2023: Year in Review

I’m sick. On the couch. Writing this on my iPhone. It’s New Year’s Eve.

Reflecting is difficult when sickness is present. The desire to return to health dominates all other thoughts. The effort required to recount the year is non-zero. Reflection and rest are usually monogamous. There’s a kind of rest that resists reflection.


I read some books this year. Surely I did. E-books count. Audiobooks count, too.

Not as many as the past. Not as many as the image of myself that I’d like to curate. Some years are slower than others.


Travel has become increasingly important to our family. 2022 was highlighted by the grown-ups taking trips. That was fun. Our takeaway was that we wanted 2023 to have a better balance of family trips.

All these trips were family trips. And they were a blast. As we close out the year we recognize the over correction. The grown ups need to get away and travel without the kids some of the time. At least once. A default of family trips is here to stay for the next decade or so.

I’m so proud of my little travelers. Their ability to navigate an airport and adapt to changing circumstances grew this year. I’m ready to plan the next adventure.

West Coast Road Trip August–November

This trip deserves a section of its own. We drove from Kentucky to Seattle, to San Diego, back to Kentucky. Our family of five in our seven-seater Tesla Model Y. No roof rack. No trailer hitch. We packed light and lived minimally in disposable housing. We stayed in different places for weeks at a time.

Some of the places we visited:

Any one of these triggers multiple paragraphs of memories. I plan to write some of them down before they’re lost to time.


I began climbing in Joshua Tree in October 2022. I’ve kept up the hobby in 2023. Mostly through bouldering at a local climbing gym.

Our grading system goes red, yellow, green, and onto colors I haven’t gotten to yet. I should know the v-ratings but I don’t. Reds are a given. Yellows are mostly flashed with a few outliers. Greens are projects that I’m challenged by. I’ve gotten a few of them. Some greens are easier than the hardest yellows. It’s an imperfect science.

Climbing in Carlsbad has become a routine part of my trips to California. Though I always find their routes substantially more difficult than the same relative ratings in Lexington. Again, it’s an imperfect science. I did my first climb over the top of a wall at Vital in Oceanside this fall. That was cool.

The bouldering gym in Bend, Oregon was excellent. I went once with my eldest daughter. Another time with the whole family. Including some extended family with my cousin and her husband. We hung out with them several times in Bend and it was an unexpected joy.

The bouldering gym in Santa Cruz was a bust. I just didn’t have it in me that day.

I have a chalk bag and shoes. The chalk bag is working just fine. I’ve worn through the toe on both shoes. I can drop them off to be re-soled. I’m going to buy a second pair of shoes before I do that. I don’t want to go back to the rental shoes. Even for a brief season of repair.

My gym has auto belays. I’ll grab a rental harness one out of ten times to sport climb. I had gotten pretty good at it for a while there. A harness of my own may be in the future.


I’ve always enjoyed running. But I’ve never been particularly good at it. I’ve ran in fits and spurts over the years.

In hindsight I realize that injury is what stopped me. Not major injury. I’d start a running routine. Then a slight discomfort would arise. My hips sitting weird. Or my toe feeling strained. So I’d stop and move onto yoga or biking.

Zone 2 heart rate training has changed everything for me. Running for arbitrary speed was my default approach for years. Running to stay in Zone 2 is different. It’s slow. Painfully slow at times.

Just last week I ran at 14:37 minutes per mile. I was still topping out of Zone 2 into Zone 3. It took over 45 minutes to run a 5K.

But! I ran a 5K. And I ran continuously for 45 minutes. And I felt great afterwards. And that’s pretty much the smallest distance I run these days. And I pretty much feel great after every single run.

I remember it being a huge feat that I ran a continuous 5K in my twenties. I was running a lot back then. But I just ran as hard as I could for as long as I could. And I felt awful afterwards. I only recall running a single 5K without walking in my twenties.

I had some great runs during our travels. Running through the Deschutes National Forest and into downtown Bend, Oregon was my favorite. At around 7 miles I took a wrong turn and gave up on a hill. If I would have kept to the flatter path I might have run 10 miles that day. I felt wonderful.

Running along the coast in Carlsbad was great. Got to run with four miles with DMa which was a highlight of joy. A solo run for 90 minutes on a Sunday morning that terminated at the farmers market was also delightful. The chocolate chip cookie and latte from Lofty was a treat after 7 miles.

Running on the beach in Seaside, Oregon was special. Had to look out for sneaker waves that never came. Four runs including a 10K. Grabbing a coffee after the 10K and walking by the Lewis & Clark salt works is etched in my memory. The mist and rain didn’t bother me one bit.

