Consider the Wildflowers

038. Jess Connolly: Chase Your Dreams, Boldly

March 30, 2023 Jess Connolly
038. Jess Connolly: Chase Your Dreams, Boldly
Consider the Wildflowers
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Consider the Wildflowers
038. Jess Connolly: Chase Your Dreams, Boldly
Mar 30, 2023
Jess Connolly

From starting a mommy blog called Naptime Diaries, helping co-found She Reads Truth, to authoring nine traditionally published books all while raising four children, launching a successful business, and starting a church with her husband, Jess Connolly is redefining what work/life balance looks like. Living wide open, she finds harmony in pursuing the things that light her up and make a bigger impact in the world. From living just slightly above poverty level to dreaming of a legacy property for her family, today’s interview with Jess Connolly will encourage anyone willing to chase their dreams. 

WILDFLOWER SHOWNOTES : shannaskidmore.com/jess-connolly

Show Notes Transcript

From starting a mommy blog called Naptime Diaries, helping co-found She Reads Truth, to authoring nine traditionally published books all while raising four children, launching a successful business, and starting a church with her husband, Jess Connolly is redefining what work/life balance looks like. Living wide open, she finds harmony in pursuing the things that light her up and make a bigger impact in the world. From living just slightly above poverty level to dreaming of a legacy property for her family, today’s interview with Jess Connolly will encourage anyone willing to chase their dreams. 

WILDFLOWER SHOWNOTES : shannaskidmore.com/jess-connolly

Jess Connolly (00:00):

I felt a lot of fear around money. I was definitely the gal who I didn't know the login to my bank account much less was I brave enough to look at it. I just didn't even want to know. I was like, I just will spend as little as I can want, as little as I can and try to be happy with that. So of course, that really came into play and kind of reared its head in a very ugly way when I started the business. Shanna Skidmore (00:25):

You are listening to Consider the Wildflowers the podcast, episode 38 from starting a mommy blog called Naptime Diaries, helping Co-Found. She Reads Truth to Authoring Nine traditionally published books all while raising four children, launching a successful business and starting a church plant with her husband, Jess Connolly is redefining what work-life balance looks like living wide open. She finds harmony in pursuing the things that light her up and make a bigger impact in the world from living just slightly above poverty level to dreaming of a legacy property for her family. Today's interview with Jess Connolly will encourage anyone willing to chase their dreams. If you dig professional bios, here goes 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.
(01:13)
She's an author, a church leader, and a coach. Okay, formal introductions over, let's dive in. Hey, it's Sha and this is Consider the Wildflowers, the podcast. For the past 15 plus years, I've had the honor to hear thousands of stories from entrepreneurs around the world. As a former Fortune 100 financial advisor, turn business consultant, I have a unique opportunity to see the real behind the highlight reel. I'm talking profit and loss statements, unpaid taxes, moments of burnout, and those of utter victory. Or as my husband says, the content everyone is wondering but not many are talking about. And now I'm bringing these private conversations to you. Hear the untold stories of how industry leaders, founders, and up and coming entrepreneurs got their start, the experiences that shape them and the journey to building the brands they have today. Stories that will inspire and reignite encourage to redefine success and build a life and business on your own terms. Welcome Wildflower. I'm so glad you're here. Jess Connolly on the podcast. Hi. Jess Connolly (02:10):

Hi. What a fun treat to get to talk to you today. Shanna Skidmore (02:15):

I have truly missed you in my life. I feel like we need a Nashville Girls weekend and to make it all happen, some good coffee. How are you? Just you? Jess Connolly (02:27):

Oh, I'm great. I'm good. You know what I've noticed, my husband has started saying this phrase when people ask how we're doing, and I don't really know what he means when he says it, but I'm going to unpack what I think he means. He always says, we're wide open. If when someone says, how are you guys doing? He'll say like, we're wide open. And I did one time, I was like, what are you saying when you mean that? And you are a car person, right? I think I remember this about you. You love a car and you love a fast car. Shanna Skidmore (02:59):

Yes. Jess Connolly (02:59):

And he kind of said something to me about it. He was basically, we're full on the gas, we're going for it. And I was like, yeah, that feels real. And so I would say, yeah, that we're wide open if life feels really full and really fast right now. Shanna Skidmore (03:18):

Yeah, yeah. Which is fun, except for then when you get into your mid to late thirties Jess Connolly (03:24):

Or above. Yeah. Does it start Shanna Skidmore (03:26):

To a little, Kyle loves going wide open, and I'm like, I could you just hit the curve a little bit slower. Jess Connolly (03:32):

Yes. Literally. Yeah. Yeah. That's Shanna Skidmore (03:35):

Good. I love that. It makes so much sense with the car reference that Yeah. Brings it together, brings Jess Connolly (03:40):

It home. Okay, good. Good. I'm glad. I Shanna Skidmore (03:42):

Love that. Hey, tell everybody, Jess, who you are for those who may not know, and then let's dive into your business backstory, how it all started and all that good stuff. Jess Connolly (03:54):

