Meet Jess Lively The Business Woman Helping Others Design a Life With Intention


About 2 years ago I was sitting in my apartment in Chicago surfing the net when I stumbled across an event that was happening the next day called “Business in the City”. This was a roundtable discussion for small business owners that would be led by business owner Jess Constable. (She is Jess Lively now at the time she wasn’t married) I was fairly new to the Chicago area and was also a new business owner, so this seemed like a good fit. I figured I didn’t have anything to lose and decided to attend. That was one of the best decisions I’ve ever made.

The event was awesome and meeting Jess was an incredible experience. She is truly special and unlike anyone else I’ve ever met. When you are around her its a simple fact, you’re just going to feel better! Her personality is infections, she’s positive, inspiring and insightful. At the time she owned and operated a jewelry line called Jess LC that she started several years back. She also blogged and did business consulting as her “side hustle”. I immediately decided to start consulting sessions with her. That was another one of the best decisions I’ve ever made. During our first session she asked what I thought about the PYP brand. Any my reply was “I think it’s great!” At the time the product was sold in plastic bags , the website was dreadful, I took website pictures with my camera phone, everything was just really bad. However, I didn’t know any better. Jess simply told me, “You need better branding.” I didn’t have much money and the idea of rebranding seemed very daunting, but I found a way to make it work. She put me in touch with the very talented Claudia of Fig 2 design who redesigned my site. I also hired Jess’s husband to develop the site (who by the way is also super awesome) Design and branding always go into my decision making these days. Check out the transformation here

Jess’s journey is incredibly interesting and I’ve learned a great deal from her. On her blog she is very transparent about her business and personal life. She selflessly shares many of her life experiences in hopes that her lessons will teach someone else. I have the utmost respect for what Jess has done not only as a business woman but as a person.

A few weeks back I had the opportunity to chat with her. I’ve shared some of the highlights from our interview below.

Jackson: Jess you are probably one of the only people I know who after undergraduate decided to forgo the traditional route of pursing a 9-5 job and went to work full time for yourself. Can you please share some of the reasoning behind that and why you found it so important to build a career on your own terms?

Lively: Thankfully I was able to learn my purpose at an early age, which was that I wanted to help people. At that time I thought I needed to write a book or have a TV show in order to help others. In order to do this, I knew I needed to be in control of my own time. I’m a high achiever and if I was given a corporate ladder to climb, I would climb all the way to the top. I didn’t want to forget about my purpose.

Right after college I took my jewelry business Jess LC full time. However, after 1 and a half years I  realized I hadn’t done anything on the purpose side which was my initial vision. I realized I didn’t need a book or TV show, so I started a blog. I began to devote half my time to my jewelry business and the other half helping people live with intention. Through the blog I created value and community.

Jackson: I know you ran JessLC your jewelry company for 5 years, why and how did you make the transition from being in the business of selling products to selling services?

Lively: When I decided to close Jess LC, I  essentially had two full time jobs. I was in the process of hiring a manager to run the Jess LC shop and the candidate I was really excited about backed out at the last minute. I listened to my gut and decided it was best to let Jess LC go and move forward.

Jackson: What are some of the important lessons you learned from running JessLC which are proving to be helpful in With Intention?

Lively: The importance of brand and design and how to do them well. My sites and brands were crappy for a very long time. Also I’v learned how to develop relationships and connect with people in the blogging community.

Jackson: As someone who has been in business for over 6 years now, what is your proudest accomplishment to date?

Lively: Quitting Jess LC. Most people didn’t want me to start my own business in the first place, then 5 years later they didn’t want me to close the business. I’m glad I listened to my gut. Letting go of that allowed me to make room for the best things that are yet to come.

Jackson: Do you have any entrepreneur heros/sheros you look up to? If so, who are they and why?

Lively: For me the Grandmother of them all is Oprah. I’ve admired her career for a while the impact she has had on so many people is amazing. Mastin Kipp from the Daily Love is also really great.

Jackson: Do you have any favorite books you recommend?

Lively: A few must reads on my list are:

7 Habits of Highly Effective People by Stephen Covey

E-Myth Revisited by Michael Gerber

Daring Greatly by Brené Brown

Jackson: What advice would you give to women who are aspiring entrepreneurs?

Lively: Start and just keep doing. There is nothing else magical about it. You don’t have to always do the same thing. Consult your gut and intuition. Do not rule with your mind and ego and you will be fine.

Jackson: Since our company is crazy about shoes, we must ask what type of shoe gal are you?

Lively: I’m totally a flats girl. I just bought a pair of gold Loeffler Randall flats that I’m in love with!

Visit Jess’s blog here

About the author


Kathryn is the Founder of luxury shoe care company Protect Your Pumps. She is passionate about entrepreneurship and of course designer shoes. She is a "smart shoe shopper" who loves to buy designer shoes and loves getting them at a great price!

Vanisha's Life in...Australia - October 4, 2013

Thank you for the introduction Kathryn. I just had a look at Jess’s blog and it is lovely, so full of inspiration! xoxox

    Kathryn - October 5, 2013

    Vanisha, I’m so glad you found Jess! She is such an amazing person. Thanks for reading 🙂

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