I ran my fastest Zone 2 pace along the beach in Carlsbad. 12:11 minutes per mile. That’s a data point I’m trying to figure out. Running on the west coast just felt easier. And the pacing seems to confirm it. Is the air just that much easier to breathe than central Kentucky? Are the slight hills making that big of a difference? Was life on the road calmer which meant for easier effort? Who knows.

Running in Seattle was melancholy. Through my old neighborhood. Passing my old house. I’m still trying to understand why it made me so sad. And so joyful. Some hard things happened when living there. Some amazing things too. Appreciating what it was and realizing it has moved on.

My running gear is pretty simple. A pair of Hoka shoes. Vuori running shorts. A bandana. A water bottle. My Apple Watch for good-enough heart rate monitoring. Whatever black t-shirt I happen to be wearing.

I plan to invest in more gear in the upcoming weeks. Tights, gloves, and a beanie so I can continue running outdoors in the Kentucky winter. Going to John’s Run/Walk shop to get fitted for shoes. Thinking about a dedicated heart rate monitor because monitoring Zone 2 has been so helpful in this first year.

Video Games

I’m a radical disappointment to my teenage self. I did play a descent amount of Tears of the Kingdom when it came out. Like all open world games, the grind eventually got to me. I played Super Mario Bros Wonder exactly once before my son beat the entire game on his own. I bought the Advance Wars reboot and started the campaign. Battling the boy in that was fun.


I reached my 10 year anniversary at Planning Center. The anniversary was rewarded with a five week sabbatical.

My second sabbatical was intentionally low key. A staycation during the school year. Joining Emily in working in the home in the era of three children. I have a new found appreciation for “stay at home” parents. The school bells ring too closely together. The seven hours between drop-off and pickup feel like three. I got some small projects done around the house. Not nearly as many as I projected being possible.

“Working from anywhere” has been theoretically available to me for 10 years. The three month family road trip put that theory to the test.

Building my mobile office was fun. My company issued MacBook Air. A Roost stand. An Apple Magic Keyboard. A Logitech Lift vertical mouse. AirPods Pro. Hard shell cases for both the keyboard and mouse. Minimalist charging options. It all packs up pretty small.

With this kit assembled I was prepared to test the theory that I can work from anywhere. I consider the results a success. As long as I have a desk with a chair and a door that can close I can effectively get work done. I loved my traveling desk. I wish I had taken pictures of its many manifestations.

There were a couple of days when I worked a few hours from the car while Emily drove. This was primarily motivated by housing transitions. Most places make you check out by 11am. And the next places usually don’t let you check in until 3pm. A four hour gap. I can take a long lunch from time to time. But not four hours long. So working from the car was the solution.

I would not recommend this strategy for putting in the work. Especially with kids in the car. While these few occurrences went off without a problem, it was stressful the entire time. There was a constant fear that something urgent would come up and I would not have the space to think, talk, and act in the way I’d need to for my team.

This artificial stress is funny to me now. When I’m home I have routines, strategies, and boundaries around time. There is rarely something so urgent that requires immediate attention. We’re mostly calm and asynchronous. But I seemed to forget that while I was on the road.

I was concerned about my road trip being perceived as having a negative impact on my outcomes. The (unhealthy) adaptation was being “always on” to a much greater degree than I am when working from my home routines. I felt like I had to respond to each Slack message faster than usual. Or hop on a Zoom call immediately instead of deferring to the office hours I’ve blocked off on my own calendar.

I recognized in hindsight that I abandoned the behaviors and strategies that have served me just fine in my 10 years working from home. All because of manufactured fears about others’ perceptions.

There are two things I will do different next time. Keeping my established schedule, adapting my office hours, and sticking to it as rigidly as reasonable is the first. It works fine from home. It’ll work fine from anywhere. The second is to either work earlier, work later, or take some vacation time if we’re going to be in the car as a whole family. I’ll accept the occasional half-day of vacation time cost for the benefit of working from anywhere.

The work itself was fine. I’m wrapping up my second full year in management. The first year was learning how to operate in the organization from a new horizon. This year was spent supporting organizational changes that sounded small on paper but rippled bigger in reality.

The biggest lesson I learned is that there is no such thing as a small change when it comes to job titles, responsibilities, and reporting structures.

Iterating via consistent and small changes works great for building software. I’m not sure consistent and small change can translate to building teams.

The literature suggests massive re-orgs are no better. So maybe organizational change is just a hard thing.

