Another milestone birthday, another existential crisis. Of course we’re going to talk about Jiu-Jitsu, but it will make sense in the context of Vibe Coding with AI soon.

My life may not be exactly what I set out to do when I was younger, but I am fulfilling the spirit of it, and in many ways, it's way better than I could have dreamed of.

As a kid, at one point I said I wanted to be a pro baseball player. That changed pretty quickly the next year when I wasn’t good enough to make the age-appropriate little league (or PONY?) team. Then I started wrestling in 8th grade on the advice of my football coach and haven’t looked back.

I wanted to make it to the California state tournament (one of the hardest in the nation) and compete at the highest level I could, I broke my hand in the second match of my senior year of high school. I was also more interested in football back then and becoming as good as I could in that. What kid doesn't dream of being a professional athlete?

Guess what, kid?

This year I got my Jiu-Jitsu Black Belt, which is like wrestling, but with submission holds, and coach twice a week at one of the most recognized, top gyms in the country, 10th Planet Las Vegas. I am lucky to call former UFC fighters and high level grapplers among my “main training partners”.

Not quite “professional athlete”, but I do know where I stand on an absolute scale in the Jiu-Jitsu world, which is “not bad”. Now I get to teach others how to achieve whatever level they desire to reach.

Here’s a text exchange I had with my coach who helped me develop from blue to purple belt, immediately after the 2022 ADCC West Coast Trials where I did unreasonably well (3 wins, 1 loss, 16th/84) for a software nerd:

This exchange was priceless, deeply meaningful, and may be the spirit of Jiu-Jitsu or any other apprentice-based profession (which is all of them). To prove that I belonged on the same mats as the highest-level athletes was the goal, and I achieved it. You can't buy that kind of experience.

It's a trope of every martial arts movie that the student is always trying to earn the approval of the teacher/coach and make them proud. It's a powerful drug.

I'm seeing this now as someone on the other side of this exchange as a coach. It is now my job to guide and affirm other people's skill in the sport. I reassure them that they are, in fact, getting better at this thing.

This year, two guys that I’ve had matches with previously (including the opponent mentioned in the above exchange) won their respective weight divisions at ADCC Trials, punching their tickets to the World Championship. I also have a win over a guy in 2022 who would later make it into the next world championship in 2024. The fact that I can point to three opponents who have made it to the ADCC World Championship (the top 16 competitors in each weight class in the world) shows me that I really did the thing. I was really out there on the competition circuit trying to test myself against the absolute best in the world.

Now that I basically achieved a childhood dream, I was left wondering, “what next? What is the next thing I'm going to ‘compete’ in?”

I found my answer towards the end of 2025. It’s related to another dream I had when I was younger. I wanted to control fleets of super powerful computers and make them do whatever I wanted.

Guess what, kid?

I did enough work at my employer in the AI coding space the past 12 months to be offered a new role on the newly formed AI Tools team. My literal job now is to live and breathe this stuff in order to enable the rest of the company.

Pretty cool. I did not see that one coming when I started taking AI coding really seriously over the past year. Becoming a relative expert in the latest technology wave in a major enterprise company wasn’t on my bingo card, but I’ll take it.

Humans always desire a certain % increase (up to many multiples, which is a different story) more relative to what they have in order to feel like they are “making progress”, whatever that means, but I have it pretty good.

I have this crazy aspirational life (to me, when I was 25) combination of a loving wife + family, a job that challenges me yet has work-life balance, and a hobby in Jiu-Jitsu that I’m halfway decent at that has a large community with many great friends baked in. I’m truly lucky to say that my life has basically looked the same since I was 30, and that was a major improvement since I was 25.

It’s the Instagram reel trend where it’s like:

Yes, yes we do, and it’s an amazing life.

Even the things that didn’t go my way, those were just prerequisites or “levels” I had to beat to advance in the game. The ecological dynamics perspective / constraints led approach coach in me says that I literally would not have learned otherwise.

The most important thing is that I haven't gone through any one-way doors that I regret.

The closest thing I had to “regret” recently is catching myself comparing my accomplishments to other people… at the very top of both of my “professions”. That’s actually nutty that I feel sufficiently skilled enough in two different fields to even begin to make a comparison. But it’s not healthy and discredits how much work those people put in to be at the peak of their craft.

Like of course I haven’t gotten the results of the work and risk that I didn’t put in. These people at the top of the Jiu-Jitsu and software development worlds are “all-in” on their profession and I’m only placing relatively moderate, hedging bets in each by comparison. And I’m still doing pretty good in each on an absolute basis, just not “elite” in either. This is more or less what I've wanted to do since when I was a kid too.

