This is where I share 3 things every week with my friends and anyone else interested.
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A picture from my life:

I went to two more Dodgers games since the last newsletter. That’s three games this season!

A thing on my mind:

What is your objective function?

The most important question just got more important in the age of AI.

In our roles now as AI supervisors, our ability to benefit from this abundant intelligence depends on how clearly we define our goals. We need precise prompts and a clear sense of what success looks like. We have to know what we want.

And…if you don’t know your objective function, you are someone else’s objective. Just like how social media algorithms are trained to maximize our time spent on their platforms against our better judgment, soon enough everyone and everything we interact with in the world will leverage AI to carry out their goals. We won’t stand a chance unless we know what we want.

I recently caught up with a friend who runs a non-profit and barely takes a salary. I asked her why not increase her salary now that it’s successful. She said something to the effect of, “What’s the point of that if you’re already doing it for the mission?” The way she said it, her clarity of purpose stuck with me.

My co-founder David is similar. He’s deliberate. When he commits, it’s 200%. David practices “full send” as a matter of habit. I make fun of him for speaking in a definitive manner on questions that I didn’t think warrant a period instead of a question mark, but I know his strategy is to constantly force clarity.

Most people I know, myself including, could use more clarifying of their objective function. It’s frustrating to hear friends say they want something only to watch them act in ways that look like self-sabotage.

My weight loss journey is like that. I’ve been tracking my weight since I was 22 because I’ve been wanting to lose weight since I first experienced a dramatic weight gain at 16.

As you can see, every year or two I’d go on a diet, lose weight, plateau, and give up. This went on until February 2023, when my “why” finally became clear. I wrote about it in “Pain avoidance machines (Ricky Weekly #94).” The gist is that the pain from carrying all the extra weight finally crossed an unbearable threshold. I couldn’t give my best to the things I care about. Later that year, when I read Peter Attia’s Outlive and came across his question—“Do you want to be able to pick up a grandchild?”—that solidified my resolve. I want to live life to the fullest for as long as possible because life is too good to half-ass.

Pain avoidance machines (Ricky Weekly #94)

Ricky Yean

·

March 17, 2024

Read full story

Thinking about times in my life when I’ve achieved major clarity, most required being pushed to the brink. That’s not ideal. You don’t want to need extreme circumstances to gain clarity.

I wish you could achieve clarity just by thinking longer, but, at least for me, that just falls way short. The next best thing is to act as if you are clear. Be like David. Use periods instead of question marks even if you are not sure. Behave like someone who knows what they want, and soon enough you’ll find out if it’s true because you’ll be moving. On the flip side, if you are not acting according to your wishes or haven’t gotten what you want (assuming it’s within your control), maybe it’s time to update your objective function.

Of course, life doesn’t always have to be so goal-oriented. Part of the fun is letting life reveal itself at its own pace. Goals are just how we play by exercising agency. The good news is that AI will lower the cost of acting as if. Our AIs will try to understand what we want even if we’re not sure, act as if on our behalf, and return with results to help us see if that’s what we wanted in the first place.

Here is a funny clip on acting as if and learning about yourself:

A piece of content I recommend:

Joe Liemandt - Building Alpha School, and The Future of Education on Invest Like the Best

Tech Twitter has been buzzing about Alpha School for a while. I first read a parent’s detailed review and thought it was great, and then this episode dropped and became a conversation topic amongst friends. As someone who brute-forced school and never thrived in that environment, there is nothing about the way school works that I’m tempted to keep other than the peer socialization component (especially the “welcome to the jungle” part). I’ve never had “that teacher” who changed my life / believed in me / saw my potential. I’ve never felt engaged. If models like Alpha School existed, I think I would’ve loved it.

Bonus Content: What Is Man, That Thou Art Mindful Of Him? on Astral Codex Ten

A funny post about building AI.

Bonus Content 2: The 3 Best Core Exercises on Squat University

I’ve been dealing with recurrent lower back issues until I started doing the McGill’s Big 3 every morning. Now when I sit, stand and move, I can feel my core engaged. That’s a new sensation for me even though so many people have told me to engage my core over the years while doing various exercises.

We have such different lived experiences that words fail us. It’s like when a dance teacher tells you to move your body a certain way and you’re like, “I didn’t even know it was possible to move your body like that…”

Other examples: I used to hate walking and never understood hiking as a hobby. Then I lost weight, my thighs stopped chafing and I started walking normally. Now I love hiking! I used to feel like I can’t control my eating. Then I eliminated most ultra-processed foods and simple carbs and realized that I can as long as I don’t consume things that hijack my brain!

