7 Stories of Dramatic Career Pivots

At some point, everybody dreams of quitting their job to do something completely different. Sometimes, those dreams fall under pure fantasy. At other times, they’re grounded in reality and hope. In the spirit of such hope, we found seven people whose major career changes worked out astoundingly well — both financially and emotionally. From a publicist who went from partying with fashionistas to washing their hair at her own salon, to a building superintendent who now owns a world-famous bakery, here are some stories of inspiring career pivots.

The Fashion Publicist Who Went to Cosmetology School

Tina Malhotra, 44, New York

I was 32 years old, slowly climbing the ladder in fashion and entertainment PR, and wasn’t happy. I could envision my future — being middle-aged, running red carpets with my little Chihuahua, doomed to singledom, and owning my own boutique PR agency filled with stress, drama, and mean girls — and it scared me.

I had a very strong feeling that I needed to get out, but I had no idea what was next. I am the daughter of hardworking immigrants and not independently wealthy. I knew I wanted to work smarter and become great at something. But what?

My mom was a hairdresser before she had me, and for as long as I could remember, she told me to “go to hairdressing school.” Her voice was always in my head, and after a few months of soul-searching, I decided to listen. It was hard to start over. I quit my job and went to cosmetology school full time for seven months. It cost $18,000, and I lived off savings and did little PR consulting jobs on the side (after a while, I started doing haircuts at home for $50 a pop).

When I got my first job in hair, I was an assistant. That meant doing laundry, sweeping hair, and handing foils to my boss. I worked at a very “cool” salon — because of my PR career, I at least knew the hottest places to work. But I was now washing hair for the fashion editors I had partied with months before. It was embarrassing at times, but I told myself that was just my ego talking and to keep pushing. Starting out at $70 a day, I had many WTF did I do? moments.

Twelve years later, I own my own hair studio in midtown Manhattan; I’m booked out three months in advance, with a waiting list; and have accidentally become the Gen X hairstylist to Gen Z influencers (and yes, my clients taught me TikTok). I make very good money, like five times what I made in PR. I own my apartment on the Upper East Side. I solo travel every few months to exotic destinations. Life has never been better.

The Actor Who Became a Financial Adviser

Claire Autran, 28, New York

My whole life I’d pursued the arts. I went to performing-arts school, and I got my B.F.A. in acting. I moved to New York right after college and pursued acting while supporting myself with a day job in audio engineering. I worked a good amount at the Juilliard School, I toured with an artist from a major label, and I was flown to L.A. for gigs all the time. Everyone was like, “Wow, it looks like you’re killing it.” But I was making no money — probably around $40,000 a year. In March 2020, a one-woman show I’d written was supposed to open at Lincoln Center. We were in my final dress rehearsal when all of Broadway closed.

Then I was unemployed. I started day-trading with my unemployment money. I had never grown up with a lot of financial literacy, so I was like, Wow, your money can make money! In June of that year, I got a call that my dad had suddenly died. He didn’t have a will. He had this condo and then, all of a sudden, my siblings and I couldn’t sell it because we didn’t have the rights to it. We were paying the mortgage on it. It was a nightmare.
During this whole process, my relationship to stability changed. I saw how generational wealth can be either built or not built, and it was so hard to understand the documents and the paperwork. It felt like a full-time job to sort through his death. I thought, I don’t want anyone else to be in this position. I wanted to bring financial literacy to my community and make it accessible.

So I started doing research. At first, I thought I needed to go to school, but then I discovered a lot of finance firms will sponsor you to get your licensing. I went to the husbands of my mom’s friends, who worked in finance. I was like, “Hey, I’m going into the finance world — what firm should I join?” There was one firm I heard about over and over that was supposed to have the best training, so I wanted to start there.

I interviewed with my now-mentor, who’s the managing director of our firm. I think I positioned myself well — I played to my strengths in my interview — but it’s also a testament to his open-mindedness that he took a chance on me. The first year was such a learning curve. I got my license and started building my practice; I had 50 clients in my first year. Last year, my third, I managed over 150 households and made close to $150,000. It has grown mostly by word of mouth, which is awesome.

People ask me all the time if I miss working in the arts. I would miss it if it weren’t such a part of my life — who I am and how I spend my time outside of work. I’m lucky to have friends who are so supportive of what I’m doing.

The Massage Therapist Turned Fashion Photographer

Melissa Presti, 45, Brooklyn

Twenty years ago, I started doing massage therapy. I really wanted a career that helped people, so that’s what I devoted myself to. I enjoyed it, and I was good at it until the wear and tear on my body became too much. The amount of massaging I could do in a day was getting less and less because I was physically so beat-up, and the less I massaged, the less money I made.