I have a memory in either middle school or high school learning about Michelangelo and the concept of a “renaissance man”. The cool kids today call themselves a “polymath” or “polyglot programmer”. I just don't think you can proclaim yourself as one. I feel like it has to be anointed to you by someone else. There's that earned approval thing again.

Nassim Nicholas Taleb (unsurprisingly, one of my favorite authors) has a less boasty idea for this, a “rational flâneur”. Someone who maximizes optionality and is interested in a broad array of subjects, but isn't rushed to "master" any of them.

I thought the concept of the “renaissance man” was the coolest thing ever when I first learned about it (also helped that his name was Michel-angelo, that made me pay attention in school). You could just do and learn whatever you wanted and cross-pollinate ideas from different fields. You weren't pigeonholed into one thing and could develop your interests organically.

That's one of the aspects I enjoyed about college was that it enforced a certain breadth across various subjects. This was once thought to be the entire point: to produce well-rounded adults. Now college is seen as just a pure ROI job training calculation, which is very unfortunate.

I have thought before that if I could just be a "professional student" and get paid to learn about everything, that would be my dream career.

Guess what, kid? lol.

As I've mentioned in a previous newsletter, the more that we know, the more we can get out of these Large Language Models. It's sort of like knowing the right words to cast a spell. The more vocabulary we know, the more variety of spells that we can cast. It will be advantageous for everyone working with these models to know as much as possible to get the largest possible return on investment on these tokens.

It's just we're currently asking them to do too small of things. For example, students asking them to write their essays for them. Instead, we could have the assignment be to connect two disparate ideas from potentially different fields to create a new third, interesting combination or application of them that is unique to each student. The new idea is the thing that is graded based on the strength of supporting evidence that the student can come up with the assistance of AI.

Testing for knowledge isn't the important thing anymore. Knowledge (a google search) and “execution intelligence” (Agents) have become commoditized now. We don't want to put ourselves in a position to directly compete with a machine that doesn't need a lunch break or health insurance.

As I've mentioned in another one of my previous newsletters (god I love citing myself), Perspective is the key differentiator on what we decide to do with AI tokens. Anyone can do anything now. It's just a matter of deciding what the most valuable thing that we could be doing at any given time. The trick is that life has always been like this, but now it's under a bigger microscope that all of the execution excuses are gone.

Testing for creativity may be what we can unlock here. And when I mean “testing”, I mean “creating a feedback loop”. Everything should be an iterative process. We shouldn't teach kids that things are ever permanently set in stone. If they're willing to put in the work, they should be able to improve their grade on any given assignment before the term end.

The real trick for job interviews is going to be testing for people's process around how they identify, prioritize, and solve problems. We can just assume any software problem can be solved. What are the highest value, most important ones to work on first? How do you work with AI tools to make that happen?

The people I’m unfairly comparing myself to at the top of my chosen fields chose their paths early on like I chose mine. I’m happy with where I’m at, and my life today definitely would not have the balance I literally just said I aspired to achieve when I was 25 if I went “all-in” on any one particular thing.

When I put it all that way, it gets me out of the “comparison is the thief of joy” trap and back into “this is my unique perspective” mindset. I get to be a “rational flâneur” as part of my job and outside of it in expressing myself through this newsletter and other forms of content. If anyone else can get something useful out of me putting stuff out into the ether, then mission accomplished.

Thinking through this comparison trap recently forced me to really figure out what I value most. If I valued those other achievements most, I would have done them, or would be in pursuit of them still. I would either be a Jiu-Jitsu world champion or in Big Tech already, there's no doubt in my mind.

Is that crazy arrogant to say? Maybe. But I've gotten pretty good results being “one foot in” both of these things at the same time. If I was two feet “all-in” either, I think I would do pretty well.

So what's this third, higher-priority thing that I value more than being a Jiu-Jitsu world champion or Tech Turbo Nerd? Autonomy.

I want to be able to do generally what I want, generally when I want. A lot of what I enjoy doing is tinkering and solving problems with technology, like Cal Poly's motto, "Learn by Doing." I want to make computers do stuff that had not yet been done before, more or less just to prove to myself that I can.

But I also want to be able to have a break from that. I want to get a full seven-to-eight-hours of sleep every night. I want to spend time with my wife and two cats. I want to pay it forward in my local Jiu-Jitsu community in the form of coaching and training. I want to lift weights, take walks, create content, read books, watch movies, go down YouTube rabbit holes, visit family, travel, and all the other things that make a well-rounded human.

