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1 day til 30

The good moments/learnings/thoughts/regrets of the decade in no particular order:

  • Meeting Micky & marrying Micky
  • Moving to California
  • Learning how to build a product
  • Luka
  • Amelia
  • Getting OpenTok built, and convincing Ian it was a good idea
  • Birthday break up
  • Growing up, and building a team at TokBox
  • Building a product that got acquired
  • Buying a house
  • Traveling to new places
  • Supporting friends in their new marriages
  • Cooking an awesome baklava
  • Keeping friends who I’ve known for a long time
  • Making new friends who I’ll have for a long time
  • Losing my fear of the unknown
  • That crazy trip to NYC for New Year’s Eve
  • My bachelor party
  • Most things to do with Las Vegas

I’m sure there’s so much more, but I just can’t remember it all 🙂

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2 days til 30

The bad moments/learnings/thoughts/regrets of the decade in no particular order:

  • Amelia’s surgery
  • Birthday break up
  • Shep leaving San Francisco
  • My family falling apart
  • How hard it is to call people on the East Coast
  • My dependence on always being connected
  • Losing touch with playing soccer more often
  • Losing any semblance of athletic conditioning
  • Being above my target weight at the end of the decade 🙁
  • Not exploring other work opportunities to better understand what I want to do
  • Not starting my own company
  • Not being a better engineer
  • Not spending enough time on charity/giving
  • When Ron got kicked out of TokBox
  • Friends getting divorced
  • Not learning to trust more
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4 days til 30

Biggest moment #4 – Amelia’s surgery

Don’t get me wrong. The babies being born were big moments. But their births don’t really define a person as much as people make it out to be. The whole, “Greatest moment of my life was my kid’s birth” line doesn’t really appeal to me. I think it’s because I don’t see those moments as terminal. They aren’t an ending. They’re a beginning.

In a lot of ways the biggest moments are actually endings of some sense. All the ones I’ve listed so far were pretty major endings to pretty major periods of my life. Amelia’s surgery was the same.

It was after she woke up, and everything was ok, that I lost all of my pessimism about the world. Because between 25 and 28 I tended to be down more than up. At TokBox especially. In my personal life outside of Micky definitely. Well…

Actually, it wasn’t pessimism… it was fear. Before the kids I was afraid of all the choices I was making, and I was even more afraid of all the ones that I wasn’t making. But not the kind of decision where you see that your 3 year old is climbing the 5 year old ladder at the playground, and they’re going to fall. I feared tomorrow. Or maybe unknown outcomes.

And more so, as I think about it, it isn’t actually my fear of unknown outcomes that ended. It was finally being able to comprehend and accept what mortality really meant. That there is a lifecycle for things, and that there is inherent risk in doing something today that may affect where that lifecycle goes tomorrow.

That we could, as loving, first-time, scared shitless, and alone (God, we were so alone) parents, that we could give Amelia to a team of surgeons, head up to the cafeteria, and just not know what was going to happen. That you could fall in love with someone so much at 10 months old that the thought of them being less than everything they could be was a worse outcome, than the thought of losing them to a surgical procedure. And yet sitting in that cafeteria eating really shitty scrambled eggs, and wondering what was normal ever going to be like again.

When she woke up, and we had faced that moment of mortality, when we had taken Kierkegaard’s leap of faith, that moment of being moments from losing everything to being free to have anything, I lost my need to hold onto today because it was to scary to look into tomorrow.

Maybe this is such a big moment because when Amelia woke up, I learned how to fly. And, in the damnedest of roll reversals, she was the one carrying me.

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5 days til 30

Biggest moment #3 – Getting married 🙂

This one had to show up as well… but in a good way 🙂

I asked Micky’s dad for permission to marry her the first time that I met him. That was scary as hell. But Mike’s amazing. First class. He said to me, “Well what if I say no”. And I really had nothing to say. But at that point, I knew it was meant to be I guess.

Then buying that ring almost killed me. I’d never spent that much of my own money on anything. Holy shit, I almost died. I brought Lauren with me to ask her if it was a good ring. She said yes… but I don’t know if I believe her 🙂

Being engaged wasn’t that different than living together. Our biggest wedding fight was over whether I’d booked the DJ or not. That one almost killed us. But we survived.

The honeymoon was my big splurge. Turtle Island was amazing though, and so worth it.

The location was a great compromise. Inviting all the Turkish mafia was meant to be a good compromise, but my parents found something to complain about anyway. That was pretty disappointing.

Mehmet being the officiant was fantastic. I thought his speech was really great. I thought the guitar player was great as well. Jill was amazing. The pies and cupcakes rocked. And the aforementioned DJ was a hit.

The rehearsal dinner was awesome. Not necessarily the event itself, but the food definitely was.

The night was really magical. I cried a lot. I think I was just overwhelmed with too much going on. The people who were there. The people who weren’t there.

There was an amazing after party, and that really capped the night off wonderfully. It will go down as one of the best weeks of my life, and definitely goes in the top three highlights of my twenties.

