the difficulties and triumphs of life beyond a white picket fence and 2.5 children by 27. The conversations were both mirrors and maps, honest tellings of living life on your own terms.

After a tumultuous upbringing, Caroline is building toward her dreams.

Caroline, 42, is an educator.

“I’m really bruised and worried, but I’ll try to stay open and flexible.”

I grew up in a family house that was pretty significantly impacted by mental illness, and still is. My parents were upfront about the whole thing. They were like, “Don’t have children. This is just a nightmare.” That really hit home, this whole sense of regret that they experienced and continue to grapple with. So I was like, Wow. This is definitely not for me. The acuity of that experience was incredibly impactful. It shaped so much in my life.

I had relationships, really great and meaningful ones, so in time, I began to think, Well, let me try to keep an open mind. I’m really bruised and worried, but I’ll try to stay open and flexible and maybe if I meet the right person, it’ll feel like the right thing. That was my thinking.

But eventually, after some difficult false starts, I changed my mind again. Now I’m 42. And going from “This isn’t for me” to “No, wait, maybe it is for me” to getting bashed and going back to, “No, this isn’t for me” has been really hard.

“Let me just give it one last go and see what happens.”

I could not give you the real deal and be like, “I’m this roving, globe-trotting, renegade lady, blazing a path, seriously independent.” There’s an element of me that relates to that sense of my own identity, I guess. But I’m human.

There’s been a major development in my life in the last year, thanks to dating apps, which I’m a total fan of. I was like, “Let me just give it one last go and see what happens.” I tried and I went on some lovely dates and I met this guy and we’re really happy together. I’m still dealing with scars and war wounds, but maybe there’s something that I can build on here. What that means in terms of children is not at all clear and possibly not possible. But at the same time, just the feeling of stability and connection and peace, and relations, community and connecting with him, meeting his friends, the shift that has come into my life through all of that has been so grounding.

To this day, I don’t see a great deal of value in being too closely committed to a map or a plan. I’ve done so much and lived so many places, but the thing I really want to do—write a book—I haven’t even done yet, but I’m building toward it. Who knows what is right? What is wrong? I’m just trying to do the best I can.

After years of prioritizing her career, Andria has found a more balanced life.

Andria, 40, is the chief curator at the Pace Gallery.

“I felt like my work became the thing I cared about the most.”

I’m from Newfoundland, Canada, which is a pretty traditional kind of place where family life is really important. The idea of finding a career that didn’t feel like work was a really big influencer for me, but I always pictured having all these new adventures ​and​ having a stable domestic life. And the reality is that it’s really challenging to do both of those things at the same time.

After graduating college, I went to Bangkok and worked for UNESCO and thought I would go into international development and policy. After that I moved back to Montreal. I debated staying in foreign policy but the art world won out and I stayed in Montreal to study art history in grad school. I went right to the Walker Art Center in Minneapolis right after grad school, and within a few years I was in New York working as a curator with the Public Art Fund.

The art world is still a place that’s challenging to navigate in terms of upward mobility, particularly as a woman curator, and you often have to change institutions to move up. I was headhunted and offered a great job at a museum, and that’s how I ended up in Cleveland for a few years. But it was a very hard move. The reality was that I was in a city where I was single at 37, no kids, where almost 95% of the people I met that were close to my age had families. All my family was living far away in Newfoundland. All my old friends were scattered everywhere and it was really lonely. I felt like my work became the thing I cared about the most and that didn’t work for me in the same way it had before. I mean, I was really enjoying my work, but it changes the way you are in your job when that’s your thing and your ​only​ thing.

I talked to Pace Gallery in New York for a long time before deciding to take on my current role. I felt like it was such an exciting opportunity, but it was also a big career transition. I took a chance and it has been an incredible year. The work that we are doing at the gallery – launching a new flagship building in New York, working with incredible artists and fantastic colleagues – it’s a dream job. I’m insanely busy, but I’m energized and inspired, and I’m happier than I’ve ever been.

For a long time, moving was really exciting to me—I am a person who loves making new friends and doing new things. But I didn’t realize how hard it was until I got a little older and stayed in one place for a while — moving takes a lot out of you. But I have great friends from all the different cities where I’ve lived, and everyone wants to visit New York, so it’s not ​so​ bad.

“I could write an entire book about the hilarious and awkward online dates I went on.”

I recently turned 40 and all these things fell into place. I feel very lucky. I’m doing some really exciting things in my work that push me to think and work in new ways. And somehow I met this amazing person in the middle of everything—I could write an entire book about the hilarious and awkward online dates I went on. I think I went on 100 dates in New York, but it was a million times harder in the Midwest. Then I met my current partner in real life through a friend and we really hit it off. He was from Detroit and owned a restaurant, but he decided to make a big life change last September and we moved to New York together. We’re getting married next year.

