Fashion Exec to Real Estate - How I traded in for my unexpected true calling


When you graduate college, you have aspirations of following your dreams and living a fulfilled existence where both your personal and professional lives are perfectly balanced. You dream of a job where you are not just surviving but thriving.

For some, this is a reality.

But if you’re like me, you get halfway to the finish line of a grueling, soul-sucking race (one you appeared to be crushing) and then boom!---you get a call and the universe tells you there’s a different plan. You’ve got rent and bills to pay, so suddenly you need to figure it out. And you have no idea what you’re going to do.

But sometimes what seems like a terrifying and paralyzing setback can turn out to be a life-changing kick in the ass. It can set you free, and onto the steady course of finding your true personal fulfillment and happiness.


I hustled to get that first break for what I thought was my dream job in fashion. I started as an intern working in the licensing department for Calvin Klein during college. I discovered the coveted internal “sample sales,” and soon attained an incredible wardrobe far beyond the means of an indebted student.

When I graduated, that internship led to a job as the executive assistant to Barbara, the president of design and merchandising for Calvin Klein. I was in. I was sharing the halls with Kate Moss and Carolynn Bessette-Kennedy, and would eventually be in merchandising strategy meetings with Calvin himself.

Most of you have seen “Devil Wears Prada”? Multiply that by ten. Barbara was a visionary who was both revered and feared. As one of her three assistants at first, my duties included walking Barbara’s dog, buying her the perfect shade of Chanel nude nail polish, and making her tea (30 seconds in the microwave, always in a mug, and with half a Splenda).

She ran a tight ship and had gone through many assistants before me. I knew I was being tested, paying my dues and soon I was able to figure out what made her tick.  She warmed up to me and six months later I was promoted to Licensing Coordinator. As far as having a cool job goes, I had an 11 on a 10-point scale. I was Barbara's protege and she was my mentor.

I learned from her about merchandising, product development, and the design process from start to finish sitting in meetings with the best in the industry. I was creating strategies, negotiating prices, following the latest trends, managing clients, traveling to factories, and shopping the world over.

When people asked what I loved most about my job, I’d say, “I work with creative people, and I get to travel worldwide.” I mean, who wouldn’t love trend shopping in Paris for a living? It wasn’t always as wonderful as one would think, and there were many late nights and weeks on the road, but I truly loved my career.

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By 2014 (almost 20 years later), I had worked with some of the best brands in the industry: Victoria’s Secret, Liz Claiborne, Tory Burch, and Ralph Lauren. I loved my life in NYC but I was ready for a change. Something in me told me I needed to be closer to my family in Boston. I reached out to fashion headhunters in the area but unless you were an active footwear maven, there aren’t a lot of fashion companies there.


As luck would have it, I got a call from a recruiter six months later. An Irish fast fashion brand was coming to the USA, and a year later they would launch their headquarters in Boston. I was asked to move to Dublin for a year and then onto Boston.

It was kismet.

This was a welcome relocation, as I had been feeling stagnant in NYC and was over the dating scene.

Dublin was amazing. I made friends quickly, and worked with super talented people who were smart, passionate, and fun. I was also having a great time traveling all over Europe and the globe. (I also became acquainted with my Irish relatives from Dingle!)

I remember meeting Marty Walsh at our Dublin HQ and discussing how excited we were to be opening up in the iconic Filene’s Store where my grandmother had shopped as a little girl. I didn’t know Boston that well but I was looking forward to living in Pats and Red Sox Nation territory, and being close to the Cape where my parents lived.


When I finally arrived in Boston, I wanted to buy a home but I didn’t know where I wanted to live. Most of the real estate agents I encountered weren’t that helpful; I felt like just another transaction to them.  

Instead of buying, I ended up renting a pricey apartment in Beacon Hill with an amazing skyline view. I fell in love with the closely-knit neighborhood and its historical architecture, which felt like I was living on a movie set.  

