10 Things I Learned in 2016

Some of the writers I respect the most have been reflecting on their years. (Hi, Ryan Hoover, David Spinks, Bo Ren, Winnie Lim, Tony Stubblebine 👋🏼). I don’t write often, but when I do, it’s worth it. Writing helps me clear my head, focus, and uncover new thoughts I hadn’t articulated even to myself. Here goes.

2016 was a year of change and introspection for me. A year of powerful breakups, lost friends, and physical injuries. We pivoted the company I co-founded multiple times, and ultimately shut it down. We were acquired, but unexpected circumstances meant most of both teams (ours and theirs) were laid off late in the year.

But I learned that in challenging times, it’s important to bring intention to how you think, focus on what’s possible, and take massive action. So, reframing: Let’s call it a rebuilding year. That’s the biggest thing I learned. Here’s nine more.

“If you’re going through hell… keep going.” — Churchill

“You might get out before the devil even knows you’re there.” — Rodney Adkins

Adversity reveals who you are. In Emissary’s acquisition (and I hear this is common) there was a lot of pressure to lay off non-technical employees. Everyone’s loyal when things are great, but times that truly test your values are rare. I stayed loyal to my team and investors, and we found a solution that worked for everyone despite advice that it wouldn’t be possible. I’m proud of that loyalty, and it was repayed. Our entire team stayed with us, even those on commission, despite the uncertainty.

Adversity also reveals who your friends are. There are friends who back away during times of loss, and there are those who run toward you. It’s a cliche, but I learned who my real friends are. Shoutout in particular to Ryan Hoover, Jonathan T., and May Alba, who consistently showed up, usually before I even realized I wanted them to.

Cliches are cliches for a reason. No one sets out to ship with low standards, hire “B players”, or make fake friends, but they still fall into the traps. It’s visceral stories (or experiences of your own) that really drive the lesson home. In 2016, I learned to seek out the deeper meanings behind cliches. Whenever something seems reductive, obvious, or even wrong, I pause for a minute, and start with the assumption that there’s hidden wisdom to find.

I learned the power of focus. “Focus” was my theme for 2015, and for me, that meant at the micro level: being present, single-tasking, and seeking flow. I picked a #1 priority for every day, then used Momentum to reinforce, and daily stand-ups for work accountability. Jonathan T. gave me a MyIntent bracelet so I’m reminded every time I look down. I haven’t taken it off since.

With big goals, think in terms of “outcomes first”. Most people start with what they’ve done before, or what they know is possible, then project forward in time to set milestones and pick a goal. “I’ve been jogging five miles a week, now I’ll do ten" or “between (these initiatives) at work, we estimate (this result) in six months”. Kamo Asatryan taught me the value of thinking in reverse. Start with a goal that seems achievable but still scary enough you’re not sure you can do it. Now, what would have to be true in order to accomplish that? What solutions do you need, what might you have to learn, who might you have to hire? Keep in mind both you and your team get better with time, so you’ll be capable of new things even six months from now, and progress will compound exponentially. Starting with outcomes first helps you stop thinking with current constraints and take advantage of that personal growth.

Consistent training gives vastly better results than the norm. One of my 2015 goals was to bike 2,000 miles (double my previous year). This fall, I was way behind my cycling goal. Due to work, life, and travel, I’d given up. “It happens — I wasn’t even home for a lot of the summer”. But I realized being one of the 8% who actually achieve their New Year’s Resolutions, and achieving this goal in particular, mattered more than I was letting myself realize. So I recommitted. I’d have to average 40km a day to do it. (Talk about outcomes first!) That seemed scary but not impossible. I fought through injuries, rain, frostbite, and bike repairs to do it. But after just four weeks of consistent riding, I was in better shape than I’d ever been, regularly doing 100K in a single ride, and on a 10,000 mile/year pace. That 2,000th mile felt incredible.

I realized a driving force in my life is helping others achieve their goals. It’s the thing I’ll do even when I’m exhausted, because their drive is infectious, and I always leave excited to watch their journey. I started remembering the obstacle course I made as a kid to teach neighborhood friends how to skate; my first “startup”, selling my class notes to other students; the long nights in college lecture halls leading study groups. In 2016, I kept my long-standing founder 1–1’s with Spinks, and organized weekly founder group sessions in SF, both to help myself and connect others. I started advising on growth for my friends’ startups and the wonderful people at The Refiners. I had a blast volunteer-teaching programming with Rails Girls, won a friend’s hack-a-thon, was humbled to speak with ex-prisoners, and open-sourced many of my side projects.

I try to remember: There’s nothing like teaching something to test your own knowledge. Even if it feels like you’re only three rungs up a tall ladder, there are others just getting on.

I went to my first Tony Robbins event in November, and was pleasantly surprised. My #1 takeaway is to control the energy level you bring to each moment or task. No matter what’s going on in your life, emotions aren’t just something that happen to you, they can be created intentionally. A number of things influence your mood: your posture, your inner monologue, your facial expression, the music you’re listening to, something as small as a hug… almost all of the factors are ones you can control.

I reconnected with live music and dance. I danced at weddings, learned partner dancing, and woke up at dawn to dance with friends. I trained with Les Twins, who tour with Beyonce and Jay-Z. I went to more live shows this year than my entire life previously, thanks to Ryan Hoover, Jonathan T., Jimmy Douglas, Suzy Ryoo, and Vina. Without fail, I leave live shows or dancing sessions feeling happier than when I started.

So all in all, I’m grateful for the deepened relationships, professional challenges, and personal growth 2016 brought me.

In 2017, I’m going to establish a much-needed foundation with a morning routine, and bike across the country (not all in one go). Feel free to hold me accountable :)

Conversation beats argument. Technical founder/advisor helping startups w/growth, research & prototyping. CTO Rupie.io. Alum of Minted, Google, others.

Conversation beats argument. Technical founder/advisor helping startups w/growth, research & prototyping. CTO Rupie.io. Alum of Minted, Google, others.