Kim Kleeman’s devotion to work/life balance has allowed her to play the roles of young entrepreneur, educator, wife, and mother. She has created a full-service, PreK–12 educational development company that not only is incredibly successful but also allows her to embrace her many roles in a unique way.

After graduating from Loyola University of Chicago with a bachelor’s degree in English and a 6–12 teaching certificate, Kleeman began her career as a teacher. During the next five years, she instructed elementary and secondary school students. Despite her love for classroom teaching, she decided to leave the classroom to obtain more flexibility for her family. 

While teaching, Kleeman discovered an alternative way to pursue her passion for education. After successfully creating a supplemental revenue stream as a part-time freelance writer, she decided to utilize her teaching and entrepreneurial skills to create a full-time business.

In 2003 Kleeman and her husband co-founded Shakespeare Squared. The educational development company provides editorial and design services for both textbook and trade book publishers. As president of Shakespeare Squared, Kleeman supervises her employees’ work on PreK–12 textbooks, workbooks, test preparation programs, and teacher guides.

Kleeman has earned numerous awards and recognitions. Inc. magazine identified Shakespeare Squared as one of the Top 500 Fastest Growing Private Companies in America. Working Mother Media also recognized Shakespeare Squared as a Working Mother 25 Best Small Companies due to its innovative, parent-friendly environment. By providing flexible hours, remote workstations, FMLA benefits, a working parent’s office with children’s room, and a stress management room complete with yoga mats and aromatherapy, Kleeman enables her employees to pursue their passions and find balance in their lives.

Kleeman continues to develop unique ways to support education. She recently founded two new companies, UpGrade Education and the Shakespeare Squared Foundation. UpGrade Education is a multimedia company that creates quality creative and practical products for students, educators, parents, and the educational publishing community.  The Shakespeare Squared Foundation is a not-for-profit organization that offers student teaching scholarships to deserving and qualified applicants. With Shakespeare Squared, UpGrade Education, and the Shakespeare Squared Foundation, Kleeman has established herself as an agent of change in education.

When you first started your career/business did you feel passion for your work?
I told everyone that I would never own my own business. But personal circumstances dictated the path to my starting and growing a small business. I didn’t know that I had the entrepreneurial gene. I discovered that I can do this!

When you first started were you able to visualize your final outcome?
I knew I wanted to be successful, but I never visualized the amount of success Shakespeare Squared has achieved since co-founding it in 2003. The company grew over 800% from 2003–2006.

What were your top three obstacles/challenges?
One of my biggest challenges was breaking into an industry (publishing) with which I had no experience. I had to network aggressively to get in touch with the key players. My other challenge is rapid growth. I address this by hiring freelancers from an untapped pool of talent: working parents and former/current educators. Also, it was hard for people I knew to translate the fact that I was going from being a teacher with no business aspirations to a full-time business owner.

How did you deal with doubt, fear, and self recrimination?
I have a great support system. Since my mother, my sister, my best friend and my sister- in-law work for me, they often give me pep talks. My husband is a very conservative person so he is a sounding board for many of my ideas. If he’s on board, then I know I can do it!

Did you feel that the traditional male dominated workplace affected you at all?  If so, what did you do about it?
Educational publishing is not a male-dominated industry. My staff of 23 is almost all female, and most of the freelancers we hire are current or former educators, publishing professionals, or both—and most are women. If anything, my industry is dominated by women.

Did you have mentors?  If not, why?  If yes, tell us about them?
My greatest source of strength is my family. I meet every morning with my parents for a cup of tea. We discuss whatever issues or challenges the business is facing and brainstorm ideas. My father, a lifelong business owner himself, understands the challenges of owning your own business, and my mom is supportive in every way.

Do you feel you were traditional in terms of your steps to your Optimal Level?  If yes, if no, please explain.
No. Business ownership was not “Plan A.” Plan A was being an educator. My husband, whom I met in college, is also an educator. But raising a family on two educators’ salaries—narrowed down to one when my husband was a student teacher—was too difficult.  Shakespeare Squared grew out of part-time, home-based freelance work that my husband and I took on to supplement our income while he was a student teacher. Also, I work very, very hard to maintain work/life balance. And to allow my employees to do the same, Shakespeare Squared offers benefits that most companies do not: customized maternity leave, flex hours, part-time and freelance opportunities, a parent’s room for employees who need to bring their children in to work, sabbaticals, and more. My goal is to build a company that helps employees achieve work/life balance and to also maintain that for myself.

As you look back, what is the one thing you wish you knew when you started?
That joining associations like WPO or Vistage would help immensely. They have aided me in working on my business more than I ever thought I would.

Any regrets?
None, I don’t believe in having regrets.  I look at each decision and each turn as being part of the path I’m on. There’s no time to look back; I am in the present, using my experiences I have learned along the way to enable me to move into the future.

Do you believe luck had something to do with your rise to where you are now?
Sometimes I think that not knowing exactly what I was getting into was a saving grace. My husband and I knew we wanted to be educators and raise a family. I didn’t know that this is how we were going to do it, but here I am!

Do you feel you paid a price to be as successful as you are now?
No, I feel I have worked hard to balance my life in a way that works for me and my family.

What is the best piece of advice you have for other women on their way to their Optimal Level?
Build your personal boundaries as you build your business. That way, you’ll have no regrets.

Do you have any other tips for career or business women?
Believe you CAN do it! Having confidence is more important than anything else.

What do you think is the biggest mistake career/business women make?
Having the what-if’s. Boldly go where no one has gone—it’s OK, what’s the worst that can happen?
I live by this quote:  “If you knew you could not fail, what would you do?”