2019 Year in Review

I will never forget 2019. Holeeeeee sheeeeeet.

Where to start?

It typically takes me a few days to find the time to capture, at the very least, some high-level thoughts about the year (this will be the 8th time I’ve done a yearly post—previous posts here: 2012201320142015, 20162017 and 2018).

The theme of 2018 was easy to identify as every single road converged, inevitably, towards friendship. 2019 was similar in the sense that most lessons learned circled the wagons of who I am and the delta between “that” person and the person I wanted to become.

The most painful and triumphant moments of 2019 were one-in-the-same; I was viscerally reminded that the most important decisions that we make are always priced considerably high, a cost that we could never, truly, appreciate (nor could we, especially in the moment).

But… but! These moments offered me a real chance at putting my principles and values into action, thus making them real operating virtues.

2019 was, in other words, the year that I codified my belief that what you do is who you are. And now it’s time to take the “training wheels” off as I look towards 2020, expanding on what I’ve learned and liberally applying it in my life in every nook and cranny.

The reason this is so damn exciting is because the initial results have been… well… very encouraging—the insights that I now have about who I am, what I’m supposed to do with myself and the superpowers that I’ve been uniquely given, have been nothing short of life-giving.

I feel a bit like Neo.

I mean, it really doesn’t get much more exciting than the moment a hero realizes that they do, in fact, have superpowers—I love those scenes in movies the most!

But that’s just the starting block! One should never conflate the knowledge of a superpower with the ability (i.e. fluency) to wield it properly, effectively, and in the right context (which I believe to be in the service of others).

What happens next in most cinematic narratives is that the heroine then spends a good amount of time practicing their newfound skills in a variety of different scenarios with varying degrees of success.

This is probably where I’m at right now as I feel as if I’ve spent the first-half of my life (at the tender age of 37) acquiring the frame and perspective, the skills, and the (starter) knowledge of the powers themselves and now I’ve got the next 37 years to figure out how to use them properly (with minimal collateral damage, hopefully).

So much is captured in these 5 minutes!

And that’s where I’ve landed for 2019 as the real gift isn’t so much about identifying them but rather an increased measure of confidence in who I am (and who I’m most definitely not).

This is game-changing for me because the difference between success and failure in every situation is not about the outcome, itself, but rather how I choose to interpret, understand, and filter it in the larger context of life.

Failure hurts (as it most definitely should) but I’m more certain than I ever have been of my ability to not only recover but to take those experiences and use them to my advantage. Failure, when coupled closely with intentional (superpower) experimentation, becomes a necessary expression of maturity, growth, and increased operational effectiveness.

So all the pain, all the hurt, all those pitch-dark moments that you and I thought we’d never recover from in 2019 can now be seen as not just important but fundamentally necessary in our inevitable march forward, onward, and upward.

I grew so much in 2019 that a single post would be a poor and ineffective expression. So, I’m not going to really try.

Instead, here are a few posts that were especially important to me and a bit of additional context, if needed. 2019 was the year that I decided that it was okay to be me, in every flavor that I have to offer, regardless of form or obvious function.

Living through this is something that very few generations get to experience—I definitely don’t consider myself “lucky”—it’s just a sad state of affairs, isn’t it? I’ve never been uber-proud of my country but this year I felt, at times, ashamed.

That’s something, isn’t it?

I’ve been trying to level-up my writing and it’s taken nearly two decades to finally learn the difference between hyphen, em dash, and en dash—and then learning to use them correctly!

This might be the most “political” post that I wrote in 2019—it’s not even that political though. I detest politics because it seems to create more division than connectedness; ain’t nobody got time for that.

Most of the pain that I experienced was my own damn fault over things that, in retrospect, are objectively dumb. But, given the full context, it wasn’t, at the time.

Holding this future perspective in tension while calmly managing the moment, in the moment, is a fucking superpower and I’m learning how to do this better.

My children consistently remind me that I can do better—I will, I promise.

This past year was a very important one for me professionally because I finally came to terms with a few mental models that have slowed me down considerably over the years.

