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A Message For The Next Decade - Shana Schlossberg, Upward CEO

Upward CEO Shana Schlossberg speaks at Upward Labs first Demo Day at Upward Hartford

It’s hard to believe that ten intense years have passed since launching my first business venture. As I look to the new decade and imagine the great change it will bring, I find it more important than ever to reflect on the important turning points in my career, in particular the clarity and direction I found precisely ten years ago.

In October 2010, after years of working myself to the bone, it dawned on me that although I was very good at what I was doing, and rather comfortable in the lifestyle it provided me, I had no immediate or fulfilling connection to the outcome of my extremely hard work.  I had reached a place where I could no longer bear the thought of working this way. And so, without wasting another moment, I resigned from my job, packed up my things, and ran away from it all. 


I found myself as far away from the life I had come to know -- in the heart of bustling Bali, Indonesia. The streets were wild, noisy, and beautifully chaotic. After enjoying a few days immersed in the welcomed distractions of this exotic destination, I felt it was time to really disappear. I settled in a remote, peaceful and quiet island called Lombok where I shut off my phone for 30 days and simply disconnected. I knew that if I created enough quiet within, I would find the guidance and direction I was seeking. The island was stunning and I spent my afternoons soaking up the sun, walking, exploring, and visiting the local villages. 

One afternoon, I came across a simple two story, stone building with no more than a mud pit as a yard. Here, playing happily in the mud were about 60 bright-eyed children who called this orphanage home. If making mud pies and chasing one another could bring them so much joy, perhaps I could really make their day by bringing some gifts from the markets I had seen in the nearby villages. I asked the staff what items the children might enjoy and the unanimous response was CHOCOLATE. While this would be an easy treat to find, I had hoped to give them something they could enjoy much longer than a sweet. I asked if they liked toys and was shocked to hear that none of these children had ever owned a toy in their life. I couldn’t help myself – I immediately rode to the town and filled my cart with anything and everything that resembled a toy.  My loot consisted mostly of coloring books, crayons, music makers, random trinkets, and, of course, chocolate.

Hours later, I returned to pass along my presents. I was completely unprepared for the realization that was to follow.  The looks these children gave me as I handed them things they had never touched, experienced, or understood filled my soul with such overwhelm.  It was far more than the simple fact that they now had ‘toys’ to play with or things to own. Instead, it was as if a gateway to a new experiential dimension had opened right there in front of me. To witness these children so genuinely experience something for the very first time -- to gain awareness of something they had never before known. To see the sheer astonishment, enlightenment, and gratitude come over the children immediately altered my trajectory forever.  I had felt first hand what it was like to be an agent of change -- to help others encounter seemingly extraordinary things for the very first time.

How could I continue to manifest the same emotion in my day to day? What would this look like back home in my environment? And how in the world could I make a living doing this?

A few days later, I had the idea for my very first venture. Six months later, I had raised enough money to hire a team of developers, and shortly thereafter we launched our product. I was officially a social entrepreneur. I had no idea what I was doing, but knew what I wanted to achieve. Today, there are many resources set up to guide new startups. Back then, in the tech world especially, it was like the wild west, where you figured it out on your own. Trial and error. A little success but mostly failures.

The last ten years have not been easy by any stretch of the imagination. Every day has provided its own struggles and lessons learned. There have been countless times when I felt it would be easier just to give it all up and return to a life of stability and sanity. But whenever it got tough, I would connect to that moment at the Lombok orphanage when everything seemed simple and achievable. A place and time when purpose presented itself so clearly. As the years went by, taking risks and making decisions that would have terrified me ten years ago have become surprisingly easy. And now, as a serial entrepreneur and ambitious businesswoman, I have finally reached a place where I am comfortable.

But we don’t grow when we’re comfortable. Enlightenment comes from discomfort and true leaders realize the influential currency that is found outside of the comfort zone.

I want to become an even bigger agent of change, and more importantly a promoter of risk. I like taking risks and I’m pretty good at it. But there’s more to risk than stimulation and short lived adrenaline. Risk is the future of the world in which we live. In the next decade, I plan to embrace this reality and use it as a catalyst for making even greater change. I am raising my own stakes, promising to create more, create faster, and bring a vision to life that many may not understand -- but one that will impact more people than I’d ever dreamed.

I am raising my own stakes, promising to create more, create faster, and bring a vision to life that many may not understand -- but one that will impact more people than I’d ever dreamed.

We can all agree that in the last ten years our world has changed significantly, in large part due to technology. That growth isn’t linear, and technology is being developed at a faster pace than ever before. The next ten years will see such an exponential shift, a hundred times over what we saw in the last few years alone. We may not recognize our world one decade from now if we continue to live life cautiously. Many will be left behind because of inevitable, technological disparities. Most of the innovation that is coming our way will likely make us uncomfortable but the only way to survive is to adapt and help others to do the same.

Thriving in the unknown and turning discomfort into productivity is this world’s next form of natural selection. Those who can adapt, evolve, and embrace risk will rise with the changes to come. A risk taker sees change like an adventure – whatever comes at them they willingly accept and overcome. We must start practicing our adaptation to change and risk immersion today.

I implore you to join me in this frame of mind and make this your approach to doing business and living your life. Teach the art of risk taking to your children -- challenge them to be the generation that does not function out of fear. By doing so, they will envision, invent, and embark on journeys of humanity we cannot even begin to imagine in this ever changing world. 

In closing, I challenge us all to celebrate the craziest of ideas and believe that everything is possible. Take one risk every day, no matter how small, and prepare for the revolutionary decade to come.

May the next ten years be filled with history making and boundary breaking adventures!

- Shana Schlossberg


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