Absolutely. My name is Jess Connolly. I live in Charleston, South Carolina. I have four kids ranging in age from 16 to 10, so that is a lot of my life and a lot of white pills wide open right now, teenagers. I actually have a 16 year old, a 15 year old, and a 14 year old, which that was really cute when they were two, three and four and four, five and six, and 7, 8, 9, but 16, 15 and 14. Anyone who has one teen or two teens knows kind of how that feels, but it's just, it's loud and it's a lot and it's a lot of life. But my husband and I also lead a church here that we started called Bright City Church that we pastor together. And I also run a small business called Go and Tell Gals where we coach women in their calling. Part of Running Go and Togas for me is also traveling to teach and writing books. So that's a part of my business. It's not technically separate from it, but for a lot of people it kind of sounds separate. So write books, coach women lead to church, mother of four kids try to sneak out for a date night once a week and make out as much as possible. Shanna Skidmore (05:01):

How long have you been married? Jess Connolly (05:04):

We have been married 17 years, 17 and a half years. Shanna Skidmore (05:08):

Wow. Yeah, I mean, that's a lot of life. Yeah. Wide open is such a good term. And is your 16 year old driving? Jess Connolly (05:17):

He is taking his driver's test, I think March 3rd, so Okay. He is on the road right now, and I would like to caution everyone. I bought a magnetic sticker for the back of my car that says student driver from Amazon, and that's helped a lot. I think just kind of warning everyone, Shanna Skidmore (05:37):

Does he resent this Amazon Jess Connolly (05:40):

Purchase? No, I think he loves it. I think he's let as many people as possible know to stay away from us. So he's aware of his own lack of capacity in the driving arena. Shanna Skidmore (05:51):

Yeah. Oh man. Okay. Jess, you have done so much. Will you take us back to life before? Jess Connolly (05:57):

Yeah. Your first Shanna Skidmore (05:58):

Business and then share about your first entrepreneurial Jess Connolly (06:03):

Journey. Yeah, absolutely. So before my first business, I was a stay-at-home mom again, you heard how close in age my kids are. And so just before I kind of dipped my toe into the water of business, I had a two-year-old, a three-year-old, and a four-year-old. And that was my whole life, honestly. I was in a really intense season. After I got married, I went through a really intense season of just feeling a lot of defeat and I remember having dreams and aspirations a little bit in high school and in college, but they kind of went to a place to die in my early motherhood. And I was in a lot of communities and cultures where women were just discouraged from working, discouraged from ambition. And so I went through just a heavy defeated phase where I was like, well, I guess this is what I'll do.
(06:55)
I'll never have a career. I'll never work outside the home again. And for people who feel called and love not working outside the home, I love that for them that I don't think that was actually what I was made to do. And so it was this heavy blanket of defeat, and that's how life felt. It felt, it felt just like every time I looked around me, I thought, this is how it'll always be. This is how it's always going to be. I'm always going to feel this way. I'm always going to feel like there could be more, but not for me. And then you want me to dive into my first business because it comes right out of that season. Shanna Skidmore (07:34):

I would love Jess. I would love that, Jess Connolly (07:36):

Yes. Okay, awesome. So in that season, again, I have two-year-old old, and I'm a stay-at-home mom and my, my daughter was diagnosed with an aggressive seizure disorder. She actually went into the I C U after a really intense grand mal seizure that caused some brain damage. And we were in the hospital and my husband and I shared a laptop and we act actually also shared a cell phone. So not only was that his stay-at-home mom, but I was a stay-at-home mom without any means of communication with outside world. And we were just in a really intensely hard financial season. So that was the best thing we could do was share a cell phone, share a laptop. But because we were in the hospital for so many days together, I had access to his laptop and I went on PowerPoint and I made what, I didn't know what to call it, but eventually I could call it a print, but I made a print of this Bible verse that people kept giving to us that they were praying for our daughter.
(08:37)
And so many people kept suggesting the same verse. It was Psalm 46, 5 that I was like, I'm going to just make something, a little piece of art on PowerPoint with this verse and hanging on our wall. And eventually she came home from the hospital, she was released from the icu, she started to heal, her brain started to heal, and I put that up on our wall, and then I made another one, and then I made another one, and then I made another one. And a friend, I was actually Skyping with a friend one day and she saw one of the prints hanging behind me and the time I didn't even have enough money to frame them, and so I just hung them up with painters tape, which is pretty hilarious. I didn't have enough money for frames, but I was just putting these printed pieces of paper all over the wall.
(09:20)
And she said, Jess, you could sell those. You could probably sell that on Etsy. And I was like, no, I don't think so. And she was like, why don't you just try? And that was April of 2011, and I started in Etsy shop, and by the end of that year, we had done about $40,000 in sales. And I was shocked and had no idea what I was doing. And so I had to very quickly learn about business and taxes. And actually I had to learn about graphic design because I was not trained and then made this on my computer on PowerPoint. So that began for me, really the beginning of dipping my toe into business. And the next few years kind of looked like throwing a lot of spaghetti on the wall to see what fit and what stuck for me and where my actual giftings were. And it's been a very, very wild ride since then. Shanna Skidmore (10:18):

Yeah. So what was that first business called? Jeff? Jess Connolly (10:21):

