How They Blog: Jessi Connolly

Quick Announcement: I just wanted to mention that I’ve made some huge updates to the Blog Planning Kit including making all the fields editable(!), a clickable table to contents, a new cover and more. You can check it out here. If you’ve already purchased it, use your original download link to access the update.

Meet Jessi Connolly

I’m going to be honest here, Jessi is one of my favorite people to follow on online, particularly on Instagram. The images she posts are inspiring, fun and sometimes wonderfully nerdy. I love the pics of her handwritten brainstorming sessions, nuggets of truth she’s gleaned during her Bible study time, and fantastic wisdom from her entrepreneurial endeavors.

There are a lot of bloggers growing and making an impact, she is doing it with a lovely combination of passion and wise restraint. We all can learn a lot from Jessi…and this week we will. Read on…

1. Intro: Give us a quick intro to you, your family and your blog.

Hi all! I’m Jessi. I’m a 28 year old, mama of four, and I’m married to a church planter. My life has been in straight up hyperdrive for the last few years and I’m looking forward to stepping into a season of developing rather than plunging forward in the next few months.

We just permanently settled in Charleston, SC after a few years of frequent moves that prepared us for church planting. We’ve been in different parts of North Carolina, South Carolina, a few cities in the Seattle area, and most recently Indiana. I’ve been blogging and navigating the online world in the midst of all our transitions and now have a deep love for the connections I see women making online.

I blog at Naptime Diaries, design for our family business – our print shop of the same name, and helped cofound The Influence Conference and The Influence Network. I also help run and write for SheReadsTruth, an online Bible study site for women.

2. Tell us your blogging story. (Is this your first blog? How did you get started? How long have you been blogging?) Feel free to share anything that might be helpful for growing bloggers.

I began blogging in 2005 or 2006 when I found out my pastor’s wife had a blog. At the time, I really really wanted to blog. I thought it would be so fun to document our life and have a space to put some words, but it seemed pretty self indulgent and cheesy so I stopped myself. When I found out my pastor’s wife blogged so that she could encourage other women and even meet new people in our city, I was totally a fan of the idea! I started a blog immediately.

I didn’t know bloggers potentially could make money and I wasn’t even sure how to tell people I had a blog. I kept writing through a tumultuous few years for our family and people kept reading. Fast forward a bit and we had three children under three and I felt a good bit landlocked by the munchkins that were a little hard to get out of the house. I realized that I could hop online quickly and have sort of a virtual coffee date – talk about silly things or heavy things or share pictures of our kids.

As people continued to read and my understanding of blogging grew, my desire to do it well and have it be a blessing for my family has grown as well. So from that simple blog, my online voice has diversified a bit. I’ve fine tuned what it is I write about, written two eBooks, started our print shop which is now our family business, and I’ve begun to focus more on encouraging women with the tools I’ve found along the way.

3. Tell us about a blogging “success” or “failure” that taught you a powerful lesson.

The past year has brought amazing success and trials in the form of partnerships. I’ve learned a lot about what an online partnership should be. I see now that when you enter into any sort of contract with someone online, they should be someone that you’d genuinely want to do life with. They should be someone you’ll willing to walk with in hard times and stand beside. They should be somewhat like minded about internet things and general life issues.

Hayley (who I cofounded Influence with) is genuinely my greatest friend outside of my family. We have a relationship founded on trust, pushing one another, and grace. I think in this age of blogging, it’s easy and quick to form an alliance, but hard to remember that alliances formed online take just as much emotional energy as ones off. We should have space in our life for them and treat them much the same.

4. What are the intangibles that have helped you succeed?

I really think my greatest key to success is intentional vulnerability. I don’t package an image to present to people online and we give a good bit of access to see who we are as a family, as a small business, and as a community. I’ve never wanted to come across as an expert at anything because I’m genuinely just not. I think women spend so much wasted time trying to be the best at something or trying to be who they think they should be, rather than just living from who God has made them to be and influence people there.

5. How do you keep your blog and home life in balance? What does a “typical” blogging day look like for you?

What I know it should look like and what it does look like are very different! I’ll be honest and say it’s pretty much a work/life free-for-all for me in this season. I do have a little bit of set work time, but work also seeps into a lot of our other time too.

Typically I wake up before my big kids, nurse the baby, and check emails from while I was sleeping. I’ll spend 30 minutes to an hour checking on all the things, scheduling tweets for the day, answering emergency emails and the like. I’ll check my schedule and make sure everyone in the family has what they need for the day. Then we head into breakfast, morning routine, and time with the kids. I may be texting the Influence or SheReadsTruth team or responding to tweets if there is time. I typically work in the afternoon and dive back into family and community in the late afternoon and evening. Once the kids are in bed and things are winding down, I’ll check my blog for the next day. If it isn’t already written, I’ll do that quickly before bed!


Come back Wednesday to read all of Jessi’s Blogging Gadget and App recommendations and on Friday she’ll share her thoughts on social media and writing. Stay tuned!

