A Brief Programming Note

I haven’t posted for a while, because I am re-working the backend of this site. I went with conventional wisdom for writers chose a fuss-free writing/publishing solution. The problem is that I like fuss.

I also don’t like the WP editor, Markdown parser, URL structure, and other assorted miscellany. I want to be able to write in any text editor, version control with Git, style, and extend the site at will. I want to own this whole thing. I want to occasionally break things, because I am a no-nothing programming dilettante. It’s fun for me. It’s also how I’ll learn.

Anyway, my day job has been busy, I’ve been traveling, and again, I’m a no-nothing programming dilettante. Thus, delay.

Please bear with me.


I highly value personal toughness. I don’t, however, expect this from everyone around me. In other words, I don’t go around hurting other people’s feeling, saying, “Hey, I’m sorry you’re offended; I’m just a straight-shooter.” No, I try to balance toughness with kindness, and I don’t pretend to be a valid arbiter of other people’s reactions.

I think one, highly-politicized example of this is trigger warnings on campus. I am largely in the Jonathan Haidt camp, in the sense that I don’t think we are helping our young people by implying avoidance is a good way to avoid pain. I think that’s akin to teaching them, “You’re too weak to handle this; you’re too weak for the hard stuff.”


If I were a professor in one of these classrooms, I would absolutely issue trigger warnings, because it is important to take care of people. Ideally, I would also sit down with the otherwise-triggered students for a one-on-one discussion after class, but I shouldn’t try to force healing or toughness on someone who’s hurting, even, or especially if I can’t understand why they are.

My toughness is also not some sort of misguided, toxic masculinity. I have all the feelings. Shoot, I cried at the end of Avengers: Endgame in a crowded movie theater, so I am definitely not calling for callousness. I simply seek toughness when the chips are down. When kindness is not offered. When toughness is required.

Another common way thinking about toughness is as stoicism. When I first heard about the philosophy of Stoicism, I was a sophomore at the Naval Academy, and we learned about it by examining the life of Admiral James Stockdale and his heroism while serving as a prisoner of war during the Vietnam War. 1 Admiral Stockdale had been very affected by the writings of Epictetus in his middle years–pre-Vietnam–as a graduate student at Stanford, and it would later sustain him during seven grueling years in the “Hanoi Hilton”.

In his own words:

On September 9, 1965, I flew at 500 knots right into a flak trap, at tree-top level, in a little A-4 airplane–the cockpit walls not even three feet apart–which I couldn’t steer after it was on fire, its control system shot out. After ejection I had about thirty seconds to make my last statement in freedom before I landed in the main street of a little village right ahead. And so help me, I whispered to myself: “Five years down there, at least. I’m leaving the world of technology and entering the world of Epictetus.”

“Ready at hand” from The Enchiridion as I ejected from that airplane was the understanding that a Stoic always kept separate files in his mind for (A) those things that are “up to him” and (B) those things that are “not up to him.” Another way of saying it is (A) those things that are “within his power” and (B) those things that are “beyond his power.” Still another way of saying it is (A) those things that are within the grasp of “his Will, his Free Will” and (B) those things that are beyond it. All in category B are “external,” beyond my control, ultimately dooming me to fear and anxiety if I covet them. All in category A are up to me, within my power, within my will, and properly subjects for my total concern and involvement. They include my opinions, my aims, my aversions, my own grief, my own joy, my judgments, my attitude about what is going on, my own good, and my own evil.²

Toughness for me is exerting rigid control over everything in "category A" when everything in "category B" is hard. I think the ultimate measure of a philosophy’s utility is how well it stands up at the limits of human experience. Stoicism has passed that test countless times throughout the ages.³

Another warrior I have immense respect for is Jocko Willink. He is impossibly intense, but also funny. Undeniably tough, but also intellectual. I’ve learned a lot from him in the few years since he emerged into public life.

Perhaps most important of these lessons is his version of what I call optimistic stoicism:

How do I deal with setback, Failures, delays, defeats, or other disasters? I actually have a fairly simple way of dealing with these situations, summed up in one word: "Good." This is something that one of my direct subordinates, one of the guys who worked for me, a guy who became one of my best friends, pointed out. He would pull me aside with some major problem or some issue that was going on, and he’d say "Boss, we’ve got this thing, this situation, and it’s going terribly wrong." I would look at him and I’d say: "Good." And finally, one day, he was telling me about something that was going off the rails, and as soon as he finished explaining it to me he said, "I already know what you’re going to say."

And I asked, "What am I going to say?"

And he said, "You’re going to say: ‘Good.’" He continued, "That’s what you always say. When something is wrong or going bad, you just look at me and say, ‘Good.’"

