Founder Blog: Embracing Change, Reconnecting with Purpose: A Reflection on Our Entrepreneurial Journeys as We Begin to Close 2024

Read Time: 5-7 minutes

By: Heather Wentler

As entrepreneurs, we often navigate the tension between self-interest and the bigger picture of our businesses. What can we learn from our 7th grade selves about growth, decision-making, and embracing discomfort? This reflection will challenge you to ask yourself: Why? And how that question can shape your success in both business and life.

As we move deeper into November, my annual reflections often center around gratitude. In past years, I’ve focused on celebrating the lessons and wins that the year has offered. But this year, I’m thinking a lot about the challenges we face, especially as entrepreneurs. And while I’m not typically one to lean heavily on optimism—I’ll be the first to admit that—it’s important to find moments of joy and thankfulness, even in the midst of the grind. These moments can be essential in navigating the complexities and the heaviness of our journeys.

A recent conversation with a friend—whose child is in 7th grade—got me thinking. Do you remember what it was like to be 12 or 13 years old? I used to love teaching middle school, but I’ve always believed that 7th grade is one of the hardest years of childhood. It’s that awkward, transformative time in adolescence, when your body and mind are in constant flux. You’re beginning to see the world through an adult lens—starting to critically evaluate adult decisions—yet you’re still trying to hold on to childhood comforts. You want to belong, but at the same time, you’re terrified of being “uncool” by holding on to things that make you feel safe.

At that age, everything is filtered through the lens of self—your needs, your wants, your identity. When you ask a 7th grader, “How was your day?”, the answer is usually “fine.” But then, through their words, you’ll hear what happened—to them. Math class was “the worst” because of how it made them feel; a disagreement with a friend suddenly becomes the world’s biggest issue because it threatens their sense of self. Everything is personal. You start questioning, “Why do I need to learn this?” because it doesn’t seem to have any relevance to your world.

Developmentally, we’re supposed to move beyond this "Me Era" as we approach adulthood, ideally by our early 20s. But do we ever really grow out of it? As entrepreneurs, we are constantly navigating this tension between personal needs and the bigger picture of our businesses. We have to advocate for ourselves and fight for our vision—but sometimes, in doing so, we can lose sight of the larger goals we’re trying to achieve. We sometimes forget that we are only one part of a much bigger system, and that our decisions—especially when made through a lens of self-interest—can have consequences beyond our own experience.

When was the last time someone asked you, “Why did you make that decision?” about your business? And did you have an answer that truly reflected the larger mission of your company, not just your own comfort or ego? If the answer is unclear, it’s time to pause and reflect. If you don’t have people around you—advisors, mentors, peers—who challenge you to dig deeper, to ask "why," then it’s time to reevaluate your inner circle.

This questioning, this “Why?”—it can be uncomfortable. I’m reminded of the times in school when a teacher asked, “Why did you do that?” or “How did you arrive at that answer?” As a kid, those questions could feel like a critique of your ability or judgment, sparking defensiveness. Even as adults, the tone of a well-meaning “why” can trigger old emotional responses. It’s natural to feel uncomfortable when we’re questioned—especially when we’re in the thick of running a business. But here’s the thing: this discomfort is part of growth. It’s necessary.

I recently had my Q4 board meeting, where we discuss next year’s strategy and budget. I deliberately encourage my board members to challenge me—to ask me why I’m considering certain moves. I know it will annoy me, but I also know I need to hear it. Because, while I live and breathe this work every day, my board members bring fresh perspectives—ones that I may not always consider. They are not involved in the day-to-day operations, which is both a strength and a challenge. They don’t experience the daily wins and challenges I face—but they see things from a broader, strategic perspective. That’s why they’re on the board in the first place.

So, how does this all relate to 7th grade?

I recently came across an old photo of myself from 7th grade and asked myself, What would I want that version of me to know? What advice would I give 12-year-old Heather today, knowing everything I’ve learned since? If I could have a conversation with my younger self, what would I say?

Would I tell her to brace for the hard things ahead, or warn her about a specific mistake? Would I encourage her to take a risk that I later regretted not taking? And what would I tell her about the impact I’m making now, in both my personal and professional life?

What if we all asked ourselves those questions? How would you answer them about your own journey? What advice would you give to your 7th-grade self?

How does your business play into that vision? How does your lived experience—both the triumphs and the failures—shape the way you lead, interact with others, and make decisions today?

As we approach the end of the year and look ahead to 2025, we all face uncertainty. The coming months are likely to bring more change—change that will feel both uncomfortable and inevitable. Some of it will feel unfair or even unjust. It’s easy to succumb to fear and uncertainty in the face of what we cannot predict.

But here’s what I know: We will make it through. We don’t know exactly how, but we will. And in the process, we’ll face some change that feels empowering, and some that feels demoralizing. The key is not letting fear of change overpower the work we’ve done—personally or professionally. We must keep our eyes wide open, stay aware of how change is impacting us, and remember why we started in the first place.

As entrepreneurs, we must never lose sight of our mission, and we must ensure our decisions align with both our values and the bigger picture of what our business is meant to accomplish. This isn’t just about surviving—it’s about thriving in a way that helps others, just as we hope to help our younger selves.

So, as we navigate these uncertain times, let’s remember to take care of ourselves and each other—and continue to ask ourselves: Why? Because sometimes, the questions we avoid are the ones that push us toward the clarity and growth we need.