Q & A with Jessi

What questions do you have about blogging for Jessi? Click here to share your thoughts or ask your question!

Read All The Interviews with Jessi Connolly

1. How They Blog: Jessi Connolly
2. Gadget and App Recommendations (Coming Wednesday)
3. On Social Media and Writing (Coming Friday)

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  1. What an amazing blogger to highlight, Kat! Jessi is also one of my favorite bloggers – I love the vulnerability, wisdom, and humor that shines through her blogs. In fact, she was a big inspiration to starting my own blog. Looking forward to the rest of this series!

  2. I’m so inspired by Jessi’s words here. I see how she has cultivated her experiences into a whole lotta wisdom. Looking forward to more info from Jessi. Thanks, Kat!

  3. Yay! I was so happy to see Jessi as this week’s blogger, I had hoped you would interview her and put her name forth for that reason.

    I am inspired and a little in awe of all that you do online and offline, Jessi. Are you an extrovert/driven person? =P I’m an introvert and as much as I love all the interacting, it wears me out. How do you stay intentional without too much burn out? I’ve been reading your blog and know this has been a tiring season for you. Do you have daily habits that keep you grounded? How did you make the leap from personal blog to a much bigger blog and online business?

    Kat, I agree with you, I love seeing Jessi’s instagrams! =)

    • Breanne, such a good question. I’m actually a HUGE introvert that can fake being an extrovert well. I’ve learned to “save up” for things that are super emotionally tasking for me and my nerdy side absolutely comes out in planning around my introvertedness:). I have an “introvert day” one day a week where I try really hard not to plan online meetings or have people from real life community over. I also have learned the little patterns and hobbies that “recreate” me. I’m not a great painter, but 30 minutes of painting before bedtime restores me a little. I’ll do that a few days a week.

      And the leap to blog and business growth was absolutely not intentional for me. When I started my print shop, I didn’t even really know what to call it:) I think for me, just pressing play on fun ideas and surrounding myself with smart women has been key!

      • Love this question, too, Breanne. And Jessi, super helpful response!

        I’m fairly extroverted but being home with littles has made me more needy of alone time. I like the idea of carving out a regular “introvert day!”

  4. Jessi, I loved reading your interview and I was intrigued by your comment: “I didn’t know bloggers potentially could make money and I wasn’t even sure how to tell people I had a blog.” I feel like I am there right now.I just started blogging this year to link up with other bloggers and now I am feeling like I need to educate myself a bit (that why I love this blog!). How did you figure out how to tell people about your blog and how did you grow? Thanks! Holly

    • Social media and just genuinely connecting with other bloggers by reading theirs and getting to know them. And truly – this is why we created The Influence Network! We created it as the ultimate answer to “you started a blog/business… now what?”! You should check it out! Hundreds of other new bloggers to connect with and support you!

  5. I really enjoyed reading this post, ladies. I have just recently started reading Jessi’s blog, and I am quite a fan. I look forward to this week’s subsequent posts – such great information and insights already in this one. Many thanks!

  6. I LOVE Jessi and her blog. and yes her instagram is fantastic too! she is also a beautiful writer 🙂

  7. Love Jessi and the many networks she’s founded 😀
    Jessi, how do you manage to pour into your kids while also dedicating so much time and energy to your different endeavors? I battle guilt and worry that I’m not giving my kids enough, that they spend too much time in front of they TV, etc. Any words of experience??

    • Such a good question. Here are a few of my big tips from someone who genuinely struggles too:)

      1. I stay tender. If I’m spending too much time working, I adjust.
      2. We do a lot of fancy footwork in our scheduling including my husband and I share a lot of kid responsibilities AND we work nights a lot. It’s taken a lot of adjusting to get used to, but for us the payouts are worth it. Also…
      3. I really try to give myself grace and not get caught up in the hype that my kids need my eyes on them every second.

  8. Greetings from Charleston, SC! So cool that you are here. I hope you love it. This is home for me, and my favorite place in the world. 🙂

  9. I live just outside of Charleston, SC; so nice to hear that you’re in the area!

  10. I have been considering starting a blog of my own, but have been struggling with the fact that I am not really an expert at anything. I too have three little ones and am a stay at home mom who splits her time by working with my husband in our family construction business. My walk with Christ is somewhat new, but I have seen God move in my life in some pretty amazing ways. I still have my share of struggles and am trying to learn how to trust in him in my daily life. I feel like it has been put on my heart to share my not so perfect walk with others, especially my friends and family who are still far from God. I enjoy writing, but don’t have the huge repertoire of memorized scripture and religious jargon that many other bloggers seem to have. My greatest fear is that I will be a poor representation of a “good” Christian mother and wife. Your advice about being vulnerable and real was inspiring and gave me the nudge that I think I needed. Whether or not anyone wil read is another story… But I would like to be a doer, not just a listener. So thanks!

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