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

This is where I share 3 things every week with my friends and anyone else interested.
—
A picture from my life:

The Dodgers were in town! It’s been forever since I’ve been to a Dodgers game. I go to lots of Warriors games, Giants games, and even went to a Valkyries game for the first time recently but NOTHING compares to cheering for YOUR team!

A thing on my mind:

I’ve been thinking about what it means to set healthy boundaries.

Without them, life’s daily “elements” seem to erode my sense of self. Boundaries are signals that I know what I need and that I value myself enough to communicate those needs clearly.

I used to think people who are sensitive about boundaries have limited capacity or adaptability. If someone got upset by harsh feedback, I’d think, “They just can’t handle the truth!” If someone needed personal space, I’d dismiss it as “rigid and inflexible.” If someone bulldozed others with their agenda, I’d label it “selfish.” I’m realizing that’s not it and wow was I judgy.

I wasn’t entirely wrong, though. Like a lot of people, childhood was painful. It felt like the world just wouldn’t stop hurting me, and no one answered my cries for help. At some point, I decided boundary-setting was a useless exercise. Instead, I needed to develop the capacity for pain and learn to adapt to any situation. You can imagine then when I met people who acted like everyone needed to respect their boundaries, I’d think, “wow it’s so unfair that they get to ask to be treated differently.” It’s even more infuriating when people would comply, myself including. I never got that treatment.

I’m realizing now though that just like capacity-building is a skill, adaptability is a skill, so is boundary-setting. Boundary-setting might be the more important skill because it isn’t just about survival; it’s about thriving. You get to learn what you need and demand it from the world. It’s giving main character energy.

For me, setting healthy boundaries involves:

1. Noticing when a boundary is being crossed

2. Confirming it’s genuinely a boundary issue and not just temporary discomfort

3. Establishing the boundary clearly to the offender

Noticing

The girl I’m dating is good at checking in with me to ask me if I’m okay with a plan or what we’re doing. She knows I’m eager to please but can get grumpy if I don’t get what I need. Her simple questions reveal how often I overlook my own discomfort. I usually struggle with answering if I’m okay, because I’m not sure! Instead, I default to the people-pleasing, “yeah, I’m okay” or even fake some enthusiasm to avoid disappointing people who want me to be happy. I’m sure we all do this from time to time. Still, her check-ins give me a chance to register if there’s an incongruence or unmet need.

Confirming

Even when I notice discomfort, it’s still difficult to tell what is a boundary and what is just a fleeting emotion (eg HALT: Hungry, Angry, Lonely, Tired) or something I can adapt to. For example, if travel disrupts my morning routine, is that boundary-breaking or can I simply adjust what I do? If someone’s comment hurts me, should I say something or am I too sensitive? If I complain, do I become the insufferable one?

Clear boundaries requires clearly knowing what I’m willing to fight for. It's taken years and considerable self-sabotage to realize that maintaining my self-confidence is a critical boundary to being who I want to be. If a physical injury is your body telling you you’ve gone too far, my emotional resilience has kept my mind from telling me I’ve injured my heart.

Establishing

Noticing and confirming boundaries leads inevitably to the hardest step: communicating them. I'm relatively comfortable communicating the uncomfortable (“I feel” statements help). The difficulty lies in the decision itself—deciding that I'm worth fighting for. If I don’t value or trust myself, I won’t genuinely advocate for myself. I have to believe deeply that “I deserve to be me” and can occupy proper space in the world. I’m practicing this now.

Acknowledgements

This was hard to write because I’m still processing it, but recent interactions with these friends have deeply influenced me:

• Jason coached me to “let Ricky cook” by getting out of my own way. His story about being too resilient to physical pain in gymnastics made me wonder if emotional resilience could similarly become harmful.

• Ryan reminded me that my younger self balanced thoughtfulness with bold, intuitive action. He used to say, "Protect your swag!" Today I think the kids would use the word “aura.”

• Kat and Amanda: Going on trips with them this summer opened my eyes to what healthy boundaries can look like.

• Nikil: For writing about how to live a confident life and setting a good example of someone who knows his worth.

Even random sports podcasts have influenced me (probably Baader-Meinhof):

Jeremy Lin said he should’ve spoken up earlier to Kevin McHale. Gary Sheffield said speaking up against rookie hazing taught him that he can demand respect.