The single biggest come-to-Jesus-moment was telling my best friend that I no longer wanted to write production-grade software full-time. Sadly, this wasn’t the first time that I’ve mentioned it but I was the most serious that I’ve ever been.

The truth is that I will never not write software—I’ll continue to put together my own personal scripts and small single-serve apps to make my life better but I don’t want my full-time job to be writing software.

Besides simply needing a break, there are also a number of professional areas that I want to spend a lot more time investing in and leveling up, like becoming a world-class leader and people manager.

I know, I know… insane, right? But, it’s true. And, I love that it’s true.

I’ll admit that I accidentally had a swig of an alcoholic cider earlier this year that I mistook for sparkling water.

Imbibing gave me a rush and a feeling that is indescribable.

My fight with alcohol will last me the rest of my life—I’m okay with that now.

Formidable would definitely be one of the Top 5 words of 2019—I can’t tell you how many times I simply said, in my head or aloud:

I am formidable.

It kind of works.

Every year I spend less time obsessing over the mechanics of my blog and more time obsessing over the how I want it all to feel. Sometimes this means changing the design but what it’s meant over the last few years is getting closer to static files and plain-and-simple html and css.

I’m probably one or two year out from ditching WordPress entirely, but, don’t say that too loudly because some people might have a heart attack.

Just kidding… I left the WordPress community a while ago.

I got some new ink done and it’s one of my favorites.

I don’t often re-read my own posts because it’s my art and, like most artists, I think my own art is shit, so, I don’t like to revisit it much.

But… on a very rare occasion, I put something together that is exceedingly useful. My post on persuasion, even though it’s been barely a month since I penned it, has been something I’ve personally referenced a dozen times in conversations with others.

So, it might be one of my better pieces of writing in 2019—maybe not.

November must have been a good writing month because these two posts have not only gotten a lot of visits (not exactly a good indicator of anything, by the way) but have also held a certain air of importance:

My post on disagreement is also something that greatly influenced my thinking in the last quarter of 2019—I imagine it will continue to be one that I return to from time to time because I am so naturally disinterested in disagreeing with people (don’t we all).

But, the message is clear: Disagreement unlocks a world of possibility when done in the right spirit and frame.

My oldest will be a high-schooler next year! I haven’t even gotten over the fact that she’s a teenager!

👆🏼— I’m watching (and listening) because it’s more than just a show, it’s a journey, an expression of being formidable.

I became a Wartime CEO this year and I loved and hated it.

I am not my emotions. I am not my mood.

Thank God for things like 90-seconds.

Walking the girls to school via public transportation is so much fun! What a great, new development in our morning routine.

Taking this approach to people has been big. Give this some thought and then try it. Seriously.

👆🏼 — This is some really neat stuff… and I have some ideas.

Irreverence is such a great word:

Joaquin Phoenix and his performance made me physically ill in the theaters and I then endured it a second time a week later.

I’ve sat down many times since watching the film in an attempt to capture some comprehensive thoughts but I’ve never been able to complete them—there’s something haunting about this movie that’s a bit too close to home.

2019 was the year where I learned what it felt like to be away from my family, intentionally, because I was sick and because I desperately needed help, healing, and a healthy dose of rest.

I came back, struggling, but hopeful—I’m still here.

I never realized how hard it would be to please myself. Or rather, I finally realized that I never will (and I should stop trying).

Building a company is like erecting a mirror, piece by piece, that will eventually look exactly like you. The process forces you to encounter every single part of who you are and begs the difficult questions as to not just what they are but, more importantly, what you will do with those parts.

Why? Because they will eventually become part of the very business that you build, whether you like it or not.

Being true to yourself requires courage, not because it’s hard to stand up to others to defend your beliefs or principles or values—it’s hard because when you really encounter yourself, honestly, you’re going to discover a lot that is just downright ugly, gross, and scary.

Again… even those parts will eventually find a point of manifestation in the culture of the business that you build.

