2019 Annual Review

This is my first year doing an annual review of myself. If you’re not familiar with the concept, I learned it from Chris Guillebeau many, many moons ago (click here to read his article about it). I’m not entirely sure how I want to structure this long-term, so for now, I’m mainly using the categories Chris uses, plus some of my own.

Two big things happened in 2019: I moved from San Francisco, CA to Portland, OR and I started The Duckbill Group with my friend and business partner, Corey Quinn.

The Big Stuff

The Move

On February 28th, 2019, I moved from San Francisco, CA to Portland, OR. This had been something actively on my mind for over a year before the move, and I ultimately decided to do in June 2019, but wanted to finish out my lease in SF before leaving.

Why move? I became increasingly frustrated with SF—-culturally, politically, safety, the costs of everything. I had originally give myself 3-5 years in SF before I moved there in 2015, and if I decided it wasn’t going to work out, I’d try Portland.

So far, Portland is growing on me. It reminds me of home (Knoxville, TN) in some ways, which is great. The rain and wetness is kind of annoying, but that’s relatively minor. I am a little frustrated that there are no direct flights on United for PDX-LAX or PDX-SEA (yes, really!).

I’m finding that the city contains most of the things you’d expect for a proper city, but then some things aren’t quite there yet. For example, the MAX (Portland’s light rail) isn’t near my house, nor in any of the neighborhoods I’d want to live in.

Portland is well-known for it’s beer and food scene, and it really is quite good, but there are some frustrations with it: there’s a heavy focus on IPAs to the exclusion of other styles (the local pub near me has 30 beers on tap, with 20 of them being some sort of pale ale or IPA). With food, there are a lot of “southern-style” restaurants that are very much not southern, good barbecue is entirely unrepresented, and the best Cajun restaurant seems to have created its recipes from hearing about a trip to Louisiana from a server’s best friend’s cousin who stopped to get gas in Shreveport once.

But, you know, overall, good city. I like it.

The Duckbill Group

I go into this below in the section on Career.

Health & Fitness

I’m not dead, so…there’s that? Honestly, this was not a good year health-wise. I’m fortunate in that I’m not sick, but I did gain more weight this year (damn you Portland food scene!), I stopped working out (damn you Duckbill!), and loneliness in a new city is a bitch (damn you moving!)

In seriousness, these are all avoidable and solvable problems and I have no one but myself to blame.

Goals for 2020

Knowing what I know about myself and my inclinations, I’m setting just two goals:

  1. Run two 5K races. I’m already registered for the Portland Shamrock Run on March 15th, and I’ll be using the Couch To 5K program to prepare for it.
  2. Hit the gym an average of 2x per week throughout the year. This is more about my strength-training workouts than running. In SF, when I worked with a trainer, I averaged 4x a week in Q4 2018, which was fan-fucking-tastic. I’d like to exceed this goal, but let’s go with something easier to hit and be pleasantly surprised in December.

I’ll be tracking my performance numbers for both my run times and lifting numbers, but the measures above are the ones I’ll be using to call success/failure at the end of the year.

Travel & Adventure

I made a total of 21 trips this year, racked up 56,349 miles on United, and spent 40 nights in Marriott hotels (and another 11 nights at non-Marriott properties). My United status increased from Gold to Platinum for 2020, while my Marriott status renewed at Platinum for the second year.

I spent ten days touring southern England with my travel buddy Kevin. We spent a lot of time in quaint English pubs, and even spent a couple days at our first CAMRA festival in Braintree, England (where we were the youngest people in attendance, with an age gap of at least 30 years between us and the next youngest person, which led to some fun conversations).

This year also changed my perspective on travel accommodations and amenities. I flew quite a bit of these trips in business class for big reason: I’m more productive sitting up front than I am in the back, and given the opportunity cost of being unproductive for a day, the additional price is worthwhile for me.

The big downside with this year’s travel is that I took my UK vacation in June, while Duckbill was still rather fledgling. I ended up working most of the whole vacation, and even had to skip one part of the trip because I wasn’t confident in the village’s cell signal and wifi reliability for some client meetings I needed to be on. 🙁

Goals for 2020

Just one goal here, which is aimed squarely at both adventure and mental health: I want to take two seven-day, totally disconnected, non-work vacations in 2020.

