Entrepreneurship requires so much to be built behind the scenes. Whether it’s financial habits that shape long-term sustainability or leadership development that happens through experience, discomfort, and responsibility. And sometimes, the rooms you eventually find yourself sitting in after years of showing up, will leave you amazed.
Over the last few weeks, I had two experiences that deeply reinforced those thoughts for me. The first was traveling to New York with Gusto as part of their Small Business Advisory Council for their Spring Summit. The second was completing United Way’s Building Resilient Entrepreneurs Spark Prize Pitch Competition. While the experiences were very different, they both challenged me to think more intentionally about leadership, sustainability, visibility, and what the next chapter of TK Consulting & Design™ could become.
We’ve used Gusto since we began hiring, and because of that history, being invited to participate on their Small Business Advisory Council felt pretty cool. But actually experiencing the Spring Showcase in person gave me a different perspective on what it looks like when a company genuinely invests in understanding the people it serves.
Gusto brought both their small business and accounting advisory councils to New York for a multi-day experience centered around product feedback, relationship building, and collaborative discussion around the future of Gusto’s small business tools. We had opportunities to preview upcoming features, test beta products, discuss product updates, and explore new partnerships aimed at making the operational side of running a business more accessible for small teams. A lot of the conversations focused on reducing friction for business owners who are already balancing so much behind the scenes.
Some of the updates that stood out to me most were the continued expansion of Gusto Money, enhancements to compliance and HR support tools, and new partnerships designed to make benefits and healthcare access more attainable for growing businesses. They also shared developments around AI-supported workflows and operational tools aimed at helping small businesses simplify administrative tasks that often take time away from actually running and growing the business. As someone who has experienced firsthand how overwhelming the operational side of entrepreneurship can be, it was interesting to see a company intentionally thinking about how to reduce some of that pressure for small teams and founders.
We were able to spend time at Gusto’s New York office, with an AMAZING view of the New York City skyline, listening to the founders share their story, participating in product intensives, exchanging feedback, and having honest conversations about the realities small businesses are navigating every day. We later traveled to Times Square to celebrate Gusto reaching 500,000 customers and saw their celebration campaign displayed before ending the evening together in celebration.
But honestly, the most meaningful part of the trip was being surrounded by other founders and professionals who understood the complexity of building something while simultaneously trying to sustain it. Entrepreneurship can feel isolating at times, especially when so much of leadership requires carrying pressure quietly. Being in a room full of people openly discussing growth, challenges, systems, staffing, sustainability, and decision-making reminded me how valuable it is to be in environments where people are learning in real time instead of pretending to already have everything figured out.
Around the same time, I was also wrapping up United Way’s Building Resilient Entrepreneurs program, which challenged me in a completely different but equally important way. Going into the program, I expected conversations around entrepreneurship, networking, and leadership development. What I did not expect was how deeply the cohort would focus on financial literacy and financial health for small business owners.
Throughout the program, we spent a significant amount of time analyzing financial reports, understanding projections, evaluating trends, and discussing what sustainable growth actually looks like beyond simply generating revenue. As a creative entrepreneur, I think there’s often a steep learning curve when it comes to understanding the financial side of leadership. Many of us start businesses because we’re skilled at the work itself, but growing a company requires a much deeper understanding of how money moves, how systems function, and how to interpret the overall health of a business beyond surface-level success.
One aspect of the program that I appreciated was the savings match initiative, where participants received matched contributions based on what they were able to save throughout the cohort. I loved that component because it reinforced the idea that resilience is not just about ambition or endurance. It is also about preparation, sustainability, and building stronger financial habits over time. As someone who has openly talked about the realities of cash flow challenges within entrepreneurship, that perspective felt especially important. A business can be profitable and still experience cash flow pressure, and I think more entrepreneurs need spaces where those conversations can happen honestly and without shame.
The program also included a pitch competition, which, if I’m being completely honest, was far outside of my comfort zone. Public speaking and visibility as a founder are still areas where I continue to grow. Even after nearly 10 years in business, there is still a part of me that feels nervous standing in front of a room and presenting my company in that way. But I decided to participate anyway because I knew growth would require me to become more comfortable articulating not just what we do at TK Consulting & Design™, but why the work matters.
What I appreciated most about the process was that it forced me to think more deeply about the larger purpose behind the company. For years, I’ve been able to explain our services: branding, web design, digital marketing, photography, strategy, and content development. But this experience challenged me to articulate the deeper problem we were created to solve.
TK Consulting & Design™ was built because there is a major accessibility gap for growing businesses and organizations. Large agencies are often financially out of reach, while relying on disconnected freelancers or trying to manage everything internally can leave businesses without a cohesive strategy or clear brand identity. We created this company to help bridge that gap by offering thoughtful, intentional creative support that helps businesses communicate clearly, launch confidently, and connect more effectively with the audiences they are trying to reach.
Participating in the pitch competition helped me better understand the broader impact of our work. In many ways, the services we provide help create stronger foundations for other businesses to grow, generate revenue, and create opportunities for themselves and the communities they serve. While I did not win the grand prize, I left feeling genuinely grateful for the experience, the relationships, and the opportunity to stretch myself in a new way. I was also incredibly inspired by the other entrepreneurs in the room, many of whom delivered phenomenal pitches and are building truly impactful businesses.
As I reflect on both of these experiences together, I think what stands out most is how much this season is shaping my understanding of leadership heading into the next decade of business. Growth is not always loud or obvious. Sometimes it looks like understanding your numbers more clearly. Sometimes it looks like building healthier systems. Sometimes it looks like becoming more visible even when it feels uncomfortable. And sometimes it simply looks like allowing yourself to continue learning instead of believing you should already know everything by now.
For the first time in a long time, I don’t feel intimidated by what the next version of TK Consulting & Design™ could become. I feel inspired by it.