When you're working in a coffee shop by day and nose-deep in textbooks by night, your 20s can feel like a never-ending treadmill with your dream job dangling like a carrot before a rabbit. But the good news is that all that hustling isn't in vain. If there's one thing we've learned in our own career trajectories, it's that every experience along the way—no matter how small or insignificant it may seem at the time—counts.
In fact, they're all crucial pieces in your own career puzzle, and the end goal won't be reached without them. Sometimes it can feel like a blur of career mistakes and job-hopping, but that's all part of the process, so trust it.
For every inch you move forward, you're one step closer to making your dreams a reality. Don't worry if you don't have it all mapped out yet. It turns out a lot of the editors and creative talents at Clique Media Group (Who What Wear) didn't either, but look at them now.
To prove it, we asked some of our own successful women to share the story behind their first job, the greatest lessons they learned, the experiences they gained, and their best takeaway tips. We all start small, but with a little grit and some confidence thrown in, you can make it happen if you really want it.
First Job: My first full-time position was when I was hired as an editorial assistant at Elle in the magazine's features department. I worked for the executive and managing editors, and in addition to supporting them, also edited the "Letters to the Editor" page, the monthly horoscope column, and wrote for my direct bosses, as well as for the beauty and lifestyle directors.
What Was My Experience Like: Working at Elle was a dream in every way: I got to be a part of this amazing team and learn from the industry's top editors. My fellow assistants became some of my dearest friends—relationships that are still hugely important to me today—and I learned how to create content. The best part of my job was that I got to work on so many things. I had an art column, wrote about music, got to travel to Spain with Bentley to write about a new launch, edited small pieces, worked with our freelance writers, and contributed to the living and beauty sections of the magazine.
My brain felt like it was growing every single day, thanks to the high level of talent I worked for. I learned how to craft a story, be a reporter, ideate, work with loads of different personality types, create compelling heds and deks, copyedit, work on layouts, write to fit—so many things I still use on practically a daily basis; it's crazy!
The Aha Moment: I knew that I wanted to be a journalist pretty early on in my life, and specifically that I wanted to work at a fashion magazine. I'd been obsessed with magazines since junior high, but it didn't dawn on me that I could work for one until about halfway through college. After I had that realization, I started interning as much as possible, and those internships really solidified my desire.
The Takeaway: Find something you love to do, and then figure out a way to get paid for it! (Which also happens to be the name of the first chapter of Kerr's book, "The Career Code".) Also, intern, intern, intern. It will help you figure out if you really want to be an editor and will also expose you to a few companies' cultures, which is also super important.
First Job: Intern at NBC throughout college; legal assistant at Kirkland & Ellis after graduation.
What My Experience Was Like: As an undergrad, I was very interested in the media. I interned at NBC every summer and studied journalism, psychology, and communication. Unfortunately, I was concerned about how to support myself after graduation on an entry-level media salary, so I evaluated my strengths (verbal and written communication) and made the decision to try working at a law firm, where I could leverage those skills in a more lucrative way.
Working at a law firm, I got used to very long hours and performing under pressure. I learned how to navigate challenging personalities and deliver against tight deadlines with flawless execution. The firm demanded an exceptional work product. This is a quality I carry with me today, although in digital, I've grown to embrace the mantra that "done" is better than perfect.
Ultimately, it wasn't the right fit for me. My experience taught me that it was important to find a positive work environment to apply my talents. I wanted to be around professionals who were creating work that they are passionate about, in a culture that nurtures talent. So as I considered my next opportunity, this became my driving criterion. Half of your career development is in identifying what it is that you don't want.
The Aha Moment: I realized I didn't want to pursue a career in law when I was filling out law school applications and I couldn't answer the very basic question, "Why do you want to go to law school?" I had earned strong LSAT scores and glowing recommendations from partners at the firm, but night after night, I found myself staring at a blank piece of paper every time I attempted to answer this question. The truth was, I didn't. Being honest about my motivations was truly a turning point for me.
That, of course, was just the beginning. From there, it was all about doing my due diligence to figure out what my next step was. Fashion was always an interest of mine, so I reached out to every fashion lawyer in New York to learn about their careers. One of the partners I contacted responded, and we met for coffee. She advised me to get experience in intellectual property law, as that's truly at the core of the practice of fashion law. From there, I sent my résumé to every IP firm and ultimately got my foot in the door at Google. Because my previous internships and undergraduate education were focused on media, the recruiter at Google suggested I join a new team at YouTube. I took a leap of faith and went for it!
