Jennifer Connolly shared their story and experiences with us recently and you can find our conversation below.
Good morning Jennifer, we’re so happy to have you here with us and we’d love to explore your story and how you think about life and legacy and so much more. So let’s start with a question we often ask: What is something outside of work that is bringing you joy lately?
Something outside of work that brings me joy is watching my son play baseball. It’s become such a meaningful part of our family’s rhythm. My husband, daughter, and I spend countless hours and weekends at the ballfield, and I love every moment of it. We get to watch the highs and lows—big wins, tough losses—and be there to help him learn from both.
There’s something special about cheering him on alongside families who have become like our own. His teammates and their parents are the people we spend the most time with now; we know each child’s quirks, strengths, and struggles, and we all play a small role in shaping who they’re becoming.
I know we’ll look back one day and realize these were the “good old days”—the dusty ballfields, the long tournaments, the tears, the lectures, the awkward car rides home, the traveling, the late nights at hotels, the shared heartbreaks, the laughs and the feeling of being part of something bigger than just a sport. That community and those memories bring me so much joy.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Jennifer Connolly, the owner of Sidekick Services and a longtime Transaction Coordinator in MA, NH and SC. I launched my business back in 2016 after realizing how much real estate agents needed reliable, behind-the-scenes support so they could stay in their zone of genius—serving clients and growing their businesses. What started as a side-hustle has grown into a streamlined, relationship-driven service that supports agents through one of the most detailed and high-stakes parts of their work: getting a deal from contract to closing smoothly.
What makes Sidekick Services special is that my entire approach is built around the idea of working smarter, not harder. I’ve refined my systems for nearly a decade so my agents don’t have to reinvent the wheel. I use my own internal processes—designed specifically for Transaction Coordinating—to create clarity, reduce stress, and keep everyone aligned, while still offering a personal touch.
Along the way, I realized how many aspiring TCs were out there trying to figure it all out alone, just like I once was. So I expanded into coaching and mentorship. I’ve helped new and growing TCs build sustainable, profitable businesses without burning out. I also train agents on workflows, efficiency, and how to scale their operations with the right support.
Right now, I’m focused on continuing to serve top-producing agents in 3 states while growing my coaching platform and resource library. If my story shows anything, it’s that busy doesn’t mean success, busy means you’re doing it wrong.
Okay, so here’s a deep one: What relationship most shaped how you see yourself?
The relationship that most shaped how I see myself is the one I had with my dad. He embodied the idea that your children should stand on your shoulders and go further than you ever could. He often talked to me about the dreams or ideas that he never pursued, not with regret, but with hope that he could be the foundation I built mine on.
He gave the kind of advice that stuck. He was my sounding board, my reality check, and the voice that told me when I was being dramatic—and also when I wasn’t pushing myself hard enough. He had such a fair, grounded way of thinking, and he never wanted any credit for anything. His only goal was for me to shine.
My dad was always proud of me, and hearing him say it made me want to keep growing and keep becoming better. That encouragement shaped my confidence and my belief in working hard and pursuing a life with intention. If I could hear anything again, it would be him telling me; “I’m proud of you Jenny, you’re doing the right thing.”
Was there ever a time you almost gave up?
Yes—after my dad passed, I came very close to walking away from my business. I didn’t know how to function in this new version of my life. I had experienced sudden, traumatic loss before, so I knew exactly what kind of emotional road was ahead for me and my family. And in those early days of grief, everything felt pointless. I remember thinking, Why work so hard if life can change in an instant? What’s the point of building anything at all?
But grief has a way of shifting over time. I started to hear my dad’s voice again—the one that grounded me my whole life. I imagined him telling me to keep going, not for achievements or accolades, but simply to live a good, full life.
In the end, that became my answer to “what’s the point?” The point is to live well while we’re here. To create a life worth experiencing, even knowing that nothing is permanent. I hope to teach my children the same.
Sure, so let’s go deeper into your values and how you think. Where are smart people getting it totally wrong today?
I think a lot of smart people are getting it wrong when it comes to how we define success in the age of technology and social media. Over the last few decades, technology has opened doors that were previously locked for so many. It’s given brilliant people—especially those who wouldn’t have had the same opportunities otherwise—a chance to build businesses, platforms, and visibility in ways that are truly life-changing.
But somewhere along the way, we became delusional about what “success” actually looks like. I attend a lot of trainings, seminars, and industry events, and keynote speakers are almost always promoted by the size of their following. So we start to believe that the goal is to impress the masses, to collect as many eyeballs as possible. But the truth is: if you’re marketing to the wrong audience, it doesn’t matter how big the audience is.
If I had a million followers but only a hundred of them were local real estate agents—the people I actually serve—then that following is meaningless. It’s noise. It’s ego-driven validation, not business growth. On the other hand, if I had just 100 Facebook friends and every single one was a potential client, I’d be in a much stronger position.
The misconception is that reach equals impact. In reality, relevance equals impact. And I think many smart people have started chasing the wrong metric.
Okay, so before we go, let’s tackle one more area. What are you doing today that won’t pay off for 7–10 years?
Right now, I’m investing in something that won’t fully pay off for 7–10 years: building generational wealth and teaching my children financial literacy. My husband and I are very intentional about passing on the lessons we didn’t learn until our 30’s. Lessons that have changed our financial path.
I grew up believing that if you wanted to make more money, you worked a second job, credit cards were “bad,” that loyalty to one company would create security, and that success was earned through hard work, not smart strategy. My parents taught me what they knew based on what they learned from their parents and the world was a different place in those generations. Financial education wasn’t widely accessible back then, and honestly, it still isn’t taught to most people.
Another phrase I grew up hearing was “money doesn’t buy happiness.” And while that’s true in the literal sense, I realize it’s also an oversimplified, uneducated statement. People who strive to earn more money aren’t chasing happiness. They’re chasing freedom. Freedom to live on their own terms. Freedom from constant stress. Freedom from the hamster wheel that keeps so many families stuck.
As adults, my husband and I learned how money actually works. We’ve learned how to grow it, leverage it and use it as a tool. And now we’re intentionally teaching our kids those same skills. The payoff won’t be immediate, but in the next decade I hope they’ll enter adulthood with confidence, choices, and a financial foundation much stronger than the one we started with.
That’s what generational wealth really is: a launchpad, not a luxury.
Contact Info:
- Website: https://sites.google.com/view/sidekickservices/home
- Instagram: https://www.instagram.com/jennconnollyrealestate/
- Linkedin: https://www.linkedin.com/in/jenniferconnolly1/
- Facebook: https://www.facebook.com/jenmulloy
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