Yeah, it was called Naptime Diaries. I had a mommy blog of the same name. So if you're wondering what Naptime Diaries has to do with Brent Subs scripture, nothing. But I had a mommy blog called Naptime Diaries at the time, and so it felt like, well, I'll just name my business that. And we ran it under that name for the next four years. Shanna Skidmore (10:42):

So did you have to figure out finding a printer and packaging prints, or was it all digital, Jess Connolly (10:48):

Yes or no? I mean, the very first ones I sold sold them when I was still getting printing them on my home printer, a eight and a half by 11 paper, not even an eight by 10 print. And so I had literally no idea what I was doing for the first few months I printed them at Kinko's. I just would go have them printed at Kinko's and thank God that paper is an incredible profit margin. It's like the best profit margin there is. And so I had a little bit of time and leeway to figure out how do I actually do this, and then how do I ship? Where do I go to the post office? Do I need a Biola maker? So I actually spent really the first few years kind of piecing it together and figuring it out. And my husband eventually came on to really help me with shipping and everything, et cetera. But those first few years, it was still us packaging every single order, just hundreds and hundreds of print orders a week, literally just printing them, labeling every single detail of the business before we brought in on any help. Shanna Skidmore (11:54):

Okay. So how did you go from zero to 40,000 in one year? I mean, what was your marketing strategy? I have to know. Jess Connolly (12:01):

Yeah, I didn't have a merit marketing strategy. I don't think I knew what marketing was. So I do want to say that I think that what came intrinsically to me in that time, I want to say I think two big things happened that year. The first one is that kind of what came intrinsically to me that I didn't know at the time I couldn't have expressed is that I'm a storyteller. So the whole time, I mean this is really when you didn't go to Instagram as an app, I was on Twitter, but I was a storyteller. And so I would design these prints that really meant something to me or that had some deep meaning in my life, or even designing them for someone else, and that it had deep meaning in their life. And then I would tell that story through my blog. I would talk about it on Twitter, I would talk about it on Facebook.
(12:48)
And so I think that's the first thing that really was, was a marketing strategy that I wouldn't have known to call it that. Yeah. The second thing, this is, again, this is actually just pure strategy, but I don't know what I was doing. I just thought it was a fun idea is at the time that mommy blogs were like the thing, so I was in the mommy blogger circuit. I knew the famous mommy bloggers, I read them, I didn't know them in her life, but I read all their famous blogs and I tweeted them and I would comment on their blogs every single day. And for a few of them, I reached out to them and said, Hey, I'd love to make a custom print with your kid's name on it and a Bible verse. And there were a few mommy blogs who did that. And so in some ways, that became a really important business lesson because my business went from me designing every print to me custom designing hundreds and thousands of prints with people's names on them, which was a really expensive and time consuming situation. But it helped us build our platform that I wouldn't even known to call it that at the time either. But it helped us build our platform and really kind of tap into a customer base. Shanna Skidmore (13:58):

Jess, I love this story so much because I think that most of us don't go into business with a plan necessarily. Yeah. I mean, we have a goal. We have a one or we have a desire. You, your friend said, Hey, frame this, and yeah, pick down your washy tape. I think that's just so beautiful. I would love for you to talk about, you mentioned, if you wouldn't mind to share the season you were in as a mom with littles at home, very close in age, how did this breathe life into you and yeah, energy and did it kind of give you an outlet? I'd love to hear you talk Jess Connolly (14:32):

About that. Yeah, absolutely. I think for me it was dual fold. It was two big things that it did for me. Number one, it really did give me a sense of purpose and possibility in my life. Again, I actually, until I sold the business, I made every single print still on PowerPoint. So the idea that I didn't need training, but that I could go within myself and use the resources I had to not only be a blessing to our family financially, but also to bless and serve other people, it felt like so much possibility. And I would say that is, even though I'm not still creating scripture prints, that is the thing I took from that business. That's the biggest gift I took from it is just this capacity to in a very scrappy and minimal way serve other people. But then in the other part that was just so important to me is almost as soon as the business started doing really well and expanding into six figure sales, et cetera, we started supporting not only our church plant and helping fund our church plant and enabling my husband to pastor for free for a time, but we were also able to help fund other church plants.
(15:45)
We were able to help fund a church plant in Pakistan and one in Amsterdam. And I think then all of a sudden 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 in my whole life. I'd never in my life lived, especially my adult life, lived too far above genuine poverty level. And so not only being able to pay the bills and feel some security financially, but being able to impact other people's lives and their God-given mission was a really big deal for me. Shanna Skidmore (16:19):

And I know, so we met Jess, was it 20 15, 16? Jess Connolly (16:25):

I think it was 25th long ago. 15, yes. Shanna Skidmore (16:28):

I think it was 2015. So you were still doing Naptime Diaries and the shop, and I remember us talking about how much impact was such a motivator for you and how it gave you energy, energized you and fueled you probably when you were tired and burn doing all of this workload. So I would love for you to talk through the transition. When did you feel like you were ready to step away from Naptime diaries? What happened next? Yeah, if you don't mind sharing about Jess Connolly (17:01):

