The Expectations vs. Realities of Owning a Small Business

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Entrepreneurs are visionary by nature. Optimistic but realistic, they’re bold risk-takers willing to gamble it all if it means building something for themselves and breaking the chains of W2 employment

But they aren’t fortune tellers.

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Unless you’ve been there before, there is simply no way you could imagine the stress, joy, exhaustion, exhilaration, disappointment and deliverance that comes with running a business until you take the leap.

The ‘Boss’ Illusion

It’s good to be boss. Bosses sit in plush reclining chairs with their feet up on the desk, cigar in mouth, barking orders at underlings who scurry to do their bidding — in the movies. The reality is rarely so glamorous. 

“We often hear about the freedom that owning a business will afford,” said Eugene Gamble, founder of weFUNDyourFLIPS. “The image of having people who do all the day-to-day activities while you are the big-picture person who delegates is common. I wasn’t naive to believe I would be sitting behind a large desk having the occasional meeting. I understood the importance of working hard, but nobody prepares you for just how hard you have to work to be successful. The reality is that as the business owner, you have the greatest responsibilities and you have to work several times harder than anyone else in the company.”

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Novices Underestimate the Minefield They’re About to Enter

Murphy’s Ninth Law states that nature always sides with the hidden flaw. This is never more true than it is for entrepreneurs — something Felix Bodensteiner, CEO of the SaaS firm TableLabs, learned the hard way.

“My expectation was that we could build and sell additional functionalities to the existing larger customer base, starting on day one,” Bodensteiner said. “However, me and my CTO had to spend the first three months — full time — on pure maintenance, such as customer service and bug fixes, leaving little time to invest in new product features.”

But ironing out the wrinkles is part of the natural growing pains. 

“We got to know the business inside out better than we ever hoped,” Bodensteiner said. “On the bright side, we are now in a much better position to decide on strategic decisions through intensive exposure to our customers and technology.”

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Everyone Seems To Underestimate the Elusiveness of Profits

Entrepreneurs naturally chase profits — but on the other side of the coin are expenses. And then more expenses. And more expenses after that. 

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“I had no idea how expensive it would become,” said Joy Gendusa, founder and CEO of PostcardMania. “In the beginning, I was just trying to pay myself. Then I hired my first person and we were working out of my house, so just her salary, and that was expected.” 

She soon had 20 employees clamoring for health insurance. 

“I wasn’t contributing at first but then that was expected, so I started to do it. Fast-forward to 300 staff and it’s $37,000 per month that I have to contribute. When you start giving perks to staff, those perks become expected. So, once you give something, you can never stop — even if things get tight.” 

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Newbies Tend To Imagine Shortcuts That Don’t Exist

If you’re considering starting a business, one of the best things you can do for yourself is to imagine how long it will take, how much it will cost and how hard it will be, and then double it. 

“My personal experience when founding a startup is that things always take longer than you first thought,” said Libby James, co-founder of Merchant Advice. “We’d always be planning for ‘this time next year,’ when in reality, growing a brand and audience to your website can be tough. Our business took a solid three years of commitment and effort to get it off the ground — no shortcuts. When excitement started to fade or doubt crept in, we had to dig deep. I think success a lot of the time is due to not giving up during those harder times, and I’m glad we didn’t.” 

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Your Business Is Your Baby — and Parenting Isn’t Easy

When people talk about entrepreneurs giving birth to businesses, their metaphor isn’t that far off.

“Owning a business is a lot like having a baby,” said Lynn Coleman of Your Epic Business. “You think you know what it’s going to be like, but before it happens, you don’t have a clue. Sleepless nights, unexpected costs, tears.” 

It’s not all gloom and doom, however — over time, pleasant surprises can make it all worthwhile.

“There’s also joy when you land a wonderful client, realize you’ve created something incredible and see your clients grow,” Coleman said. “I started my business because I realized I couldn’t work for a boss anymore. But what I found was a far deeper freedom than being bossless. Now I choose where I take my company. I make my own mistakes. I get lost and find my way back. There’s no one to blame or complain about. The buck stops with me and that’s exactly how I like it.”

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Last updated: June 22, 2021

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About the Author

Andrew Lisa has been writing professionally since 2001. An award-winning writer, Andrew was formerly one of the youngest nationally distributed columnists for the largest newspaper syndicate in the country, the Gannett News Service. He worked as the business section editor for amNewYork, the most widely distributed newspaper in Manhattan, and worked as a copy editor for, a financial publication in the heart of Wall Street's investment community in New York City.
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