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  January 23rd, 2021 | Written by

5 Questions to Ask Yourself Before Taking the Leap to Entrepreneurship

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As COVID-19 causes layoffs and extends uncertainty about employment in 2021, many people are considering new options, reinventing themselves, or trying to decide whether working for themselves is more desirable than finding another 9-to-5 job that might not last.

Entrepreneurship brings a lot of freedom, responsibility, and risks, and before people commit to taking that big step there are several important questions they should ask themselves, says Tim Mercer (, ForbesBooks author of Bootstrapped Millionaire: Defying the Odds of Business.

“Entrepreneurship is a career that offers a kind of freedom and personal satisfaction you simply cannot get from traditional 9-to-5 employment,” Mercer says. “You will never know if you have what it takes to be an entrepreneur unless you take the leap of faith and experience it yourself.

“It’s a big decision, though, involving many factors and inherent risks. There is a lot to navigate and endure en route to reaching your dream destination of professional and financial freedom, and many don’t make it because they simply weren’t cut out for the challenge to begin with.”

Mercer thinks people who are considering entrepreneurship should first ask themselves these five questions:

Why do you want to do this? “Let’s be honest,” Mercer says. “If the business endeavor is just about us, we will want to give up on ourselves when things get hard. Your why, which is your purpose, has to be much bigger than yourself. You must believe in a vision of why you want to be an entrepreneur and develop a plan for how you will involve others in your vision. Sustainable entrepreneurship requires the efforts of other people.” Mercer thinks it’s imperative to write down your ‘why’ and keep it in front of you as a reminder when tough times come.

Are you being realistic? One can get swept up in the emotion of starting a business, but Mercer says it’s vital for every potential entrepreneur to be realistic in their business projections for the first two years of the startup. “Answering this question before you open can prevent some unpleasant surprises as you try to build your company,” Mercer says.

Do you have daily discipline? “You are the boss, and only you can hold yourself accountable,” Mercer says. “If it’s hard for you to stay on task or stay motivated, and you think being an entrepreneur is a fast ticket to easy street, entrepreneurship definitely is not for you.”

Can your relationships survive the sacrifices? The time commitment, Mercer notes, to starting one’s own business and getting it running efficiently goes well beyond a typical 9-to-5 job. Relationships can suffer. “All entrepreneurs have to understand that they are going to be forced to make sacrifices on a personal level with their family and friends,” Mercer says. “You have to stay focused without letting your dedication to your entrepreneurial pursuit harm your relationships with those you are closest. Communicate with them and mutually come up with adjusted expectations as you build the business.”

Can you withstand the struggles? Rejection and failure, Mercer says, are realities that new entrepreneurs have to get accustomed to and learn to overcome. “You need to understand how many times you’ll fail before you’ll succeed,” he says. “You’ll get turned down by prospective customers constantly and your self-value will be tested on a daily basis. Is your why strong enough to keep you going?”

“Overall, deciding whether you are an entrepreneur or not boils down to how comfortable you are being uncomfortable,” Mercer says. “Only time will tell if you have the people skills and business skills to be a successful entrepreneur, but rest assured that you will have to endure periods of real discomfort.”


Tim Mercer ( is the founder of IBOXG, a company that provides technology services and solutions to government agencies and Fortune 500 corporations. He also is the ForbesBooks author of Bootstrapped Millionaire: Defying the Odds of Business. Mercer was inspired to pursue a career in IT as a consultant after he became a telecom operator while in the U.S. Army. After growing up in difficult economic circumstances in the rural South, Mercer achieved success as an entrepreneur, then recovered from the financial crisis of 2007-2008 after starting IBOXG. The company has accrued over $60 million in revenues since its inception in 2008.