Autonomy has been a throughline in my work life. Ever since I was a junior engineer, I always valued being on an autonomous team, or at least having sufficient autonomy on a team (the manager trusts me and gives me enough leash to run), to just do cool, hard, and inherently valuable stuff that I am interested in. It sucks to have to be spoon-fed every task, but sometimes that’s what the business calls for.

It's only because of this recent comparison trap that I even identified that I value autonomy above basically everything else in my life besides my family. This is probably an extension of me valuing time above all other resources. Autonomy is the ability to spend that time how I want.

Another way to think of Autonomy is Mobility, as in "ability to move". I talk about this in Jiu-Jitsu coaching because, as a wise coach Greg Souders says, “Jiu-Jitsu is the game of immobilization that leads to strangulation and breaking”. Mobility (the lack of it) is the first property that he talks about. You need to be able to hold people still to make them submit. Otherwise, they squirm around too much, stand up, and then run away from you.

If they can get away from you, then that means they are autonomous. They still have a choice or say in the matter. They can choose to disengage or re-attack at will. Jiu-Jitsu is all about increasing or maintaining your own autonomy and decreasing your opponent’s. Maybe this is why this autonomy lesson is ringing so clear now.

Further analyzing this comparison trap, if I went down the path of a singularly focused purpose, I may have missed out on a lot of the beautiful texture of life.

If you listen closely, you hear all these MMA champions say, "I sacrificed everything for this." I believe them. Many times I have heard and read fighters talk about how they've missed important events in their family and friends’ lives (birthdays, weddings, funerals, etc.) in pursuit of their singular goal.

I have also similarly heard the same type of “I sacrificed everything” speech made by singularly-minded businesspeople; entrepreneurs and corporate types. They ate ramen, slept on a couch, and scrapped to get by in order to fund their dream. Notice how we only hear from the ones who make it.

My hot take is: if someone brings up how much they sacrifice to win, I think, by definition, some part of them regrets it. If they're still keeping score of all the things they gave up in order to achieve a goal, then the goal was not all-encompassing or rewarding enough to make up for everything they missed out on.

It's a one-way door that they can't buy back. Their repeated chest-thumping about how much they gave up in order to achieve their goals really is just a warning for others to steer clear unless they’re willing to pay the same price.

To put it in numerical terms, why are you thinking about the $20 you had to give up for a million dollar payday? But maybe, just maybe that $20 wasn't money and was an irreplaceable, sentimental thing or experience, or worse, time, and you can't really put a price on it. That will fuck you up.

I try to live life minimizing regret while maximizing optionality. I want to be able to say I lived life fully and did everything I wanted to on terms I found acceptable. Someone wise once told me, “you get what you tolerate”. Meaning we should tolerate nothing less than things that feel good or even great for ourselves. If we tolerate less than that, and we actively, consistently dislike something in our lives, it will eat away at us.

This is just my perspective. I might be wrong. Please hit “reply” and maybe we can have an interesting conversation.

My favorite phrase for myself when I'm hungry to get things done is “Become Undeniable”.

As I mentioned before about Jiu-Jitsu is that I have undeniably achieved some level of skill at it on an absolute scale. I know more or less where I'm at in my particular niche of the sport. Most people don't. They never test themselves and they never truly know where they stand. They only have some vague relative sense of where they're at compared to others, who are compared to others, who are compared to others.

I try to tie myself to objective, undeniable things and achieve them. SMART goals, or something.

Another part of this is removing things that do not serve me anymore to make room for things that do. One way I'm doing this is by deleting social media apps off my phone and only accessing them on the web browser on my laptop. This really reduces the addictiveness of unlimited doomscrolling. I also want to just limit the negativity and focus on things that I can control and create, such as this newsletter.

35 feels entirely too serious of an age. Halfway to 40. It doesn’t get any more adult than that. Diseases start showing up then by how I treat my body now (and how I have been treating it so far, which isn’t all bad, but isn’t good either). I need to get under 200lbs and stay there for the rest of my life. I had some notion of lifting to be strong and always increasing weight on the bar, which is still a valid goal, but not at the expense of excess body weight. I can't afford a powerlifter “dreamer bulk” anymore.

Now that I'm not competing and not training as intensely in Jiu-Jitsu, the ultimate purpose of exercise for me now is just future disease and death prevention. Not the most fun or motivating thing in the world, but health underlies everything else fun that I want to do.

