He Spoke to 3,000 Entrepreneurs and Learned They Were All Asking the Same Question 'Am I going to be okay?' is a universal anxiety shared by most business owners.

When Dan Nicholson left a prestigious career at Deloitte to become an entrepreneur, he started noticing something strange. Some business owners seemed to win consistently, while others—despite having similar skills and opportunities—kept spinning their wheels.

"After more than 3,000 conversations with entrepreneurs across industries, I discovered they were all essentially asking the same question: Am I going to be okay?" says Nicholson, a three-time global top 40 accountant under 40 and the Wall Street Journal bestselling author of Rigging the Game.

That universal question sparked a years-long project: building a system to help purpose-driven entrepreneurs reduce financial anxiety and make better decisions. At its core is a formula Nicholson calls the "anxiety equation": Anxiety = Uncertainty × Powerlessness.

"Most entrepreneurs experience financial anxiety because they're unclear about their priorities," he explains. "And they don't have systems to make decisions that reduce uncertainty or help them feel in control of outcomes."

So how do you reduce both uncertainty and powerlessness? Nicholson has developed a framework rooted in four key principles.

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1. Aim for closer, not just more

The instinct when things get tough is to pursue more—more revenue, more clients, more growth. But that's not always the best move.

"Instead of defaulting to more, focus on getting closer to what actually matters to you," Nicholson says.

He shares the example of a client who wanted to hire someone to reclaim ten hours a week. The assumed solution was to increase revenue by $10,000 a month. Instead, the client moved their office five minutes from home—saving ten hours of commute time for just $2,500 a month.

"The right move wasn't more money," Nicholson says. "It was a better alignment with their priorities."

2. Know whether it's a binary or preference-based decision

"Most business decisions don't have a right or wrong answer," Nicholson says. "They're about preferences, not absolutes."

He suggests a simple test: Can this question be answered by Google? If not, it's probably a preference-based decision—and that means the "right" answer depends on your goals.

For example, two identical businesses might choose opposite strategies. One owner may want to grow aggressively. The other may want to take more time off. Both are valid.

Nicholson says recognizing this distinction helps entrepreneurs avoid chasing someone else's version of success.

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3. Every business decision has financial consequences

Too often, entrepreneurs separate business and finance. Nicholson believes that's a mistake.

"I talk to founders all the time who say, 'I'll focus on the business, and someone else can handle the money,'" he says. "But every decision has financial implications. You can't afford to ignore that."

Whether it's hiring, marketing, or expanding, Nicholson encourages founders to assess the cash flow impact up front. That shift can prevent surprise shortfalls and keep priorities in focus.

4. Look for Asymmetric Opportunities

"Take bets where the upside far outweighs the downside—and never risk total failure," Nicholson says.

He borrows a mental model from Jeff Bezos: if there's a ten percent chance of a 100x return, that's a good bet.

To evaluate opportunities, Nicholson runs them through four filters:

• Does it save time?
• Does it act as a forcing function (i.e. push other things forward)?
• Does it reduce costs?
• Does it generate revenue?

"For my companies to pursue something new, it has to check at least three of those boxes," he says. "Even if it doesn't drive revenue, it's still a win in other ways."

How to put it all into practice

Nicholson helps founders implement his framework using a simple three-step process:

1. Define your profit priorities. That means setting specific personal goals with timelines and dollar values attached.
2. Engineer your cash flow. Restructure how money moves through your business and accounts to reduce impulsive decisions.
3. Optimize before you maximize. Before chasing growth, look for ways to keep more of what you already earn—through tax strategy, cost-cutting, or better systems.

"Most entrepreneurs are shocked to learn they don't need more revenue to reach their goals," Nicholson says. "They just need to make smarter decisions with what they've already got."

For entrepreneurs who feel like they're constantly hustling with little to show for it, Nicholson's system offers an alternate path: one built not on growth for growth's sake, but on clarity, intention, and repeatable decision-making.

"Winning consistently isn't about luck," he says. "It's about making decisions that move you closer to what matters most."