That. Absolutely. So for me, the transition occurred when very early into running Naptime Diaries. Other women would come to me and ask for insight or advice or even coaching. And in those early days, I know you can resonate with this and probably agree, even meeting me in 2015, I really had no business giving any advice. I was learning as much as I could. I was trying to get a business degree from Google. I was learning as much as I could about business and leadership and finances, but I still knew so little, but I loved helping other women. And I realized that actually what lit me up the most was seeing other women move forward in what they were called to, which is not normal for a lot of people who already have a platform and are already doing their own thing, running their own business.
(17:54)
But I realized a great day in sales for me was not nearly as exciting to me as a great day in sales for someone I was giving help to, which was just really interesting to me. And I started in just brave, quiet places, telling people in my life, I really don't want to run a print shop forever. I actually know that I'm not a graphic designer. I am really pretending right here right now, but this is not the thing that sets my soul on fire. And I think there's probably an expiration date to this. And so that kind of was a long lead time for us. We ended up selling the majority of our business first and co-running it with another family for a season, which was really life giving and also so good for lessons. But all along that amount of time I was also coaching and learning what coaching looked like and how I could do it and developing a rubric that I could take other women through.
(18:49)
And so there was a season where I was doing both, actually. We were still running the print shop, and I had started Go Tell Gals, which is where I knew I wanted to host most of my coaching. And so I was doing both for a season until ultimately just kind of everybody in my life and everybody in the print shop business too felt like We've done what we came here to do, we're good to say this was a great season and we're ready to shut it down. So that is really truly what the transition looked like for us. And there are days, I have to say, I super miss running a print shop, and there are days where I miss feeling excited and passionate about just one more of truth. But on those days, I remember now I can go make my own print, I can have it professionally printed, I can put it up in my house, and that's really life giving and it's now a fun passion project side hobby that has nothing to do with income. Shanna Skidmore (19:47):

Yeah, I love that. I want to talk about go and tell gals and coaching and writing a book, but you mentioned something that I have to circle back to about your background, I would say with money. Jess Connolly (20:00):

Yes. And Shanna Skidmore (20:01):

Would, if you don't mind to share, Jess, I would love to hear more, and I'm just going to frame the question that way. Tell me about your background with money. Yeah, Jess Connolly (20:09):

Yeah. Well, I was raised by a single mom who was the hardest working person. She still is the hardest working person I know. I tell people all the time, if you think I'm busy or if you think my life is full, you should see my mom. I look like a sloth compared to her. She is a hustler in the best way, and she just killed it providing for us and taking care of us. But I will say I even growing up I through just even maybe internal messages or messages that I internalized, I felt very lack when it came to money. I felt like scared of it. It felt intimidating to me, and I definitely worked under the assumption that I would never have it. Yeah, I also didn't do great in high school, wasn't a great student. So especially in those high school and college years, there's just kind of this assumption made about you.
(21:00)
If you're not great at books, if you're not great at studying, if you're not great at wooing teachers or you're really dynamic, you start to see this trajectory in front of you that is not super profitable. And so I just started to make some assumptions about my life and then adding into the to that I got married really young. We were both interested in ministry and there's definitely that banner over ministry. If you're going to be a pastor, if you're going to be in ministry, you are going to be poor. What's going to happen? And so that was just kind of a message I internalized this is how it's going to be. And because of that, I felt a lot of fear around money. I was definitely the gal who I didn't know the login to my bank account much less was I brave enough to look at it.
(21:43)
I just didn't even want to know. I was like, I just will spend as little as I can want, as little as I can and try to be happy with that. So of course, that really came into play and kind of reared its head in a very ugly way. When I started the business, I had to get brave and I had to get courageous about money. I had to start to ask serious questions about the complications I felt around earning money or accumulating wealth or savings, or even really not just immediately giving it away. As I said earlier, a large part of our story in the print shop was supporting other church plants. And so I had to even look and ask is sometimes my giving even counterintuitive to supporting my business and supporting my family sometimes, and why am I doing that? So yeah, it was a really very complicated relationship with money that's taken decades to sort out and feel a little healthier about. Shanna Skidmore (22:44):

What are some ways that you have seen positive change when it comes to that mindset about money? Jess Connolly (22:51):

Oh, that's a great question. I didn't prepare you for that, did I? Yeah, I love it though. It's a really good question. I think the biggest thing that has helped me, and I don't know if anyone hearing this maybe is going to be really freed up by this. I think 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. And I think for the first few years of business, I really felt like that was the only way I was going to get out of this. And so I thought I'll find out how other authors or teachers spend their money or how they use their money and see if that is inspiring to me.
(23:38)
Or I'll look at other business owners and try to understand how much they have in savings or how they do profit dividends and I'll learn from that. And what worked best for me was really getting quiet and accessing desire and vision about my financial life. So I had to really access my personal desire. 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? Because actually for me, it's not going to be nice pillows. It's not going to be incredible drapes. It is going to be for me, just being totally on the table. For me, it is a legacy property. I want to a place my kids can come and vacation or bring their kids that actually matters to me. So I had to access some real desire and then also some vision.
(24:29)
Where do I see this whole thing heading when I open my eyes wide and I stop kind of squinting and shutting my eyes and turning this off and pretending it's not happening, where do I see this going? And back to the desire, where do I want it to go? And I have to say what's interesting about both of those things is I still don't know that I know anyone else or that I've met anyone else that manages their wealth, manages their money, that gives in the exact type of way that I want to. And that actually now is beautiful to me that we all have such different desire and vision for how we're going to handle it. Yeah. Shanna Skidmore (25:05):

