Thinking of Starting Your Own Business? Planners Share Their Biggest Challenges

Every year, millions of people start their own businesses, despite the fact that, according to the Bureau of Labor Statistics, 20% will fail in their first year, half will fail after five years, and 65% will fail in 10 years.

Among those taking the leap are meeting planners who decide to set up shop either by choice or because they have lost their jobs or been forced into early retirement. 

Challenges faced by independent meeting planners include budget constraints, cash flow issues, and finding skilled staff. For Eric Rozenberg, who started Event Business Formula in 2017 to help other small businesses, the need to do everything himself almost led to his downfall.

“When I started my first business, I made a classic mistake: I thought, it’s my company, my brand — nobody can do it better than me.

“For two years, I ran projects entirely on my own. It was exhausting and unsustainable. I was stuck in a hamster wheel: Finish one project, scramble for the next, and repeat.”

It wasn’t until he hired a team and learned to delegate that things began to change. He recalls spending his first weekend off since starting the business doing nothing but worrying that something would go wrong. “Guess what? It didn’t,” he said. “My team delivered, and I finally had the time and mental space to focus on growing my business instead of just surviving.”

Cash Flow Issues

According to SCORE, a nonprofit organization that provides free business mentoring and resources to small businesses, 82% of small businesses fail due to cash flow problems. The majority, roughly 64%, choose to handle their own bookkeeping using accounting software.

Hiring an accountant from the start is a smart move, said Steve Hoffman, a former IRS Agent for 15 years who specializes in tax advice for universities. Meeting planners who have always had their taxes withheld by employers may struggle to file estimated quarterly taxes, and failure to do so can result in penalties from the IRS.

Small businesses often overlook basic deductions, such as mileage, by not keeping accurate track of expenses. “Getting professional advice early on can save time, money, and headaches in the long run,” he said.

Flexibility is Essential

Caryn Taylor spent 28 years at the technology and investment firm SEI, working her way up to vice president, events and experience. She started her own meeting planning and strategic planning company, The Caryn Taylor Network, in January. Her major challenge, given her extensive years of planning experience, has been to stick to the specific services she offers.

“On one hand, having a clear focus allows me to carve out a niche, establish a strong reputation, and create streamlined processes. On the other hand, limiting my scope can be restrictive, especially when I can imagine the potential opportunities that are beyond my initial vision.”

After being laid off last month from her position as director of convention and meeting planning at a global religious organization, Fiona Nieman established her own meeting planning company, Indaba Events. She is already experiencing how different it is from planning meetings, which she has been doing for almost 30 years.

“I soon realized I would have three different roles within my company: the entrepreneur with the vision, the manager of the business, and the employee — the person doing all the work,” she said. 

“As a meeting planner, it’s so easy to revert to what you know and love best: meeting planning. Yet as a business owner, you have to take a zoomed-out approach to your business and see it not just as a series of events to plan, but as a business to build, nurture, and strategically grow for long-term success.”