I love the question posed in my title.
I really don't know.
It's one that I started hearing with regularity when I started working for Petro-Canada (now re-christened Suncor after our merger with the "old" Suncor). The head of Petro-Canada's downstream business was fond of talking about opportunity development areas as items that "kept him up at night". I thought that was such a great way to explain what others might term "pains in the a*s" or "who is bringing us down so we can fire them?". It made issues seem not quite trivial, but certainly worthy of being resolved through brainstorming and perhaps a good night's sleep!
So what keeps me up at night?
I think the fear of not being relevant when my life's work is done is what does it for me. This isn't to say that I'm so caught up in my own importance - or lack thereof - that I will ignore any other success I'm part of (if not entirely responsible for), nor does it mean that I won't be happy until I'm as famous as Barack or William Gates...no. However, I have set out certain targets that I would love to accomplish between now and the time I'm 35 and others yet that culminate in my 40th year on this earth. None of the goals are necessarily earth-shattering, but I believe they are relevat, not only to my ego, but also to ultimate good of this world - in particular the African continent and peoples of African descent. I realize this does appear to defeat my ego-less pretentions, but rest assured, my intentions are purely altruistic/nationalistic.
By the time I'm 35, I would like to:
- work for myself
- be considered materially successful
- achieve my dream of social entrepreneurship in Africa and perhaps the Caribbean as well
- be able to point to concrete, life-saving (or improving) projects that I've been part of
By the time I'm 40, I would like to:
- work because I want to, i.e. financial independence
- do some missionary work every year, if I'm so led
- expand from where I was at 35, vis-a-vis infrastructure development in developing nations
Of course, there are other personal goals which I won't necessarily elaborate on now :-)
I realize that as time goes on, other things - family, kids, health, mortality and the other realities of life are more likely to keep me up at night, I recognize that a time will come when the small pleasures - walking, talking, eating, sleeping - will matter as much as the big dreams...but I'm happy that I'm still at the stage where big dreams are possible, and I look forward to working to make mine come true. In the meantime, I'll keep working on dreaming up the breakthrough :-)
What keeps you up at night?