For instance, a leader who is a closet lacks a healthy dose of self-respect (e.g. privately hates themselves) will inevitably create a culture where respect, at best, is superficially-shared. A leader who is cavalier with their finances will create an organization that struggles to manage burn (I know what this is like… ugh!). It’s really not rocket science.

But, I don’t want to beat myself up either! I’m not perfect nor is that really the goal in company-building. I need to hold both views in tension, simultaneously. Hey, that’s life.

I walked my team into a non-profit accelerator only to quit 3-months later. Those people were not my people and that was an important lesson to learn. Just because you may culturally share a larger sphere doesn’t mean that you will immediately find a comfortable spot to commune.

My search for a spiritual community that makes sense for me and my family’s unique needs continues, tirelessly. I oftentimes wonder if it’s all worth the effort.

I’m not a betting man, but, if I was, I’d still put it all on the cross—it’s just a really good fucking bet.

This is the first of 25 posts that detailed, visually, our road trip from San Francisco to Atlanta and back. It almost killed us, at least emotionally.

The memories are painful, to be honest. I was not in a good place during most of this trip. I’m glad we were able to have some neat moments that weren’t completely bombed by my misbehavior.

If there was one writing technique that got a major upgrade this year it was due to this post and Scott Adams.

My writing, overnight, changed. So grateful.

I started another newsletter and it has a few hundred folks subscribed. It’s not much and I don’t imagine that it’ll get too large, but, the writing canvas always feels intensely personal and I enjoy that.

Becoming someone’s friend is so much work! I imagine that this is why most of us don’t give friendship-building much of our (intentional) time.

But, the return on investment is entirely outsized. I can’t stop talking about this, mostly because I learned it a little later in life and I regret not indexing more on it earlier. Perhaps I can help others focus on relationships more and make the world a better place.

We got a fucking slide in the house. I tried it. I wasn’t supposed to. I won’t do that again. Another amazing product purchase in 2019 were these headphones which are the best headphones I’ve owned as an adult.

I don’t count my Sony Eggos back in the mid-90’s because… I wasn’t an adult. But, I did have them into college… I think? Whatever happened to those things… … …

This is the only way that I know how to “do life” at this point—I simply don’t have anyone to copy and not many contemporary comparables. The zigs and the zags of life keep things exciting.

A bit of anxiety mixed in there… but, yes… exciting all the same.


Sometimes I doubt that I believe this, but, I keep going anyway:

Writing is what I do. Is it who I am? Perhaps.

I’m proud of my kids. Always. But, there are moments that… 😂 … just make your heart… so… big. So proud of Roenne and her final project work earlier this year!

This was really fun:

I had no idea how prescient this was for me in 2019:

I worked through a number of pivots in my life but this one has been the hardest and heaviest. I started the year with 19 folks on my team. Now, I’m the only member left standing.

In a way, I’ve been avoiding the posts about how I’ve felt during this transition because… well… it’s just complicated—there are a lot of moving parts and people’s lives that are involved (but it’s much more about the personal relationships than the professional ones).

It is lonely. Why? Because I’m the only one! I’ve felt all types of emotions, including guilt, grief, and shame. Why? Because I failed and I failed a lot of people and it wasn’t their fault; it was mine.

I do plan on unpacking a bit more of these things in the coming weeks and months as I clear a mental pathway forward—I’m very excited about it because I know that life is on the other side of it all.

God, this is everything. Knowing the difference and the fact that it’s a never-ending struggle is important as it gives meaning to the struggle.

Our youngest had a seizure and it was one of the scariest moments of my life. I hope it never happens again.


Thinking through this dynamic really helped me give up some older relationships that I had been holding onto for a little too long. Not surprising is the fact that both parties are happier now with a bit more clarity in tow. Go figure.

This was really fun:


It’s crazy to read this post from almost a year ago! I thought that I was “rebooting” the company into the next phase and I had no idea that I’d have to really do that hardcore just a year later.

But, I feel even more equipped to think through company-building with a clear mind and a very big and open heart.

Oh, and I really love Hawaii and we need to go back. This was 2019?! Yikes. Feels like forever ago!

And that’s that. See you in the new year.