Oh, Jess, that's so good. I think you may not remember this, but I'm going to tell you a story from when we first chatted that stuck with me. I am not known kind of as the money girl, and I love helping and teaching people about money, but people are always surprised that in all of my curriculum and everything I teach, the very first step is vision. And I believe that you have to define what your values are before we even create a plan with your money. And I love that so much. And I don't know if you remember this, but when I taught at that conference we were at, I spoke about defining your enough, and you said to me, you said, I got little chills because it has transformed my conversations and I share about it all the time. You said it's like the place where abundance and contentment meat is this place of enough. Wow. And Jeff, I mean spoke truth. I have never forgotten that and I never will because money is both aspirational. Something to get excited about, especially as entrepreneurs, we can do such good things, but it's also a place to find contentment in what you want and your desires. And you're so right. When you define that for yourself, it changes how you view and handle your money. Jess Connolly (26:27):

Yeah. Well, I want to say very clearly, there is no doubt in my mind that encounter with you was pivotal for me. And not only do I remember that session, and I am of course now, well of course this was a part of me healing my fear and anxiety about money and starting to tap into some vision. But also, I don't exactly remember what we talked about, but I remember after your session, I literally think you unfolded an envelope and you just started writing numbers. You were really helping me. Do you remember this? You were doing math wildly on a scrap piece of paper and trying to help me figure out, this is how you can make it work. This is how we can figure it out. And I, here's how you work backwards. And I think, again, I literally don't even know if you just used cars and as an example, and that's why I said I think I remember that you're a car girl, but even literally, I want you to know how impactful it was to me because I just had a conversation last week with someone about how freeing it still is for me right now that multiple of multiple, many of my employees have way better cars than I do.
(27:37)
And I think for a lot of bosses that would feel really intimidating. And I'm like, no, because cars are not my thing. I love my Honda pilot and I love that I pay you enough for you to get your dream Telluride in Jesus name. But I love that. I love a Honda pilot, and that is right for me. And that meeting you that time and learning from you was so wildly pivotal for me. And yeah, I'm just super grateful for your work for that exact reason. Shanna Skidmore (28:07):

Same. And I do remember that. I do remember that envelope. And then I'm pretty sure you flipped it over and wrote down the title of my book, defining Enough the Place where Abundance Jess Connolly (28:18):

Me Shanna Skidmore (28:19):

If for everybody listening who just Jess Connolly (28:21):

Freaked. Shanna Skidmore (28:21):

I don't have a book, but Jess. Yeah. Jess Connolly (28:22):

But it was, you are going Shanna Skidmore (28:24):

To, if I ever wrote a book, Jess's already titled it. Nobody steal it. Jess Connolly (28:27):

Don't steal Shanna Skidmore (28:28):

It. So I just that conversation. Anyways, so all this to say we need to hang out. I have missed you. We too. Thank you for sharing that. That means the world to me. I do have a tendency to scribble math for people. Jess Connolly (28:40):

Love it. I love it. Shanna Skidmore (28:42):

That is my gift in my calling. Let's talk about Go and tell gals, and when we met again, I think you were right at this transition where you were starting to coach. You had not written your first book yet. Yeah. So tell us about this next journey with coaching and writing and become That was a dream, becoming an author. Yeah. How's it gone? How's it going? Yeah, tell us about that. Jess Connolly (29:06):