I’ve been a part of this company growing from 20’ish people to 150+ people. Growing pains have been a through line of small changes and big changes alike. So maybe organizational growth is just a hard thing.

Planning Center is a bootstrapped and profitable company with zero investors. Much of the literature about engineering management is speaking from and to the experience of venture capital and hyper growth. The incentives are different. The structures are different. The behaviors are different.

I’m looking forward to finding a better way in 2024. Within the boundaries of time and mental energy that should go to work. I have a bad habit of letting this pillar of life bear too much weight for purpose and identity. This shows up in where I spend my time and where I point my thoughts. I don’t want to think less of my work. But I do want to think about my work less.


I love my crew so much. Being out of the changing diapers stage and into the kids in school stage is a huge upgrade. Watching kids figure out the world with their best guess theories is refreshing.

Inviting them into my hobbies is fun. I share video games with E. Climbing with H. S is up for anything. We haven’t found our thing yet. But we have the most time to find it.

Emily and my marriage goes on strongly. Double our years of marriage and all the kids will be out of the house. Or at least of a legal age where they could be out of the house. I won’t kick them out but I do aspire for them to launch earlier than later.

I’m not wishing away this season of rearing children. If anything I’m trying to slow down and appreciate it more. But I’m aware that it will end. I am looking forward to being happily married beyond the immediate shared responsibility of raising children.

In the immediate I’m trying to embrace the season we’re in, not fast forward to what comes next, and not long for the seasons that have passed.


Still identifying as Christian. I’m just about 10 years removed from the nonsense that was Mars Hill Church. I still walk with a limp. And cannot fully separate the wheat from the chaff. But I haven’t given up on the premise yet.

I served as an elder at my church for about eight months. I thought that responsibility might kick start my spiritual renewal. It didn’t. And because we were planning so much travel I resigned. It clarified that I believe in an embodied presence as the necessity of church leadership.

I tell my kids that Jesus didn’t stay dead, and that doesn’t happen very often, and that’s why we’re still talking about it two-thousand years later. I also tell them that no one has ever seen God. But when we love one another God lives in us and his love is made complete in us.

I want to love the one another as well as the other. Love your enemies and pray for those who persecute you and all that. The greatest of these is love.


I decided to try on sobriety in October 2022. It wasn’t difficult once I had resolved to do it. I’ve taken substantial breaks at different times in my life. I’ve never struggled to stop when I’ve chosen to stop. I’ve never pursued excess for the purpose of excess. There’s probably a clinical term about being a high functioning social drinker. Whatever the case I was tired of feeling routinely disconnected, tired, and uninspired. It felt right to try on sobriety.

I felt my feelings and slept great. I found more time to do creative things I enjoy. When I sat down to write the words flowed more freely. When I sat down to listen I could give my full attention.

That is the thing I hate most about being under alcohol’s influence. The feeling that I am not fully available to my friends in moments of conversation. Drinking puts listening, comprehension, and being present on hard mode.

“Addiction is the opposite of connection” is a phrase I latched onto. It rings true in my experience. The missed opportunity of real social connection in moments of buzz is what I grieve the most.

Sobriety improved my connections but it did not fix my life. I thought it would be a silver bullet even though there are no silver bullets. Except for Coors, the beer as cold as the Rockies.

Sobriety clears the room. The real work of healing builds on that clarity.

On a Sunday in June I was craving pizza and beer. I ordered an IPA and a slice of pepperoni. This meal ended my eight months of sobriety. It felt like a non-event. It tasted great and I felt fine.

I’ve been consuming alcohol on a regular basis for the past six months. And if I’m completely honest the eight months of sobriety that preceded them were superior in most every way. It’s a thing I think about a lot. It’s time to grab my resolve again.


I’ve been writing it without releasing it. The current incantation of my website feels inadequate for hosting it. I want to find an afternoon or four to invest in typography, structure, and everything else that goes into presenting words in the ways they need to be framed.

I also want to get my poems from Instagram out of the walled garden and onto my site. In time.

2024: Year in Preview

2024 is a big one. I turn 40. Emily turns 40. Our marriage turns 15. E turns 10. 25% of my life has been experienced as a parent. That’s weird math to think about. We have a lot to celebrate and be thankful for.

We’ll celebrate with travel and making memories. I’ll climb, run, read, write, and overall be present to whatever is going on.

I don’t set hard target goals much. And I’m not about to start now.

I’m sick. On the couch. Writing this on my iPhone. Health is all I want in the new year.

Published: 2023-12-31

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