This as-told-to essay is based on a conversation with Ann Parnes, the 48-year-old founder of After Hello Matchmaking in New Orleans. The following has been edited for length and clarity.
I became an attorney because I wanted to positively influence other people’s lives. I spent a lot of my career prosecuting juvenile offenders and handling emergency-removal proceedings of children who were mistreated.
I did feel like I was changing the world, but I didn’t realize how heavy it all was. I was handling very traumatic cases around abuse and neglect of children, and it was hard to shake off. I had two young kids at the time, and it started to feel like a dark world to live in.
I began flirting with the idea of changing my career in 2013
I started thinking about other skills I had that I could develop into a career. For as long as I can remember, people in my life have called me at all hours with their relationship problems. I brainstormed what type of business I could start around love.
I got a coaching certificate while still working as an assistant direct attorney and started coaching single people on how to ease back into dating. Everyone I worked with had one common problem: They were all frustrated with online dating. This gave me the idea to start my own matchmaking company.
In 2017, I quit my 14-year career as a lawyer and became a full-time matchmaker. I’m so glad I did — it’s more fulfilling than my old job ever was.
Leaving law was a big risk, but I was willing to take it
Before this career leap, I had no business training. I knew there would be a big learning curve, but as I started immersing myself in the industry, I learned a lot from those who already had this type of business.
I went to conferences, found a private Facebook group for matchmaking professionals, and reached out to matchmakers around the country to ensure I understood what it took to succeed in this business.
Because I was leaving a salaried job to become an entrepreneur, I initially took a pay cut, which was feasible primarily because of the financial support from my husband at that time.
It took me a year before I was able to pay myself. Before that, any money I made went back into the business operations.
I found clients through word of mouth and digital marketing
I landed my first handful of clients because I was very connected to the New Orleans community since I lived there most of my life. People I knew helped me spread the word about my new business.
My first client was someone I played tennis with, and my second client came as a recommendation from my trainer at the gym. I found ways to be present at local activities in the neighborhood, chamber-of-commerce meetings, and networking events.
I also leaned in to digital marketing. I hired someone to build my website and handle the search-engine optimization. I started using social media, which was new for me at the time. Having a presence on Instagram, using location-targeted hashtags, and putting out valuable content helped me land clients.
I work with a variety of clients who usually have a similar lifestyle
My clients range from 29 to 77, but what they all have in common is they’re professionals who are usually very busy and believe they can spend their time more productively than scrolling on dating apps.
When I work with a client, I have them fill out a detailed questionnaire so I can understand what they’re looking for. I want to clarify their vision and values, as well as the characteristics they’re looking for in a partner.
After that, I look in our database and chat with other matchmakers to find people who would be a good partner for my client. I’ll tell my client about the prospective match, and if both people agree to meet, we’ll set up their first date.
I also help clients figure out what to wear and prep them with conversation starters that could lead to a more meaningful connection.
Being your own boss requires focus and structure
As a business owner, you don’t have due dates or a boss telling you what to do. You need to create your structure each day and practice discipline to ensure that things are done on time. I typically work 50 hours a week.
After running the business on my own for six years, I just brought in a partner who has complementary skills to mine. Together, we’re rebranding and expanding the business.
The biggest benefit of having a business is your earnings have endless potential. I’m now making more money than I ever did as an attorney.
My new career isn’t so different from my old one
There are many similarities between being an attorney and being a matchmaker. In both professions, communication is critical. Whether I’m talking to a witness as a prosecutor or a matchmaking client, it’s important to lead with empathy, listen to their story, and read between the lines.
I’ve noticed that people don’t always say everything they want to, and being a good communicator is figuring out motivations and emotions while you get them to open up more along the way.
In my old job, working with many different kinds of people in varying situations helped me become comfortable in almost any setting. There’s nothing someone will say that will surprise me after what I’ve seen as an attorney, which helps me work with clients now who might be embarrassed or shy about their dating preferences or needs.
If you want to change careers, don’t limit your ideas for what you could do next
If you’re looking to try a new career, start by asking yourself questions about your natural abilities, values, and interests. Ask your friends to help you brainstorm.
Once you have an idea, find people doing your desired career and ask them questions about their jobs and how they got started, then jump in.
If you’re working a job that doesn’t make you happy, you’re not serving yourself by going through those motions day after day. There will always be things you don’t like about your job, but when the negatives outweigh the positives for an extended period of time, it could be worthwhile to change careers. I’m forever glad that I did.
