Today’s Feature Friday covers someone I was lucky enough to meet during my days at Cornell. Jessica McSweeney and I briefly spent time together at Alpha Xi Delta, and thanks to the power of social media, I’ve been able to watch Jess take her business to amazing heights. She is one of my role models when it comes to dedicating time & passion to what you love to do.

Jessica McSweeney is the owner & artist of Poppy & Scooter, a Baltimore-based wedding stationery & calligraphy company. She creates beautiful pieces that have been featured in Southern Weddings Magazine, Geraldine Magazine, Flutter Magazine, Weddings Unveiled, Washingtonian Bride & Groom, Style Me Pretty, Wedding Sparrow, and Magnolia Rouge. And get this, she has only been in business for two years! The growth of her business has been incredible!

Special thanks to Jess for participating in this interview and for spending time and attention on this. Here we go!

TF: Can you tell us a little about yourself? 


JM: I’m currently based in Baltimore, Maryland, but I work with couples from all over the country on their wedding stationery. I’m originally from a really small town in Connecticut and went to college in New York, but got hooked on Maryland living after spending the summer here for an internship with a local wedding planner. I moved to Baltimore after I graduated about three years ago and haven’t looked back! I sadly don’t have any pets (yet!). I don’t think I’m fully ready to be a responsible dog or cat mom, but hopefully soon!

TF: What does your typical day look like (or do you even have a typical day)?

JM: At this point I don’t have a typical day, but I’m working hard to establish more routines for time management on the advice of other entrepreneur friends. I usually wake up around 7, grab a gallon of coffee, and dive into whatever project is on the top of my to do list. I’ve found my hand and mind are sharpest early in the day, so I like to do calligraphy and design work in the morning and tackle my inbox and nitty gritty things around midday or afternoon. On certain days I’m not in the studio at all; in any given week there are several deliveries, supply runs, and client or vendor meetings on the schedule. It’s definitely still a work in progress!


TF: Were you always involved in calligraphy & stationery, or did you start out in another industry? When did you start working in wedding stationery?

JM: I’ve always loved art and paper — my dad was a painter and a woodworker, and he taught me the importance of creativity from the second I could hold a paint brush in my hand. My mom has always been a big greeting card enthusiast, too, which inspired my love for stationery specifically. When I got older I appreciated how one small piece of paper could transform someone else’s day, even if it was something as seemingly trivial as a Happy Arbor Day card. It communicated that someone was thinking of you, even if it was for no particular reason.  

I started out in the wedding industry on a total whim. One of my sorority sisters told me that a fellow sister from another chapter had started an event planning business in Baltimore, and a few months later when I was looking for a summer internship I decided to cold email them because it sounded like a fun job. Luckily they agreed to take me on, and I had a blast working with their couples on month of wedding preparation and day of execution, as well as a few corporate events, too. They offered me a more permanent position as a designer when I graduated the following year, and over the course of about a year working for them I was exposed to every part of pulling together a major event as well as small business ownership. Wedding planners are one of the only vendors who touch on every aspect of the day, from major elements like rentals and venue communication to smaller details like paper and favors. I had the opportunity to talk to and learn from beauty specialists, florists, stationers, and DJs every day, and through those interactions I actually picked up another part time job as a bridal consultant at a local boutique.

I happened upon calligraphy as an art form through one of my clients, and took an online class to learn as a hobby. It quickly became an obsession, and I started doing a few place cards and signage projects for my clients and the brides I met through the boutique, too. The more work I did, the more I knew that stationery was the place for me in the wedding world. Looking back it all sort of makes sense, but finding the specific area I wanted to be in took time and exploration. I’m really grateful I had a first job that allowed me to do that.

TF: When did you realize you wanted to have your own business?

JM: I don’t think there was a specific moment when I realized I wanted to be my own boss. When I think about it now I just can’t imagine it any other way, and in the wedding world most people are entrepreneurs or a part of a small team. I’ve always had an admiration for the tenacity, spirit, and community-driven purpose I saw in entrepreneurs growing up. My uncle is a self-employed carpenter and contractor, and I’ve looked up to him as someone who made his own way and has done well by his clients on his own terms. When it came time to think about my career, I naturally gravitated towards positions with small businesses. For me there was an allure to working with people who valued personal client relationships and who set their own standards for what they wanted to accomplish and create. When I found what I loved doing every day, no other model made sense.

TF: What was the hardest part about growing your business?

