On this day, at this time (roughly 1pm) ten years ago I was at my apartment (Allston, MA) preparing for New Years Eve at my friends John and Kris Cain’s house, over in Melrose, MA. That house holds some of my fondest memories of last decade, the 1990s. That year, however, was not one of my favorites. My indie label dream was ending and my life in the music business was over. I knew it was right, but I wasn’t happy about it. I had also been dumped in the summer and it left me reeling a little. Then – get this – my ex-girlfriend moved away and I, like a moron, moved into her vacated bedroom. A word to the wise, people: if you’re trying to get over a breakup, don’t move into your ex-girlfriends bedroom. Don’t do that. I also was very very sick that fall. Not sure if it was mono or something, but it was scary. One night I had such a hard time breathing that one of my roommates, bless her soul, gently knocked on my door at like 3am and asked if I needed an ambulance as I was wheezing and throwing up out my window. I probably did need an ambulance, but not for the physical sickness.

Luckily, by late-autumn of 1999 I was bouncing back. The sting was gone and the scab had started to fall off. I performed my first (and last) physical makeover. Chopped the hair off. Got new glasses. Worked out more. I got a job at an internet startup that was quite ridiculous, but it was “good enough for now.” Most importantly, I started stabbing the shovel into the near-frozen snowpile of debt I’d amassed from starting the record company. Turns out the roommate situation was really ok and the rent was INSANELY LOW for such a big house. I have great memories of our Sunday night Scrabble games and endless amounts of joking around. It helped. More than they ever knew. I do wish they could have seen more of the real me, but such is life.

So I headed over to my friend John’s house feeling a little dread, mostly because of the year I’d just had, but also because there would be three couples there – and me. Myself. Of course, after ten minutes being there, I didn’t care at all and of course, they never cared. They were my dear friends. We laughed all night, ate well, played cards and video games, got drunk and paused in great anticipation to see if the house would explode when the new century hit. Y2K. Then we laughed some more. Boy, did we laugh.

And that’s how I entered the Naughts. A little bruised, but optimistic. I didn’t know it at the time, but two weeks previous to that party, I had re-connected after many many years with the person who is now my wife. I moved to another internet start-up that was a better business idea, but much like other start-ups at the time, doomed to failure. The sun, however, was figuratively shining a heck of a lot more. By February and March, I was dating Stephanie and it was terrific. I can type all day and all night about what she means to me, but you’d just get bored. In short, it changed the whole game for me. We all have regrets. I have lived, learned and grown from previous relationships – that is, after all, what you’re supposed to do – take the lessons learned from failures of the past and apply them to the future to make yourself a better partner and person.

This decade has been the most transformative of my entire life and I owe a lot of it to her. I’m not saying I was a dick before that and gosh, I hope all you folks who knew me in the ’90s wouldn’t say that, but I can say that I became much more thoughtful, considerate and more importantly, aware and sympathetic of other people’s feelings. I’ve made myself learn a lot about the world – past and future. Some of that is my own interest in history and people’s stories, but a lot of it comes from her – that desire to understand and if possible, to help. Yeah, part of that comes with age anyway, I know. But her presence in my life, geez, I’m not sure where I’d be today if it wasn’t for her strength, solitude and selflessness. I can’t sit here today and tell you that I’m a charity machine or that my actions speak louder than these words. Yet. But I hope to soon.

On the music side, the naughts brought me back to the 1980s – just being a fan. Let me tell you, just being a fan of music – and only a fan – is much more fun than trying to make money (and a living) off of music. I met some awesome people in the music business and I can’t imagine I’ll have more pure, drunken, stupid fun than the fun I had during my tenure in it. But being a fan is better and I still have much of those friendships.

Professionally, my goodness. I would have never guessed I’d work at Ask for 90% of the decade. I don’t know that anyone is ever completely satisfied with what they do for an entire decade in a work environment. Personally, I think it might be impossible. But I don’t have much to complain about there. Some of the people at Ask will be my friends long after I (or they) are gone and that to me is the most important part. Connecting.

Of course,in addition to my marriage, part of this hugely transformative decade is the arrival of Nathan & Zachary, my now 2.5 year old twin sons. As all of you parents well know, the job is thankless, exhausting, humbling and at times, difficult. EVERYTHING changes. But for me, the joy can’t be matched. The smiles every day, the hugs, the butchering of the English language (at this stage), it all makes for a collection of memories that is outrageously worth it. I love them so much.

I always told my friends I’d be the last to marry. I always told them I’d probably never have kids. Honestly, I don’t know why I always said that, but I did think it to be true. But time – and people – change. I am not the person I was in 1999 and I won’t be the person I am today in 2019. All I can hope is that a) I’m still around and b) I have the same (and more) people in my life who have enriched it so much this decade. You know who you are.

Happy New Year!