We’re excited to introduce you to the always interesting and insightful Jessica Shershenovich. We hope you’ll enjoy our conversation with Jessica below.
Jessica, so great to have you with us today. There are so many topics we want to ask you about, but perhaps the one we can start with is burnout. How have you overcome or avoided burnout?
As the owner of Pop Up Picnic Long Island, avoiding burnout has been all about balance, boundaries, and staying connected to my passion for event planning. Running a creative, client-focused small business can be demanding, but I’ve learned to schedule intentional downtime between bookings, which allows me to recharge and come back refreshed for each picnic experience.
I’ve also streamlined my setup process and client communications to be more efficient, making it easier to manage multiple pop-up picnic events without feeling overwhelmed. Delegating tasks when needed and building a reliable support team has helped me stay focused on the big picture—creating unforgettable moments for couples, families, and friends across Long Island.
What truly keeps burnout at bay is seeing the joy on my clients’ faces when they arrive at their setup. It reminds me why I started Pop Up Picnic Long Island in the first place—to bring people together in a beautiful, stress-free way.
Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?
At Pop Up Picnic Long Island, we specialize in creating luxury, custom-designed picnic experiences across Long Island. From surprise proposals and romantic date nights to birthday celebrations and family gatherings, we transform everyday outdoor spaces into unforgettable, Instagram-worthy moments. Each picnic is thoughtfully curated with stylish decor, comfortable seating, tableware, and optional add-ons like fresh florals, grazing boards, 8 ft. teepees, and more.
What makes our brand truly special is the intentionality behind every setup. We don’t just set up picnics—we help our clients create memories that last a lifetime. We tailor every detail to the occasion and the people we’re celebrating. It’s about more than aesthetics; it’s about creating connection, celebration, and joy in the most beautiful way.
One exciting new addition is our growing list of themed picnic packages, which include unique options like paint-a-pot picnics, Kid-Chella, The Boatnic, The Truck-nic, and proposal packages complete with chalkboard signage and romantic lighting. We’re also partnering with local Long Island businesses to elevate our offerings—from picnic-friendly catering to live musicians.
Whether you’re planning a beach proposal, bridal shower picnic, or just want to do something different for your next celebration, Pop Up Picnic Long Island is here to bring your vision to life—effortlessly.
We proudly serve all of Long Island. You can learn more or book your next picnic at www.popuppicniclongisland.com
If you had to pick three qualities that are most important to develop, which three would you say matter most?
As a female entrepreneur and founder of Pop Up Picnic Long Island, building this business from the ground up has been a mix of creativity, hustle, and constant learning. Looking back, three qualities shaped my journey—two that empowered me, and one I had to grow into:
1. Creative Vision & Attention to Detail
As a woman in the creative service industry, I leaned into my natural eye for design and event aesthetics. Every pop-up picnic I created was an opportunity to turn a blank space into a beautiful, meaningful experience.
–Advice: Don’t shy away from your creative intuition—it’s your superpower. Study trends in event planning, but make sure your unique touch shines through.
2. Client Connection & Communication
One of the most powerful tools we have as women in business is empathy. I prioritized clear communication, personal touches, and exceptional customer service to create lasting relationships with clients. That level of care built trust and led to repeat bookings and referrals.
— Advice: Focus on the experience, not just the service. Respond quickly, listen closely, and treat every client like your first.
In the beginning, I tried to do it all—by hand and by heart. From managing bookings to setting up picnics solo, I was wearing every hat without systems to support me. It nearly led to burnout.
— Advice: Invest in tools and processes early. Whether it’s booking software or a simple checklist, setting up systems will give you room to grow—and breathe.
My biggest takeaway as a female business owner on Long Island is that success doesn’t come from doing everything perfectly—it comes from staying passionate, being resourceful, and learning as you go. Pop Up Picnic Long Island was built with heart, hustle, and the belief that women can create something truly magical from the ground up.
Tell us what your ideal client would be like?
Our ideal client at Pop Up Picnic Long Island is someone who values meaningful experiences, loves attention to detail, and wants to create something unforgettable—without the stress of planning it all themselves. Whether it’s a romantic beach proposal, a surprise birthday picnic, or a luxury bridal shower, our clients are looking for a high-end, fully customized experience that reflects their style and vision.
We work best with clients who:
1. Appreciate aesthetics and thoughtful design
2. Are excited to celebrate life’s special moments—big or small
3. Trust our creative process and are open to curated recommendations
4. Communicate clearly and value professionalism
5. Want a stress-free, turnkey event setup
From couples planning their engagement to moms throwing that perfect baby shower or best friends organizing a beach brunch, our ideal clients are people who want to elevate their celebration—and trust us to bring the magic.
Proudly serving clients across Long Island for pop-up picnics, proposals, bridal showers, birthday celebrations, and more. Let us handle the details—so you can focus on the moment!
Contact Info:
- Website: https://www.popuppicniclongisland.com
- Instagram: https://www.instagram.com/popuppicnic_longisland/
Image Credits
Joanna Stuba Photography
Brooke Walsh Photography
Amber Dawn Films
so if you or someone you know deserves recognition please let us know here.