My company quickly learned that opening a new chain of stores in a country with no brand recognition was extremely difficult. The lack of brand awareness, no advertising, and the shifting landscape from brick and mortar to e-commerce were challenges facing the company. Sadly, our numbers and sales projections just weren’t there.

In May 2016, after almost two years with the company, suddenly and without warning a few other executives and myself were let go. It wasn’t performance based, they said. It was a business decision. “Nothing personal.” They slid the compensation folder across the table.

Oh. My. God. What am I going to do now? I thought. How could this happen to me? How did I not see the signs?

I didn’t want to start over and I felt panicked. Thankfully, I had saved plenty of money so I knew I wouldn’t be destitute---but I didn’t want to be unemployed for too long. I knew there were few fashion jobs in Boston (at my level and salary), and I also knew I didn’t want to leave the industry. I had worked too hard to get to where I was. I was accustomed to my lifestyle, and at the same time I had serious bills to pay. In a few months’ time, I wouldn’t have any income coming in.

My NYC friends assumed I’d be moving back but I didn’t want to. I couldn’t. Boston felt like home and moving a third time in three years (and back to a place I was so ready to leave) wasn’t an option.  

One of my colleagues found a job at a discount retailer near Boston, and he urged me to do the same. But my heart wasn’t in it. I wanted to feel excited about my career, not deflated. I was convinced I would find a job.

So I took most of the summer off and looked. I thought for sure something would turn up. I would get phone calls from HR people asking why I was applying for positions where I was clearly overqualified and the pay was less than half of my previous salary. I had to ask myself the same question.

The months passed and my bank account was hemorrhaging for rent, car payments, and other expenses still coming in. I hadn't had a paycheck in six months.

It was starting to get uncomfortable.


My mother (a former real estate agent) urged me to think about real estate but I was hellbent on avoiding sales. I just didn’t see myself in the role. I wanted a steady paycheck and the security that brings.

Meanwhile, I couldn’t move and downsize to a more affordable apartment because I didn’t have a job (so I couldn't submit an application with no income).  I was stuck.

I didn’t travel, didn’t go out as much, and I certainly didn’t buy any clothes. But I also had the time to get to know the city and create friendships with an amazing group of people all around me. I didn’t know that this lively group of Bostonians would also become my clients.

I started to think more and more about getting out of the industry that I loved, and one that felt like second nature. I went to a career coach who told me, “You have all these skills and knowledge. Lots of companies would be lucky to have you. You’ll figure it out.” (Thanks for the sage advice, which amounted to nothing.)

That year Trump was elected. I became angry. How did that happen?

I thought about going into politics but when I researched what a starting salary in politics pays, the future looked bleak. I couldn’t go back to making what I made when I was 25. I had become accustomed to my lifestyle.  

Again, my mom urged me to consider real estate. And still I said no. I thought for sure something would turn up.

Renewed optimism arrived when I interviewed with the president of a Boston sports consulting company. I would have a team of six direct reports, he said, and I would be flying all over the country doing damage control as a consultant interfacing with the leadership team of heavy-hitting, well-known brands.

We chatted for over an hour.

I could sense the excitement in his voice and I thought, Finally, I can breathe! I am going to be okay! Yes! I don’t have to move in with my parents.  

But he waited to discuss salary at the end of the conversation. I thought it would be decent or in the ballpark of what I was looking for (which, even then, was well below where I had been). So when I told him my minimum, it was not even close to what they were offering. He exhaled an audible breath and explained that “six figures would be a stretch” for the position.

At that moment, I was done. It had been 10 months since I had a job and a paycheck. I didn’t have the luxury of time to continue hoping for a magical, high-paying job that might present itself. I slammed down the phone, bit the bullet, and enrolled in a real estate course that would start the very next day. Like it or not, this was happening.

How did I feel? Sad because I loved what I did for a living but also excited about the prospect of being my own boss. I was leaving the fashion industry, changing what defines me, and starting a new career as a real estate agent in Boston (something I never thought I would do).


