What business are you going to open up when you grow up


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?”

After running my video distribution business for 20 years, I don't know what my work in the world is.

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.)

I could not imagine the synchronicity that would happen next.

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

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.