Retirement Reflections

I am now done with my first career, and I did not realize the time between the old thing and new thing would be so hard. I don’t have a routine. I don’t have any particular goals. It’s weird.

When I kicked off this project at the beginning of the year, I figured that once I was done with the Navy, I would easily go into a research mode, regularly write, and produce weekly posts that would rival the work of my favorite online writers. Instead, I am home, and I see how much more I can be in my family’s life. I know this is better. It’s why I retired from the Navy, after all. Somehow, I nearly forgot that fact, and I would lose my way if I went back to that original plan.

So, what now?

Fortunately, I named this project This Will Be Hard, because it is, and I therefore remain on-message. I am still going to write here, but I am going to remember my goal is to write what I think. To shape and share my philosophy of everything. This site will be a reflection of me. It will be what I want my kids to know, in case I can’t teach them myself.1


  1. Concluding my first career has also been a very effective memento mori. I didn’t see that coming either. ↩︎

Small Identity, Simple Core

So far, we have set the goal of this project and defined success, but we still have to figure out how to effect change. Self-improvement is hard, and we are best served by taking into account who we are before trying to become who we want to be.

I previously used the metaphor of working with the grain, because many aspects of ourselves are particularly resistant to change. When working with wood, this manifests in the grain, and these comparatively weak wood fibers can easily deflect the path of a metal saw or chisel. Bringing this back to people, our grain is manifested by our identity.

Paul Graham has a great essay entitled, “Keep Your Identity Small.”

More generally, you can have a fruitful discussion about a topic only if it doesn’t engage the identities of any of the participants. What makes politics and religion such minefields is that they engage so many people’s identities. But you could in principle have a useful conversation about them with some people. And there are other topics that might seem harmless, like the relative merits of Ford and Chevy pickup trucks, that you couldn’t safely talk about with others.

The most intriguing thing about this theory, if it’s right, is that it explains not merely which kinds of discussions to avoid, but how to have better ideas. If people can’t think clearly about anything that has become part of their identity, then all other things being equal, the best plan is to let as few things into your identity as possible.

If our identity affects our reason, we who value reason are well-served keeping this identity small. If we can do this, everything beyond the very core of our being can evaluated and changed. We can change when circumstances change, and we can move from who we are to who we want to be.

Another related idea that has long resonated with me is having strong opinions, weakly held1. I have always tried to be changeable, and I beyond claiming this, I try to make sure I use the actual words, “I was wrong,” lest I fool myself when forming the memory. Although this is hard work,2 I take a perverse sort of pride in being proved wrong. I think by now this is a part of my identity. I hope it is.

What is at your core? What do you want it to be? I think our identities can change, but it has to be done slowly and self consciously. Step one is honestly defining the starting point. Every conscious and unconscious part of our minds rails against what threatens our identity, but this war can be won when we know we’re fighting.

Keep your identity small, and know this will be hard.


  1. This link is to Jeff Atwood’s blog, and he is the first one I remember encapsulating this idea so succinctly. ↩︎
  2. My wife surely knows how often I need to recommit myself to this goal. ↩︎

 

What Does Success Look Like?

In my role as Commanding Officer, I always tried to begin any new project with the simple question, “what does success look like?” Air-to-air combat is a complex and somewhat hard to define skillset, so we sometimes knew a pilot wasn’t doing well enough, but it was often hard to define the problem. A joking, but not-quite-unserious admonition Navy pilots often give to each other before a check ride or important flight is don’t F it up1 Because of all this, I tried to explicitly define success when counseling or setting policy.

As set out in my first post, the audacious goal for this project is working out how to live. This broad a goal easily devolves into a series of platitudes or aphorisms, and while this can motivate or encourage, it rarely teaches.

So, what does success look like?

First of all, success itself is a terrible measure of a life well-lived, but the only potentially worse ruler is wealth or making money. There are simply too many external factors that affect success or failure, and we can’t always move those levers ourselves. We do not all inherit the same set of tools, nor do we all have the same opportunities in life.