Everyone says, “Your thirties are so hard.” And it’s true, they are really hard. I think a lot of women, if they’re single, reach a point in their mid-to-late thirties when some deep thinking has to happen on how they want their life to go. That was true for me. At one point I thought maybe I really needed to slow down and just focus on my personal life, but I was also excited to walk through the door of a new career opportunity, and so I did. And things shifted into place in a way I didn’t imagine.

When I turned that corner to 40, which seems like a cliché, something re-aligned. I do feel a different kind of confidence or security. That’s not to say that there won’t be really, really hard times ahead, but I think the whole point is that now I know that I can deal with it.

Post-divorce, Patty is ready for motherhood on her own terms.

Patty, 45, is the marketing director for a food hall.

“I gave up a very comfortable life in Chicago and found out so much about myself.”

My career sent me on a lot of different trajectories, but I always wanted to live in New York. One of my first jobs out of college was driving the Oscar Mayer Wienermobile! It was great for a while, but I realized I had to get a real job and pay my student loans, so I ended up at an advertising agency in Chicago. After that, I was a DJ for Radio Disney Chicago for 10 years and it was amazing.

Eventually Radio Disney offered me a huge promotion, but it was in LA. I never wanted to move to LA—the dream was always New York—but LA was where the job was. I took it, which was the scariest thing I had ever done. I gave up a very comfortable life in Chicago and found out so much about myself. I don’t think I would have evolved as much as I did if I didn’t make that move.

A few years later, I started thinking ​I need to go to New York now.​ ​I’ve wanted this since I was 17. I need to do this.​ So I quit my job, moved to New York, and couch surfed at the age of 39. I was happy and excited, but also scared. I couch surfed for a year, took random jobs, did some consulting, worked for free, did whatever it took. A friend said, “Trust in your journey, trust in life itself.” And I thought:​ What does that mean? I’m 39, I should know myself by now. ​The whole experience taught me that I’m always evolving.

I’ve now been in New York for six years. I got the food job of my dreams (I love to eat), I’ve got my own place. Uprooting my life was terrifying, it’s still sort of terrifying, but it’s what I’ve always wanted.

“I didn’t understand what self-love was until this year. I didn’t know I didn’t have it.”

In college, I had the best boyfriend, but we were young and I wasn’t ready to be settled down at 21. At age 26, I was in another serious relationship in Chicago, and all my friends were getting engaged and getting married, but it just never felt right for me. We broke up and I was single for a few years and when I moved to LA, within the first couple of months I met another amazing guy. I was 33 or 34 at that time, and he was 23 years old so I was like, ​this is not happening.​ But we ended up sharing a beautiful love for three years. We had this great relationship, and then he got deported, and it was awful.

I didn’t really date anyone else in LA after that, but I met someone a year after I moved to New York. And at an NYC pace, we fell in love fast, moved in together got married, went through 6 rounds of IVF to start our family. Ironically, I got pregnant naturally last summer during the time when our marriage faced its biggest test. The person I loved showed his true self and we were no longer compatible. I had miscarried my most wanted baby and we got divorced. So this past March, I just had to start over again.

I didn’t understand what self-love was until this year. I didn’t know I didn’t have it. Coming out of the divorce people would say to me, “Take time for yourself, pamper yourself, love yourself,” and I didn’t know what that meant, I didn’t know how to do it. I know I’m affected by love and I don’t regret any part of that. I loved fully and authentically, but right now I think my path is figuring out ways to love and take care of myself because I’ll only be a better mom, friend, daughter, and sister if I take care of myself truly. I must say that I couldn’t have done it without the love and support of my amazing tribe of family and friends.

“This​ is what I want. This is what I am ready for.”

I want to be a mom more than anything else. I’ve wanted it since I was six years old. After I watched Baby Boom with Diane Keaton, I told my mom I wanted kids before I’m 15 and she shut that down quickly. I wanted to be a young mom and now I’m 45 and I’m thinking, ​shit.​ But getting pregnant naturally last year was a reminder that I became a mom and I will be a mom to someone else no matter what.

At the end of this year, I’m hoping to start my own family. You can be all things, and not be confined to one thing or other people’s expectations. When people say, “Oh, you’re not married?” I say, “No, I’m not​.”​ I’m not dating, it’s not what I want. ​This​ is what I want. This is what I am ready for.

I hope if you, like I, still feel a certain amount of pressure to follow a certain path, that these interviews spoke to you. There is no right way to live a life so I hope to follow my path and see where it takes me based on what I want and need at the moment, not what I’ve been taught is the “right” thing to do. We’re never too old or too young to stake a claim in our future.

If you want to talk about all of this IRL join Man Repeller, SK-II, Andria, Caroline and myself for a rousing real-life discussion about life, love and choosing your own path and making your own timelines at our Good Evening event on August 22 (more details to come – check back Wednesday for the event link and information).

Photos by June Kim

Nora Taylor

Nora Taylor

Nora Taylor is the Editor of Clever. She can frequently be found knocking things over in the greater New York City area.

More from Archive