My “Why”

There is a difference between thinking about change and recognizing that change is no longer optional.

For most of my life, starting a business lived in the space of “someday.” It was an idea I returned to periodically, something I could imagine myself doing when the conditions were right—when I had more time, more clarity, more energy, more certainty. It existed as a possibility, but not yet as a decision.

That distinction—between possibility and decision—is easy to maintain when life feels relatively stable. Even dissatisfaction can be managed when it is familiar. A steady job, predictable routines, and incremental progress create the illusion that there is always time to adjust course later. There is always another year, another opportunity, another moment when things will feel more aligned.

But part of the reason I held onto that belief for so long traces back much further, to the way I understood work itself as a child.

I grew up thinking that entrepreneurship was not just possible, but commonplace. My father was a successful cartoonist who worked for himself, and from my perspective, that was simply how a career could look. His office was in the attic of our home, a space that felt both ordinary and quietly significant. That was where the work happened—where ideas became tangible, where deadlines were met, and where a livelihood was built without ever leaving the house.

He had clients like Kraft and General Mills, illustrating food products that filled grocery store shelves. Characters like Count Chocula and the Nesquik Bunny were not abstract brands to me; they were part of the world my father helped create. His work translated into something visible and familiar, something I could point to and recognize. And beyond that, it supported a life that, by any reasonable standard, was comfortable. We lived in a beautiful home on the shore of Connecticut. There was a sense of stability, of provision, of having what we needed and more.

From the outside—and certainly from a child’s perspective—it looked straightforward. He worked for himself, he was successful, and life followed accordingly.

What I did not understand at the time was how much nuance existed beneath that surface.

With that early impression, I moved through school carrying a quiet assumption that things would work themselves out. I struggled academically, though not in a way that drew significant concern. I did “well enough,” consistently landing in the middle space where effort and outcome never quite aligned. I often felt that I understood the material, at least conceptually, but when it came time to demonstrate that understanding, it rarely translated into results that reflected it.

That pattern followed me into higher education. I attended Parsons School of Design to pursue illustration, a choice that felt both natural and inevitable. Again, I did well enough. I moved through the program without failing, but without ever feeling fully anchored in what would come next. There was always a sense that I was capable of more, paired with an inability to consistently translate that into something concrete.

After graduating, I attempted to build a freelance career, focusing on mural work and children’s book illustration. In hindsight, both paths were misaligned with the realities of the degree I had earned and the market I was entering. More significantly, there were two critical gaps in my education that I did not fully recognize at the time: I had not been taught how to build a business, and I lacked meaningful computer literacy.

The timing, in that respect, was particularly unforgiving. I graduated in the late 1990s and early 2000s, just as digital tools were beginning to reshape the illustration industry. What I had been trained to do—hand-drawn illustration—was slowly becoming less central to commercial work. Opportunities that might have existed a decade earlier were becoming less accessible, and the industry was shifting in ways I was not prepared to meet.

Even my father’s career, which had once seemed like a clear model to follow, was changing. The demand for hand-drawn commercial illustration was diminishing, and the clients who had once relied on that work were turning toward digital alternatives. The path I had assumed was stable was, in reality, narrowing.

In many ways, I entered adulthood with an incomplete understanding—not only of how to build a business, but of how quickly the ground beneath you can shift if you are not actively adapting.

So I did what many people do when faced with that kind of uncertainty: I chose stability where I could find it. I built a life that worked on paper, even if it did not fully align with what I had once imagined for myself. The idea of starting something on my own never disappeared, but it remained just out of reach—something I associated with a version of success I had witnessed, but never fully understood how to recreate.

Years passed that way. Responsibly. Predictably. Safely.

I leaned into what I could rely on in myself and found a path in corporate sales. It was not a natural fit in every sense—I struggled with organization, with structure, with the expectation of fitting neatly into predefined systems—but I learned how to use other strengths to compensate. I was recognized for my emotional intelligence, for my ability to connect with people, and for a natural inclination toward teaching and mentoring. Those qualities carried me further than I might have expected, and over time, I was promoted into management roles.

From the outside, it looked like progress. I was moving up, gaining responsibility, and achieving a level of professional recognition that suggested I was on the right path. And in many ways, I was. But the motivation that kept me there was increasingly tied to something specific: the paycheck. The financial reward became the primary driver, the justification for continuing to push forward even as the work itself felt less aligned.

