I visit Facebook.com each morning to type “birthday!” onto friend’s profiles as appropriate. Earlier today I also noticed a post from a friend celebrating his 5th wedding anniversary. “One of the best decisions I ever made” was a partial description of the nuptials. Made me think – what are the most important decisions I’ve made in my life thus far?

1. The decision to have a child

Prior to marriage, my wife and I had discussed our views on family. We clearly both wanted children but as we got down to business later, I dragged my heels. What if I wasn’t a good dad? Could I be successful in my work and my family – where would I get the time to do both as well as I wanted? It also so happened that conception was initially more difficult due to my lazy sperm. But I knew I was just afraid and that fear wasn’t fair to Caroline or, ultimately, to myself. So we went forward with an IVF and very quickly found ourselves with a great little kid that makes every day more meaningful and interesting.

2. The decision to marry Caroline

I was a  serial monogamist but always found my relationships hitting walls – sometimes at three months, sometimes six, etc. The furthest I’d gotten before was ~15 months. With Caroline there was never a wall, never a hesitation. Relationships in my mind aren’t about finding the perfect person randomly. It’s about finding a special person at the right time in both of your lives. We’ve been together for 14 years and married for 10 of those.

3. The decision to *not* stay on Conan O’Brien

I don’t spend a lot of time thinking about my career path, especially the “what ifs” – I love what I’ve had the chance to work on and where I’ve ended up. BUT the most dramatic split in my career tree involved not trying to stay with the Conan O’Brien show, where I’d been working my senior year of college. Note – I’m not saying it was right or wrong to have left – this isn’t ‘best’ decisions, it’s most important decisions. Staying with Conan could have unlocked an equally interesting path fulfilling creative pursuits but it almost certainly wouldn’t have led my into tech, google/youtube, homebrew, etc.

4. The decision to restart therapy in 2011

I was pretty confused the second half of 2011. No longer running product at YouTube, a pregnant wife, physical pain from some repetitive strain injuries in my arms/hands. Blah. I’d tried therapy earlier in my life and it was helpful for a particular phase. So I returned to it with a new psychiatrist and he helped my find lots of clarity. It’s something I continue to pursue because I’ve found it to be like training – you stay with it, through ups and downs, for maximum results.

5. The decision to go to Baghdad in 2009

It would have been easy to turn down the chance to visit Baghdad in 2009. There was a war going on. None of my family members were particularly enthusiastic about it. Work was busy and this would be a week away. But I went. And it was amazing. It’s become a reference point for me about how saying “yes” to things always leads to better, more interesting possibilities than no. And how there’s a positive momentum you build when you lean in, when you take risks.

So there you go. I wonder how these might change looking back five, 10, 50 years from now….