Because of my organic interest in fashion, I cultivated expertise in digital fashion media working with fashion and beauty vloggers on YouTube, and even some larger brands like W magazine. This ultimately landed me a role at Condé Nast, launching a video strategy for the publisher's print publications, brands I'd never dreamed I'd be able to work for: Vogue, GQ, Glamour, and Allure.
The Takeaway: My father always told me, "Pursue your passions; the money will follow." I feel so fortunate to have received this advice. Looking back, I didn't know where I'd end up when I transitioned from law to digital media. What I did know was that I believed in myself, my ability to work hard, and my ability to put in the hours. I approached the decision without letting fear stand in the way.
You have the ability to shape your career out of ambiguity by relentlessly pursuing your passions. Outside of work hours, I'd read anything and everything I could to learn more about the digital media landscape, and how fashion brands and publishers were innovating in the space. This helped me become a thought leader. I carved out opportunities to lean further into the fashion and digital media niche and cultivated a strong body of work and expertise that drove me forward.
First Job: Story development intern at DreamWorks SKG.
Growing up in the '90s, DreamWorks was borderline mythical. The studio's first animated film was with Woody Allen. It was a haven for artists entirely driven by talent bent on shaking up the commercial model. I'm still in awe of the way Jeffrey Katzenberg runs a studio. It was a unique environment, and for a 20-something, it was pretty much Shangri-La. It's also why I put off my own writing career for close to 10 years.
What My Experience Was Like: I was 19 at the time. I had no idea how to get a job and zero "Hollywood" studio connections. I was a kid from Texas. What I did have was multiple talents and academic scholarships, a perfect GPA, and enough doe-eyed naiveté to blithely breeze into an interview assuming that was all I needed to get hired. I cold-faxed (yes, faxed) out 65 résumés to pretty much every studio in town. I wrote 65 separate, unique cover letters. I got one callback, one interview, and one offer in the room. It happened to be with my first choice of employers: DreamWorks.
The Aha Moment: I hired writers and workshopped scripts in film production for a long time, both in live-action and animation. When I was young, I couldn't get my head around the fact that in many ways, writing is a service gig. You're delivering for a brand. You're a gun for hire. In my 20s the notion of not having total creative control over your work or voice felt terrifying. I thought I'd rather be the exec protecting the talent, fighting to keep their vision intact. I also didn't personally know a lot of wildly happy, creatively-fulfilled writers—at least not ones who could pay their mortgage.
Ironically, it wasn't until I fell into a gig as a full-time senior copywriter for a brand that I decided I was dead wrong. Writing for brands informs your personal work in a pretty brilliant way. Delivering art that's meant to sell, especially in advertising, teaches you the business. From there, you just rank your priorities. Do you want to be in show business or show art? A case can be made for both. Much of what I might have considered "selling out" in my 20s turned out to be just "marketable skills" in my 30s. When I was starting out, I was pretty wrapped up in having a discernible path and in climbing a corporate ladder with tangible goals.
First Job: My first job out of college was working at the fancy hair salon in the penthouse at Bergdorfs—the John Barrett Salon. While I worked there, I freelanced. So, yes, I was working seven days a week in order to make ends meet and add to my résumé. I had to answer phones, schedule appointments, make coffee, and show people to their chairs. Then I would write during my lunch break. It was a ton of running around (in heels), but it was fun and I loved watching everyone work.
What My Experience Was Like: It came about by chance (a girl I had interned with worked there too), but it turned out to be completely serendipitous. At the time, I thought I wanted to work in fashion, and I didn't really know beauty was an option. After working around the seasoned, wonderful, and divinely talented stylists, colorists, and makeup artists, I knew beauty was my thing. We began to play games at the front desk, guessing who had styled each client as they came to settle up. We gossiped in the kitchen. It really was like a family.
Of course, it was exhausting. The salon would see hundreds of clients in a day, all paying high prices and expecting great service. I tried my best to always keep a good face on, as I was the first thing people saw when they walked through the doors.
I learned all about the ins and outs of makeup, hair, and skincare from many of the industry's most celebrated experts. I saw what happened behind the scenes and how much hard work goes into each and every client. That's been immeasurably helpful to me in my job as a beauty editor. I know how important it is to tip, to be on time, and to be kind. I also picked up a few great tips and tricks along the way.
