How to Balance Enterpreneurship and Personal Life: Penny Wing


A Serial Entrepreneur

Ep. 30 - Penny Wing Starting a business isn’t always easy – but when you can start, grow and sell your business, it’s a great opportunity! Described as a Serial Entrepreneur who has created and sold several businesses, Penny talks about how to deal with the work-life balance when you have aging parents with health issues, a business that needs a new home, and keeping a still-young marriage alive.  In this episode, Penny talks about her success in the travel and hospitality industry, business risks and issues, and handling family issues. Listen in to learn how to recognize your professional strengths as an entrepreneur and enhance them to succeed. You will also learn how to stay sane by adopting the right attitude when life hardships and struggles get the better of you.


  • Taking the opportunities to grow professionally by learning under a successful person
  • How to get to know your professional strengths and weaknesses as an entrepreneur
  • The things you need to know before investing in a technology company
  • How to mentally readjust and keep sane to deal with the struggles of life, family, and work
  • Find something that you love and enjoy and figure out how to make money out of it

"When you start a small company, you can choose to stay small or take the opportunity to learn from someone else how to make a larger company." -Penny Wing

In this episode you’ll discover:

Penny talks about her childhood and educational background experiences with different cultures [1:40]

Her experience studying mathematics as a Caucasian woman in Japan in the 70s [5:32]

How she first became aware of racial and gender inequality in the business world [9:49]

She explains her success in the travel business, especially with group travel [12:19]

Why she bought, build, and sold travel businesses plus her love for building businesses [18:26]

She explains her challenges in business management as opposed to building a business [23:23]

How her parents influenced her successful career plus how she balanced her work and life [27:33]

She narrates the story of her life as a stepmom to 3 girls, marriage life, and living in England [31:31]

Penny explains why her technology company is the hardest business decision she’s ever made [36:06]

How her life is changing juggling caring for her aging parents and a struggling tech company [44:36]

How to have the right attitude when balancing the hardships of family, life, and work [48:13]

What Penny would do differently as an entrepreneur, investor, and as a wife [55:02]

The importance of finding a career that you truly love to enjoy your professional life [1:08:18]


Penny shares the story of her globe-trotting life from England and Germany to Japan and back to America. She describes making the challenges associated with the transition between a variety of countries cultures. She shares with us the experience of working with Professor W. Edwards Demming; the guru credited with the beginning of quality, productivity, and competitiveness.

She has started and sold three businesses and is now CEO of Plan the World, a travel incentive and event planning company. She is President / Co-Founder of and CEO/Founder of Brojure LLC.


Penny Wing has a graduate degree in Mathematics under Professor Demming of the W. Edwards Demming Institute in Japan who is credited with the beginning of quality, productivity, and competitiveness.


Plan the World Website



Cristine Crandell

Andrea Stevenson Conner

Jamie Amelio

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