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The 5 Things Keeping Small Business Owners Up at Night

Robb Todd

Robb Todd

Business Columnist at Fundera
Robb Todd is a freelance writer and editor at The New York Times, Fast Company, and elsewhere.
Robb Todd
Editorial Note: Fundera exists to help you make better business decisions. That’s why we make sure our editorial integrity isn’t influenced by our own business. The opinions, analyses, reviews, or recommendations in this article are those of our editorial team alone.

Good help is still hard to find—and it’s getting harder.

Of the many things small business owners lose sleep over, “finding and keeping skilled employees” top the list as the fastest rising problem they face, according to a survey by the National Federation of Independent Business. That problem leapt 16 spots to 14th last year from 38th in 2012, the last time the NFIB conducted the survey. That was followed by the equally grim (and somewhat redundant) issue of “locating qualified employees,” which jumped 12 places from 32nd to 10th.

The other problems that keep small business owners awake at night: the cost of doing business, politics, cash flow, and work-life balance.

Here’s what five entrepreneurs had to say about what’s causing their sleepless nights.

1. The Help

Losing great employees tops Casey Meehan‘s list of worries.

“I am lucky to be able to work with some super-talented people,” says Meehan, the co-founder of, a publication that rates and reviews online trading platforms. “These people are what makes our business successful. I have read many business books that say, ‘Your business should not rely on one person.’ I think that is easier said than done!”

He’s also losing some sleep over stagnant growth and getting so caught up in the day-to-day that he finds it difficult to find time for innovating the company’s services.

“There are so many new things that I want to implement,” he says. “But as my business grows, I am continually facing decisions or unique duties that no one else in my organization is trained to handle.”

Then there’s the not-so-small worry that today’s political climate threatens the global economy.

“We work with many international companies who are increasingly concerned about doing business with a U.S. company because of their negative feelings toward Donald Trump,” says Meehan. “They are starting to put their money where their mouth is and break ties with U.S. companies in favor of more local options. We also hire overseas contractors and have seen evidence that this might be getting more difficult in the near-term.”

2. The Cost of Doing Business

The cost of doing business is the biggest concern for Anthony Cirone, president of Li-Lac Chocolates, which was founded in 1923 and is Manhattan’s oldest chocolate house. Being based in New York City is a big part of that cost, and Cirone says it’s only getting worse on multiple fronts.

“So many regulations make it difficult to do business,” he says. “Higher rents, rising labor costs, increasing paperwork, restrictions on signage, and, in general, just keeping up with the myriad of regulations that you aren’t even aware of. We are always adjusting and making necessary changes to our business to keep abreast of the changing conditions.”

Political uncertainty is an issue, too, because of situations that could arise that would hurt his business. It also makes it difficult to plan. Among those potential problems are higher import duties on components or ingredients they buy from overseas, new regulations like the proposal for bag tax in New York City, and increasingly burdensome labor law regulations that require time-intensive paperwork requirements

“These type of activities and costs pull us away from focusing on the business,” Cirone says.

And, like so many other businesses, it’s difficult for Cirone to find qualified employees.

“We struggle to find people who have even the basic skills for some of our entry-level positions,” he says. “We are surprised by how many people can’t seem to get themselves to arrive for their shift on time, or who have issues that prevent them from working a regular shift, or who don’t seem to have the ability to concentrate and focus on the work they are doing.”

3. Politics

A lot of small business owners are excited about President Trump’s views on the economy and his proposals to reduce taxes and regulations. But some are wary of how a regulatory pull back will directly affect them.

Katharine Halpin, founder and CEO of The Halpin Companies, a business optimization and strategic alignment consulting firm, says she has some concerns.

“I’m afraid that the deregulation will cause so much damage to our environment, our roads, etc., that we will pay more in the long run,” she says. “I also think that the tax breaks, while they should benefit us small business owners, will mostly be geared to higher net worth individuals.”

Still, what goes on in Washington, D.C., isn’t her biggest concern. That would be cash flow because, like all businesses, the doors close without it. A business also needs adequate revenue, she says, “so you can afford to support your family, purchase adequate health insurance, build retirement savings, build reserves for future investments.”

If a business is lucky enough to find and keep talented employees, it’s just as important to have the right people “in the right roles, focused on the right priorities,” Halpin adds. “Without this, you will work longer hours, experience undue stress and intensity, and significantly sabotage the potential of your small business.”

4. Cash Flow

Cash flow is always the biggest worry for Kimberley Rudd, president of Rudd Resources LLC, which focuses on business management, marketing, and communications.

“There are times when my bank account looks fantastic. and then, once payroll is processed and consultants are paid, I’m wringing my hands hoping that nothing is lurking around the corner to surprise me,” she says.

Among her other major concerns are whether she’s properly insured and retaining talent.

“I cannot afford full-time employees, and so I’m aware that my team is prone to moving on to new challenges,” she says. “I have always approached this concern with a proactive stance of anticipating that some staff won’t stay long—usually, younger staff.”

She tells these types of employees that she’ll groom them for their next job while they work for her “so that I get the best from them, and them from me.”

One thing not keeping her up at night is the political climate. She sees some possible benefits, at least for her business.

“If Trump means what he says, then his drive to grow the economy will be good even for micro-businesses like mine,” Rudd says.

5. Work-Life Balance

The thing that keeps Duncan Murtagh awake at night is the fear that he’s not working enough.

“Should I send a few more sales emails or watch WestWorld?” says Murtagh, co-founder of Vetter, an online employee suggestion box software company. “Do I have time to jog, or do I need to prepare for that demo call? Can I browse Facebook during lunch, or should I read that industry article I have saved?”

He says that whenever he reads about famous entrepreneurs, they all spent every waking moment on work.

“We don’t hear so much about those folks that had balance in their lives along the path to success,” he says, “so we end up thinking that you’re doing it wrong if you are not going full speed, working 80-plus hours a week all the time.”

Despite his own success, Murtagh still wonders if he’ll ever be content with the progress of the business.

“We grew almost 100% for the last few years, but I get no great satisfaction from it,” he says. “That’s not because I am some kind of driven winner like Michael Jordan or something. It’s just the nature of founding a business I guess.”

To help cope, Murtagh tried meditation—but kept falling asleep. He’s found more success with hiring a business coach and setting goals. He also has some built-in buffers that help him balance work and life like walking his oldest son to school every morning and meeting him at the bus in the afternoon.

Still, he often finds himself worrying about how he can attract new business.

“I wrote to Santa in December to ask for more leads,” Murtagh says. “I got a Fitbit instead, though. I suspect my wife intercepted the letter.”

Robb Todd

Robb Todd

Business Columnist at Fundera
Robb Todd is a freelance writer and editor at The New York Times, Fast Company, and elsewhere.
Robb Todd

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