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6 days til 30

Biggest moment #2 – The break up that rocked my world

It had to show up at some point.

There were only really two relationships in my life during my twenties. The one that worked, and the one that failed spectacularly. It just took five years to get there.

When Giana broke up with me (on my 25th birthday, over the phone, while I was at work), I was destroyed. I took half of December off of work claiming to be “burnt out”, and just went home to try to figure out what the hell had just happened.

It really messed me up, and there are parts that I’m definitely still unable to piece together.

But holy smokes was it the best decision for both of us. Not simply because of Micky and the kids and how wonderful everything is now. But because we were actually awful for each other.

Giana would have held me back, and I would have drowned her. Our families would be even more incompatible than I assumed at the time. And I think we ultimately wanted very different end games out of life, and that would have led to a lot of friction.

I couldn’t have seen it then, but Giana was right to end it. And I genuinely think we’re both better off five years later.

It’s crazy that this will end up on both the best and worst things to happen to me this decade lists, but I guess time and reflection have an amazing way of painting such a picture.

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7 days til 30

Biggest moment #1 – Moving to California

The biggest moment that I can think of… the one that really defines all of the rest is moving to California.

I never wanted to stay in North Carolina. It was never going to be a big enough pond for me. Matt Davis was already out in California, and I wanted to join him, and then the two of us were going to take over the Valley.

I was interviewing like crazy.

I got to 2nd round interviews with Mint, first round with Apple, second round with Google, and I just couldn’t close the deal. I interviewed with agencies, hedge funds, and everything in between.

I read TechCrunch religiously, and applied to every company that showed up (well, every company at Series A and lower).

I was desperate to get into the ground floor, and ride the roller coaster to the top of the Silicon Valley dream.

After 20 some odd interviews, I walked in the doors on Tennessee Street, and convinced the TokBox crew to hire me.

I don’t think I was that good… I just think they were desperate. And sometimes that’s all it takes.

Shep got a job out in San Francisco as well, and we moved out together. My parents didn’t want me to have a room mate, but I didn’t want to be alone. Having Shep was huge for me. It got me through so much that first year.

And then everything else just falls from there.

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8 days til 30

Out of nowhere while I was reading my blog back log on Amplifize, I came across this blog post on Kottke.org. Apparently 1984 was quite an awesome year for music, movies, and the 1980s in general.

The article failed to mention that I was born in 1984, but I’m sure that will be added at the appropriate time 🙂

Up next are a few days where I dig into the biggest moments of the decade.

Then I’ll finish with two lists – the worst moments of the decade, and the best moments of the decade.

It’s been a really introspective time, and I’m really excited that folks have read it, have been a part of it, and I look forward to writing all of our stories over the next decade.

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9 days til 30

Holy shit we’re in single digits

This idea was contributed by one of my most loyal readers who has asked to stay anonymous. But he’s got a full list of great ideas that I’ll be using over the next few weeks. If you have an idea, then please let me know it!

How do you feel about being so much more privileged than most of the world knowing that you’re probably pooping in the water they drink?

If you know my anonymous questioner, then you’ll know that this question is straight in her/his alley.

The truth is that I didn’t realize this until very, very recently.

I was on Quora (I think), and the topic was why was the image for Human in Wikipedia the one that was chosen. The editor involved said when you think of the world’s population, then you realize that most of it is in Southeast Asia, most of it is below the poverty line, and that most of it survives on subsistence farming.

And that blew my mind.

Because I’ve never been in a situation where a McDonald’s wasn’t 10 minutes away. Or not having running water wasn’t a choice.

I then remember reading that the cheeseburger is truly a modern invention because you never could have all the ingredients fresh before refrigeration, global trade, and year-round growing cycles.

And it wasn’t that I wasn’t intellectually aware of starvation nor of drought & disease’s ability to ravage a nation.

It’s just that practically I didn’t realize how many people it affected. I didn’t realize how big of a lottery win it is to be born Caucasian, in the US, middle class, and never really needing a helping hand from the weather, the soil, and randomness.

And so the feeling that comes to mind is awe. I’m in awe of how lucky I am. And I only really realized it in the last few years.

Stunning isn’t it?

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10 days til 30

This past weekend we headed back to Asheville, and got to spend time with some of my closest, oldest friends.

I really miss NC. I haven’t made the kinds of friendships out here that I thought I would mainly because I haven’t found a way to make everything work. And the thing that’s suffered the most is building relationships in CA that don’t revolve around TokBox.

And when I get back together with this crew (and now the +1s that are starting join), I realize how great good friends really are.

They bitch with you about things that don’t matter, and there’s no need to fix it.

They tell stories about when you were an idiot, and how they contributed to that moment in ways that only they could.

They make you laugh, and cry, and think about how lucky you really are.

This weekend was a great reminder for me that you can go home, and it doesn’t mean you didn’t make it.

Gosh I love these guys. And because of this weekend, I appreciate the crew I have built in CA that much more.