Laura Bogart

Mon, Jun 2, 2025, 7:08 AM3 min read

Running a successful business feels like an art form. You’ve got to assemble all the right pieces in all the right ways to create a masterpiece. And sometimes, along the way, you’ll make mistakes. But these mistakes don’t have to make the canvas irrevocably ugly — if anything, they’ll teach you how to work with your materials to create something lasting and beautiful.

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With so many decisions to make, from managing client expectations to choosing the best insurance, most experienced business owners will admit they have a few regrets. But the successful ones didn’t let those missteps smudge their long-term vision. GOBankingRates spoke with some entrepreneurs who’ve faced those regrets head-on — and built thriving businesses despite them.

When Merilee Kern, MBA, a brand and product marketplace strategist, analyst and pundit, began Kern Communications, she believed that “constant availability leads to effectiveness.” Being in the PR world, it’s understandable why she thought she had to respond to every request or communication immediately.

However, she soon learned that the pressure to deliver rapid-fire responses can lead to rushed, shallow work — and burnout that can absolutely scorch your creativity and strategic thinking. To avoid this, she restructured her business with intention.

“Immediate responses to every notification and email and direct message can actually decrease the capacity to achieve high-quality results for clients,” she said. “So we have structured deep work blocks to disable notifications while dedicating time to strategic high-value tasks. This strategy includes curating an internal culture that provides recognition for results achieved — not just quick response times.”

To free up even more creative and strategic thinking time while still ensuring timely client responses, Kern’s company also developed standardized templates for common interactions, like intake forms and reports.

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Starting a business — especially one as robust as VIQU IT Recruitment — involves a lot of work. And sometimes, things fall through the cracks. Unfortunately, Matt Collingwood, founder and managing director of VIQU, learned that the things you overlook can eventually become costly.

“Sadly, we tragically and unexpectedly lost one of our major shareholders in 2020,” he said. “In order to move the business forward, we were required to purchase the shares from the estate of our deceased shareholder. That transaction took over 18 months and placed significant strain on the business, particularly on our cash flow and growth opportunities.”