Well, prior to officially coaching, I would get this same question that so many entrepreneurs and Interneters are getting DMed every day. Can I pick your brain? Can I just ask you a few questions? And I wanted to be a generous person, so I would always say, absolutely. You can pick my brain. I'll give you anything. I'll tell you what's worked for me. I'll give you any kind of insight. And not only is that not a great use of your time when you have four kids and a small business and a church that you're running, but also I realized two things about just constantly letting people in my brain, number one, when I was just telling them how to do what I had done, I was not serving them well because they aren't me. And so what worked for me is not going to work exactly for them.
(29:53)
And number two, I was also not serving them well because when none of them were paying, none of them were actually taking my insight. They had no skin in the game. And so I was just giving free advice that A wouldn't work that well, and B, they wouldn't even take because they didn't pay for it for the most part. For the most part. So I was like, man, this is crazy because this kind of lights me up, but I got to figure out a different way to do it. So again, driven by financial desire, this is why I love what you do so much. In the spring of 2018, I had recently moved into our house, which we had purchased. We love so much, it was a dream to be able to purchase a home in downtown Charleston. And we had this great back porch and no furniture on it, and we had just sunk every bit of free money that we had into moving into this house and doing some first things.
(30:43)
And I went to my husband, I was like, listen, I really want some back porch furniture. And my husband was like, great, we'll save up for a few months and we we'll set aside some money and you can get some back porch furniture. And I was like, okay, well, the problem is it's February and it's only nice to sit on the porch in Charleston like April, may and June, so I don't actually want to save up for it and then not use it for a whole nother year. And he was like, well, let's think about what we could do. And I was like, well, actually, I have a great idea already. I'm going to host a few all day coaching sessions. I'm going to tell people that they can pay me a thousand dollars to come spend the day with me and I'll coach them.
(31:21)
And if I do a few of those, I'll get some really nice patio furniture. And he was like, you are such a hustler. I love you. Go for it. So I went on social media and said, guess what guys? I'm hosting all day coaching sessions. I have three spots open. You can join, and three people booked. And then I thought, wow, now I have a serious issue because I don't know what I'm going to do with these people for all the whole day and they're going to fly here and spend a thousand dollars to spend the day with me. So I need a plan really quickly. And at the time, I was at the very beginning of writing my next book, which is called You Are The Girl for the Job. And again, I was at the very nebulous starting stage of You are the Girl for the Job.
(32:02)
But I knew the book was going to be about really understanding our capacity in light of God's power. So it was the book for any girl who didn't feel like she was the girl for the job, but that wanted to take a brave step forward and use what she had. And so as I'm working on the book, I'm realizing I kind of think this book has six steps to it that I actually think would be great steps to take anybody through in an all day coaching session. And I used really the outline of the book to make a rubric for what a day of coaching would look like. And then I did those three all day coaching sessions and I thought, I love this. I'm obsessed with this. And what's more, I felt like it was actually fruitful. I felt like the steps I had helped develop really actually helped women make movement forward.
(32:52)
And so from there I was like, I think this might be a thing. I think that I could do this in other forms. And so around that same time I had, then I got the idea for the name of Go Tell Gals, and I got the Instagram handle and I bought the domain and I still wasn't super sure what to do with it. And I just kind of sat on it. And that summer I was done writing. You were the girl for the job. I had hosted my three sessions, gotten my back porch Patio furniture, which I still have. I have not replaced and really probably should because it's been five years. But I was playing Put Butt Golf with my family that summer, and we were on vacation, and a friend of mine who was an aspiring author was texting me some coaching questions. And really, she was again, just kind of picking my brain and I could feel the phone buzzing in my pocket as we played put putt. And I really wanted to be engaged with my family and pay attention to them. But I really wanted to answer her questions.
(33:50)
And I just thought, man, I should be doing this. But what she really needs is other women also to talk to what she really needs is a community of other women who've already published books or who are also interested in publishing books because I can't be the only source of insight for her. And so from there, I developed my first group coaching program, which is called Go Teams, which we now still host every single year through Go Intel Gals. And so since the start of Gwen Tell Gals, we're just kind of constantly asking how can we best come alongside women? Is it through one-on-one all day coaching, which I still do. Is it through a group program? Is it through a coaching pdf? And then the newest way that we've been doing the last few years is now certifying and training other women in our six steps in our coaching process. And I realized that also just really, really, really lights me up because of the exponential impact, the capacity to not only coach the coaches, but coach the women that they coach as well. Shanna Skidmore (34:53):

Yeah. Oh, I love it. And you are such a passionate encourager of others and of their dreams. I love the name Go and Tell. It's so fitting for what you do. I love it. Tell me about writing the books. Has that, I know that was such a dream and speaking, but tell me about writing the books. Jess Connolly (35:15):

Well, I think that there are a lot of different authors. There's a lot of different types of authors right now. And I'm going to be honest, I've told you guys a little bit about my backstory. Barely graduated high school, didn't do great in college, didn't have a lot of expectation or anticipation for my life, but I did know that I was a good writer and I knew that this was the best way I could communicate. If I ever wanted to convince my parents of something, I wrote a letter. If I'm ever super sorry and need to apologize to my husband, I write 'em a letter. Even parenting, my favorite phase of parenting is right now because I can text my kids so I can send them a very encouraging text in the morning. So I knew I was good at writing. And I always preface that because when people say I dream, I one day dream of writing a book, what is really interesting about me is a kid with very little worldly potential.
(36:11)
From the outside. I knew I was going to write a book one day. There was no, I dream about it. And in so many other areas of my life I had just extreme defeat and didn't think I'd ever do anything but about this one thing. I was like, oh, no, that's going to happen. I know I'm going to write a book. And that's just always been interesting. It's just this one area of my life where I've had a lot of confidence and just assurance. And so that being said, there are a lot of different types of writers and there are writers who are just like, I know I've got a book in me. I'll get it out one day. More people who are are just kind of right and are not totally sure where they're going. And I am on the far other end of the spectrum where for me, writing is serious business.
(36:56)
And it's serious business for a few reasons. I mean, number one, it's a very large part of our family's income and my business's income, but also it's serious business for me in that I make a lot of time to do it. I make a lot of time to do it efficiently and to try to do it really well. I bring a lot of processes to it to try to do it as best as I can. And I unashamedly try to sell as many books as possible because I absolutely believe that the books help people, and I want to help as many people as possible. So I met you in 2015. I think I I was just about to start writing my first book then. Yeah, wild and Free. Wild and Free was my first traditionally published book. And right now in 2023, I'm working on my ninth traditionally published book.
(37:47)
Stop. I don't even think I knew it was nine. Yeah, Jess, I've just a feel so counting, counting Bible studies and devotionals, which I do because they've all been a process. I've been able, this will be my ninth traditionally published book. And again, it's because there is no, we'll see if it happens. For me, I take it really seriously. I take my relationship with my publisher really seriously. I take deadlines really seriously. And I do all of that, not only because I think it serves people well, but because it's really important for my mental health and for me to feel the most alive that I can. I just love it. Yeah, I love writing. So yeah, I'm currently working on my ninth book. I write for about an hour and a half every morning before I come into work, and that's how I've been able to work and run and lead a business and also get some manuscripts done. Shanna Skidmore (38:42):