Financial – Income

Despite starting a new business that solves a problem I’m not an expert in, business revenue is at a record high and my personal income is as well. This was both a nice surprise and validation of something I’ve been thinking for a while: you don’t need to be an expert in a technical area to build a successful business solving a technical problem. Building a business is a whole other set of skills from, say, being an expert in application monitoring or AWS architecture.

Goals for 2020

Increase my personal income by 40% over 2019. It’s a stretch, but I’m optimistic. I do have an unfair advantage in that I own (half of) a business, so this is easier for me than it would be for, say, a full-time employee.

Financial – Giving

I used to think I’m not a naturally-generous person, but I’ve come to understand that’s quite true. Rather, I give and receive differently. To draw from The Five Love Languages, I give with service but receive by affirmation.

Most people seem to equate “being generous” with giving of money or gifts. I definitely do those things, and I don’t have any Scrooge McDuck views on them, but neither is ever top-of-mind for me. When it comes to giving, I enjoy being generous with my time. Cooking dinner for someone, giving advice and perspective over coffee, etc are my natural inclinations, though I sometimes fear people view me as being ungenerous.

I don’t know that I’m quite ready to lean into my preferred mode of generosity. In the meantime, I want to try to be more mindful of other people’s preferred ways of receiving, and when I can’t know them (eg, business relationships), be more intentional and varied.

Goals for 2020

I’ve spent some time thinking about an appropriate goal, but I can’t seem to find one that makes sense. Instead, I’m going to build a personal system that ensures I’m able to followup regularly with friends, family, and business associates.

Financial – Savings

2018 was a rough year for my business (the business before Duckbill Group, that is), and that carried over into 2019. While I didn’t burn through any of my personal cash savings, I did end up with some sizable credit card debt. I paid all of that off in 2019, thankfully, but it also means I wasn’t able to add any additional savings to my investment accounts or cash holdings.

Goals for 2020

I’d like to max out my eligible retirement account contributions in 2020, expand my medium-term investments (3-5 years) with the equivalent of one year of expenses, and maintain my cash savings at six months of expenses. The larger goal in mind is a multi-year effort to reach a certain level of personal liquidity.


Of all the categories here, this saw the most solid increase across the board.

I started the year running my application monitoring consulting business, the Monitoring Weekly newsletter, and the Real World DevOps podcast. I had begun to pivot my business toward an industry analyst role when Corey Quinn asked me to help him turn his AWS cost optimization business into something more. Truth be told, Corey and I had been looking for that 1+1=3 partnership opportunity for over a year without success, but here it was staring us in the face the whole time.

As our new company began to grow, I found my mental energy for Real World DevOps and Monitoring Weekly begin to wane. I shut down the podcast in June after six months of running it, and I put Monitoring Weekly on hiatus in late August. They were painful decisions at the time, but very good decisions in hindsight. I’m still hopeful I can find someone to take up the mantle of writing Monitoring Weekly, as it’s a solid service to the monitoring and observability community.

I was also extraordinarily fortunate to be an organizer for a small, private community event. I’m a member of a small business owners Slack-based community, and we held our first community event in 2019. It was a lot of work by a few talented and dedicated people, and I’m honored to have had the opportunity to contribute my share to organizing it. I view this sort of thing as my way of helping grow new business owners and in fostering community—both things I’m starting to think are core to my purpose.

Goals for 2020

Keep on keepin’ on. As I run a business, my career and the business are intricately linked. The business’s success is also my success, so I’ll leave it at this: my goal is to grow Duckbill this year with more service offerings, more amazing clients, and continue to build a wonderful team.

Family & Community

Along with Health & Fitness, this category took a pretty bad beating. Moving to a new city in your 30s is hard—harder than you would think, if you’ve never done it before. While I made a few fantastic friends in Portland this year, it hasn’t been quite to the level I envisioned it. And that’s entirely on me.

On the flip-side, I’ve also deepened relationships this year with existing friends, which has been an absolute joy.

Goals for 2020

I’d like to be more social in 2020. Rather than set some arbitrary metric like “number of new friends made,” I’m going to measure this with a leading indicator instead: consistency of putting myself in places where it’s possible to make new friends.

In essence, this really comes down to getting back into old hobbies and joining new social groups. This will definitely be a category that’s more ambiguous to measure, but it will be pretty easy to decide success or failure here.


And that’s that: my 2019 Annual Review. All in all, a pretty solid year with its share of good and bad, but overall I feel okay with the accomplishments this year. I’m definitely looking forward to doing my 2020 Annual Review and seeing how close I got to my goals (and which ones I exceeded!)

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