“I guess I got my swagger back!” - Jay Z

A piece of content I recommend:

The Materialist written and directed by Celine Song (Past Lives)

Past Lives was my favorite movie of 2024, so I had to watch Celine Song’s latest—and it did not disappoint! Past Lives explored longing for a multiverse of what-ifs. all those coulda, woulda, shouldas we carry until we surrender and embrace the present. The Materialist dives into the infinite possibilities of the present and how we struggle to decide what’s truly right for us. “Dating is hard and love is easy,” but can—or should—you trust what’s “easy” when your brain tries to protect your heart by trying to check all the boxes?

Bonus Content: Ocean Vuong Was Ready to Kill. Then a Moment of Grace Changed His Life from The Interview, New York Times

When this interview dropped, my friend Katie and I both separately listened to it right away. Then Katie called me and I said, “Ocean Vuong on The Interview!?” She was like, “Yessssssssss.” That’s how good it was.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

This is where I share 3 things every week with my friends and anyone else interested.
—
A picture from my life:

I went on a bachelorette party trip! I feel special being part of a bridal party. Boys and girls can be so different it’s a fun topic to think about.

A thing on my mind:

Whenever I’m down about work, I like to say to myself, “I CHOSE this.” It’s a powerful reminder of my tremendous luck and privilege to do what I love to do, and that I can always choose something else.

Then I ask myself if I still love what I do. People have asked me, “is this your life’s work?” I hope it’s not that serious. Sounds like a trick question to me, as if we are only meant to do one thing. My answer is always, “who knows!”

I fell in love with startups in college. 15 years later, I know much more about it and I still love it. Most days I wake up excited because I get to do something challenging that has potential to teach me something about how to shape our world. Business is a big, competitive game with very few rules that affords me maximum degrees of freedom and scorekeeping to tell me what I’m made of. Can I fall out of love with it at some point? Sure. It’s really hard and I’ve sacrificed a ton. So I have to always be checking to make sure it’s still worth it.

Am I good at it? No. Not yet, at least. I’m not nearly as good as I believe I could be. One of the hazards of this job is that you can’t easily get the reps to improve a particular skill (ie if your startup isn’t scaling, you don’t get to work on hiring skills). Another one is that the actually important skills are too meta* and hard to work on (eg seeing opportunities and knowing how to capture them). Either way, regardless of how good you get, luck plays a very significant role in the outcome, which makes this all very unsettling but also very appealing. You have to constantly be working to figure out what actually matters for your business, charting paths to your best ability for those around you, and being willing to run full speed ahead of everyone knowing where you’re going is most likely off the cliff.

Should you succeed as a founder, you’d have created a system. You can hire employees to operate with reduced uncertainty for a predictable result, and they get to showcase and refine their skills in that context to produce the result more effectively. But at the end of the day, the uncertainty is only reduced for everyone in the system to the extent the business is successful. Job security is a fantasy. Markets are alive and changing faster than ever. Just over the last few years we went from one of the longest bull markets in tech to massive layoffs due to economic uncertainty and AI disruption. The founders are the ones staying up every night in good times and bad studying the market and thinking about the customers to figure out how to move in the direction of opportunity. Founders trade certainty and security for resilience and agency.

Still, founder life is hard. I’m plagued by insecurities. What’s been useful for me over the years is to stop believing in the successful founder archetypes. Bill Gates. Steve Jobs. Jeff Bezos. Mark Zuckerberg. Elon Musk. Their successes have led to an entire industry pattern matching for roughly the same type of brilliance: intellectual horsepower/rigor, precociousness, brazenness/daring, visionary-ness, a little unhinged with a side of the tism. As an ambitious nerd, this is admittedly what made Silicon Valley feel like home to me. These are qualities historically undervalued by society. But it’s a trap to think they’re the only attributes that hold any predictive power. For too long I’ve discounted many of my strengths for not matching up to this archetype. Now I know better. Among all the pattern matching, founders and companies need to be differentiated enough to win. I think for me to really do that well, I need to embrace who I am.

*Footnote: the “meta” skill of business is not so meta according to this article by Cedric Chin. It’s a different type of learning that you can think of as “sensemaking” — useful when learning from real world experiences where feedback loops are noisy, delayed, might not even exist. There are ways to get better at “sensemaking” through constant reflection and being agile enough about updating your priors. Here’s a related article from Brian Lui on the dangers of tight feedback loops. Really, really cool stuff.

