Entrepreneurship is often romanticized as the ultimate path to freedom—being your own boss, setting your own hours, and building something meaningful from the ground up. But according to entrepreneur and philanthropist Shalom Lamm, that freedom comes at a price that many never anticipate until they’re already in too deep.

Having spent decades in the business world, building ventures and leading impactful nonprofit initiatives like Operation Benjamin, Lamm understands both the visible and invisible tolls of leadership. “People see the title—founder, CEO, entrepreneur—but they don’t see the anxiety, the long nights, or the financial strain that often come with it,” he says. “Being your own boss can be rewarding, but it’s far from easy.”

In this post, we explore what Lamm calls the “hidden costs” of entrepreneurship—those emotional, mental, and logistical burdens that don’t show up on spreadsheets but can weigh heavily on even the most passionate founders.

1. Time Isn’t Really Yours

Entrepreneurs often start their journey seeking more control over their schedule. Ironically, many end up working far more than they ever did at a 9-to-5.

Shalom Lamm shares that during the early stages of one of his ventures, he routinely worked 80+ hour weeks. “You’re not just running the business—you are the business,” he explains. “That means you’re wearing ten hats at once: marketing, HR, operations, finance, and sometimes janitor.”

The cost? Time away from family, missed events, and mental fatigue. Unlike clocking out from a job, being your own boss means the business is always with you—emotionally and psychologically.

2. Financial Risk (and Stress)

There’s no guaranteed paycheck when you work for yourself. Lamm emphasizes that many new entrepreneurs underestimate how long it will take to become profitable—and how much of their personal capital they’ll need to risk in the process.

“People often think starting a business is the fast track to wealth,” Lamm says. “But in the beginning, you’re more likely to go into debt than make a dime.”

From bootstrapping and funding your own payroll to losing sleep over expenses, the financial strain is real—and it doesn’t always come with immediate rewards.

3. Emotional Isolation

Leadership can be lonely. When you’re the one making the big calls, there’s often no one to turn to when things go sideways. Shalom Lamm recalls how the pressure of responsibility can isolate even the most social individuals.

“You don’t want to burden your team or your family with the weight you carry. But that silence can start to erode your own well-being.”

That’s why he encourages entrepreneurs to build a strong support network—mentors, fellow founders, and even therapists. Having someone who understands the journey can make a world of difference.

4. Your Mission Must Ground You

One of the reasons Lamm has maintained perspective through the highs and lows of entrepreneurship is his dedication to purpose-driven work. He co-founded Operation Benjamin, a nonprofit dedicated to identifying Jewish American soldiers buried under Latin Crosses and correcting their headstones to properly reflect their heritage and sacrifice.

“The work we do with Operation Benjamin keeps me centered,” says Lamm. “When you’re facing uncertainty in business, remembering that you’re capable of creating real-world change gives you strength.”

Lamm believes that every entrepreneur should anchor their work to something bigger than themselves—whether that’s community impact, innovation, or solving a deep problem. Purpose becomes fuel when money, energy, and confidence run low.

5. Freedom Isn’t Free

At the end of the day, being your own boss is a form of freedom—but it’s a freedom that must be earned through sacrifice, strategy, and endurance.

“You trade one kind of pressure for another,” Lamm says. “You’re not answering to a boss, but you are answering to your clients, your team, your vision—and your own expectations.”

For those who thrive on autonomy and purpose, the hidden costs may be worth paying. But no one should go into entrepreneurship blind. Recognizing these less visible burdens upfront can make the journey not only more manageable—but more meaningful.

Final Thoughts

Entrepreneurship is not just about making profits—it’s about managing pressure, risk, and responsibility. Shalom Lamm reminds us that while being your own boss comes with undeniable rewards, it’s not the carefree dream often portrayed on social media.

But with awareness, resilience, and a mission like Operation Benjamin to stay grounded in, those hidden costs can transform into powerful lessons—and lasting impact.