2016 Year in Review

Wow, what a year.

Honestly, I wasn’t very interested in doing my Year in Review (as I’ve done in the past for ‘15, ‘14, ‘13, and ‘12),  but I eventually overcame my general inertia about it and sat down to give it some thought.

Honestly… where to start (and what to include)?

Previously, what I’ve done to jog the memory is walk through my archives and copy and paste titles and then expand on them. But, today, I feel like that is cheating (and I can’t tell you why).

There’s a part of me that wants to just write what first comes to mind, which might mean that the things that first come to mind are the most important or perhaps more poignant memories of the year. Perhaps… both?

I’ll start at the beginning, I suppose… … … …

When January 1st, 2016 rolled around I was gainfully employed at an early-stage startup and what would eventually (quickly) become the third failure to “land” here in Silicon Valley. I would be fired exactly one week later on January 8 and the reason I remember this date in particular is because it was the 5th birthday of my youngest.

Getting fired on someone’s birthday is never cool, especially if it’s your own (ewwwwww)… but it’s just as bad when it’s on your kiddo’s bday. It really sucked. And although I experienced a number of different emotions I was, above all, angry.

The next day I resolved to start my next company. I wrote a bunch of posts around that day including this one about the value of leadership and how to spot good leadership (and leaders) and this one about starting something out of frustration (or even hate) and especially this one about fooling oneself.

Long-story short, I fooled myself not just three significant times in 2015 but I started off 2016 by deceiving myself once again and I started putting together a new project out of anger.

(Oh, and I could write a book on why those three attempts failed and, if I did, this is where I’d start – that’s all I’ll say about that… for now…)

Sure, it looked like a good idea (and it was, and is…) but anger is never sustainable and it’s just not something that I can easily weaponize into something meaningful. Others might be able to, but, I can’t, and that was a big lesson for me to learn.

I went on to build multiple prototypes, get term sheets, fire my cofounder, and then get hired as my first Entrepreneur in Residence at an early-stage VC Firm. Success and failure all wrapped neatly in a big, red proverbial bow, getting a bit closer to “Person/Market Fit,” as I like to call it.

I’d be remiss if I didn’t say explicitly that I’m incredibly grateful for everyone who had to interface and deal with me during the first 6 months of 2016 – I was moody, shaken, and a bit stirred up. I especially appreciate the close circle of friends, colleagues, family, and mentors that didn’t give up on me.

Self-deception is real. Add any layer of emotional instability and it’s a concoction best avoided at all costs and last year I found myself inebriated and deeply hung-over with it. If I’m honest, I’m probably still recovering. The wounds are still painful to review.

In the middle of all of this I found footing in my family, the long-list of scheduled events around soccer, hackschooling, and other fun activities (a lot of eating good food). There’s no way that I would have been able to successfully weather the storms that I walk into (and create for myself) if it weren’t for them.

I also spent a ton of time meeting new people, dedicating myself to filling my calendar and expanding my IRL social network as much as I possibly could. My chief motivation was to reduce the insanity of working on another venture and the other half was because I had spent the first year of my time in SF building products instead of relationships.

I wanted the pendulum to swing the other way and I also wanted to spend more time giving back and booked out a number of coaching and mentoring clients quickly. I don’t always have good advice but, I tell my clients, I do have stories, rich narratives that span the emotional gamut. Sometimes the stories matter more than the prescriptions.

I invested so much of my time into the relational components that I had to give up some more of the technical ones; so, for a time, I shelved my award-winning app, Desk, and told folks that I was done. I lied. Or, rather, I ended up just taking a break and 5 months later it was back on the menu.

I reserve the right to change my mind (you should too). Strong opinions, weakly held type of stuff. Move things forward quickly, strongly, and with conviction. But, when given new information or things significantly change in your surrounding environment then, as a natural consequence, your mind and body should follow, in wisdom.

A very visceral and obvious example of this was when I started my vlog and then quit and then started it again. And, again, I reserve the right to start and quit a thousand times more before I get to the very end.

But hey… along the way I celebrated 11 years of marriage, my oldest turning a decade, and a corporate decision to renew a year lease on our apartment in San Francisco. It meant that we were here and committed to be here and to make and build our lives and our future, as successful or unsuccessful as it might turn out to be, here. A big step, one of cautious, optimistic faith.

Finishing out the year was packed with routine. I say that in the best way possible as that’s what I needed more than anything, especially considering the first year of landing in SF/SV. There were a few family “firsts,” like using an EpiPen and a few new experiments, like making failure normative and turning anxiety into excitement as well.

And as I meandered a bit, practiced putting people before everything else and putting into practice the principle that our actions create the very things that we believe, it gave me the courage to do scary things and developing a rhythm that is unique to me.

Finally, If I am to look back at most of the writing that I’ve done it’s so lopsided on self-discovery and new awakenings of self-awareness that it’s deeply frightening. This means, among many things, that when I first started the 2016 year, I hadn’t the faintest clue of who I was and what I really wanted to do.

It means that, as I begin this 2017 year, it’ll probably be a bit more of the same; maybe more than I’d like to admit. 2016 was a year of desperate self-improvement, an unwelcome gift that slowly became a truly unforgettable year.

And I hope that I can write the same thing a year from now, if I’m to be so fortunate, blessed, and lucky.

Also published on Medium.