What I eventually found, somewhat unexpectedly, was that reaching higher levels did not necessarily bring greater reward. In some cases, it brought less—less financial upside, less flexibility, and less direct connection to the parts of the work I actually enjoyed. At the same time, my personal life was shifting. When my first son was born, my priorities began to change in ways that were both subtle and profound.

The ambition that had once fueled my movement upward began to lose its intensity. The trade-offs became more visible. The cost of time, energy, and attention required by those roles no longer felt justified in the same way.

So I made the decision to step back down into an individual contributor role.

On paper, it may have looked like a step backward. In reality, it was an attempt to recalibrate—to find a version of work that felt more sustainable within the context of my life. But something shifted in that transition that I had not anticipated.

The value I had placed in the company, the trust I had put into the corporate structure, began to erode. The sense of purpose I had once been able to derive from my work felt diminished, and in its place was a growing awareness of how transactional the environment could be. At the same time, I was navigating the demands of motherhood—exhaustion, responsibility, and a level of emotional investment that far exceeded anything I had experienced in my professional life.

The contrast was difficult to ignore.

Where one role required everything of me and offered unconditional meaning, the other began to feel increasingly hollow. There was little flexibility, little understanding, and little acknowledgment of the broader context of my life. The disconnect between what I was giving and what I was receiving became more pronounced, and with it came a quiet but persistent questioning of whether this was a structure I wanted to remain within indefinitely.

It was also during this period—after my second son was born, and before my own diagnosis—that another layer of clarity began to emerge within our family.

It became increasingly evident that my oldest son was struggling with attention and focus. While I was navigating my own challenges—feeling scattered, disorganized, and often overwhelmed by even simple routines—I began to recognize similar patterns in him. Mornings, in particular, became a reflection of that shared struggle. I was trying to hold everything together, to get us all out the door, to manage the logistics of daily life, and he, in his own way, was struggling just as much.

There was a moment of realization in that—not one of frustration, but of recognition.

He could not compensate for me, just as I had spent years trying to compensate for myself.

We had him evaluated, and when he was diagnosed, it forced me to look at my own life through a different lens. The feeling I had carried for so long—the sense of being “good enough,” but never quite fully capable of reaching what I believed I should—suddenly took on new weight. It was no longer just about me. It was about what that same internal narrative might become for him.

I understood, perhaps more clearly than ever, how deeply those quiet beliefs can shape a person’s confidence and sense of possibility. And I was confronted with a question that felt both urgent and unavoidable: what would it mean to support him not just in managing those challenges, but in building a life where they did not define or limit him?

That question extended beyond emotional support. It became practical.

Because alongside everything else—motherhood, career uncertainty, and the growing awareness of my own limitations—I was also facing a reality that was impossible to ignore: financial vulnerability.

During my cancer treatment, I found myself relying on my 401(k), which, after 14 years in what I had considered a successful sales career, amounted to roughly $50,000. It was a sobering realization. The safety net I had assumed I was building felt far less secure when it was actually needed. Resources that were meant for the future were being pulled into the present, and the margin for error was shrinking.

And with that came a thought that was both simple and overwhelming:

What if I am not here tomorrow?

It is a question that reframes everything.

What happens to my family if I am gone?
What supports are in place?
What foundation have I actually built?

For the first time, the idea of a “safety net” took on a meaning that extended beyond my own stability. It became about ensuring that my children—particularly a child who might face challenges similar to my own—would have options. That they would have support. That their ability to build a life would not be limited by the same uncertainties I had carried.

I did not just want them to be okay.
I wanted them to be secure.

And more than that, I wanted them to grow up without the quiet fear of not being enough.

That desire reframed everything I had once considered risky.

Because continuing on the same path no longer felt like the safe choice. It felt like avoidance.

Beyond my own reluctance to remain confined within a structure that never fully fit, there was now something larger at stake. The idea of building generational stability—of creating something that could outlast my own time and effort—was no longer abstract. It was necessary.

The diagnoses I received did not introduce new ambitions, but they did something far more significant: they removed my ability to delay them.

Time was no longer an abstract idea. It was no longer something I could assume I had plenty of.

That shift was immediate and clarifying.

For years, I had told myself there would be a better moment—more time to prepare, to feel ready, to take the leap under the “right” conditions. That belief made staying where I was feel responsible.

But it wasn’t.

Because waiting is still a decision.

And what became undeniable was this: continuing to wait carried its own risk—the risk of never doing it at all. Never being certain I had set myself up for the future. And never creating a path of financial security for my boys.

Once that settled in, the urgency was no longer optional.

It was real.
And it demanded action.