And I said, "Well. I mean it. Because that is how I operate." So I explained to him that when things are going bad there’s going to be some good that will come from it.

  • Oh mission got canceled? Good. We can focus on another one.
  • Didn’t get the new high-speed gear we wanted? Good. We can keep it simple.
  • Didn’t get promoted? Good. More time to get better.
  • Didn’t get funded? Good. We own more of the company.
  • Didn’t get the job you wanted? Good. Go out, gain more experience, and build a better resume.
  • Got injured? Good. Needed a break from training.
  • Got tapped out? Good. It’s better to tap out in training than to tap out on the street.
  • Got beat? Good. We learned.
  • Unexpected problems? Good. We have the opportunity to figure out a solution.

Beyond the Stoic ideal of an imperturbable rock, Jocko points out that bad news is just an opportunity to get better.

I love this reminder to ignore what’s out of my control and to instead focus on what I do control. I especially like it as a one-word reminder. In my day-to-day life, I put that one word in between action and reaction:


  1. Depending on your age and pop culture IQ, you may associate Admiral Stockdale with the jokes about him after the vice-presidential debates in 1992, when he was Ross Perot’s running mate. Please spend some time learning about the actual man. Dennis Miller gave perhaps the best counterpoint in his own comedy special in 1994: “Now I know [Stockdale’s name has] become a buzzword in this culture for doddering old man, but let’s look at the record, folks. The guy was the first guy in and the last guy out of Vietnam, a war that many Americans, including your new President, did not want to dirty their hands with. The reason he had to turn his hearing aid on at that debate is because those fucking animals knocked his eardrums out when he wouldn’t spill his guts. He teaches philosophy at Stanford University, he’s a brilliant, sensitive, courageous man. And yet…he committed the one unpardonable sin in our culture: he was bad on television.”↩︎
  2. Courage Under Fire: Testing Epictetus’s Doctrines in a Laboratory of Human Behavior], Hoover Institution, Stanford, 1993, p 7.↩︎
  3. If you’d like more inexpert opinions on Stoicism, Erik and I discussed the topic at length on our old podcast, Seasons.↩︎
  4. Jocko Willink, Discipline Equals Freedom: Field Manual, 2017, pp 58-59.↩︎


I am not a "goals" person. That’s nebulous, so let me explain. My brother-in-law loves to ask people, what’s your 5-year goal? Your 10-year goal? I don’t work that way. I’ve explained before how I define success, and as I implied then, this is not "vision board" kind of stuff.

In his book The Practicing Mind, Thomas Sterner discussed how goals often cause adult learners to self-sabotage.

If you have never considered it, think about how everything we learn and master in life, from walking and tying our shoes to saving money and raising a child, is accomplished through a form of practice, something we repeat over and over again. For the most part, we are not aware of the process as such, but that is how good practice manifests itself when done properly. It carries no stress-laden anticipation, no internal question, “When will the goal be reached?”

We have a very unhealthy habit of making the product—our intended result—the goal, instead of the process of reaching that goal. This is evident in many activities in our everyday lives. We become fixated on our intended goal and completely miss out on the joy present in the process of achieving it. We erroneously think that there is a magical point that we will reach and then we will be happy. We look at the process of getting there as almost a necessary nuisance we have to go through in order to get to our goal.1

When we only consider some future end-state a success, each effort short of that end feels like a failure. At some point after childhood, we lose the joy of discovery inherent in erring. Children are not troubled by falling while having fun; they pop right up again. When an adult falls, we check for witnesses before we check for injury.

And now we’re back to my goals.

I want to be content, within the bounds of what I think is right. My personal ethic, were I to boil it down to something pithy, is be kind and be tough. This means I try to care intensely and elaborately for everyone in my orbit, but you don’t need to worry about me. I’m good.

I further refine it–at the risk of losing pith–with seek micro over macro. This circumscribes my aforementioned orbit to my family, friends, and the people I come across day-to-day. This is based on my mistrust of any systems that purport to be universal. Said another way, I know I can treat my waitress well, but I know I can’t help all the waitstaff in the world.

I think small.

This valuing the micro over the macro makes my "goal" singular. Namely, I want to always get better. It is perfectly okay for me to get just a little bit better. It’s preferred, even.

This a continual process that places a big emphasis on the present moment. Sterner continues:

In order to focus on the present, we must give up, at least temporarily, our attachment to our desired goal. If we don’t give up our attachment to the goal, we cannot be in the present because we are thinking about something that hasn’t occurred yet: the goal. This is the goal shift I spoke of earlier. When you shift your goal from the product you are trying to achieve to the process of achieving it, a wonderful phenomenon occurs: all pressure drops away…

This awareness of being where you are and in the present gives you the constant positive reinforcement of reaching your goal over and over again. However, when your mind is only on the finished product, not only do you feel frustrated in every second that you have not met that goal, but you experience anxiety in every “mistake” you make while practicing. You view each mistake as a barrier, something delaying you from realizing your goal and experiencing the joy that reaching that goal is going to give you.

