6 Questions to Ask Before Making a Break for Entrepreneurship

By Susan Reilly

As the year came to a close and 2016 launched so many are wrought with emotion, reflection, hopes and dreams. Maybe as you swirled your favorite drink anticipating your midnight New Year's Eve kiss, you suddenly were haunted by the reality of your career. And today, your alarm rang through your head along with that voice saying, "The holidays are over and in a few hours I have to return to that job!" That other voice in your head kicked in your soul and said, "I have to get out of that place,  I am choking!" 

Maybe you get a moment of exhilaration when dreams of launching your own business start dancing in your head? Your vision is clear and 'the angels you have heard on high' take you to the thoughts of following your dreams.  

Take your daydreams a bit further and ask yourself these six simple questions before making the break for an entrepreneur's life.  

1. What Motivates You?

Many people think that entrepreneurs are motivated by money. While making money is certainly necessary for survival, the truth is that many of us are more motivated by freedom—the freedom to push the bounds of creativity and take risks in pursuit of a passion.   

If you are solely driven by money and already have that security, think hard, because you may not see any income for a while. In addition to causing great anxiety, a stalled cash flow could also mean you have to humbly take up residence on a friend's couch or maybe in your childhood bedroom. 

2. How Hard Are You Willing to Work?

If you think you are going to work less and only when you feel like it, think again. Prepare to work harder than ever. The most successful entrepreneurs set very specific office hours—namely, twenty-four hours a day, seven days a week—and our brains churn relentlessly with ideas and concerns.   

Some of my best ideas have been conceived in the midst of pulling weeds or in the early years of Reilly Connect, changing a diaper. 

While Reilly Connect has evolved from a traditional public relations agency to an integrated marketing agency over the years, in the beginning I was a solo practitioner tapped for my expertise as a media trainer and for my strengths as a writer.

Most of my writing began late at night after putting my kids to bed and continued into the wee hours of the morning, when I often woke up with my face plastered to my kitchen table.

3. How Much Do You Care What People Think?  

Are you willing to sacrifice the enviable prestige and comfort of that great office you have for the modest means and environs that accompany freedom and the pursuit of your own dreams? Test your tolerance for public and parental scrutiny.

I left a coveted job and an office with a jaw-dropping view of the Chicago River to start Reilly Connect. My friends and coworkers perhaps thought I was making a rash decision because my life was in a period of tremendous upheaval at the time. I had  three kids in diapers and was suddenly single again. My father knew better. His words still regularly ring through my head: "You will soar!" And I knew he didn't just mean financially.  

Though I obviously cared what my family thought, as time went on, my liberating discovery was that I did not want to be defined or held back by societal norms. I wanted to make a living and do my own thing. Not every entrepreneur has to achieve the success of Richard Branson or Steve Jobs. While the sky's the limit, this level of achievement and financial success is rare yet women are making great strides as business owners.  In fact, according to a report by the Kauffman Foundation, women-owned businesses represent 30% of all firms and could be the catalyst for economic growth in the United States.

Determine what you need to live the way you want. Most entrepreneurs don't give much thought to what people think because we are driven more by internal than external motivations. I remember my brother saying, "Follow your heart and the money will follow." You just need to know what constitutes "enough" based on the lifestyle you want to lead and your obligations. 

4. How Much Are You Willing to Sacrifice Financially?

While our culture is infatuated with wealth accumulation, the entrepreneurs I know (myself included) were initially willing to give up everything to make their dreams a reality.  

Many started with nothing. No trust fund. No MBA. No "C-Suite" connections. Before I made the final decision to launch my own firm, I went through every single expense and asked myself, "Can I live without this? Am I willing to move to cheaper housing with three kids if I have to?"  

This was a freeing exercise. We really don't need a lot to live. If you currently work for someone else, this is an essential exercise. You might find that you want all of the perks that an employer provides, which is fine.  

I was already working 70 hours a week while raising my kids. Taking into account my salary, my child care costs and my cost of living, simple math revealed that that I needed to make every hour of my professional life more profitable and fulfilling while being a devoted mother. Something had to give. I needed flexibility, and I wanted freedom.  

Being a parent adds an extremely challenging dimension to any career and therefore must be carefully considered. The price is subjective. My decision to venture out on my own was a highly-calculated risk.  I decided that if I could provide for my family as an entrepreneur, I was confident that in the end, my kids would look at my life and my accomplishments and say, "She was an amazing Mom." That seemed most important to me.  

It is impossible to have it all but I felt the flexibility of having my own business made the likelihood of good success at both motherhood and a viable career even more viable.

Those of us in the parenting club know it's the most demanding and rewarding job you will ever have, but if you can't or don't want to join the club, you will simply have more time to devote to your business. 

However, don't make the mistake of thinking that you will work less. Expect the opposite. You will have to work hard and smart to balance your work with your lifestyle demands, but knowing you are trying to achieve a dream will leave you more satisfied than working in a job you hate or never trying at all. 

5. How Hard Are You Willing to Hustle?

Work doesn't land on your doorstep. You have to tirelessly seek it and tenaciously secure it. Having innate talent helps, but there are plenty of people with mediocre skills who've built successful businesses.  

At the time of Reilly Connect’s launch, the Internet was not what it is today. As integrated marketing communications and social media influencer experts, technological developments have made building awareness and branding so much more efficient than in the early years of our business.  

Regardless, technology is only one part of getting work. You need a solid business plan with specific goals, timelines and target customers, and you need to stick to your timeline while networking to sell yourself and your business. Many people have failed miserably here.  

Simply put, you need to know what you are selling, and you need to hustle to get the work. And unless you have stockpiles of cash, wealthy parents or investors with deep pockets, you may have to take on jobs that are slightly below your skill level or get a part-time job to pay the bills. Leave your ego at the old office. 

6. Can You Take Out the Garbage?

If you are starting from the ground up, be prepared to do it all. The days of having a cushy office environment may be over at least for a while. All of those daily tasks handled by other staff members that made the day flow smoothly are now up to you.  

Put on your rubber gloves and be prepared to clean up your mess after a full day of following your passion. And if you have a team crammed into a small space, the slobs can't help but reveal themselves before long. This can be fun for a while—kind of like the first week in a college dorm—that is, until the flu hits.

Just remember the garbage pickup is the city's responsibility. All you have to do is get it in the can.


This month, Reilly Connect celebrates our 19th year as an independent digital communications agency. My kids are no longer in diapers, and I don't have to take out the garbage any more.

You will occasionally find me emptying the dishwasher in the company kitchen while eating a late-night snack.