Sabbath Year – A Year Later

A little over a year ago I finished our sabbath year and began the process of reentering normal life. After taking that sabbath year to rest and reflect, I had learned a few lessons which I documented in this blog post. Now, a year-ish later, I want to reflect on how those reflections have aged.

The following line up with the decisions & changes I discussed in the aforementioned review post.

1. We decided that the next few years aren’t a period for taking on big risks or flirting with overcommitment.

This has held true. It turns out the role I took at Google was a lot more involved than I had originally envisioned, but this is mostly in my control. I tend to dive into things head first and put myself in the center of the action, which I’ve done here. Despite that, our lives feel fairly maxed out, despite minimal risk exposure. Margins are thin and so maintaining a relatively predictable lifestyle has remained important and effective.

2. We decided on having Seattle be our long term home with plans to snowbird (or rainbird) in southern California in the winter eventually.

We have remained in Seattle and been pretty happy with that. The time of year of my writing this is the harder time of year, but it also the time of year I find myself most inclined to do indoor hobbies like writing.

We had explored ramping up our San Diego plans this year by spending a month or so down there in an AirBnB. In the end we decided not to, though I have made a few quick trips down. I think the jury is still out on if we will desire rainbirding enough to do it. Some of me suspects that with the right adjustments we might be able to handle Seattle, but then again, it is still February – we’ll see how I feel come May if we have an extended winter.

3. I changed my work mentality from that of trying to retire early to realizing it is good for me, personally, to work.

This has proved the biggest change from our sabbath year. I entered this new period with a nearly 180* rotation in my mentality on work. I had previously been striving to free myself from having to work as soon as possible. I now hope I can find jobs interesting enough to me that I can work until I’m unable.

Currently, I think of my job (on most days) as the most realistic boardgame I could possibly play. Instead of a stack of cardboard coins, I get to play with a $10B/year business. The competition is fierce, the rules and complex but the measurement is clear. Sure, parts of my job are difficult, but in the end I’m encouraged to learn to fix those aspects and get to the fun strategy parts. Most days I remember that given a billion dollars of my own, I would probably still be doing something similar.

I also mentioned that as a result of this change we were going to value our time more and become more willing to spend money when it would save time. That has remained constant. Funny enough, though our spending has increased dramatically as a result of some things like hiring a nanny and ordering food more, our income has similarly increased such that the savings ratio is similar. The way the math works out that means we’re actually saving a good bit more than before. That won’t be impactful if we keep up this current level of spending, but if we ever do want to retire to a less expensive locale, that extra money will go even further which is nice.

4. After two years away from being a product manager, the role that leads a software team in prioritizing what to build, I decided to return to that role.

I think product manager means a lot of different things depending on where you work. What I get to do at Google is exactly the type of stuff I love doing. I don’t think it is a coincidence that the CEO of Alphabet came from a product management track. They design the role to build thoughtful leaders and I’m enjoying absorbing that culture.

On a daily basis I get to unify the interests of dozens of different stakeholders and design creative solutions to solve them in an efficient manner. I have a real impact on the ability of our $10B/year business to maintain (or increase) its 50% YoY growth rate. I could do similar things under different titles at different companies, and someday I will, but for now, this title and company are a great fit for me.

5. In my searching and exploration phase I exposed myself to a lot of ideas that helped me reject some false tradeoffs I’ve long held. One is a lie I’ve believed for a while that the highest paying corporate jobs at the biggest companies are stodgy, un-impactful and dehumanizing.

I now work for a trillion dollar company. On top of that, I’m having a lot more impact on the company than I would have expected when I joined – both in terms of within the company and on the industry as a whole. On top of that, I am part of work running group, I have people I regularly play boardgames with at lunch and I did a team bike ride around Mt. Rainier last year. I have so far found it to neither be stodgy, un-impactful or dehumanizing – so I’m glad I gave it a chance.

