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Five Years With Hart

A conversation with Jennifer Hart about her first five years as a business owner. Compiled from frequently asked questions throughout her tenure as a lady boss.

Kate: What is it like to run a business? Is it what you expected?

Jenn: Have you ever run a marathon every day? Kidding. The beginning for me was a little intense. It was a lot to throw myself into and learn. I enjoy learning so that helped. I didn’t sleep much in those first couple of years (laughs). I don’t know what I expected, but it was just one of those things that is unpredictable until you are in it.

Kate: Anything you would change if you could go back?

Jenn: Maybe just to accept the imperfection a bit more–especially in the beginning. Learning to prioritize what needs to be perfect and what is good enough was huge and is still something I struggle with. Details are part of what makes a good designer. It’s hard to turn that part of my brain off that is trained to look for spacing off by an 1/8 inch (laughs). It's important to keep it in check though in order to get things done.

Kate: So, then what do you think is the greatest learning in five years? Is it not being a perfectionist?

Jenn: After five years, I can honestly say I still learn something new every day. That really is the truth. It was a huge shift to go from working in agencies and in-house departments to freelancing on my own and then hiring people to help me run my business. I knew design, but the rest was new to me. I don’t think it’s one thing learned–It’s hundreds of little things learned along the way. How to set up a business license, write a contract, find talent, and discover being my own IT person–the latter is still my least favorite. Shout out to the IT professionals out there! We appreciate you! It’s one day at a time, one obstacle to tackle at a time.

Kate: It sounds hard. Why do it?

Jenn: I wouldn’t use the word hard. I think learning new things is always challenging, but the reward of building something for yourself far outweighs any of the tough stuff. It’s fun most of the time. And it feels so good when you figure out each piece of the puzzle. It puts fuel in the tank to keep wanting to learn and do more.

Kate: I think people starting out are probably curious about how you get clients?

Jenn: To quote a very smart friend of mine, “One at a time.”

Every single handshake and job counts, whether it's a business card or an entire advertising campaign. I do my best to treat every client and every collaborator with respect. I want people I work with and those who work for me to feel seen. Their project is important to them, so it needs to be equally important to me. I show this by giving each one the attention it deserves. If my efforts are successful, they will tell their friends, and so on.

Kate: Ok, but how do you get the first client?

Jenn: With a smile and a cup of coffee. Above all, I believe this business, and any business, is about people. I approach my work like I approach life. Do good work, be decent, and try not to take anything too personally. I was in the graphic design industry for many years before I struck out on my own. I built relationships along the way just because that's what you do when you work with people. I didn't know that those same people would help support my company later.

Just be nice and do good work. People make what we do every day possible. And they tell other people with people that tell people–With a little luck.

Kate: Do you think your biggest accomplishment has been building these relationships?

Jenn: They are part of it, for sure. I’ve been fortunate to work with some fantastic brands and equally amazing people in my life. I couldn’t pick a favorite piece of work or a project even. They are all meaningful and teach me something. So, I guess I would consider my greatest accomplishment the company itself. Watching and participating in its growth has been incredibly rewarding.

Kate: Is there any piece of advice you’ve ever gotten or given that might help others working on their own self-made projects?

Jenn: I love quotes, and there are so many great ones. One I repeat often came from a book, “Big Magic” by Elizabeth Gilbert. I’m paraphrasing, “There’s no reason not to go for it because if you try something new and you fail, you can always go back to doing whatever it was you were doing before.” This spoke to me at a time when I needed to hear it, and I continue to parrot it to others.

Kate: You are also an author and illustrator. How do you make time for it all?

Jenn: It is challenging, of course (laughs). Being the conductor of my own time is at the root of why I went into business for myself. That and having my dog within petting distance all day. I treat this part of my creative soul with just as much importance as the design piece. They overlap in many ways. It’s just like anything else important–Family, career, me-time. You have to do your best to balance and make time for it. I try to mind the scales to make sure one isn’t tipping over too far. At least for me anyway.

Kate: Is there anything you are looking forward to in the next five years that you can tell us about?

Jenn: Oh. Lots (laughs). But nothing I can share yet. I am excited to keep building Hart House and collaborating with businesses. I also hope to introduce some new things in the coming year that will be really fun. I am just looking forward to more creating.

Interviewer: Kate Frabbiele

Interviewed: Jennifer Hart


Connect with Hart House Creative and Jennifer Hart about your project by emailing

JULY 27, 2022



Hart House Creative, its employees, partners, The Squeeze, and guest writers make no guarantees for results. Methods and marketing suggestions are based on prior knowledge and with the intent to inspire business owners and other creatives. Every client is different with different goals. None will be held liable for any negative results achieved from implementing suggestions from our website.

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