Cherry Leigh Woodburn & Borderless Thinking LLC
From fearful kid to fierce warrior.


I started out in life scared. At the beginning of each school year I was terrified to return – a new teacher, a new classroom – my stomach was filled with knots. I’d end up in the principal’s office crying. I didn’t participate in extracurricular activities because of paralyzing fears.

So how did I get from there to here – a successful entrepreneur for over two decades who has to sell herself and her work; a professional speaker standing up in front of hundreds of people; a workshop facilitator conducting training across North America?

 My answer is three-fold:

1.     Coming-of-age during an era of protests when the questioning of doctrines, government and belief systems was de rigueur

2.     My first professional job and the expectations of my boss

3.     Becoming a single mom when my older son was 2 years and my younger son was 6 months


My childhood was difficult. I’m not elaborating because I don’t want that to be my story. What’s important to understand is that I was frightened much of the time, shy, smart, and a talker.

In 1968 I attended Lebanon Valley College because my parents said I wouldn’t succeed at a larger school or one further from home because of my “emotional weaknesses”. I accepted their definition of me while containing a defiant powder keg within me waiting to ignite. The 1970’s provided the spark.

The 60's and 70’s were marked by protests: against the Vietnam War; for Civil Rights; and for Women’s Rights.  I was gripped by a continuous dialogue that questioned belief systems and stereotypes. Debating ideas and challenging prevailing assumptions was stimulating and became my drug of choice. It also made me question my parents belief systems about me – epiphany - I was actually very strong. Inquiry and dialogue became part of my genetic code (discussion #1), hence the name of my business today – Borderless Thinking® LLC .

 I became a Community Organizer - ready to change the world. However, (today I chuckle at my naivete ) the position was with a Redevelopment Authority (RA), funded by Housing and Urban Development, which meant I was to organize the community in support of urban renewal, including the government's big-stick: eminent domain.

I was flying solo at the first point of contact with people in the urban renewal area and my boss told me I needed to make decisions as necessary. He continued, saying he wouldn't be angry with me for making the wrong decision; we’d just work together to fix it. However, he explained, he would be angry with me if I made no decision. What a great thing to be told when launching a career. I learned that mistakes require a resolution not blame and to make decisions without waiting for a boss’s direction. [Discussion #2]

Another Aha-moment came when meeting with homeowners protesting the condemnation of their entire neighborhood under eminent domain. Their homes were to be demolished for green space and building projects that would “renew” the city. At age 22, white, blond hair, blue eyed and the RA representative, I walked into a tension-filled room comprised of people much older than I, with black skin, black afros, and mostly males. Their spokesperson was outraged because he/they believed their neighborhood was chosen for demolition as a way to break up the black community. He understood there was a system for purchasing their houses but they liked their row homes and the new home(s) each family found would be scattered throughout the city, thereby losing the community they had within their neighborhood.

It was an eye-opener for me, realizing that I’d projected my white, middle class values on them – assuming they would want what I wanted: a single detached home with space away from my neighbors.  I also questioned if, in fact, HUD did want to break up the black community. Divide and conquer. Diminish their strength by dispersing them throughout the city and beyond. I became unsure of what I knew and believed.

I left my job to obtain a Master’s in Public Administration (MPA). Upon completion I worked in more grant-funded programs but became frustrated with the funding process and decided to transition my career into the business world.

Obtaining a job in Employee Relations with GE, I stepped into the culture of assembly lines, manufacturing quotas and labor relations. It was all new to me so I wasn’t burdened with stereotypes about union members but quickly learned they had stereotypes about me because I had “joined” management. Many management members also had their preconceived notions about the union and work ethic among the employees. When production numbers weren't met they assumed the primary problem was the people rather than looking at all the contributing variables within the system. Their knowledge of variability and data analysis was old-fashioned because they had not yet heard of Dr. Deming's work,  TQM and what became the Six Sigma movement.

In hindsight, it was another lesson in the importance of questioning assumptions and belief systems. As Grace Hopper said “The most dangerous phrase in the language is, “We’ve always done it that way.” [Discussion #3]

I became pregnant at the same time GE was flying me to job promotion interviews. My husband and I decided that a new job, a new geographic area, and a new baby was not what we wanted. It meant I had to quit GE, which led me to choose to became a stay-at-home mom. [Discussion #4]

My marriage ended when my sons were 2 years old and 6 months old. It was a watershed event, primarily because I decided that come hell or high water I wasn’t putting my sons in day-care full time; they had “lost” their father and they weren’t going to lose their mother to a professional job that inevitably required more than a 40 hour work week. [Discussion #5]

My drive for the work/life balance I wanted led me to all types of freelance writing jobs. It meant writing at home at any hour of the day as long as the deadline was met. As the kids grew and I wanted more challenging work I became proficient in conducting statistical problem solving training and team dynamics as well as process consulting. When it came time for the teams to develop their hypothesis, I did what I loved and helped them surface and dispel outdated paradigms that were keeping them from an innovative solution.

I remained an independent contractor to maximize my flexibility. I had jobs across North America and spoke at conferences on continuous improvement, Six Sigma, team development and communication skills. It worked well for me for almost two decades.

Professional issue

When my sons began living on their own, I changed my work to my passion: helping women question their belief systems and assumptions regarding how they see themselves and the role of women.

Through professional relationships and the mentoring I received as part of the SisU pilot mentoring program at the George Washington University School of Business, I improved my business and marketing strategy. However, I realize I've been resisting certain aspects of implementation because of fear.

It’s back-to-my-childhood, almost cliché-based, fears:

  •   Who do you think you are wanting to have a successful business doing what you love…especially during a recession.
  • Who are you to set high financial goals?

I know these fears are fairly common among females. When I experienced them before, I plowed through my fears because my goals were related to my children. Now, however, the work and success I want are clearly mine and for me.

It's a paradox: afraid to step out and be who and what I want to be and also knowing that I'm a strong, powerful, bright woman. [Discussion #6]

Personal issue

It's easy for me to isolate. I live alone, I mostly work alone. My income is greatly reduced due to changing careers and the recession, so I can't afford to do a lot of activities that would take me outside of my home.

This can cause me to ruminate on life's daily challenges; it keeps me from having stimulating debates except on-line, which doesn't have the immediacy of in-person dialogue. I don't have my viewpoint challenged nor meet the diversity of people and situations that I need to grow both personally and professionally.

Paradoxically, often when I'm with people I find they're not interested in engaging in dialogue and debate. Some see it as conflict, others exhibit a sound-bite mentality, not knowing about a subject beyond the headlines. [Discussion #7]

Wrap Up

I need to accept and live with paradoxes and the contradictions inherent in them. If I've learned nothing else in my life I know that things are not black and white. It's accepting that it's also true within my own life.