Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Jillian Penney, owner of Jaye Designs, located in Alliston, ON, Canada.

What's your business, and who are your customers?

Jaye Designs is a design studio that offers unique, fully-custom wedding stationery and modern calligraphy for couples looking for bold design choices that wow their guests from the moment they open their mailbox. By connecting one-on-one with you, we deliver wedding invitations, signage, event calligraphy, and stationery designs that reflect your personal style, tell your story and bring your vision to life.

Tell us about yourself

I’m a calligrapher, lettering artist, stationer, artist, wifey, and mama of two, delivering wedding stationery and event calligraphy throughout the Greater Toronto area and beyond. Between it all, I wear a lot of hats, but my passion is creating one-of-a-kind event stationery and modern calligraphy tailored to your unique point of view.

My journey started as a passion project after planning my own wedding. After creating all of the stationery, wedding invites, and event signage for my special day, I dreamed of one day being able to help others create stationery designs and event signage that reflected what made them unique! Finally, my dream came to life, and now I specialize in hand-painted, hand-lettered designs ranging from watercolour wedding invitations to fine art calligraphy, event stationery, calligraphed signage, and everything in between. That is to say that my products are 100% customized and unique to each client! Drawing on what makes you and your story special, I pride myself on my ability to lend a personal touch to every piece I create, so you can’t find my stationery designs just anywhere!

In 2009, I graduated from Ryerson University with a Bachelor of Design in Fashion. After graduating, I worked as a graphic artist and fashion designer for over ten years for several leading fashion manufacturers, including Bluenotes (YM Inc.) and Amerella Fashion International Inc., whose major clients include Wal-Mart, Target, Sears, and The Hudson’s Bay. I now channel this creative energy and passion for style and art into the stationery, fine art calligraphy, and hand-lettering I create today, giving me a unique point-of-view that allows me to create boldly designed pieces to wow you and your guests.

What's your biggest accomplishment as a business owner?

I think every small step of building a business is a huge accomplishment. Every step I take leads me somewhere in this, and I love watching it grow. I still get excited with every booking I make.

What's one of the hardest things that come with being a business owner?

Every single part of it! As a business owner, you wear ALL of the hats. Since day one, I have been learning something new every single day. I am a creative person, so for me, all of the back-end business sides of things are always the most challenging part. Things like book-keeping, scheduling, emailing, building invoices, quotes, contracts, etc... The more you do them, the easier it gets, but it is all a learning curve.

I also find balancing work and home life challenging when you run your own business. I work from home, and I have two small kiddos, so between school drop-offs, extracurricular activities, taking care of the house and family, and getting work done, I'm go go go from early in the morning to late at night.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Don't be afraid to hire a professional if you feel out of your element for certain things. That is one of the best decisions I have made this year for my business. Hiring an accountant, a professional web designer, outsourcing printing, etc... It will save you time and be done properly the first time. Investing in yourself and your business is so important if you want it to succeed.
  2. Open a separate bank account! Trying to do taxes without a separate account is a huge headache. This was my first step after I registered my business.
  3. Do your research. Explore the market and your competition. See where there are holes and how you can fill that need. Reach out to your competition... There is room for everyone, and a lot of people are much nicer than you expect and are willing to chat or give advice. Building community with other like-minded people is a great way to build a network. If you have a group of people in your field, you always have someone to reach out to if you ever have questions, need advice, or support.

Is there anything else you'd like to share?

I am so grateful to get to do what I love every day. I have put a lot of hard work into building this business, and as it grows, I am so proud of what I have accomplished. I cannot wait to see where Jaye Designs is in a few years.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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