Ten Strategies I Used To Move From Teacher to Entrepreneur

“There are lots of bad reasons to start a company. But there’s only one good, legitimate reason, and I think you know what it is: it’s to change the world.” – Phil Libin, CEO Evernote

When I was a little girl, I wanted to be a teacher, a journalist and an author. In high school, you could find me staying up late at night under my covers with a little book light writing a narrative or translating the Canterbury Tales from Old English to New English. I fell in love with words by the time I was ten years old. The sounds, feelings and the power that came alive on a page naturally enlightened my universe.

It was in my junior year in high school, when my English teacher, Dr. Dieter, first noticed a few of my narrative pieces. Dr. Dieter was an icon in our school and was well known for her tough-love pedagogy and unyielding strategies to stretch the minds of all of her students. She paved roads with soft notebook paper and provided the opportunities we needed to find our strongest pens. To this day, our woven relationship brought together in that classroom remains.

When it was time to look down my path toward college, I wavered between journalism and teaching. I became an elementary teacher and taught public school for six years and went into higher education for another five.

Every academic year, Dr. Dieter would come to my classroom and read to my fourth-grade students for Dr. Seuss’ birthday. Her encouraging words to continue writing never left my side. And the pen remained.

My Continued Love for the Written Word Never Ceased

Over the years, I continued to write, not because I wanted to, but because I had to. Writing is part of my unique build, like a nucleotide within my DNA. Most of my early work was about my childhood. I found these stories challenging to share; they were about my father, a man I never knew well nor did he know me. He walked away from my family when I was 11 years old, leaving behind a crater of poverty and pebbles of the unknown.  

Loss, fear and childhood insecurity permeated the narratives I wrote. Nevertheless, these anecdotes were filled with moments of triumph, flashbacks of smiles, and a bond between a mother and her children that couldn’t be expressed in words.

Regardless of these uplifting outcomes, I only shared my work with a few close family members and friends. The stories notably moved those around me. However, I kept these narratives close to me, rarely letting anyone else into this space.

I didn’t believe my work was worthy enough to be shared, and I was afraid of judgment and adverse reactions. This is where my mindset stayed for quite some time.

In 2011, I had to make a difficult to choice to leave higher education. I learned about web design and chose to focus on writing about my great passion for education. I began interviewing innovators and game-changers in the education field. At the same time, without realizing it, I was reinventing myself as well as my career.

Although LinkedIn noticed a vast amount of my work over the past few years (which I am eternally grateful); it was at this point when others outside of my circle began to notice my work. Ouch, my comfort zone was starting to shake.

Enter The Word: Entrepreneur

Did you know that some teachers make the best entrepreneurs? According to Rod Grimshaw, the CEO of TES Global, “Some of the best innovators, fundraisers, and problem solvers are often found at the front of a classroom. There’s another, much simpler reason the education technology market is taking off: the teachers pioneering this market make great entrepreneurs.”

Here are Five Reasons Why:

1. Sales And Marketing Come Naturally
2. Teachers Are Natural Fundraisers
3. They Know When To Throw Out The Playbook
4. Teachers Know What Students Want
5. They Care-They aren’t in it for money

And Then It Happened. Someone Called Me An Entrepreneur.

He looked just like this guy.

However, I was still struggling to refer to myself as a writer. In my mind, I was a teacher, end of story. The entrepreneur world was part of an entirely different orbit. My thoughts about myself or how I could grow continued to hold me back from leading my career journey toward its full potential. I went on in this manner of, what some may call denial, for quite a long time.

Until Something Magical Happened. Hello, Brené Brown.

Over the past year, Brené Brown’s life-changing work came into my life. Her research about vulnerability altered my entire mindset. If you haven’t seen her TED Talk, The Power of Vulnerability, I suggest you watch it. In a recent article on LinkedIn, Brené said it best, “We need braver, more authentic leaders. We need cultures that support the idea that vulnerability is courage and also the birthplace of trust, innovation, learning, risk-taking, and having tough conversations.”

I was hiding in this space of vulnerability; and it was at this moment, that I began to work on believing in myself. And every day, I take an organic step forward toward changing my mindset and continuing my reinvention.  

If you’ve struggled with these changes or haven’t reached an “ah-ha” moment, I hope these tips I’ve learned can help you.

Ten Strategies I Use To Reinvent Myself And My Career

1. Meetings with Vulnerability: I have meetings with vulnerability. I walk slowly toward it, and I am now able to share a little bit more about my personal life in my work.  
2. Believe: I work on believing in myself. If I don’t believe in my work, who will?
3. Speak and Write: I talk about what I want in life, and I write it down (similar to The Secret). I wanted to work in education and journalism, and here I am today. I also wanted to work with smart, talented and exceptionally friendly people (you’ll meet him below).
4. Pay Better Attention: I listen more carefully to my inner voice.
5. Listen to Others: I listen (instead of hearing) to the voices around me, especially from those who are non-biased. I take notice of people who take the time to offer advice or compliment my work.

A Focus On Others

I want to focus on #5 because many people had a tremendous impact on my life as a teacher, a writer, and dare I say an entrepreneur. Their words inspired me to move when I didn’t want to glimpse. I believe when people with more experience take the time to compliment your work (sans an agenda), it is a good idea to pay attention, to be thankful and especially, remain humble.

Here are a few people I want to thank because they changed my life for the better through their words of encouragement. There are far too many to add here, so please know I appreciate all of you who have played a role in my life.


Susan Cain, whom I met through LinkedIn, had a tremendous impact on my personal life. After reading her book, Quiet: The Power of Introverts in a World That Can’t Stop Talking, I had a tremendous awakening in reference to self-reflection, understanding my introverted traits and especially bringing my passion of writing and painting back up to the surface. And most of all, Susan is so nice and especially encouraging.


You can read the rest of my journey on LinkedIn.

About Me:
You will find me on LinkedIn’s new application among Influencers via the education technology and management channel. I am also the Editorial Director at MindRocket Media Group. Please reach out if we can help you tell your story.

I also manage ED News Daily, contribute to the Huffington Post and was recently featured on Cision’s Influencer Blog. Please follow me here or via Twitter.