Jess Connolly understands the power of staying committed to your goals. Her dedication to her dreams has helped her start multiple businesses, lead a church, and publish nine books – all while raising four children.
Women like Jess are redefining work-life balance and what it means to chase your dreams. If you’ve been struggling to stay committed to your goals, this interview will remind you why you started and encourage you to keep going.
Press play to hear our full conversation or keep reading below!
Although Jess Connolly had plenty of career dreams back in high school and college, after getting married she found herself in a community where women were discouraged from working. That social pressure led her to become a stay-at-home mom.
“It was a really intense season of defeat,” she says, looking back. “All of those dreams went to a place to die in my early motherhood.”
“Every time I looked around me, I thought, this is how it’ll always be. I’m always going to feel like there could be more, but not for me.”
But just when Jess felt herself sinking into a place of acceptance, their family was rocked by a health crisis that changed everything.
After suffering a grand mal seizure that caused brain damage, Jess’s three-year-old daughter was diagnosed with an aggressive seizure disorder.
Jess suddenly found herself stuck in the hospital with nothing to do but worry. She noticed that several of their friends kept recommending the same Bible verse to pray for their daughter, so she made a printable piece of art to hang on their wall.
When their daughter was released from the hospital and began to heal, Jess made another print – and another, and another.
“I was Skyping with a friend one day and she saw one of the prints. She said, ‘Jess you could sell those.’ That was April of 2011, and by the end of that year we’d done $40,000 in sales.”
Jess found herself thrown into the world of entrepreneurship, teaching herself everything she could about business, taxes, and graphic design. “The next few years looked like throwing spaghetti on the wall to see what fit and what stuck for me.”
That first business was called Naptime Diaries, after Jess’s mommy blog. It took off quickly and it wasn’t long before her husband joined in to help with shipping and packaging orders.
Without any formal training in business or marketing, Jess Connolly credits her early success to her innate storytelling skills. “I would design these prints that meant something to me or had some deep meaning in my life, and then I would tell that story through my blog.”
Another strategy she used was to reach out to other mommy bloggers and offer to create custom prints for them. “That helped us build our platform and build a customer base.”
Naptime Diaries gave Jess back a sense of purpose and possibility in her life. Her biggest takeaway from that business was that she didn’t need formal training to look after her family financially and serve other people – she could get scrappy.
Once the business began bringing in six figures, Jess and her husband were not only able to support their local church but also fund churches around the world.
“All of a sudden I saw this bigger picture of I can do things with money, I can be generous and impactful in a way that I’ve never been able to my whole life.”
After spending most of her adult life not far above the poverty level, not only had Jess found financial stability, but she was also able to use that money to impact others.
Jess Connolly was raised by a hardworking single mother and internalized a lot of lack messages about money. “It felt intimidating to me, and I definitely worked under the assumption that I would never have money.”
When she married young and decided to pursue ministry, those messages were reinforced. Many told her that going into ministry meant she would always be poor.
Because of that, Jess felt a lot of fear around money. “I didn’t know the login to my bank account, much less was I brave enough to look at it.”
All of those limiting beliefs reared their heads when Jess started her business. “I had to get brave about money. I had to start asking serious questions about the complications I felt around earning money or accumulating wealth.”
The biggest thing that has helped Jess navigate her fears around money was to stop looking outside of herself for answers.
“A lot of times when we’re looking for our relationship with money to change, we feel like we need to look at other people and we need to find someone who handles money or uses money in a way that is aspirational for us.”
For the first few years of business, Jess focused all her energy on trying to understand how other entrepreneurs handled their finances.
When that didn’t work, she learned to get quiet and access her own vision for her financial future. “What do I want to do with money? How do I want to feel about it? What is going to matter to me when I’m 80?”
For Jess, those things weren’t fancy home furnishings. What she truly wanted was a legacy property – someplace her kids could vacation and one day bring their own children.
We all have different desires and visions for our money, and what matters most to someone else may not matter to you.
This is why both my Blueprint Model and Blueprint At Home courses start with how to create a vision for your finances. Before you can create a plan for your money, you need to define what your values are.
Jess shared an example of how freeing this concept has been in her own business: “Many of my employees have way better cars than I do. And I think for a lot of bosses that would feel intimidating.”
But cars aren’t Jess’s thing – and she loves that she’s able to pay her employees enough for them to buy their dream cars.
Early into running Naptime Diaries, other women began to come to Jess for advice or coaching.
“I had no business giving advice. I was trying to get a business degree from Google, but I loved helping other women.” It wasn’t long before Jess Connolly realized what lit her up the most was seeing other women move forward in what they were called to.
“I started telling people in my life, I don’t want to run a print shop forever. This is not the thing that sets my soul on fire and I think there’s probably an expiration date to this.”
After a season of running the print shop alongside coaching, the business naturally came to a close. “Now, if I want to make a print, it’s a fun passion project that has nothing to do with income.”
It wasn’t long before Jess started offering coaching sessions. She used the outline of the book she was working on, You Are the Girl for the Job, to make a rubric for all-day coaching days.
But eventually, she realized that her coaching wasn’t enough – what these women truly needed was a community.
Under the new name Go + Tell Gals, Jess Connolly launched her first program and the business took off from there. They now offer one-on-one coaching and group programs, as well as training other women in their six-step coaching process.
“I realized that really lights me up because of the exponential impact, the capacity to not only coach the coaches, but also the women that they coach as well.”
Despite not performing well in school, Jess always knew she was a good writer, and she always understood the power of staying committed to your goals.
“I knew I was going to write a book one day. There was no dreaming about it. There was no ‘we’ll see if it happens.’”
Since 2015, Jess has published eight books and is currently working on the ninth. She takes her process very seriously, writing for an hour and a half every morning before starting work.
“I do that not only because I think my writing serves people well, but because it’s really important for my mental health and for me to feel the most alive that I can.”
Between writing books, running multiple companies, and parenting four kids, you may be wondering how Jess juggles it all.
“My life is not even slightly balanced, but I do believe there’s great harmony and a lot of peace.”
The biggest thing that’s helped Jess achieve harmony is creating no work zones. “Know what’s sacred to you,” Jess says. For her, that means no phone in the bedroom, on date nights, or at her kids’ sports games.
Her other tip for redefining work-life balance is to ask for help. Jess Connolly has never been afraid to hire people, even if that impacts her profit margins. “I would rather lose a little bit of the money and keep a lot of the peace.”
At home, her husband does the majority of the cooking and cleaning because he enjoys it. Passing off those tasks allows Jess to pour into other areas of her life. “My life is full, but I’m not busy.”
When Jess started her printing business, she never could have imagined the journey that would lead to her becoming a coach, author, and church leader. If she could go back and tell herself one thing, it would be, “It’s going to be better than you think.”
To hear the rest of the story and what Jess Connolly is up to now, press play on the player above for the full interview or click here to download the transcript.
RESOURCES MENTIONED :
Powersheets by Cultivate what Matters
Jess Connolly is a woman who wants to leave her generation more in awe of God than she found it. She is passionate about family, God’s Word, and seeing women take their place in the kingdom. She’s an author, a church leader, and a coach.
March 30, 2023