It's slightly unclear whether the OP is talking about risk assessment and reducing unknown unknowns, or simply advocating becoming more well-rounded in your problem domain.
Also, I would argue there's much more to consider before offhandedly determining anything you don't know "is the riskiest part of your business". The real answer probably lies in the question: Can I hire somebody to do this, or is it important enough to distract us from other goals? If yes then do it, otherwise reconsider when resources free up.
Money aside, it's great you've created an awesome product for a group that really could use more assistance. Thanks for building something to better the human condition, and showing others they don't need to sacrifice everything to do it!
Fellow "serial over committer" here. I find it preferable to accept all new opportunities, but make sure stakeholders/I understand my availability. After prioritizing, nobody's surprised when some projects complete and others don't gain momentum. If you're letting others down, they probably overestimated your time/resources.
Having used it for a while now, I'm still blown away by how simple (yet effective) it is for getting tasks done. I wish I could escape the world of email, Fogbugz, and Pivotal Tracker... and bring everyone with me to Orchestra. Congrats on the great coverage, hope my wish becomes realized!
Great article, though I would take it one step further and strongly nudge more designers to take on more engineering roles (as many engineers also work to broaden their skill set).
You know, after 2 failed upgrade attempts to Rails 3... we eventually came to the understanding that we shouldn't attempt to simultaneously make "improvements". Because without a green test suite, we had no idea if the failures were new or upgrade related. That was the cause of 99% of worry until we said "fuck it, let's just fix everything first."
While I love this is FOSS, there's is a $1 paid-app that is almost entirely 1:1 with the Snow Leopard (plus features) called "Classic Color Picker". Totally worth it IMO.
Also, I would argue there's much more to consider before offhandedly determining anything you don't know "is the riskiest part of your business". The real answer probably lies in the question: Can I hire somebody to do this, or is it important enough to distract us from other goals? If yes then do it, otherwise reconsider when resources free up.