One thing I reflect on is whether I made the wrong move by not coming to a place like Google right out of college. My current thinking is that for me, it took a while to find my path and so small companies that let me fluidly change roles were a great place to slowly gel. If I were to advise a new grad today though, I would recommend giving big companies a try early in their career, especially if they know what role they want to spend the next few years in. It is hard to undervalue the benefits of a well known name, a network, structured management processes and well defined expectations. Start ups are a lot of fun but they aren’t for everyone. I saw plenty of people flail and fail while working at a startup that have since gone on to bigger companies and done great – sometimes explicit structure and expectations is valuable.

6. Along with rejecting some ideas I’ve held, I also became more comfortable explicitly accepting some beliefs I’ve loosely held. One is that that doing high quality work is in itself good, even when the task seems far from the objective.

I work on the billing systems for a cloud. This is a far cry from what I consider “good work” like developing cures for cancer, solving poverty ending human trafficking, etc. But, despite that, every step forward we take at making our cloud serve customers better will bring one more step of progress to the world. Either our cloud will serve customers needs better or it will force another company to find a way to do even better than that. Either way the world is going to see progress and I’m really excited about that. I might not be curing cancer, but people that are working to do so, like the Mayo Clinic, are using our cloud and benefitting from the projects my team works on.

7. I wrestled with the notion of identity and how hobbies played a role into that.

This has been an area I have been much more intentional about. Hobbies have remained a big part of my life but I’ve intentionally made some hobby decisions based on my life circumstances rather than letting my hobby dictate my life circumstances. I’ve generally found this to be effective. I’ve been able to transition to some new hobbies I find just as engrossing as my previous ones. I think that is part of why I’m less inclined to spend as much time as possible in San Diego. While I still love surfing, I’ve found I can replicate parts of it that I enjoyed in other activities if I take a bit of a reductionist approach. In the end, surfing is just some outside time, alone, moving fast, without full control, with variable rewards, some unpredictability and a lot of tactile stimulation. I can recreate that in other ways.

2020 Focus: Action Economy

With the start of a new year, I take the time to set my focus for the coming year. I believe that by being selective about where I direct my energy, I can achieve results that are exponentially greater than if I split that energy across many different goals.

More details about the process are in this blog post and you can review the results from past years (2013, 2014, 2015, 2016, 2017, 2018, & 2019).

2020 Theme: Action Economy

My theme for 2020 is action economy.

This is a phrase I’ve borrowed from board gaming where it describes the ability of a player to utilize their limited turn actions to maximize their ability to score points.

The real life application of this is efficiently using my resources (time, skills, knowledge, network, money, etc.) to achieve the goals that I’ve selected for myself.

This is the second full year of my sabbath cycle focused on preparing for my calling. As I think about achieving goals over the long term, and I realize how thin I am stretched, effectively using my resources has become a top priority for me. I need to get better and doing more with less. This year I want to spend some time thinking about that and building heuristics I can lean on in the future.

This year will be centered around learning how to effectively measure the inputs needed to achieve outputs, how to more accurately predict them ahead of time and how to reduce them.

2020 Challenge: Develop a Strategy Evaluation Model

For my challenge this year I am going to develop a model that I can use to evaluate various potential strategies for achieving a goal. I want to be able to use this to quickly (and hopefully accurately) predict the costs of each strategy, so that I can select the best one.

Some things I want to think through as part of this are; what is the value of my time?, how should I factor in risk potential?, how can I account for other externalities?, what other outputs do different strategies have? and how should I value them?

The end result, I hope, will be a model that lets me answer questions like; is it better to mow my lawn myself or pay a neighbor kid to do it?, should I take on a high paying project that uses my current skills or invest time learning a new skill?, or should I go on another training run before trying to run 93 miles around this volcano? (hint: yes)

2020 Habit: Run 13 Projects & 52 Common Tasks Through the Model

My habit will directly pour out of the challenge. I want to apply the model I develop to 13 of my 2020 projects and 52 of my common tasks. My hope is that by doing so, I’ll find out that some of the ways I spend my time or money are best handled in another fashion.

For the former, I will look at projects I take on during the year and use this to estimate the cost and effectiveness of the strategy, which I will then compare to the reality after the fact. I use GTD to organize my life and usually have ~6-10 projects that are active at any point – things like planning a vacation, getting a new job, buying a house, learning to stand up paddle, etc. These projects range in complexity and duration but what they all share is that they are things I want to have accomplished and if I can accurately define what it is that I want to accomplish, I can better optimize how I get that done.

