How I Reinvented Myself and Changed Direction: Ten Strategies That Took Me 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

As a child I wanted to teach, write for newspapers and publish books. By high school I was staying up late under the covers with a book light, writing my own stories and even translating the Canterbury Tales into contemporary English. I fell in love with language early — the sound of words, the feeling they create and the transformative power of a page opened my world.

In junior year, my English teacher, Dr. Dieter, noticed my writing. She was known for her tough-love approach and for pushing students to stretch intellectually. Her encouragement and relentless faith in the craft helped me find my strongest voice. That classroom relationship shaped much of my future.

Facing a choice for college, I wavered between journalism and teaching. I chose teaching and spent six years in elementary classrooms and another five years in higher education. Every year Dr. Dieter would come back to read to my students for Dr. Seuss’ birthday and remind me to keep writing. Her words remained with me, and so did my pen.

My Ongoing Love of Writing

Writing has always been part of me — not an obligation but a necessity, like a strand of DNA. Much of my early work revisited childhood memories, including stories about my father, who left when I was eleven. Those stories were rooted in loss, fear and insecurity, but they also contained moments of triumph, laughter and the unspoken bond between a mother and her children.

For a long time I shared those pieces only with close family and friends. Though the stories resonated with others, I doubted their worth and feared judgment. That doubt kept me quiet for many years.

In 2011 I made a difficult decision to leave higher education. I learned web design and focused my writing on my deep interest in education. I started interviewing innovators in the field and, without fully realizing it, I began to reinvent both my career and myself. LinkedIn began to notice my work, and gradually people beyond my small circle did too. My comfort zone started to shift.

Teachers Make Natural Entrepreneurs

Many teachers bring skills that translate well to entrepreneurship. As Rod Grimshaw, CEO of TES Global, observed, educators often become innovators, problem solvers and natural fundraisers because they understand how to motivate and connect with people.

1. Sales and marketing come naturally.
2. Teachers are adept fundraisers.
3. They know when to throw out the playbook.
4. They understand what learners need and want.
5. They genuinely care — they’re motivated by impact, not money.

Despite the evidence, I still hesitated to call myself a writer or an entrepreneur. I defined myself as “teacher” and nothing more. That internal narrative held me back until I encountered work that changed how I saw vulnerability and leadership.

Vulnerability and a New Mindset

Brené Brown’s research on vulnerability was pivotal. Her message — that vulnerability is courage and the birthplace of trust, innovation and learning — helped me move out of hiding. Embracing vulnerability allowed me to believe in my voice and to take consistent, incremental steps toward reinvention.

If you haven’t seen the TED Talk “The Power of Vulnerability,” it’s worth exploring. For me, the ideas it presents were a turning point in learning to accept uncertainty and to lead more authentically.

Ten Strategies I Used to Reinvent My Career

1. Meet with vulnerability: I intentionally open conversations that include personal details. I move toward vulnerability slowly, sharing a bit more of myself each time.
2. Believe in myself: I practice confidence in my work. If I don’t believe, who will?
3. Speak and write my goals: I say out loud and write down what I want. Declaring my ambitions — to work in education, journalism and with brilliant people — helps make them real.
4. Pay attention inwardly: I listen more closely to my inner voice and instincts.
5. Listen to others: I truly hear feedback from trusted, unbiased sources and those who take the time to offer advice or praise.
6. Notice the signs: I stay alert to opportunities — emails, conversations and chance encounters that point the way forward.
7. Respect fear: When fear appears I quiet it, but I also recognize it as a sign I’m in a new and growing place.
8. Take action: I act when signals are clear and also create forward motion when things are uncertain. Confidence has taught me to be assertive without being aggressive.
9. Allow mistakes: I accept that errors are part of learning. Making mistakes is essential to growth.
10. Practice saying no: As a recovering people-pleaser, learning to prioritize my time and set boundaries was transformational. I still help others, but I do so more intentionally.

The Power of Others’ Encouragement

Listening to people who offered honest encouragement had a big impact. A few individuals whose feedback mattered to me:

• Susan Cain: Her book Quiet helped me understand my introverted tendencies and reclaimed my passion for writing and painting. Her support was kind and inspiring.
• Tom Tuohy: A social entrepreneur and friend who encouraged me to consider the start-up world and recognize the broader value of my skills.
• Daniel Roth: Executive Editor at LinkedIn, who consistently encouraged my writing and offered public and private praise that motivated me to continue.
• Edith Moricz: When I initially declined an interview, she gently invited me to share my reinvention story in the future, validating that my path was entrepreneurial.
• Louis Salguero: A friend who took the time to share heartfelt feedback on my writing, which helped me feel seen and appreciated.

And of course I’m deeply grateful to my mother and my husband for their steady love and support.

Want to Share Your Story?

This is a bit of mine. I’d love to hear yours. If you’re on social platforms, you can seek me out by name on Twitter and LinkedIn to connect and continue the conversation.

Reinvention isn’t a single leap; it’s a series of small, deliberate choices: to listen, to act, to fail, and to keep moving. If you’re contemplating a change, start with one of the strategies above and build from there. The path shifts when you choose to step into it.