We caught up with the brilliant and insightful Jessie Silva a few weeks ago and have shared our conversation below.

Alright, Jessie thanks for taking the time to share your stories and insights with us today. Do you take vacations? How do you keep things going – any advice for entrepreneurs who feel like they can’t step away from their business for a short vacation?

As a wedding photographer, my schedule fills up about a year in advance. As I book weddings and extra gigs, I will frequently check my calendar for gaps of time and decide from there if I want to fill them or save them.

It’s so important to take mental breaks for yourself, even if it’s not a full vacation, just some time off to do nothing. I have two hard and fast dates I do not book any weddings for – the weekend of my husband’s birthday, and the weekend of our anniversary.

It can be difficult to know how to keep things going when you’re away, but there are so many great ways to automate your business while you’re gone. If I get an inquiry, I can set up my CRM to automatically reply with a link to a scheduler. The best thing is to look at what parts of your business you are good at and enjoy doing the most. Then look at what’s left, and outsource those tasks. The first thing I outsourced was my editing. The amount of time it takes me to edit versus the cost does not balance out. I can leave for vacation knowing when I come back, the images I sent to my editor will be 90% done. One time, I was enjoying lunch with my grandma when I got an email that my images were done! Nothing felt better than that to know my business kept going even when I was spending important quality time with loved ones!

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?

I originally went to college for photography, but after a disappointing experience, I needed to find my own pathway. I found a local workshop for photographers, learned a lot, and made some great connections. It really helped me hone in on what I really wanted to do.

After getting married, my husband and I relocated, where I met a photographer who took me under her wing. She gave me tough love about my skills and kicked me into shape. It was around that point that I realized my heart lied in wedding photography.

In 2020, I needed a change that included a full rebrand and new name. But a lackluster design and Covid had other plans for me. After grieving my losses, I found another designer and copywriter who together helped me nail the exact vibe I wanted. The difference I’ve seen in attracting my ideal clients has been so heartwarming and encouraging! Nothing makes me more excited than when someone tells me how fun their time with me was!

Weddings have so many moving parts, and it can be super stressful! It’s my main goal to help my couples have a fun and stress-free experience from the first call to the album delivery. Before they even sign a contract, I draft up a timeline to make sure nothing feels rushed. Throughout the planning, I’m there to help my couples find their perfect vendors and organize the list of family photos. Afterwards, I pre-design an album and help them finalize it, as well as offering their images in an online gallery that they can share with their friends and family to download/order prints.

Have you ever had to pivot?

I’ve had to pivot multiple times throughout my career. I started my business in Michigan in 2007, and got married in 2011. My husband was in the military at the time, so we immediately relocated to Virginia after our wedding. I had to start from scratch when I wasn’t fully established to begin with. At the time, Craigslist was actually a pretty good source of gigs, as well as local Facebook groups. I was able to work with many different photographers as a second shooter, and then would get referrals from them when they were unavailable for inquiries. That helped me build up my own reputation as well.

Then a couple of years later, it was time to relocated again! This time, I joined those local Facebook groups before I was in the area so I could hit the ground running with a whole new set of photographers.

We moved a final time back to Michigan in 2017. I was able to lean on my previous clients as well as, yet again, Facebook groups to get my business back running.

What’s the most rewarding aspect of being a creative in your experience?

Nothing makes my heart sing more than when my couples tell me how much fun they had! I’ve often had couples say they’re “not camera people”, “we don’t get photos taken”, “we’re not photogenic”. It’s those sessions when I know we’re going to have a blast! I love it when I’m able to shake up their expectations, get them to loosen up, and really show their true selves! After all, getting married is some of the happiest times of their lives, so why shouldn’t they be anything but happy?? The biggest compliments I hear are “we had so much fun!” and “you can really see the love we felt that day”.

Contact Info:

• Website: www.jessiesilva.com
• Instagram: www.instagram.com/jessiesilvaweddings
• Facebook: www.facebook.com/jessiesilvaweddings
• Twitter: www.twitter.com/jessiesilvawed

Image Credits
Jessie Silva