03/19/2014 12:06 pm ET Updated May 19, 2014

Success and Failure in Entrepreneurship, Part 2: The 'Glass Half Full' Outlook

In the Exponential Age smart, established companies will find ways to work with innovators vs. looking only internally for new products and services. Smart investors will make bets on women entrepreneurs. And of course, passionate women entrepreneurs will dream big, work smart, and move fast."

-- Carol Realini, Serial Entrepreneur, World Economic Forum Technology Pioneer

"My advice to my fellow entrepreneurs? Follow your flow, cherish crazy ideas, and experiment constantly. Treat your business as a permanent 'beta' version."

-- Guido Kerkhof, Entrepreneur, Innovator, and Marketing Consultant

I grew up in the golden age of Disney films and in the aftermath of the Challenger explosion and the birth of the Apple computer. I'm part of the can-do generation raised after the Equal Rights Amendment was debated in Congress, and during the rise of the supermodel and the gradual fall of communism. I'm someone who actually knew about Aliza Sherman when I became a MacGirl Evangelist in special education in the '90s, and that it was just a matter of time before the first leg of the Technology Revolution changed our lives forever, starting with the dot-com boom.

All along, friends and colleagues called me Pollyanna Penina, a euphemistic nod to my optimism. Pollyanna is actually a noun defined in the Merriam-Webster Dictionary as "someone who thinks good things will always happen and finds something good in everything." I guess it's because I'm someone who believed Steve Jobs when he said, "the people who are crazy enough to think they can change the world, are the ones who do."

Right after graduate school, I joined the ranks of professional folks who "think different": about education, about technology, and recently, about entrepreneurship -- and I've never looked back. I'm a proud member of the human race, composed of different people and different outlooks. It is through personal experience, i.e. partaking of the collective story, that I have gained a better understanding of the entrepreneurial process, and all its feats and foibles. Of the intangible traits one needs to hone to achieve success; empathy, conscious and unconscious time management and sequencing, and honesty; with oneself and with others.

Success today means embracing that humanity but balancing it with technology; psychologically and intellectually.

It means redefining busyness vs. being busy. It means learning to be truly productive, reframing one's successes and failures, and actively pursuing increased self awareness and coping strategies. Why? To counteract perfectionism and multi-tasking; the banes of our entrepreneurial existence and the silent self-employment killers.

Results matter, especially in entrepreneurship, when one's service/product is measured by profit margins, metrics for social media marketing, and the size of one's client base. But a founder's outlook matters more, in the initial phases, and in the long run, when obstacles appear, setbacks occur, and failures happen.

In my last post here, I touched on the anatomy and benefits of experiencing failure in entrepreneurship. Something that has historically happened to some of our greatest leaders, inventors, thinkers, and writers, such as Theodore Geisel aka Dr. Seuss, whom I also wrote about previously. His life's work is both a study in failure deconstruction and psychological warfare, especially if you interpret his prose for his Cat in the Hat using your entrepreneurship lens.

Failure has also historically been experienced more frequently by female entrepreneurs than their male counterparts. Why? Is it our risk aversion (and if so, is that biological or societal)? Is it due to an ongoing quest to capitalize on originality while still producing a Minimally Viable Product? Is it because of the continued "glass ceiling," the "good old boys club," and the "youth culture" mentality, all still prevalent in venture capital and tech-hub circles such as Silicon Valley?

Whatever our perceptions of success in entrepreneurship, let alone women entrepreneurship, it is clear that the process, the journey, contributes to that success, not just the end product and outcome. It is becoming more apparent in this Digital Age, i.e. Exponential Age we live in, that this outlook, this distinction, is more crucial than ever. It's greater than employing a growth hacker or being technologically connected.

True success in today's startup culture is about creating an ecosystem with multiple entry and exit strategies. A collaborative, creative, and socially and morally balanced milieu where an entrepreneur can survive, thrive, and actively dampen perfectionist tendencies. So that success becomes a true "sum of its parts", not a linear (that's a myth!) outcome of shortsighted thinking and actions that result in the pursuit of profit above purpose. Something we've seen time and time again in the afterglow of CES hype and in the recent letdown and realization that WhatsApp users can be hacked.

Do I have all the answers? Did I ever write a definitive to-do list like some others have? Do I know the secrets to success, especially in entrepreneurship? The answer is an emphatic and thankful no. Emphatic because authenticity and humility are integral to the human experience. Thankful because remaining a work in progress, to forestall fear of mistakes, boredom, inertia, and stagnant thinking, are all integral to the human experience as well.