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Updated: Sep 2, 2019

While describing my upcoming extended career break to my friend Eli, he understandably asked “Why?”. And as I embark on this new chapter in my life, I’ve tried to answer that question, both for him and myself.

But first, let me put some things in context.

I just ended an incredible five-year adventure as the co-founder & CEO of (You can read some posts from this period.) Five years of joy, of doubt, of ups, of downs, of excitement, of fundraising, of awards, of risks, and of walking this thin line that separates success from failure. It ended very recently – not in the way I could have imagined 5 years ago – but we definitely grew the business to a point I never thought we would when I first started with my partners.

On the personal side, I became single in January after five years with my ex-girlfriend.

Sometimes there are many signs around us that are telling us something very specific if we are open to hearing and seeing them. Somehow today, the constraint of running a large business and the obligations of a long & committed relationship are no longer a part of my life.

So I have decided to go away – Six Months – Far – Remote. In very simple & probably challenging ways. The six months started a few weeks ago, and as I write this from France, where I am visiting my family before the big travel begins, I feel the urge to answer Eli’s question: “Why?”.

In a country like the US, where the average American takes just two weeks holiday every year, taking six months off is often considered “extraordinary” or even “crazy”. To quote a few of the reactions I’ve heard: “Aren’t you afraid to go so far away?” – “Don’t you think it’s risky to leave the work scene for so long?” – “It must feel scary to go alone for such an extended time.” – “Isn’t it dangerous to go to some of those countries?”.

Fear, fear, fear. In the US we live in such a fear-based culture. Just turn on the TV or open any newspaper if you ever doubt this. So making a decision that is NOT based on fear is a challenging endeavor in many ways.

So Eli, here are my answers:

1. I felt the urge to give back. After having the incredible chance to build Totsy, receive all those awards, and meet & work with some of the most incredible technologists and e-commerce people, I wanted to find a way to give back my time and my skills to those who need it the most. So part of this extended travel is going to be spent working for various NGOs – from taking care of dying people in the organization of Mother Theresa in Calcutta to teaching English to young monks in a Tibetan monastery in Nepal. And also raising awareness and $$$ for my favorite NGO,

2. I felt the urge to step back. When you are working 24/7 for so many years, especially in a city like New York, you can lose sight of a true or more whole vision of the world. You see things only through your close environment. And like a fish in a fish tank, you start to believe that the fish tank is the ocean. So going away allows you to realize the ocean is just a little fish tank. Ok, not a bad one I agree, but still, a fish tank.

3. I felt the urge to look at things differently. This is probably the most difficult thing to do when you are “trapped” in a career. How can you filter opportunity – like hearing a story from a friend in a very profound & very different way than your usual outlook on things? Our brain is hardwired in such a way that our thinking process is automated to such a point where we are not in control. Think about the cappuccino you have every morning and try to resist passing your local Starbucks and not have the desire to buy one.

4. I felt the urge to question what I really should do next. In some ways this is linked with the need to step back and look at things differently. But this is where putting myself in places where I will have time to investigate myself is needed. So part of my time is going to be in retreat places where you are “forced” to do nothing but to look inside.

5. I felt the urge to mark this new life transition with a big symbolic trip. There was a time, and there are still places, where “rights of passage” were/are an essential part of a persons development. As a child in some tribes in Africa, you had to go kill your first animal alone and with the most simple of knives. This was done to force you to face your own fears. The inside “beast” we had to fight was in fact much more dangerous, and invisible, than the lion we had to kill.

So are you ready to ask yourself WHY not take this step?

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