The Aha Moment: It's hard to pin down an exact moment. There have been so many I can't believe this is my job-type of situations. I remember when I was freelancing, I was assigned a story that covered cancer survivors and how they regained confidence and felt sexy in their skin post-treatment. We took them all out to get their hair and makeup done, and I interviewed them while they sat in the chair.
Watching each one of these women leave the salon—hair bouncing, smiles from ear to ear—I realized the very real impact beauty has on a woman. It's not always about this season's lipstick or learning to cover your flaws, but rather feeling good in your own skin. That was a huge turning point for me. I love that our writing can actually help people, and since then, I've been trying to be as "real" as possible when I write—whether it's about my hair, skin, or experiences with body image.
The Takeaway: You have to hustle; you will never get around that. To be successful in this field is to work hard. Build relationships. It's a small industry, and those relationships will be more helpful than you realize. Most jobs I've gotten have been through a former colleague, boss, or word of mouth. I owe so much to a few wonderful mentors that have helped me endlessly over the years.
Take every opportunity that comes your way.
The reason I took that first salon job was that my dad imparted this wisdom, "You just have to get a job; it doesn't have to be the job. No matter what, it will help you." Those words couldn't have been more accurate, because, after eight months at John Barrett, I accepted my first full-time beauty gig.
First Job: Associate buyer at Bloomingdale's. I started in the training program group, where we learned a lot of the basics: retail math, learning the retailer systems, forecast planning, pricing, etc. I shadowed a buyer and team in the women's contemporary department. I ended up being placed in the men's department, focused on designer suits and sports coats. The role consisted of monitoring sales and markdowns, assisting in forecasts, and selection of product per store.
What Was My Experience Like: I had a wonderful experience in my first role. I consider myself lucky that I was able to participate in a training program with a group of fellow graduates and learn some fundamental skills that are key to any job. It was a nice transition into the real world. I was also lucky to have an incredible boss who acted as a mentor. She not only taught me a lot, but she showed me how to be a mentor to others, the value of building a good team, and fostering growth in others who are coming up in their career. I learned a lot of analytic skills that I was able to parlay into my role in product management once I transitioned out of fashion and into the world of e-commerce.
The Aha Moment: Although I had transitioned into the ticketing industry working in e-commerce as a product manager, I knew that I ultimately wanted to bridge the two worlds back together. One of my favorite things about being a product manager is that you can actually see the results of what you do. You can point to a screen, app, or tool and show what you helped to create, and better yet, have data to demonstrate the value it provided to the business, consumers, peers, etc. I knew I liked product management but wanted to do e-commerce for a fashion company so that I could also tap into my personal interests.
The Takeaway: For someone trying to get into product management/e-commerce, my tip would be to know your user and let data guide your decisions. There is always a laundry list of projects that can be executed, but the key part of the role is helping determine what the right projects are and where the focus should be to really move the needle.
First Job: Editorial assistant at The Zoe Report.
What Was My Experience Like: I had interned there for about a year beforehand, and right around the time I graduated, they offered me the job. I was so over-the-moon excited about this new position, not just because I didn't have to tell people I was "still figuring it out" after college but because I was able to see my hard work over the past year pay off. That was a great feeling.
As the editorial assistant, I was writing 12 stories a week for the site across the categories of fashion, beauty, and lifestyle. I helped oversee our team of interns, supported the other editors in any way needed, and was responsible for a lot of the delegation and training of our freelance team. I learned so much so quickly at this job.
Although at times I felt overwhelmed, it was that healthy pressure combined with the support of the company as a whole that taught me the most and then led me to my role here at Who What Wear. I truly don't think I could have entered this position as prepared as I was if it wasn't for that job.
The Aha Moment: There wasn't really one moment per se that assured me I was on the right track, but it was a summer internship. Since I was about 8 or 9, I knew that I wanted to work in fashion, but I didn't really have a grasp of what that meant. All I knew was that there was something so inspiring about the industry and the place that it inspired me most was in the pages of fashion magazines.
When I was a sophomore in college, I got an internship at Marie Claire in New York. I moved to the city by myself for four months and prepped by Googling "what to do by yourself in New York for a whole summer" (I'm a pessimist at heart). I was interning under the then-associate accessories editor Elana Zajdman, who the other interns told me on the first day either loved you or hated you, and that she was a hard one to crack. So naturally, I took on the challenge of getting her to like me for the rest of the summer. It paid off more than I knew.
