If there were a high-stakes test for business management, marketing or making money, I would be sent to remedial classes, stat. I have been failing in my business daily and flailing all over the place trying to figure it all out.

I failed so much that up until about 2 months ago I had choking anxiety over a scene that played over and over in my head – my husband, daughter and I sat on cardboard on the sidewalk of 5th Avenue (a very fancy street in Naples, FL), and begged strangers for change. My daughter’s tiny, dirty hands held up her Styrofoam cup as people walked past ignoring our pitiful gaze. My husband shaking his head while I apologized over and over again for ruining our lives, for making a decision that landed us on the streets.

To me, avoiding homelessness was a miracle. I started ConversationED one year ago as I took the biggest risk of my life. I walked off the job as an assistant principal. I had benefits, I had a substantial paycheck (for public education), and I was living in a Florida style, stilt home across the street from the beach. It had shutters and porches and tall ceilings and curtains that swayed in the breeze. I left it all for this dream that soon became one failure after another.

I had no team except a partner I thought for sure would leave because we made no money. I alienated every professional contact I had made in the last 7 years in public education. With nowhere to go and no one to talk to I tried everything. And everything crashed and burned.

I launched a webinar for leaders, it was free and only 15 people signed up. I also launched a social media course for the classroom, also free but cost me close to 500 bucks to produce. Only one person signed up for that. I had to write her an email and cancel the class. It was humiliating.

More failure came when we pushed to grow a high-stakes testing opposition movement and sell #boycott t-shirts. I bought 300 and 20 sold – the box is sitting pitifully in my office as a reminder of this disappointment. Most of my blogs went unnoticed, uninspired, unread, and unshared. My husband and I even dipped – by dipped I mean dove – into our savings to realize my dream, ConversationED. To this date, ConversationED hasn’t made a dime.

All the while, my husband went to work every morning, walking out the door encouraging me to keep going as I fell on my face over and over again.

As the New Year approached, I took the tree down, cleaned up the house, and decided to tidy up my digital clutter along with the holiday carnage.

I flipped open my Mac and came across a document on my desktop that said “goals”. I opened it, thinking they were most likely exercise goals I hadn’t come close to achieving in 2014. Did I mention I gained 20 pounds as I flailed and failed?

There on the page I saw my goals for ConversationED or my Painted Picture. This was an exercise I attempted after I read some heady business book that outlined how you should visualize what you want your company to look like – see it vividly in your mind so you can manifest it. Give me a break, I thought as I scrolled down the page.

  1. Be self-employed.
  2. 500 likes on Facebook.
  3. 500 Subscribers to ConversationED content.
  4. 500 twitter followers.
  5. Talk to important people.
  6. Help parents, students, teachers and anyone else stand up and fight for what is right.
  7. Publish consistently.
  8. Keep moving forward and don’t look back.

I remember number 8 vividly because it was an attempt to open the blockage in my throat and the knot in my stomach I felt every morning when my feet hit the floor as I got out of bed. I had nowhere to be, no job to go to, no team to lean on, no students to talk to in the hallway. Just my computer and me, in a house near the beach I could no longer afford.

I squinted. Were these really my goals? They seemed so easy to achieve now. 500 likes on Facebook? We have close to 2500 likes on Facebook. 500 Twitter followers? We have 1050 Twitter Followers. 500 subscribers to our content? With all of our email lists combined we have over 2000 subscribers.

“Number 5, talk to important people?” I asked out loud and chuckled. Since last January I had met with legislators, governors, school board members from all over the country. I also went to Dallas several times to meet with someone I thought for sure I would despise, but later fell in love with, Glenn Beck. We now call each other friends.

As far as helping parents and students, ConversationED, along with other groups like Opt Out Orlando and Opt Out Lee County, has mobilized communities to storm district and state buildings, demanding changes in testing policy. We provided a free webinar, that lots of people showed up for, to help parents understand high-stakes tests and how to refuse the tests. We even convinced a district to “opt out” of all state mandated tests. They later opted back in, but that’s not the point. We had crushed number 6. We had grown a movement.

Number 7, publish consistently, was happening as well. For a year I published a blog and newsletter every week. I posted a podcast every month and we engaged our audience on social media, daily. Now we have other writers who provide us amazing content as well (thank you writers!).

I leaned in and stared at goal number one – to be self-employed. Well, I’m definitely self-employed. I can’t pay myself but I’m not homeless.

Far from being homeless, December was ConversationED’s best month in 2014 with over 80,000 views. To my surprise, in the first 5 days of the year, January has beaten out every other month with over 140,00 views. When I quit my job a year ago only 3 people were reading my blogs and one of those people was my husband.

Finding that list banished my feelings of inadequacy and I felt a deep desire to share my failures, so students, parents, and teachers can embrace the failure we are desperately trying to avoid in education.

When measured against other online media businesses or the “standard”, I’m a colossal failure. When measured against myself and measured against the realistic goals I had set and achieved, I’m a huge success. Most importantly, the struggle to learn and pick myself up from these failures has made me a titan.

We should all fail and fail big. And when we pick ourselves up, fail even better.













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