Then I had a kid. I was 34 years old, my body was falling apart, and I couldn’t make enough of an income. The final straw was that I got Lyme disease and was basically paralyzed for two years. We had to use credit cards for everything and went into major debt.

I kept asking myself, When I get out of bed, how can I change my career? How can I make money? How can I do something I love that is lucrative? Photography was always my hobby. Whenever I was having a hard day, taking pictures made me feel centered again. So I did a deep dive researching every single aspect of becoming a successful photographer, from the business end to the different niches to lighting to marketing. I practiced studio lighting from bed. I knew I could either be depressed and bedridden or use the time while I was healing to develop a new career.

As I got healthier, I slowly built up the business. I decided to focus on photographing kids because I’m the happiest when I’m with children. Kids, fashion, styling — it all came together. I started contacting kids’ modeling agencies and taking pictures of child actors and models for free just for the content, to showcase my style and quality of work. When enough people started to notice my work on social media and trusted me as an artist, I finally began getting paid for my services, and the work got more elevated and professional. I started building a team — hair and makeup — and now I’m hired to shoot real campaigns for major brands. Right now, I’m working on two campaigns where, in one day, I’ll make the same as if I did 20 massages. I now come home worn out in the best way. By the end of the year, I will have tripled my income.

The Woman Who Quit Big Pharma to Become a Cheesemonger

Lauren Toth, 38, Boston

I come from a big family of health-care and pharmaceutical workers, so, naturally, after college I started in health-care communications. It never felt right. The culture did not suit me. The work was intensely serious, and everyone was so buttoned-up; every day was dealing with the minutiae of regulatory issues, legal concerns, and soulless corporate jargon. There was so little joy in my day-to-day life of 14-hour workdays.

I had just gotten married and it was supposed to be the happiest time of my life, but it wasn’t. To cheer me up, my husband would always take me to Murray’s Cheese. I was born cheese-obsessed, and it felt like I was in heaven there. It was my happy place. We would take all the classes and sign up for all the events. I remember one time when I had just turned 30, the cheesemongers at our lesson were singing ’80s rock, and all the women were wearing cool hairnets, and I thought, Could I ever work here? Could this be a real job possibility for me? All the weirdness and coolness and cheese passion just resonated with me so much.

What it took in the end was my taking control of my own life. I quit my pharma job and got an internship at a Murray’s cheese cave. I worked up to it slowly. Since I had volunteered to work a few of the company’s public classes, I asked the manager of the public-education program to pass on my application to HR and then I got an interview. I started a few months later, after wrapping up some big projects at work. Right away, I was wearing a lab coat and hairnet and rain boots to protect me from the sanitizers on the floor, and I was just like, This is the best moment ever. Plus, as I quickly learned: Cheese people are, like, the nicest people you’ll ever meet.

I was very privileged to have flexibility because my husband and I share finances and had enough in savings to take the risk for a year or two. We had to get our health insurance through the public marketplace, which was a big investment but not something I was willing to forgo. The internship was unpaid but part time, so I freelanced for the pharmaceutical company during the internship and my first year as a cheesemonger.

It’s been eight years. Now I’m the director of curriculum and talent, which means I oversee all the training initiatives. The money is about the same as I was making in my old role, though my peers who stayed in pharmaceuticals are now making a bit more. But I work significantly fewer hours, and my quality of life is 1 million times better. At least once a week, I take a step back and think, How did I get so lucky?

The Building Super Who Opened Her Own Bakery

Janie Deegan, 36, New York

I come from a theater family and thought I’d be a writer or director. Instead, I became an addict. I couldn’t cope with the fear of the unknown. I didn’t know how to transition out of childhood. After years of floundering, alcoholism, and addiction, I found myself homeless at 24. I got sober at 25. To get myself out of homelessness, I got a job as a building superintendent in the East Village — taking out the trash, fixing things up. It felt so good to have a job with basic tasks.

I stayed sober, but I still had so much shame. I had trouble looking people in the eye. Baking was something I credit to my early sobriety. It was my bridge back to life. While working as a super, I would bring baked goods to people I worked for. It made me feel like a person again, someone who could connect with people. They’d say, “You should open a business doing this!” But I was like, “A business? I don’t have an M.B.A. I don’t come from money. I’m not a man.” I couldn’t even dream of it. There were so many barriers to entry.

Then a friend who could afford any cake she wanted asked if she could buy a cake from me. From me! She wanted to give me money. It gave me that first seed of confidence I needed. I slowly built the business. I started taking orders. I had to figure out how to make it legal and viable.