A piece of content I recommend:

Why Relationships Die & Which Ethnicity is WORST in Divorce on Flagrant by Andrew Schulz and Akaash Singh

I’m a new fan of Andrew Schulz and Akaash Singh, so I’ve been gobbling up all their content. The podcast’s pretty sweet. Good comedians have superpowers because they can cross the line and take conversations to places they don’t normally go. The topic of divorce is not something people like to talk about and here’s two and a half hours of it in exhilarating depth with a wide variety of perspectives. Another good episode is the one with 50 Cent talking about…Diddy. Yup. They’ve also talked to politicians like Bernie Sanders, Pete Buttigieg, Eric Adams, Vivek Ramaswamy if you’re into that.

Bonus Content: I have a bunch this time, so a sentence to introduce each.

• If you love San Francisco, you’ll love this explainer of SF’s map and how it came to be.

• This is like Jiro’s Dreams of Sushi but for ramen lovers.

• A Chinese YouTuber interviews her grandfather about growing up in the communist revolution. I think this is a pretty rare first-hand account.

• A very adept conversation about trauma between Peter Attia and Jeff English.

• A fun reminder that we are the source of our problems (and the title of this newsletter).

• If you’re looking to eat better, Eric Topol interviews Kevin Hall who used to be a Senior Investigator at the NIH and looked into ultra-processed foods, among other things in our food environment.

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

This is where I share 3 things every week with my friends and anyone else interested.
—
A picture from my life:

Went on a breakfast date with my friends’ kid (and her parents). We loved watching bigger kids and trains go by!

A thing on my mind:

I’m at Thorough Bread and Pastry enjoying their almond croissant (one of the bests in the city). This is my 100th Ricky Weekly. Even though it hasn’t been a “weekly” for some time, it still gives me joy whenever I make the time to write what’s on my mind to share with you all. The fun is in how writing helps me think. I always have a lot of thoughts swirling around in my head. They keep swirling because I feel like if I just pull on their threads a little more, they’ll reveal something about themselves that will change the way I see the world.

I had mentioned that I might stop writing this newsletter at No. 100. The thinking at the time was to pivot myself into higher impact projects in my free time. I crave impact and was belittling this newsletter for its mostly selfish nature, but maybe that’s too harsh. When I look at all the things that make me happy, writing for fun is right up there near the top. The desire for higher-impact work is still burning, so I’ll do that anyway, but I’ll also keep writing here.

So, what’s been on my mind?

I’ve been re-learning that I have agency. A new friend was remarking that I am a high-agency person, which matches my own self-narrative. But a closer examination would show that I contradict myself and act low-agency in lots of situations. If there’s benefit to choosing differently to produce a better result and I don’t choose it, that’s infuriating. Of course, easier said than done. Being high-agency feels virtuous because it’s hard, like waking up at 5 and starting your day with a workout. It’s not the end-all, be-all of course. Nothing ever is. But re-learning that I have agency in many more situations helps me practice it more frequently.

I’m un-learning that I have to hold myself to sky high expectations in all aspects of life. For as long as I can remember, I’ve set a very high bar for myself. The reasons are complicated, but the consequence is I’m always failing and beating myself up over it. I was watching the latest season of F1: Drive To Survive, and Fred Vasser described Charles Leclerc as “over-motivated” and that struck a chord. Obviously very different context but the idea that you can be “over-motivated” is a nice reminder. In an email with my friend Jason Shen, he wrote, “Research shows that beginners need positive feedback and reinforcement, while experts benefit more from constructive criticism about gaps they need to address” as a way of reminding me that I can be more adaptive with how I set expectations to not deprive myself from ever being a beginner. I’m a beginner in almost everything I try to do!

I’m learning that I might have an “addictive personality.” I was being very self-critical with my fitness coach about falling off the weight management horse for two weeks when it was only supposed to be a weekend. Not the first time it’s happened, so he pointed out that I may have an addictive personality and will experience more polarized behaviors. For example, after two years of work, I got to a point when I’m “on” (the proverbial horse) I can stay very disciplined and eat a healthy diet, but when I’m “off” I swing hard in the other direction and engage in unhealthy behavior that can verge on disordered eating. Depending on how long I had to stay disciplined, what my brain needs to feel like I’m really off is a lot more than just a cheat meal or two or three. Combine that with the addictive chemicals in bad food and my other addiction to beating myself up when I’m down…things can get out of hand. I’m not sure if “addictive personality” is even a real thing but it does explain a lot outside of my relationship with food and why I prefer a simplicity, a bit of structure, and minimal living. Either way, it’s useful learning to help inform adaptive strategies.