I'm currently around 240 lbs and I need to get down to "One-derland" as soon as possible. I think I can get there by Christmas in 6 months. The number on the scale determines a host of other health factors that will be under control once I achieve this. I'm always going to enjoy lifting weights to some degree, so I'm not concerned about losing muscle or strength as I lose weight. Any amount of weight loss at this point is probably going to be predominantly fat, and even if it isn’t, it’s healthier than the alternative of staying the same weight or gaining. Momentum is the goal.

The thing I've struggled with my whole life is choosing to eat healthy foods. If I was naturally gifted in grappling and software development, I was not naturally gifted in the enjoying healthy food stat point dice roll.

The times I have been able to successfully lose weight and get down to a certain healthy level has been specifically for Jiu-Jitsu and wrestling tournaments. Those are built-in time-oriented weight class goals that force me to adopt certain behaviors, otherwise, I don't compete.

I tolerated those behaviors because they led to a bigger goal. Notice how I didn't use the word “sacrifice”, it's not that dramatic. The goal was big enough for me to want to eat primarily meat and low-carb for certain stretches of time. But then the competition came and went, and I reverted to just eating whatever I wanted.

I need to find alternatives to food habits that I enjoy. Remember the whole “not sacrificing” bit earlier? I recently found out that I enjoy pineapple. A lot. I’ve never been a big fruit person, but I will ensure that my future kids will be. Having a fruit that I can keep on hand and that I actually want to eat, without guilt, makes me feel like I'm not missing out on more calorie-dense sweet treats like cookies and ice cream.

I had a big 32 oz pack of cut pineapple today for $7. It was 450 calories and very filling because it's not just sugar, but also 12g of plant fiber. A single Crumbl cookie has more calories than that and costs just about the same. And you can never have just one.

If you don’t have a favorite fruit as an adult, do yourself a favor and buy a variety pack of pre-cut fruit and try them all. If you still can't find one, try one fruit from the store every day until you do. I never got this actionable advice, so I'm trying to pass something on.

My next challenge is to find meat that I can consistently cook well and enjoy while hiding veggies in there somehow, while also minimizing dish use.

How does this relate to AI? You want to give agents closed feedback loops with constraints. Meaning they can make a tool call to enact a change and then observe the effects of their change, and then they can iterate on that. My closed feedback loop is the scale. The times in my life where I've lost the most weight, I weighed myself first thing in the morning every day. The times where I've gained it back, I stopped doing that.

Basically everything I write about is from my personal perspective and experience, but all of that is in the context of being a teammate in my marriage. It's important that you're an individual and you feel good about things you do by and for yourself individually in order to be a whole person to your partner.

Even though my wife and I both work from home and we see each other throughout the day (which is way more than any other time possible in modern history) we still have our own separate individual jobs, hobbies, interests, friends, etc that keep us as whole people. I think it's dangerous when you put your entire identity into another person, and that other person puts their entire identity into you. Now neither of you have identities and feel like you're giving up yourself for the other person and start to feel resentful, even though what attracted you two together was your separate individual identities.

I love my wife for who she is. I want her to continue to be her and I want to give her space to do that. At the same time, when we're together, I can do a better job of being fully present. I've had this competition mindset around work for the past 6-9 months or so, and it's a little bit all-consuming. If you're here reading this, you kind of already know.

Everyone in the tech sector is trying to wind up on the right side of the K-shaped economy for themselves and their families. This is why I'm writing this newsletter on a Sunday evening, and I've been writing most of the day. My wife is out of the house today, so that's my excuse.

Nobody wants to lose, nobody wants to fall behind, but at the same time, we still have to live. It is still real time passing every second. If you're determined to end up on the correct side of this K-shaped economy and “win” this AI thing by putting your head down for the next five years on work and doing the bare minimum everywhere else, you may not have a partner to share in your spoils by the end of it.

Suffice to say, I want to be a great husband and be mentally and emotionally present whenever I am with my wife to the greatest degree possible. This includes doing stuff around the house to maintain it; which is part living space, part office, and mostly cat playground.

Having such an integrated environment where I'm currently writing on the couch with two laptops doing three different streams of work while my cats are running around the living room playing may not be the most biologically or energetically natural thing to do, (aka, it’s freaking exhausting) but this is part of how I want to live my life. All of it together interleaved, but I may have to work on some boundaries to ensure that I can decompress at some point so I can show up for my wife better.

