1871’s Kaylin Berg Shares Why Connection Is at the Heart of her Purpose Pillars

By Kaylin Berg, Director of Events, 1871 Chicago

Let me begin with this: I am not an entrepreneur, nor am I an aspiring entrepreneur (yet!), though I have the opportunity to work closely with those in the thick of building a business—either as founders or as part of the team—every day in my role as Director of Events at 1871 Chicago. 1871 is the top private incubator in the world, and our mission is to inspire, equip, and support entrepreneurs and those accelerating their businesses and personal development across any stage of company development. 

Entrepreneur or not, every person has and acts with purpose. Purpose is what drives us forward, what makes us tick, what defines how we interact with people in every aspect of our lives. Reading Pete’s book, Purpose First Entrepreneur, I was stunned by the connections I made and the inspiration I felt. It caused me to take a look back at my roots and examine those guiding Pillars that have always been in the background and have alternated focus through the different stages of my life.

To get to the crux of my current purpose, I find myself going all the way back to what defines me at my core. For every “two truths and a lie” or “fun fact” team-building activity, I always choose “I’m an only-only”—in other words, an only child and only grandchild. This uncommon identity has remained a shaping part of my identity, even after marrying into a family of four with about fifty grandchildren between both sides.

I am the only daughter of a single mother. My mom is a leader in her family (she’s the oldest of six—yes, the odds of my being an only-only were astronomically small), her friend group, and her school, where she taught as a beloved reading specialist for 35 years. In fact, when she finally “retired” (she still volunteers there, eight years later), the school named the carpool lane after her. 

I spent the formative years of my childhood at her school—for meetings, events, or simply helping other teachers set up their classrooms—at bunco, or along for ladies’-night dinners.  Throughout that all, I watched and soaked up how my soft-spoken, 5’3” mother flexed her iron will—all while making people feel loved and listened to. Looking back now at all that time spent at her side, I see how my mom’s Purpose Pillars influenced and shaped my own. As I grew up and entered the professional world, my Purpose Pillars looked a little something like this:

These Pillars guided me through college, where I stayed true to myself and my upbringing, while allowing myself the grace to grow socially and emotionally. They took me through my search for my first job—and the years working there—where I lost my sense of balance.

During that time, my Pillar of Honor took over, and my guiding lights of dependability, hard work, and loyalty outweighed my Wellness Pillar. I found myself sacrificing my emotional, mental, and physical well-being and giving the company more and more of me—until there was very little left. One day, my husband helped me take an objective look at the situation, and I realized that while my company told me I was valued, I clearly was not. If they had truly valued me, they would have recognized that I was tapped out and close to a breakdown. It was time to move on.

After a short search, I stumbled across a nonprofit called the Illinois Technology Association and found myself getting back to the core of my upbringing—community-focused work, aimed at bettering the lives of others. All of a sudden, my Pillars shifted back into balance, with self-respect and valuation promoted from the background to the main stage in my Honor Pillar.

As I settled into my work with ITA, my pillars continued to develop in response to my life experiences. When my mom had to have open-heart surgery in October of 2019, there was no question from my leadership team that I would take nearly two weeks off to be there for her surgery and initial recovery. I felt supported by my team and know that my Pillar of Honor, which drives me to be dependable, loyal and empathetic to others, allowed my team to put faith in me and to know that I would get my work done—even if it was on a strange schedule those weeks.

My professional life continued to be blessed by empathetic and kind leaders, even as ITA underwent an acquisition by 1871 in the spring of 2020. As we were merged into the team, I immediately saw that our new CEO, Betsy Ziegler, truly cared for us as individuals and professionals. She constantly tells us “own your life” and exemplifies that through the flexibility and understanding she provides to her team members.

My Purpose Pillars underwent their biggest fundamental shift in late 2020 after my first child, Allison, was born. Halfway through my pregnancy, we learned that Allison would be born with a congenital birth defect, requiring a long NICU stay. She battled—and us with her—for seven months before her health issues became insurmountable.

During that time, I realized that those guiding Purpose Pillars that drove me to be loyal, create friendships, forge connections, and care about the people over the task had created a solid web of wonderful people who supported me. I was given every possible flexibility in my job at 1871—being able to keep my job and have adult conversations about nonmedical things was a godsend—and came to realize that the best leaders truly care for their teams. I will always remember two professional connections that I had meetings with after returning from bereavement. I was touched when, after hearing about Allison’s passing, one woman and her company inquired about and donated to the charity we chose to honor Allison through and the other sent a beautiful bouquet of flowers.

Both actions—though small—proved to me that simply doing a job is not enough. By taking the time to connect with people—chit-chatting before diving into meetings, sending notes just to say hi even when there was nothing I needed—I had formed meaningful connections with people who truly cared. After Allison, and my collective experiences as a young professional at ITA and 1871, my pillars shifted to:

In my mind, what it boils down to is this: the job will always be there. The people, not so much. It doesn’t cost a thing to be nice to someone, to ask a question about them, to spare a kind word. The fruits of those small labors can blossom into something that means an incredible amount to the people you interact with.

I watched, for years, as my mom was unfailingly kind to people, believed in them, and guided them to be their best. She was everything that I wanted to become. I hope that in some small way, I am on my way to achieving that.