A piece of content I recommend:

An Expertise Acceleration Experiment in Judo and Mental Strength in Judo, Mental Strength in Life by Cedric Chin

It was intriguing to read about someone’s journey to compete in high-level Judo in their mid-30s after taking more than a decade off from the sport. The most striking part to me was how the author’s coach identified “mental strength” to be a limiter to his progress. The author writes a successful business blog, which takes mental strength to accomplish, so I would’ve thought the same mental strength would translate to working on Judo if he’s completely dedicated to it. That’s too simplistic. This is what got me to email my friend Jason who knows the author, and he reminded me that our attributes (eg mental strength) are domain-specific.

Bonus Content: Court of Gold on Netflix

USA vs Serbia and USA vs France were two of the best games I’ve ever watched in my life so just to re-live those two games would’ve made this worth watching but it definitely delivered way more. If you love basketball, you’ll love this. Fuck it we ball.

abortedfetus133

A post shared by @abortedfetus133

Bonus Content 2: Another Harry Mack Freestyle. Enjoy!

@alex.ontiktokRick Glassman gives a task to Harry Mack: come up with a “Girls At Guggenheim” freestyle — amazing! Is there any other rapper that could do something like this? #flowstate #freestyle #rappers #hiphop #improvisation #podcast #legend

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🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.

This is where I share 3 things every week with my friends and anyone else interested.
—
A picture from my life:

Found a mushroom, a banana, and a shark at the farmer’s market.

A thing on my mind:

“What’s your biggest fear in life?”

A friend asked me this recently. At this age, a lot of my fears have subsided. I don’t feel much more courageous, but I’ve stopped spooking myself as much as I used to.

I told my friend my biggest fear is not living up to my potential. Not becoming the best version of who I can be. I know I sounds like a typical overachiever. How would I even know if I’ve reached “my potential?” All the conventional markers of success are arbitrary. Startup IPO? Win the EGOT? Own a home? Build a loving family? Just different games of our choosing (or “different adventures” since “games” feels like a neg and I don’t mean to trivialize how we find meaning).

For me there’s no finish line, meaning I’d probably have this intense desire to be better until I die. Striving is a lifestyle preference, and playing the startup game to challenge myself still feels right because it has a tight feedback loop. I’m challenged to be better every single day.

As part of the improvement, I’m working on overcoming moments of FUD more quickly. When I feel FUD, experience has shown me that there’s something valuable on the other side, but I don’t feel like I’m moving swiftly enough through them. So really, like FDR said, “the only thing we have to fear is fear itself.”

Jeff Bezos’ Regret Minimization framework resonates. I don’t want to look back on my life and regret not doing what I want even if it’s scary. I’ve been really enjoying the latest Silicon Valley mantra, “you can just do things” because it’s a wonderful reminder.

Talking to my friend about how I arrived here, I can give you countless stories but the original sin was probably spending my entire childhood hiding in fear and helplessness until I took control and began living. I remember the day like it was yesterday. I was 14, and it felt like someone flipped on the light switch. I realized that I can poke life and mold it to make it better. Only after that did I start to really perceive the world, register the experiences, and remember the people. Everything I have today is because of that fundamental realization, so the goal is just to get better at the poking and molding.

A piece of content I recommend:

Jerry Seinfeld on Blocks w/ Neal Brennan

There’s not one thing that stood out in this conversation. The whole thing was great. I love it when comedians talk to each other because to be good at their job they have to see life very clearly, from all the angles and all levels of depth. Even better they’re both writer types, so they can articulate what they see.

Bonus content: I saw someone recommend a book called “Don't Believe Everything You Think” and thought the title was great but I’m probably never gonna read it. Then Baader-Meinhof took over and I started seeing similar ideas everywhere. Here’s a good clip from Mel Robbins on how ruminating or venting to friends can be counter-productive, asking what if you simply do not allow it?

melrobbins

A post shared by @melrobbins

Here’s research that suggests we can inhibit negative thoughts and improve our mental heath:

Bonus bonus: This Frank Ocean cover together with drone shots of LA is immaculate vibes. Reminded me of HBO’s Insecure.

blxst

A post shared by @blxst

🤗

—
As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.