Yeah. Jess, you are an incredible writer. I'm going to link your books below because in the show notes, because I love them. So life giving, I just want to talk to you so much. We are getting close to that time, and I want to make sure I ask you something before we go into a quickfire round. Yes. And I would love to hear Jess, in the things that you're doing, writing books, publishing books, running companies, you have four kids and are also leading a ministry and helping others start ministries. So will you just tell me one or two, maybe if you can boil it down for anybody listening, how do you feel like you've been able to find, or any tips or things you hold onto regarding life and work harmony? What are some things you like that create harmony in your house? And again, this is going to be different for everyone, but I would just love to hear for you, how do you do that? Jess Connolly (39:39):

I mean, I love the way you word it because the first thing I'll often tell people is that my life is not even slightly balanced there. It doesn't look like the American dream. It doesn't look like what other people would probably assume balance looks like. But I do believe there is great harmony and there's a lot of peace. I feel. I always tell people, if anyone ever says like, oh, you're so busy. I'm like, I am actually not busy. My life is full, but I'm not busy. I'm not hurried, and I don't feel frantic. I feel very sure about where I'm at. I would say the biggest thing that has helped me is having no work zones in my life. So I have physical zones in my life that are no work zones, and I have emotional places that are no work zones and theoretical places that are no work zones.
(40:30)
But I think knowing what is the most sacred to you, because that is going to look different for everybody else, has helped. So this is as simple as literally never a phone in my bedroom, ever, ever, ever, or date nights or my kids' sports games or practices. Just knowing the places for me that this is it. This is sacred, and nothing comes here. And then I would say the other biggest thing that has helped bring a ton of harmony is asking for help. I take a lot of help on the home front. I take a lot of help at our church, and I take a lot of help in business and in business, obviously financially, that means I'm doing a lot of profit sharing. I am hiring other people, money that could be going into my pocket because I know that I could probably do some of your work, but I would rather pay you lose a little bit of the money and keep a lot of the peace for me.
(41:24)
But also on the home front, this looks like kind of crashing the ideals of what I think the norm should be for me as a and a mom. So just full disclosure, I don't cook and I don't clean. I clean for fun, but my husband does the bulk of the cooking and the cleaning, and it's life giving for him. It's his favorite thing to do. And we learned a few years into this business church hullabaloo that he was like, Hey, you actually hate cooking. You don't like it. You feel exhausted, but you feel like you should do it, so why don't you let me cook? Because I'm actually great at it and it's super giving for me after a long day. So that's a small example, but I just ask for it and take a lot of help on all fronts. Shanna Skidmore (42:10):

Okay. Jess, thank you for sharing that. As a mom with Madeline turns two next month, I'm always gleaning wisdom. And I love the idea too, of no work zones, whether that's physical, mental time, whatever that looks like. That's so good because my brain, I have realized works well in compartments. It needs to Jess Connolly (42:33):

Be, yeah. Shanna Skidmore (42:34):

So some people integrate all the things so well and so beautifully, but for me, I need that structure. So thank you for sharing. This has been such a joy. I want to spend so much more time with you. Same. Let's do a fun little hot seat kind of quickfire round. Jess Connolly (42:50):

Ready? Shanna Skidmore (42:51):

Ready, ready. Okay. Number one, what is one thing you would be embarrassed if people knew? Jess Connolly (42:58):

I have horrible teeth. I just like the worst teeth. They're just a hot mess. I, I'm currently working with nine cavities, and that is after I have gotten a lot of work done on my teeth recently. I mean, I have bad teeth. Shanna Skidmore (43:14):

And is that just the most frustrating because part of that's just like you're born with it. Jess Connolly (43:21):

You can't help it. You can't help it, but it feels shameful. You're like, what is wrong with me? Yes. Yes. Shanna Skidmore (43:26):

Sweet Kyle, my husband takes the best care of his teeth. All dentists listening, he is like poster boy for tooth care and Jess Connolly (43:36):

Bless. Shanna Skidmore (43:37):

Bless. Yeah. I know. He gets the cavities and the things, and he gets so frustrated because he's like, I take better care of my teeth than you. And I'm like, I know it's born with it. Born with it. Okay. I love it. Number two, innate regrets or wish you could do over moments Jess Connolly (43:55):