JM: I’m only in year two of business so the early growth stage is still very real to me! There’s a great community of wedding artists that I’ve had the chance to connect with (thank you, Facebook!), and we have a lot of conversations about struggling to set our pricing and personal boundaries based on our value as artists, experts, and human beings who need to have lives, too. I know I tend to make a lot of emotional decisions about pricing and my time — it’s hard not to when your clients are planning such an important moment in their lives and you want to give them the world.

I had a real wake up call this year when I realized that my business would go under if I didn’t start charging what I needed to to live, and I would go under if I didn’t stop working until 3am every night. It’s important to know what your financial picture actually looks like, and to not avoid it out of discomfort for a long time like I did (I think a lot of creative business owners can relate). I outsourced my bookkeeping and accounting because numbers make me queasy, and having that outside perspective and set goals keeps me on track. It’s allowed me a little more freedom to know what I can realistically do to cultivate the experience I want for my couples and what creative projects I can take on, too.

TF: What is your favorite part of having your own business?

JM: To quote Braveheart, “Freedom!” There’s really nothing like the feeling of business ownership, even with the chaos and responsibility that comes with being the head honcho. Doing the creative work you really want to do, and the satisfaction of knowing you’re making it happen for yourself and others — it’s just the best. Also, I love being able to run errands at 10am on a Wednesday. Empty grocery stores are a major part of my company benefits package.

TF: Do you still have another job in addition to your business? If so, how do you manage the work-life balance (or should I say work-work balance)? If not, could you tell me what it was like taking the plunge into your business full-time?

JM: I worked full time (Tuesday-Saturday) at a bridal boutique while running Poppy & Scooter until this past fall. I was very lucky, though — my boss at the boutique is my small business mentor and a close friend, and she let me work on my projects while on the clock if we had down time and made sure my schedule was as flexible as I needed it to be. She also supported my growth by allowing me to letter all of the gown tags in our store and sending mutual clients my way. I still help out on Saturdays when I can because I just love being there and spending time with my coworkers and our brides so much.

Having spent about two years in the industry before going full time and working for another small business owner who was invested in my success, I didn’t feel very nervous when it came time to dedicate 100% of my time to Poppy and Scooter because I had such an awesome community surrounding me. It would have been a lot tougher transitioning from a 9-to-5 job, and I admire anyone in that situation who is working their butt off to make their business happen. The biggest thing to know is that a lot of other people are in your situation, too, and oftentimes emotional support is what makes the difference between making it and breaking it. If you can join an industry-specific Facebook group or local community, and if you’re lucky enough to have a good support system around you of friends and family, that can be everything.



TF: If you could give your pre-business owner self a piece of advice, what would it be?

JM: Be way less hard on yourself about having it all figured out and being perfect immediately! I still don’t have it all figured out, and I’ve come to see it’s a lot better that way. The possibilities are endless if you don’t force your path, and as cheesy as it sounds, the path you find usually leads somewhere way better than you imagined. It’s also really rewarding to see how far you’ve come and how much you’ve learned as you look back at your life. If you allow the need to be perfect to stop you from getting started — even if it’s a wobbly, baby deer standing up for the first time kind of start — you’ll regret that forever.  

TF: Finally, how did you choose the name Poppy & Scooter?

JM: A lot of people assume they are my dogs (seriously, one day!), but the name is actually about my dad, who passed away when I was in high school. He was an avid gardener and our favorite movie to watch together was The Wizard of Oz, so “Poppy” represents his love of art and how he passed that along to me. “Scooter” was his nickname for me as a kid, and to me that represents the family connection that’s the core of my business’ mission statement. Weddings are about building extended families and celebrating with those you love, and celebrating him while doing that work just feels right.

Thanks again to Jess for being so accommodating and letting us see a glimpse into her entrepreneurial life! If you’d like to learn more about what Jess does, take a look at her website Poppy & Scooter or check out her Facebook Page. She also has an amazing Instagram with beautiful photos of her products.


Join the conversation! 2 Comments

  1. Therese! Awesome article. And wonderful to hear the story behind the amazing work I see online by Jess! Nice work to both of ya 🙂


  2. Thanks Sarah! It was so fun interviewing her and Jess put it all so eloquently. 🙂

    Liked by 1 person


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About Therese Fess

Tech researcher, Army Reservist, aspiring weightlifter, aspiring minimalist, writer, wife, pet mom, and fountain of profanity. I'm obsessed with wellness and helping others.


Creative Work


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