Entrepreneurs, Don’t Lose Sight of Your Why

by Jay Jacobson, LUTCF, CFP, CFSP

The grind is seductive. As founders, we convince ourselves that long hours equal progress. We wear exhaustion like a badge of honor, pointing to growth charts and revenue numbers as proof that the sacrifice is worth it. But if we’re honest, the grind often isn’t about building at all—it’s about hiding.

Dakota Robertson shared a powerful story of how the very passion that once gave him life—writing—turned into a prison when his business scaled. He had built freedom only to discover captivity. His days were filled with tasks he hated, his creativity shrank under the weight of obligation, and his success began to feel like someone else’s story. His insight cut straight to the truth: burnout doesn’t come from working too hard; it comes from working too long on the wrong things. The cure isn’t stepping away—it’s realignment.

Jean-Paul Gonios added another layer. He wrote that the grind masks the hardest questions, the ones we avoid because they strike too close to the core. Why do I feel empty when the numbers say we’re winning? Who am I when I’m not “the founder”? What relationships am I trading for the sake of growth? Those are not business questions. They are life questions. And by the time many leaders face them, it’s too late. Health is in shambles. Relationships are distant. Identity has vanished into the role. No exit strategy can buy back what’s been lost.

Susan Braund reframed burnout in a way that resonated deeply with me. Burnout is not exhaustion—it’s erosion. The erosion of meaning. The slow loss of connection to the very work that once inspired you. And that erosion is dangerous, because it convinces you that what you do no longer matters. But she also reminded us that burnout is not the end; it’s a signal. A signal to recalibrate. To realign with your values. To release what no longer fits and protect the space that renews you.

Even Adam Grant, the Wharton professor and bestselling author, is weighing in. He recently described “quiet cracking” as the new form of silent disengagement—a slow breaking of the spirit that’s nothing less than burnout. He points to the same causes we see every day: being overworked, undervalued, and disrespected. His reminder is sharp and clear: leaders have to make it safe to talk about burnout if they ever hope to solve it.

These voices converge around one truth: success without alignment is hollow.

At Jay’s Cookies, we’ve lived this lesson. About five years into our journey, an opportunity arose to expand into multiple retail locations. On paper, it made sense. The numbers projected well, the demand was there, and more than one advisor told us we’d be foolish not to scale. Around that same time, we were also approached by a well-established business with an offer to buy them out—a shortcut to rapid growth and regional presence.

In moments like these, it’s easy to be dazzled by what looks like progress. Bigger footprint, more revenue, larger staff. But when we paused, we realized the cost: our days would shift from baking, creating, and connecting with people—to managing leases, payroll, and spreadsheets. The very things that gave us joy would be traded for responsibilities that drained it.

So we asked ourselves the hard question: Would growth bring us closer to what we loved, or take us further away?

We chose not to expand. We chose not to buy. Instead, we stayed close to the craft—hands in the dough, face-to-face with the community that had supported us from day one. That decision has been our guardrail. It allowed us to protect our “why” and reminded us that growth, if it causes you to lose sight of your foundation, is no growth at all.

For entrepreneurs, this is the hidden challenge: not every opportunity is the right opportunity. Sometimes the bravest decision is saying no to the kind of growth that leads you away from your purpose.

This is where Simon Sinek’s wisdom—Start with WHY—becomes more than a phrase. Your why is the compass. It is the guardrail that prevents achievement from turning into emptiness. In Lead by Legendary Example, I wrote that values form the foundation on which we build our lives and our organizations. Without them, we climb ladders only to discover they’re leaning against the wrong wall. With them, we grow without losing ourselves.

Because the real measure of a business is not what it produces. It’s who you become while building it.

Every founder will face this reckoning. The only question is whether you will face it on your terms—or when it’s already too late.

So pause. Reflect. Ask yourself: What part of your work no longer feels meaningful, and what would you replace it with?

And with so many thoughtful voices—from entrepreneurs to psychologists—raising the alarm about burnout, perhaps it’s time for all of us to step back and look hard at how we structure our days. Maybe the greatest challenge isn’t how much we can do, but how clearly we can prioritize what matters most. And maybe the best way to begin is the same choice we made at Jay’s Cookies: to measure every opportunity not by how big it makes us, but by how true it keeps us to our why.