February 2, 2020
Reflecting on 2019: The Year in Review

Here are the previous annual review posts: 2014, 2015, 2016, 2017, 2018.

Looking back, twenty-Nineteen was a great year of learning, growth, and executing. Looking back, that’s a pretty common statement I use when reviewing the prior year.

While I didn’t hit my Big 10 goals that I set earlier in the year, I achieved 4 of them and made a lot of progress on the others.

I’m reflecting on the same things this year, but doing it in a more focused way. The 5-pillar approach is something I use in my weekly habits and retrospectives so I thought it’d be worth doing annual reviews in a similar vein with more detail. I’ve begun to track more consistently about each area of life below so starting with my 2020 reflection, I will have statistical reports and results from those efforts to share.


We continued to attend Life Church and Lauren continued to serve in 252 (kids ministry) as well as the Family Life check-in team. I applied to use my guitar and musical talents for the worship team but haven’t used it on Sunday quite yet. We tithed fully and were blessed in so many ways.

I’ve been more habitual in focus on the first things first every morning; devotional (using YouVersion bible app),. prayer, gratitude (5 Minute Journal), and meditation (Headspace).


We also invested in a small home gym in the basement that includes a Peloton, two adjustable dumbbell sets, a jump rope, ankle bands, stretch bands, a medicine ball, and some multi-purpose resistance bands.

It’s been able to help me work out with less notice and cut out the ~20-30 minutes round trip to the gym every time. It lets me plug in early in the mornings or late at night really effectively.

I’ve never been more convinced and focused on the quality and quantity of sleep that I’ve been getting. I started using AutoSleep for the Apple watch and iPhone, and it’s been helping shine a light on how exercise, food, and stress play into how rested I am through the readiness feature.


This year seemed like we really started to hit our stride. Things became familiar, patterns emerged, and an understanding helped to steady the constant changes as well.

At home, I’ve been able to spend more time with my wife, our daughter Violet, and Keona. We went on vacation to Lanikai, Oahu, HI and rented a pretty amazing place in the hills, just under the Lanikai Pillbox. It was our second time on the islands with Violet, and this time she was healthy and we all had a blast.

We also found out that we were growing our little ohana (Hawaiian for family) by one and that Violet was going to have a sister! Spoiler: we welcomed Olive June to our family on January 19th at 7:19am.

Photo by Kinetic Bear.


For Headway, 2019 was a great year of growth for us. We just about doubled the team from ~17 to 31 crew members, and all in the span of about 2 months over the summer as we ramped up for some great partners. In April, we moved into our 3rd office building and I lead the interior design of it along with Eric and Jon, as we code-checked with the architect on the project.

In September, our team retreat brought us all down to converge in Gatlinburg, TN for a week of team activities, learning how we work best together, and the outdoors.

Headway team poses for a group picture in Gatlinburg

It’s been amazing to see how the culture morphed and changed through the growth. At Headway, we continued to roll out EOS to the entire organization and it’s been helping us to focus and fight off new and shiny distractions.


With family and work taking up most of my time, I feel the relationships in my life got a bit more distant. I didn’t make time or even text regularly to keep up with friends that I normally had in the past. This is something I’m focused on improving in 2020.


I consider wealth to be knowledge and investing in the right things that help me grow, in addition to how I manage and direct my money.

In 2019 I read 27 books between a mix of printed, audible, and kindle. As much as I’d like to declutter my office shelves from printed books, I find the tactile experience the best way I digest new content, and the kindle’s transitions and e-ink display feels a bit too delayed with friction for reading efficiently.

From a financial standpoint, we were able to continue doing the Dave Ramsey debt snowball and pay off some more loans and other debt.