We recently connected with Jessica Hill and have shared our conversation below.

Jessica, looking forward to hearing all of your stories today. What sort of legacy are you hoping to build. What do you think people will say about you after you are gone, what do you hope to be remembered for?

When I first started Dear Summer I didn’t have a full business plan, just a dream and love of the industry. In the event world, you either love weddings or you hate them and I was for sure on the love side of the coin. There really is nothing better than being a part of a couple’s special day and having them trust you with their vision and life memories. It’s a great responsibility that I cherish and my hope is that all of my clients remember their day fondly. To be remembered as a calm presence on a day that can be very much the opposite of calm is always the goal. I have been lucky to have some amazing clients and families and I hope the name “Dear Summer” is a name they associate with kindness and care because that is what they mean to me.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My whole life I’ve loved anything creative. My mom would always dressed me in outfits with accessories to match so style and coordination was engrained in me from a very early age. In high school I would go thrift shopping turning old clothes into something my own so as I got closer to deciding what to study in college, Fashion Design was the natural choice. I started at The Art Institute of Washington with a major in Fashion Merchandising but halfway through my freshman year my life changed. I got pregnant with my first son and had to make the tough decision to leave college and start to work so I could provide for this little life I had coming.

As a single mom I was working any job I could find, sometimes two at a time. One day my best friend came to me and said “I’m leaving my event planning job and I’m getting you an interview for it, you can do this”. The role was to plan all social member events at a private business club. I had never planned a real event before but I figured, why not?! I immediately fell in love with the high that came from seeing other people enjoy themselves at something I planned. It made me want to learn everything about the event industry so I made it my mission to work in jobs of every aspect of it, including hospitality, non-profit and corporate offices. I loved it, planning an event was feeding my creative brain in a way that fashion design used to.

After years of experience in the industry I got tired of making money for other people so I took the leap and started Dear Summer! I didn’t know much about owning a business but I knew what I was doing and getting over the imposter syndrome was honestly the hardest part. Dear Summer started as a side hustle that made me a few hundred dollars to being fully booked a year out. The heart of the business is weddings but my passion for art, music and philanthropy has also allowed me to branch into planning other types of events including art exhibits, music festivals and non-profit galas. At my core there is hard work, passion and dedication and that is what I try to have shine through from my initial interactions with clients to the finished product.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

The biggest lesson I had to unlearn was that uncertainty was bad. I think there is a culture with our parents generation that is very much rooted in stability, which for me was instilled from a young age. Not taking chance or making big decisions because of how it could affect your life, that was the mentality that drove me for so long. No one in my family had owned a business or had a side hustle, and so for me to be doing something like that as a single mom was completely foreign. I was working a good “stable” job but I just knew deep down that I was supposed to be doing more. Taking that chance and spending money that I did not have on an idea that I didn’t know was going to be successful was really scary. Those fears that were projected onto me from society were hindering my gift and I had to realize that there was beauty in uncertainty. There was beauty in taking risks and that it really is what life is about. I had to stop listening to other people’s fears and even those fears inside my own head telling me that I had to be “safe”. When I did that, I was able create something not only profitable but also something that allowed me to grow as a woman, mother and business owner.

Can you tell us about a time you’ve had to pivot?

My business originally started in my native town of DC and then blossomed in Richmond after our family moved there. For years I grew relationships and partnerships with vendors and venues that made Dear Summer a common name for weddings. We were on the cusp of our most successful year yet when my husband got a job offer from San Diego State University. It was such a double edge sword because while moving to California sounded so exciting for our family, leaving behind the foundation that took years to grow was devastating. Not to mention I had never lived that far from my family and also pregnant with my second son, so it was a ton of change in a very short amount of time. After many discussions, spreadsheets and family plans, we decided to make the jump and move to San Diego. The first year there I knew that learning the city and adjusting our family to this new change was the priority. I slowly started networking and worked a few weddings which helped me meet local venues and vendors. It felt like I was starting my business all over again! Even though it was terrifying, it also became a great way to rebrand, re-envision and restart with a new purpose and business model. Getting out of yet another comfort zone and pivoting allowed me to expand Dear Summer, and myself, in a way that I could not have expected. I still maintain my relationships with my Richmond crews and now consider myself a bi-coastal planner! It has been a journey and a gift all at once but that makes life fun and I am so grateful for it.

Contact Info:

• Website: https://www.dearsummerevent.com
• Instagram: https://www.instagram.com/dearsummerevents

Image Credits

Kenzi Flinchum Photography
Leah Miessler Photography
Casper Photography