I have been down in DC the last few weeks, among other things, talking to lawmakers and regulators about cryptonetworks and cryptocurrencies.  As part of that, I've been spending a lot of time with attorneys -- specifically securities attorneys -- getting into depth on issues like the definition of an "investment contract" and case law like Howey, Reves and Forman. Separately, I've spent a bunch of time over the past 9 months helping USV portfolio companies getting ready for the EU's new privacy regulations, the GDPR.  As part of that I have spent a bunch of time with tech teams, attorneys and others unpacking not only what the regulations require in different cases and what it will take for companies to comply, but trying to think about ways to make data security and privacy compliance easier for small startups, assuming that new regulations in the US are looming. This is not a post about cryptocurrencies and whether all ICOs are securities, or about how we should be thinking about solving privacy and security problems online.  It's about getting comfortable in that sweet (& sour) spot where you know a little (or a lot) less than everyone else in the room about whatever problem you are trying to solve. I am not an attorney, am not a PhD computer scientist, am not an economist or monetary policy expert, and am not an MBA and don't have a background in finance. Yet every day I find myself in the middle of some set of issues drawing on all of these specialties, typically with people who are seasoned experts in one area or another.   It can be intimidating, but it's also incredibly stimulating and exhilarating. There have been many times during my career where I have stood at that crossroads and had an opportunity to either stay in the comfort zone or wade into the discomfort zone (starting at USV 6 years ago was one of those moments).  I'd like to say that I've always headed straight to the discomfort zone, but I can't say that that's true. It has taken time for me to get comfortable being uncomfortable. One of the great things about working in the discomfort zone is the ability to be honest about your limitations -- in a room full of lawyers, leading with "i'm not a lawyer and you guys are the experts, so..." can be really freeing.  Once you can do that, you can open yourself up to lots of interesting and important situations. A while back, I tried using this heuristic for prioritizing my time: what's the hardest thing I can be working on right now?  That has helped me guide myself to the discomfort zone more and more, which I will keep doing as much as I can.