I worked full time as a nanny for the first year and a half I was building the business and then I continued to babysit on weekend evenings to pay my personal bills. Pretty much everything the business made went back into the growth. Plus I had a built-in customer base for custom cakes because of the families I met while nannying.

In 2021, about two months after we opened our first store, I went on Watch What Happens Live With Andy Cohen. He had a booker reach out to me after trying a cookie from a friend. The result was incredible — it launched my business in a way that would have taken years to do otherwise. I got over 12,000 orders in one night. We were back-ordered for about five months and had at least five bakers on any day working in the back to bake, pack, and ship. It was total mayhem, but it was such an exhilarating time. I now have three shops in New York City. I own 100 percent of my business. I’ve never had investors. We are profitable. I used to think of myself as a meek worker among workers, and now I’m an entrepreneur. A few years ago, I literally had to Google what that word meant!

The Freelancer Who Opened a Poshmark Store

Rachel, 44, Brooklyn

After college, I was accepted into the NYC Teaching Fellows program and completed a master’s degree in special education. I wanted to help families. When I started working in the school system, I adored my students, but the job wasn’t a good fit. I was making about $50,000 with great benefits, but it just wasn’t my calling. I wanted to be a businesswoman. I’ve always had an entrepreneurial spirit — but what could I build?

I quit and tried a few other jobs. I worked in magazines and in the fashion industry, all while doing private tutoring. But when I got pregnant and had kids, my family became my main focus. I was very lucky that my partner at the time supported us financially, but even during those first years of motherhood, I was searching for the right idea. All I knew was that I wanted flexibility and I wanted to be an entrepreneur.

They say “Do what you love” — what did I love? Well, retail therapy runs in my family. I grew up going to tag sales in Massachusetts and hunting through markets and bazaars wherever I was. I’ve always been passionate about thrifting, sample sales, and scoring deals on expensive clothes and accessories.

About five years ago, I heard about Poshmark from a friend and ran to the site. I posted a few things on it just for fun and sold them fast. I was hooked. I started obsessively hunting all around the city and beyond. I’d go to church sales, to every Goodwill, to stoop sales. I turned over every stone in search of an authentic Gucci key chain or Céline wallet. Within a few months, I had about 2,000 listings up on my site and was making a couple thousand dollars a week. I made a friend through the app, and she became my mentor who helped me with descriptions, photography, and marketing.

When my kids are at school, I’m either looking for treasures to sell — via online sleuthing, thrifting, estate sales, and Facebook Marketplace — or communicating with buyers, sourcing specific items for them, and updating social media. Some weeks, it feels like a full-time job, and other weeks, I can pull back and focus on my kids if I need to. What boosted everything was starting live shows on Poshmark, which really changed my life financially. I now make well over six figures a year.

The PE Teacher Who Went Into Tech

Samantha, 37, Boston

I was a public-school teacher for about eight years. Most of my career was in middle school teaching physical education, health, and wellness. I loved giving back. At the time, I was making $60,000 a year. I knew I wouldn’t make a ton of money teaching, but I had a few other expectations — like being supported, valued, and appreciated — that didn’t pan out. I do think in general the teaching profession has been undervalued, but especially after COVID-19, there were shifts. Our classroom sizes were getting bigger. I think one of my classes was 34 kids; I couldn’t even fit them in a classroom. Kids who should have had aides accompanying them didn’t have aides. Kids who had severe behavior problems didn’t have the support they needed.
At some point, I had to think about my well-being, my mental health, my physical health. Is this worth the money? It was sad to have to say that.
In 2021, my wife — who is very good at seeing my strength — was like, “I think you should make a career change. If you hate it, you can go back to teaching.” She and my friends kind of guided me. With my personality — I was a college athlete — sales naturally came up.

First, I took a “bridge” job in an entry-level sales position. I initially wanted to get some firsthand experience. About six months later, I got another job, training salespeople. I used LinkedIn and my network to apply. All the jobs I’ve gotten post-teaching have been through referrals — for me, getting a referral is key to having my résumé looked at. Then from there, I made sure I was the most prepared candidate for every interview.

In my current role, my salary is $93,000. I love what I do now. Not only do I get paid more but I’m valued for my work. I’m treated like a professional. Also I’m fully remote; I can go to a doctor’s appointment during the day if I need to. I think if I knew then what I know now, I would still go into teaching and coaching — I had such an amazing experience, especially for a few years. But I really can’t put a price tag on the work-life balance I have now.