For the latter, common tasks are something I track via recurring ToDos. I have ~100 that I undertake with various frequencies; 40 yearly (like this blog post!), 10 semi-annually, 17 quarterly, 9 monthly, 6 biweekly, 5 weekly and a few at various other increments in between. Those will be potential place for big impact, especially the tasks that take a significant amount of time due to the compounded impact of saving effort on a task that I repeat many times.

2020 Exemplar: Warren Buffett

I still struggle to find good Exemplars. I need someone that demonstrates the quality, that has documented their thoughts about it and/or that has had a lot written about them. That tends to limit me to famous and successful people. That doesn’t seem altogether wrong – successful people often get there due to the same good choices and behaviors I want to emulate. But they also get there by making certain tradeoffs and I’m worried I’m overexposing myself to those tradeoffs. I am also concerned that this pool of people is disproportionately white men – something that will limit the experiences I have a chance to learn from and relate to.

That said, I’ve chosen a successful, famous, white man this year because I had a hard time thinking of anyone that has had more success prioritizing and think about the value of things. I know essentially three things about Warren Buffett

  1. He has made a good bit of money investing in companies he thinks are valuable, when others don’t see the value
  2. He is an advocate of ruthless prioritization
  3. He has simple tastes and plans to give all of his money away

These things all seem like they fit with this year’s theme of action economy quite well. Buffett’s success and contemporariness also means there is a ton written about him.

Interestingly Buffett is the first exemplar I’ve selected who is still living and I’m actually only two degrees away from him socially – people I know have met him. I don’t think that means I’ll have a chance to spend 1:1 time with Buffett this year to learn from him directly, but I have thought about selecting exemplars I’m closer to in the future as a way to learn more directly from them. This feels like a step in that direction.

2020 Bucket List Item: 100+ Mile PNW SUP & Trail Running Adventure

This year for my bucket list item I’ve decided on the general flavor of what I want to do, but I haven’t yet figured out the specifics. I am going to combine two new loves of mine into something new (to me at least), awesome and thoroughly PNW.

The area I currently live is made up of mostly two things, bodies of water and wilderness areas with trails. I’ve been enjoying both over the past few years – running on the trails and SUPing in the water.

I decided to combine those into a single adventure by undertaking a 100+ mile SUP (stand up paddling) and trail running adventure.

By combining these two modes of transportation, I will be able to get to anywhere within ~100 miles of my house, including many remote spots that there is no easy way to go to via a single mode of transport. By land or by water, I will cut a path and get there. There is something really cool about that idea and it might open up some new camping options for the future.

It is also nice that these two activities utilize different parts of the body, so preparing for both of them should offer me some well rounded fitness this year.

I’m excited to figure out where I can go and then get there. The last time I went SUPing in the sound I had an encounter with a pod of jumping orcas and the last time I went for a trail run I bumped into a mountain lion, so combining the two sports feels ripe for adventure.

2019 Focus: End Of Year Review

With the start of a new year, I take the time to set my focus for the coming year. I believe that by being selective about where I direct my energy, I can achieve results that are exponentially greater than if I split that energy across many different goals.

I detailed my 2019 focus here (read that first if you want more context). I’ve posted a few updates throughout the year (quarter year, half year & three quarters) and now is the time to do a final review.

2019 Theme: Long-Suffering

Self Grade: 9/10

2019 was my best year ever for executing a yearly focus. Part of this is certainly due to everything I have learned from having mixed results in the past. I kept my challenge, habit, exemplar and bucket list item all tightly nested with a topic that I was getting plenty of time to think about from everyday life anyhow. That resulted in a nice synergy – never before would I have thought I would use Nelson Mandela as motivation to help me press forward while running around a volcano by myself at 4am, but here we are.

2019 Challenge: Fasting in the Wilderness

Self Grade: 8/10

In December I went out in the wilderness of Joshua Tree National Park and fasted for 48 hours. I wrote some thoughts on that experience here. Funny enough, the picture that I decided to use last January is from Joshua Tree, even though I originally had planned to do this closer to Seattle.