If I was going to do this, I was going to give it my best shot. I dove in and took a 12-class real estate course over the next month. I took online tests over and over again until I was ready for the exam. I interviewed agents, brokers, and team leaders in the industry and got the inside scoop.

I was told repeatedly: “The first year is very hard and you won’t make a lot of money but just hang on…soon, it will snowball into a full-blown business.”

Well, bring it on!--- because I needed something I hadn’t seen in a long time: income.

Between 10 brokers, I narrowed it down to two. One was a successful, former real estate coach and broker and had just set up a luxury boutique business. I liked that it was a small, female-run organization, and it felt like an intimate environment where I could learn. The other was one of the biggest agencies in the U.S., and their training was second-to-none.

I was so torn between the two but I ended up choosing the boutique agency.

My first task was creating my SOI (sphere of influence): put everyone you know into a database and start marketing yourself and your business. I was also encouraged to network, go to events, and meet people for coffee (all things I am very good at).

It’s not easy convincing your SOI to buy or sell a $1M condo with you (when you've never done a deal). My group of friends and network in Boston was just taking off, and I was making new contacts daily. So I just kept working hard and learning about the real estate market.

Before when I was looking for a job and couldn’t find anything, I was worried about money.  Now, after getting “a job”, I still worried about money. My savings were going fast and the phrase “fake it until you make it” was pressed upon me. I looked, dressed, and spoke the part but I wasn’t getting clients to trust me with such an important purchase. Why would they? I had never done a deal.

My broker told me my first commission might not come until next summer. This was June, and I couldn’t fathom that. Something had to be done, and quickly! It was shaping up to be another difficult year without income.

My broker and I had a sit down and mutually decided that this was not the right fit for me. I realized I needed to be on a team where I could get the hands-on training I was lacking. I gave Duncan, the broker from the other agency, a call. He asked, “How soon can you start?”


Things started to click. Duncan was another mentor to me and, like Barbara, he involved me in every phone call, communication, and conversation. He shared his 17 years of real estate knowledge with me, and I absorbed it all. I loved that every day was different.

My first deal was with a couple set on Charlestown but we found a property in the South End for them, negotiating the winning offer though multiple rounds of bidding. The timing and strategy of it all was my favorite part. There are so many ways to navigate the offer on behalf of your client, and one false move could prevent them from getting the house they had fallen in love with.

Not long after my first offer was accepted, I found my good friend her dream apartment on the waterside of Beacon Street with a terrific view of the Charles. It was my second deal, and again we entered into a multiple bidding situation and won. The phone call to share the news and hear her shrieks of delight was addicting. I wanted to do it again and again!

Soon more friends came to me and asked for help to buy their dream home. I treated every client like I was buying the house myself. It’s the most important purchase one can make.

I had finally hit my stride.


January 2018: I’ll never forget my first real estate paycheck, which was a handsome sum (more than two months’ salary in my previous job). My team leader had written “Oh yeah!” on it. Hell yeah, oh yeah! I thought to myself. Finally some income.

I could've bought a house; I could’ve moved in with my parents; I could’ve left Boston; I could’ve taken a job that I hated. But at that moment, I realized I had done the right thing and stuck to my intuition.

If I had bought that house when I moved here, I would have been forced to take a job that I would have hated, making a paltry salary because I was desperate. I also frankly would still be in that fretful fashion industry headspace that now plagues many of my friends (always fearful of “restructuring” or being “aged out” or laid off for someone who was willing to do your job but is half your age and would take half your salary).

I had made it through the worst and was hopeful for the future. I would go from making $900 last year to breaking six figures and being so busy that time flew. It felt amazing. I had more and more clients and transactions. The “snowball” my real estate friend had told me about was moving down the hill, getting bigger and bigger.

I am now finding myself on a new journey that feels exactly how I pictured it would be: good; purposeful; in control. Any energy I put into the process comes back to me, and I get to meet so many wonderful people along the way.

No more Sunday Scaries. Every day is a good day when you do what you love, with the knowledge you can do it on your own terms, and do it forever.

In TransitionKim Conant