It’s 2006 when my attorney calls and says, “Alana, your company is officially sold!”
I respond flatly, “Oh ok, thanks,” and end the call.
Suddenly, I feel like I’ve been set out to drift in space and just received the last communication from Earth. I know all the business calls and emails are over.
My friend says, “That’s amazing. You sold your company! What do you want to do now?”
I reply, “Get an ice cream?”, but all I’m thinking is, “Who I am now? What do I do with my life?”
I grew up in New York, a relentlessly curious child with a father deeply intent on raising an entrepreneur.
“What business are you going to open up when you grow up Alana?” he would often ask. He didn’t care if it was a hotdog stand as long as it was mine.
My curiosity first showed up in my deep interest in philosophy and studying the ancient wisdom traditions. Instead of watching TV, I would sit, read, and research, in all-consuming fascination.
So ingrained was my thirst for knowledge that when I was 11, I went to the library almost daily for a year and studied all the world’s religions. (At year’s end, I proclaimed myself a Taoist philosopher).
I grew up to be an entrepreneur, but my insatiable appetite for ancient wisdom got left on the sidelines. I saw no way to put the two together. Until one day…
It was 1996, and I’d just joined EO, a network for entrepreneurs.
At their requisite training day, I sat enchanted as the man leading it taught us special communication skills that had roots in the Eastern wisdom I’d learned about in the library.
The content and the setting set my soul on fire.
I thought, “OMG, this guy is getting paid to teach these wonderful tools to entrepreneurs! … I wish I could do
that one day!”
I ran my video business for 10 more years before selling it in 2006. I’d recently completed a deep and diligent clarification of my core values, but I felt lost as to where to apply them in the world, how to turn them into a business and a meaningful life.
I was living in New York, Italy, and London at the time. On a flight from New York to Marrakesh for an EO event, I had two thoughts. “I need to meet an EO member from London.” (I knew I could network.) And, “One thing I’d love to do with my life is lead forum trainings.” (This was a wishful thought without feasibility.)
When I arrived in Marrakesh there was one empty seat left on the shuttle. I sat down next to a tall, blonde woman who introduced herself, “Hi, I’m Julia. I’m President of the London E.O. chapter.”
That was easy, I think to myself!
Then 10 minutes later into our chat, she says to me, “I don’t know why, but I have the sense that you would be great at leading forum trainings. I’m going to nominate you!”
As I filled out the application, I wanted the opportunity more than anything I’ve wanted in my life.
Becoming an EO Forum trainer showed me my life’s work.
It wove together the strands of who I am on the deepest levels.
For 12 years, through EO, and my own retreat company, I’ve worked with thousands of people around the world doing what I love.
In 2009 I founded MI6 Academy and Stiletto Spy School, additional ways to do my work in the world.
Today my answer to my Dad’s question about what kind of business I’m going to own when I grow up is simple,
Dad, I own a business where I am a guide on the path to present and self-aware leadership – and I’ve never been more fulfilled.
Alana Winter is a serial entrepreneur, creative thinker, and guide on the path to self-aware leadership.
A master at helping others unearth their roadblocks, Alana runs retreats, workshops, and one-on-one trainings to help transform the lives of business leaders and their teams. Her unique efforts have helped thousands of people worldwide become their best selves.
She is recognized as a leader of leaders for her extensive work with Entrepreneur’s Organization and Young President’s Organization forums. Ms. Winter built and operated several entrepreneurial businesses, including a fashion accessories company in Australia and three successful video distribution companies in the United States.
She is also the founder and President of MI6 Academy and Stiletto Spy School, where participants learn to see challenges in new ways, overcome fears, blow through obstacles, make calmer, clearer decisions, and achieve success in the boardroom and life.
Alana’s programs and businesses have been featured on NPR, The Today Show, E!, CBS Morning News, ABC, the Wall Street Journal, Psychology Today, NY Daily News, Men’s Fitness, Tyra, and many other major news and media outlets internationally.
Ms. Winter earned a B.A in psychology from Wesleyan University and has lived in Australia, London, Italy and New York. As a child she got thrown out of every ballet school in New Jersey.