When it was recently announced I was leaving Ashoka most people assumed I had something specific lined up, that I would only make this announcement, this leap, if I knew exactly where I was landing, that I would land on my feet. But I don't, and I feel okay about that. Humans are hardwired to generally dislike uncertainty. We hold off on making decisions in the face of it, or avoid risky life choices all together, missing opportunities as we do. We have constructed complex religious mythologies around filling all possible uncertainty in the cosmos (repeatedly!).
I'm sure we all know or have known people who are unable to leave a job until they have another assured. Indeed I've known people who could not leave their partners until another came along, even if the passion had gone out of the relationship.
However this is not true for everyone. Amongst many other traits entrepreneurs have an unusual capacity for uncertainty. If you're going to make a bet on the future, and your capacity to make that future, you're going to risk being wrong. But taking that risk is the only way to create the future you desire, to live your dreams and make a difference.
For me I feel my life has taught me that it's vital to commit myself to the path I wish to walk. If I had not been prepared to focus my time and energies into Vibewire, sacrificing the comforts of a proper paying job and, potentially, years of my life, neither it nor I would be where we are now. For years I never had more than a few months worth of funding to pay myself. Once it got down to two weeks reserves before new funds arrived. Uncertainty was a constant.
Now you certainly can't do that forever. But going through times of uncertainty is usually (perhaps always) a necessary part of the most exciting and rewarding journeys. When we left Australia and came to America I didn't have a job confirmed. I had some good leads but knew I had to be here to finalize them. I bet on my success and came over. And now I am prepared to do it again.
I also think it's critical for organizations to accept the uncertainty that comes from trying new things. Especially when technology is involved I think an iterative approach to change, constantly tweaking and experimenting as you go, constantly being in beta, is the only sensible approach.
Humans don’t like to take risks. We are evolutionarily designed to be risk adverse. But good philanthropy, just like good investing, requires taking risks. Maybe a Zen approach to evaluation isn’t just a new age joke. Maybe accepting discomfort rather than trying to overcome it is the key to navigating uncertainty.
Having said all that I normally would not announce my departure from a job without another lined up. The reason I did so this time was more for Ashoka's sake than mine. While we had been quietly looking for a possible successor for a couple of months I felt we needed to accelerate that process by announcing that we were looking. My job is the most outward-facing one in the entire organization and it is essential that there is continuity. As a result of the announcement we've had several strong applications and I'm hopeful of finding someone in time.