Elana took me under her wing and gave me more responsibility than I sometimes knew what to do with, but I had to make work. She let me do everything from attending her market appointments and doing her scheduling to assisting on cover shoots and actually sitting in for her in my last week as she was out of the office. The rush I experienced that summer is incomparable, but once I experienced it, I knew editorial, whether print or digital, was the only path for me.
The Takeaway: My main tip would be to intern at as many places as possible in as many departments as possible. You often don't know what you want until you experience it, and an internship is a great temporary way to test out any job you're interested in. I also encourage anyone going into any field to be as resourceful as possible. You will be surprised how much you can teach yourself if you take the time to try and answer your own questions before relying on someone else.
First Job: Actuarial analyst at Hannover Life Re.
What My Experience Was Like: My first job was as an actuarial analyst at the world's second-largest reinsurer. I ran statistical models on large populations to predict future outcomes. The type of work—researching and engineering big data studies—was very rewarding.
The Aha Moment: While my statistical and analytic knowledge was being leveraged as an actuary, I knew I needed to nurture the engineering skills I had acquired from my undergraduate education in computer science. This led me to my first position at Clique Media Group as a junior web developer. I was definitely able to sharpen on programming skills by being a part of the feature development for all CMG sites. Since then, I've been lucky to grow both identities of analyst and engineer with the company.
The Takeaway: Be open and flexible to nurturing multiple talents and identities. You'll be working for a lifetime, so don't rush to put a label on yourself. If you are getting started specifically in programming, my tip is that the struggle is real. However, it's often when you are struggling that you are on the cusp of reaching that next plateau of knowledge. If you like to create or are curious, programming is very rewarding when you reach those plateaus.
First Job: I worked as the junior editor and salesperson for This Month magazine. This free home-delivered publication featured articles on local businesses and various events in the region. I sold ad space for the magazine by visiting small businesses door-to-door, and once they were signed, I interviewed the owner and wrote a small article (better known today as an advertorial) about them to accompany it.
What My Experience Was Like: This job definitely had its ups and downs. It was a family-run, family-owned business, which meant the team was extremely small and tight-knit. This also meant I was given a larger scope of responsibilities that most fresh-out-of-college graduates might. I thrived in this environment. I worked across all departments, from sales to ideation to editing to planning. It was a huge learning experience, but after a year of knocking on business doors, cold emailing, and calling, I knew that the sales biz wasn't for me and that writing was my true passion and calling.
Without that experience, I wouldn't have had the confidence to cold-call the features editor at the Gold Coast Bulletin newspaper and ask for a job. Despite my tenacity, I was declined many times, and I even received a typed letter in the mail (which I still have as a reminder), but it didn't stop me. He finally caved and decided to meet up with me. I won him over, and within a month, I was offered a job on the copy desk assisting other editors before finally being offered a cadetship a few months later.
The Aha Moment: Being a cadet is really hard work. You're treated like a junior with no experience and reminded of that fact daily. It's brutal. I was assigned to the newsroom, where I'd sit with the other cadets listening to the police and ambulance scanners waiting patiently for a chase or an accident to report on. We also had to call the ambulance every hour to check-in, just in case we missed something over the scanner. As soon as we heard something big, we'd grab a photographer and race to the scene. It was crazy. I will never forget the day I arrived before the paramedics at a major car accident. The driver died before being pulled out of the vehicle. The silence that followed was eerie and gut-wrenching. I knew from that moment that hard news wasn't for me.
They soon moved me to the features department, where I started writing about fashion, beauty, and various lifestyle topics. I worked directly under fashion editor Lauren Barker, and she taught me everything. I learned so much during that time and had so many amazing, memorable experiences, including reporting on Mercedes-Benz Fashion Week Australia in Sydney. When I returned to work after a year off from having my son, Lauren had moved on and I was promoted to the role of fashion editor for Tuesday, the newspaper's weekly magazine. It was a dream come true.
The Takeaway Tip: If you really want something, go for it, and don't take no for an answer. Besides, what other choice is there? I think it's also really important to remind yourself to trust the process. Everything happens when it's meant to, as long as you let the universe know what you want and don't give up.
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