I am only giving myself 8/10 for two reasons. First, my total fasting time was exactly 48 hours and wilderness time was ~42. That was the bare minimum of what I had hoped to accomplish. My leaving was mostly due to scheduling issues and not inability to continue so I don’t feel like I got as close to my max as perhaps I wanted. The second reason, which likely resulted from that first, is I didn’t get quite into the headspace that I wanted to. I’m not sure if it just takes me longer to get there now because I have more in my head or if I’m unwilling to go there, but I don’t feel like I quite did it.

2019 Habit: Minimizing Digital Entertainment

Self Grade: 8/10

I ended up averaging 1.98 hours per week of digital entertainment, just slightly under my goal of 2 hours. I stayed under my target amount (which varied by quarter) on 37 of the 52 weeks.

I had been making great progress into the summer but saw a bit of a regression this winter. Some of that is expected seasonal patterns. I had originally hoped to maintain my low summer levels of digital entertainment as winter set in, but ended up relaxing my target a bit as reality kicked in. Even with that, I can tell I regressed a little more towards the end of the year. I had a plane ride where I watched shows I didn’t even care about and I signed up for Disney+ which got me hooked on one show I hadn’t planned on (The Mandalorian).

Here are the results from Q4. In the beginning of 2019 I had planned on having Q4 have a 2 hour per week target, but after a successful summer I decided to shoot for one hour. After the first few weeks, I decided two revert to the original 2 hour plan – mainly due to the reality of long, dark, cold days (and Baby Yoda).

Here is the full year’s worth of data, including the average line, which finished at just under two hours.


Related to this, in 2018 I had tracked a secret goal that I wrote about before and after to reduce the ratio of consumptive vs productive entertainment activities.

Previously in 2017 & 2018 my ratios were 1:2.5 & 1:3.95.

In 2019 the ratio changed to

Books read: 8.5
Books listened to: 0
Significant blog posts written: 5
Total Productive: 13.5

Movies watched: 24
Video Games Played: .5
Graphic Novels Read: 6
TV Show Seasons Watched: 2
Consumptive Total: 32.5

Ratio – 1:2.4

So this is forward progress.

Interestingly, the consumptive number was actually down a lot from the previous years, and I read more books than either of those years. The thing that hurt me was not writing as many blog posts. It turns out but I didn’t read as much as I had those years. If I had written three more blog posts, my ratio would have dropped to under 1:2. I think that means my weighting is a bit off as I can usually write a blog post in a night or two where as reading a book often takes me a few weeks to get through.

2019 Exemplar: Nelson Mandela

Self Grade: 9/10

This year I learned a good bit about Mandela and in July I published my exemplar review for him.

One of the things I learned from him was the ability to remain engaged in a debate but to let time, rather than talking, win it.

I’ve gotten a chance to put this into practice a few times at work. One recent & unannounced project is near to my area of expertise and it was originally heading in a direction that would have resulted in a lot of extra work for my team and frustration for customers. I didn’t own this decision and due to the number of things on my plate, wasn’t able to devote a major portion of my time to it to help steer it.

Instead I was clear about my top concerns and a better solution. I periodically communicated that 1:1 to the right people, even when it seemed like the critical mass of people involved were spinning a bit. The end result (so far, we’ll see for sure when it finally goes live) is essentially what I was pushing for. Getting there took much less of my effort than being deeply engaged would have though, which was the big win.

2019 Bucket List Item: Run the Wonderland Trail at Mt. Rainier

Self Grade: 9/10

Sometimes you achieve something because you put in the hard work preparing for it. Sometimes you achieve something because you’re stupid and stubborn and just keep pushing through pain. My run around Mt. Rainier was the latter.

Despite encounters with a mountain lion, two bears and a sprained ankle, I managed to complete the ~93 mile run, self-supported in under 48 hours. It wasn’t pretty, but it counts. Read the adventure report here.

As a bonus bucket list item, also appropriate to the long-suffering theme, I rode my bike around Mt. Rainier. The one day 150 mile ride, called RAMROD was something I’d had my eye on for a while and when a few coworkers signed up, I decided to join them. Read the ride report here.