As I’ve also mentioned before, earlier this year, my wife and I had a very early miscarriage (also called a chemical pregnancy). We want to be parents, and we're doing all the steps necessary to make sure we're both healthy to do so.

Weirdly enough, I don't feel as freaked out about this now. For about two days, my wife was pregnant and our lives were on a one-way train leaving the station. It clarified what was important to me and it brought a new sense of purpose to life. There was a new mission and shared goal to get the house ready to welcome the baby in nine months.

Unfortunately, that didn't happen. We're undeterred and hopefully by this time next year, I'll be a father. That's another reason why I'm motivated to lift this “generational curse” of this eating healthy food issue. I'm realizing more now that my kids are going to learn more by observing what my wife and I do, normalize and habituate, than what we'll ever tell them verbally.

Our future children will feel the rhythms of our life first, and that basic momentum more than anything else will carry them forward into whatever adventure they are called to in adulthood.

I would also like to think that, given my coaching background and Constraints-Led Approach bent, I am much more open to letting my kids fail at low-stakes, appropriately scaled challenges. We learn by doing at all ages. They have to get used to interacting with their environment and associating cause with effect; perception with action.

They can't rely on the environment of mom and dad to bail them out every time when something gets a little bit too challenging. The whole idea of this parenting process (from what I can observe) is to bootstrap children into becoming fully capable adults, and that starts with building their confidence in achieving the smallest things and scaling up from there.

I don't know, maybe that's just me talking tough before I have a little person who melts my heart and I would do anything for. I'm seeing it a little bit now with our cats and how half of the living room is taken up by their toys. It's their world. We're just living in it.

I think past a certain point of physical/career/”life” maturity, where you had the opportunity to go after your childhood dreams and it either worked out or it didn't, life continuing to be exclusively about you becomes a little bit boring, stale, and less interesting than investing in others.

I think after a certain point, at least for me, part of my purpose is to care for gentle things that can't take care of themselves. For right now, that's cats and maybe white belts, but in the future, that will be my kids. Something something yin yang, being strong for the weak, etc.

Alright, everybody who's been waiting ever so patiently for another mention of AI gets one right at the end here. I've been jamming on two other projects while I've been writing this newsletter. I think this is the real power of Agentic AI technology. The power of kicking off long-running async tasks.

The ability to just give an agent a goal and a reliable closed feedback loop where they can judge whether they are getting closer to or further away from their goal. I heard on the “Code with Claude” conference live stream that they call this “hill climbing”. I have more or less hill climbed two very different major projects over the past week with the help of Claude's latest model, Fable (RIP).

Fable really was a different beast. It was able to have an incredibly rich context window, crunch so many actions per turn, and write so much code to get exactly what it needed. It was an amazing sight to behold. It was very slow, but I viewed it more as a lumbering giant ready for battle than a slow grunt reluctantly taking orders.

I want to keep pulling on this thread that any and all software is now essentially solved, and now it's just a matter of what should be worked on. I feel like my kind of eclectic “Jack of all trades” type of experiences yield a unique Perspective on the world that is seemingly valuable to a certain number of you reading this. If you’re still here, thank you so much.

One more thing: my wife just threw me an incredible birthday party last weekend with tons of friends (mostly from Jiu-Jitsu, but a few outside of it!) who came to enjoy a dressy Vegas-themed evening with no-stakes blackjack and roulette over bartender-served Old Fashioneds at our house. My wife planned the hell out of it, and the event was a huge hit.

I was particularly struck when my wife brought the Black Belt Jiu-Jitsu-themed cake out and ~30 people started singing "Happy Birthday." It's rare to have that many people, as an adult, voluntarily sing happy birthday to you, and it meant something more to me than ever.

It struck me because everyone was there because they cared about me. They were there out of their own free will. They didn't have to be there, but they wanted to be there on their Saturday night. These are earned relationships.

After saying the same thing in four different ways, it's still hard for me to process that many close friends showing up to my house in nicer-than-Jiu-Jitsu clothes. I said it in my short “thank you” birthday speech, but I really felt all of the love in the room and everyone was there just to have a good time.

All of the expense, preparation, hassle, and planning for this party were made worth it by seeing those 30 people, singing in a simple act of care. Something that we have done as a society since we were kids. I don't know, it just means more as an adult now because these people don't have to be there, they aren't your family, but are instead a chosen family.

It has made me want to be someone who shows up for others even more. I show up for my friends for important things, but I'm sure there's other ways I can be there for them in more mundane parts of life.

This is kind of the whole point of being human: to love and be in community with others. Let's not forget that in the age of AI.