When, instead, your goal is to focus on the process and stay in the present, then there are no mistakes and no judging. You are just learning and doing. You are executing the activity, observing the outcome, and adjusting yourself and your practice energy to produce the desired result. There are no bad emotions, because you are not judging anything.2

I don’t worry about making sure every new opportunity will help me achieve a discrete goal. I instead approach each new endeavor as an opportunity to grow.

Maybe I can make some money. Maybe I can gain a new skill. Maybe I can brighten the day of a DMV clerk by simply treating her as a human being instead of as an impediment to my Getting Things Done mojo.

I apply a better check at all decision points.

Better is good enough.

  1. Sterner, Thomas M. The Practicing Mind: Developing Focus and Discipline in Your Life: Master Any Skill or Challenge by Learning to Love the Process. Novato, CA: New World Library, 2012.↩︎
  2. Sterner.↩︎


In the next several posts, I am going to spend some time highlighting my favorite decision tools and ways of thinking. These are all concepts I consciously call to mind with a certain word or phrase, and I’ve taken to calling the lot of them incantations.

I use incantations to shift my thinking all at once, and that is why use the same word or phrase every time. This forces a pattern interrupt in my monkey mind, which helps me carefully filter incoming information, break a cycle of destructive thoughts, or consider circumstances from a different perspective.

My list of incantations is not yet complete, nor will it ever be. I hope to keep growing and improving them as long as I live, and I expect I’ll also need to prune this list sometime in the future. That’s all part of the fun.

P.S. Many readers may be thinking of mental models by now, and that is the more normal way of talking about metacognition. No one is here for normal.

P.P.S. Long time readers will recognize some of these from my past work. The good stuff sticks.


One of the most useful shifts I’ve made in my own thinking is the conscious use of chunkingIn my own words, chunking is a way utilizing a stand-in word or phrase to bring an entire, complicated concept to mind.

I picture this being like when Neo in the matrix “learned” new skills.


This chunking enables me to build a fuller understanding of new concepts in the same way that an expansive vocabulary can enable a fuller verbal explanation.

As I have considered what and how I want to learn and study, I’ve wanted to figure out how to capture notes and preserve what I learn. I realized today I don’t really care about the “how”–Evernote, DEVONthink, etc.–of this process, and knowing myself, if I go down the tools rabbit hole, I won’t actually get anything done. HTML is going to be my storage method. I’ll also post this external brain online here, because I know I’ll do better work if someone might be reading along with me.

This brings me back to chunking. I am in the habit of processing new information gleaned from books or podcasts based on the vocabulary I have developed over the past few years. I’ve found this to be a valuable way to evaluate new ideas and figure out where to hang the good stuff on my own mental framework.

As I now rededicate myself to more deliberately learning, I first want strengthen my vocabulary. To that end, I am going work through my favorite terms here for a while, so that’s what you can expect to read next.

P.S. – I’ll have to add in some css to make gifs stop animating, if I keep using gifs. Kinda distracting.


Shamelessly Motivating

I accidentally found myself motivated today by my past writing.

Although it surely could be a shameless plug for the old project, spending some time in the archives helped me remember why I spent all that time writing. It was hard work, but I now remember I can do good work. Starting again doesn’t feel as daunting having been reminded I’ve done it before.

The motivation must be kicking in a little already, because I started and rejected two drafts earlier today. I was planning to just try again tomorrow, and yet here I am ready to hit publish for the second day in a row.



More Problems

The biggest problem with setting out on a journey begun with a grand purpose is knowing what to do when you don’t feel grand. When you’re not sure where to look for grand. When you don’t even feel good.

This is where I have been living since my last post. Lots of up and downs–mostly ups–but I haven’t been able to find a coherent thread between my ideas. Nor have I had the right combination of time and brainpower required to build a bridge between my roaming thoughts.

So I haven’t written at all. This isn’t what I want, but it’s also not something I could fix.

So, I’m going to pivot again.

I am going to record the mess, before I figure it out. This means I may someday actually figure it out. My overarching mission statement remains true. This will hard. The “it” is just now going to be “where do I go from here?” I completed my Navy career, and I need a new mission. I have a job, but it’s not my mission.

I’ve always liked Bill Gate’s quote, “Most people overestimate what they can do in one year and underestimate what they can do in ten years.” I don’t know where I’ll end up, but I can wait a while to evaluate where I’ve been.

You’re welcome to follow along.

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) ↩︎