Money does not buy happiness,2 sure, but I don’t think happiness is the hallmark of the good life, either. For some of the reasons above, and many more besides, it is easier for some of us to be happy than it is for others. This leads to a sort of set-point for our happiness level, and movement of this level is subject to what’s commonly known as the Hedonic Treadmill. Simply stated, we adapt quickly to changes in our happiness, even after very large, positive or negative life changes. The desires of our hearts rise or fall in line with our ability to fulfill these desires. Nevertheless, seeking happiness first is better than pursuing money or success under the impression it will result in happiness.

Instead of money or happiness, my basic goal is contentment. This contentment often looks a lot like happiness, but when circumstances make it hard to smile, I can still be content. This is often the result of knowing an experience is hard, but that I’ll learn from it, but sometimes it is only the result of knowing something is temporary. When I’m not sure how temporary something even is, there is a military saying that helps: “embrace the suck.”3 This boils down stoic ideals quite nicely, in my opinion.

So is that is what success looks like? Contentment? I think so. At first glance, contentment seems pale in comparison to happiness, but contentment also has the benefit of being always within reach. We read our circumstances and adjust our minds. We don’t look to our circumstances and expect them to enable happiness. In fact, as we’ll see in the coming months, we will sometimes seek out tough circumstances.

Lastly, realize we won’t be perfect anytime soon.4 We don’t need to be. We just need to get a little better every day.


  1. It’s effectively-never censored as “F,” but I don’t like to swear. Also, your buddies will often encourage you after a bad performance with a rousing, “next time, suck less.” You’re only in trouble if people stop teasing. ↩︎
  2. Let’s except the extremes of poverty for now. I think you need to have a certain amount of money before this discussion matters in the least. ↩︎
  3. Read David Goggin’s book if you want to turn the corner on you own self-discipline. This is also a case where the audiobook is even better than the print version. There is a lot of information presented in-line with the narrative that adds to the story in all the right ways. Highly recommended. ↩︎
  4. (or ever) ↩︎

Why This Will Be Hard

My wife and I are raising four children, age 10, 8, 6, and 4. As they have grown, I have had to confront the fact that I still don’t know the secret to being grown up. I don’t know how to get them from where they are now as children to becoming happy and successful adults.

At about the time of this realization, I began my With the Grain project. I began it, because I was struck in a rut. I needed to get better. As I went to work on myself, while also trying to cultivate a writing habit, I continually butted up against the frustration of not being able to see how all my disparate improvements and new ideas fit together.

Richard Feynman often talked about the significant distinction between two types of knowledge: you can know something by name, or you can understand it. In order to foster understanding, he had his own learning technique:

  1. Choose a concept
  2. Teach it to a toddler
  3. Identify gaps and go back to the source material
  4. Review and simplify (optional)1

As I continued to work on With the Grain, I realized I was only ever able to demonstrate this depth on the small details, not when I zoomed out. In other words, I realized how little I really understood. This began to make my brain itch and two times caused the project to grind to a halt. I knew I needed to work more on this, if I wanted to do things right, but I was unable to create enough time in my day to make it happen.

Two things are changing for me. At the end of January, I will turn over my job as a squadron Commanding Officer, and shortly after that I will retire from the Navy. I selected my next job because it allowed me a lot more autonomy over my time, and I have been thinking about how I want to fill that time. Mostly, I want to be with my wife and children more, but I also want to be a better husband and father.

Our culture loves get-rich-quick schemes and life hacks. Even as I was writing this, The Atlantic published an article about how much money folks have lost trying to get rich selling consumer products on Amazon.2 The same goes for diet plans which all promise results in x days or y weeks, usually trumpeting how little time you’ll need to spend in the gym or how you can enjoy your favorite foods while still losing weight. None of this really works. Real improvement takes time and is difficult. Real improvement comes in fits and starts.

My goal for this site is to completely define my personal philosophy, while also improving it. I want to describe how to live a good life, while figuring out how to. If I succeed, I will meet Feynman’s test of real understanding, by being able to describe life to a toddler, to my own toddler.

This will be hard.


  1. I think Farnam Street provides the best full discussion of the “Feynman Technique.” I highly recommend Farnam Street in general. ↩︎
  2. No judgement. A year ago, I bought a $10 ebook on this very same topic. It’s a seductive concept. ↩︎