Specifically in business, Shanna Skidmore (43:57):

Right? Nope. Anything goes, Jess Connolly (43:59):

Ooh, yes. I would not quit my very first full-time job. I quit my very first full-time job out of college. I was actually a manager at Anthropology, and it stressed me out just a little bit, and I thought I could make more money elsewhere, and I would go and stay and learn the lessons I needed to get there. Shanna Skidmore (44:24):

Yeah, yeah, Jess Connolly (44:25):

Yeah. Shanna Skidmore (44:26):

Hindsight. Yep. Okay. Number three. What is a big win or a pinch me moment? Jess Connolly (44:32):

Ooh, I'm going to be honest. I'm not saying this because it sounds like the right thing to say, but there have been a few successes for people that I've coached that have genuinely meant more to me than my own. Actually, one of the first gals that I really coached through writing Anonymous anonymously to getting a book deal, her first book deal was bigger than my first book deal. And I was like, man, that felt good. Yeah, that felt good. Yeah. Shanna Skidmore (45:06):

That's so fun. And I feel the same, Jess, it's funny, sometimes I feel similar with my clients when I see their storefronts, their physical stores, and I walk by them, or especially when my family members are see somebody that we have worked with. It's just really cool because people sometimes just talk. It's a big deal. Don't really know what you do sometimes when you work online. Yes.
(45:30)
Or we have a couple of past clients and students who are on TV now, and it's just really, really cool. I have no aspiration to be on tv. I mean, sometimes Have you seen the show The Prophet? I'm like, if no, Joanna Gaines called me and said, we want to show start a show similar to the Prophet with you. I'd say, yes, hands down. It's an awesome show. You would love it. It's kind of like Shark Tank, but it's about business and anyways, okay, moving on. I love that, Jess, thanks for sharing. All right. I would love to hear best advice or really good advice, and this can also be from the Lord Jesus that you would like to share. Jess Connolly (46:07):

Don't trade your core competency. That is the best advice I've learned in life and also in business. The thing that you are very good at, don't give it away, keep it. Shanna Skidmore (46:18):

What do you mean by that? Jess Connolly (46:19):

So I think especially in life and in business, in business, as we scale and as we grow, it's weird, but I watch people do it all the time. It's really easy to say, well, I need to grow. I need to bring on other people. So I'll ask, I'll let other people do this thing that I'm good at or that I'm, or I'm even just that I just love doing. But I feel like we also do it in life a lot. We feel like this season means we can't keep doing this one small important task. This is a very dumb example, but it's the one that just popped into my head because I lead at our church. One of my core competencies at our church is that when we go on retreats, I'm really, really good at room assignments, whether it's a staff retreat or a leadership retreat or women's retreat. I am very good at picking who should be in what room and how that will impact the culture of the event. But as our church grows, that's such a small thing that people will be like, let us do that for you. But I'm like, actually, this is a gut instinct thing that I have. You need to let me keep doing it. Shanna Skidmore (47:21):

Yeah. Ooh, that's so good. Because I'm thinking of a couple right now that I should probably outsource, but I hold it and yeah, and I think it's life giving. It makes me better at my actual job. Jess Connolly (47:34):

Yeah. Cause Shanna Skidmore (47:35):

It's a creative outlet for me too. Okay. That's good. Jess, thank you for expanding on that. Yeah. All right. Last quick fire question and then I'll have you send us off. What are you working on now or a resource you would like to share? Jess Connolly (47:47):

Oh, I love both of those. What I'm working on now is my next book, and it will be out in spring of 2024. I can't yet share the title, but I can share that it's on realistic rest. So we're going to be talking a little bit about how to fight spiritual, mental, physical, and emotional exhaustion in a very real way and love it. A r thank you so much. A resource that I love that I really can't quit is the Power Sheets by Cultivate What Matters. I'm, I'm pretty sure when we met, I was really into them and I still am seven years later. I love, it's a goal setting workbook that cultivate what matters makes that I love so much. Shanna Skidmore (48:31):

Yeah, I love that this thing intentional planning is so, I'm such a journaler. I'm such a, that's helpful for me too, so love that. Yeah. Okay, Jess, let's send it off. This has been such a joy. I would love for you to share, just to send us off, what would you tell yourself on day one when you decided to print your print from your home computer and sell it to somebody else? What would you tell yourself on day one of your business? Jess Connolly (49:01):

I love that. I would say it's going to be better than you think, and I think that's probably a message most of us need to remember. It's going to be better than we think, even if it's harder. Shanna Skidmore (49:12):

I love it. Jess, thank you so much for coming on and sharing more of your story. It's just been a joy to catch up with you. I've missed you. Jess Connolly (49:19):

Oh, same. Thank you so much for having me. It's a huge honor. Genuinely. Shanna Skidmore (49:24):

Hey, wildflower, you just finished another episode of Consider The Wildflowers the podcast. Head over to consider the wildflowers podcast.com for show notes, resource links, and to learn how you can connect with Jess. One final thought for today from Seth Godem, the only thing worse than starting something and failing is not starting something. As always, thank you for listening. I'll see you next time.