Thoughts for the Second Half of 2025

In-the-pocket? Morning routines? The Virgin Mary? Dogs pissing themselves?

In-the-Pocket vs Out-of-the-Pocket

“You’re definitely in the pocket”, he told me. I felt offended.

I had just jumped into a conversation with some half-drunk friends that were giggling about a little game they were playing. They were looking around the Airbnb guessing if people at the party were “in-the-pocket” or “out-of-the pocket”.

“Five years ago when you quit your job to start Interview Query, you were out-of-the-pocket. But right now you’re in-the-pocket”, he said. “I’m also in the pocket. But our other friend, he’s WAY out of the pocket”.

I was bewildered and demanded an explanation but never got one. After five minutes, we moved on, but their comments started living rent free in the back of my head for the next couple of weeks.

What did they mean by being in-the-pocket?

There was something offensive to me. Like I was following the crowd, being a normie, maybe a vanilla type person that wasn’t taking any risks. And it felt true in the moment, running Interview Query was quite comfortable even if building a business was still sometimes stressful.

But not taking risks felt contradictory to my own perception of myself. I didn’t want to be seen as someone who was just going along with things. It irritated me to think that if the options were to be in-the-pocket vs out-of-the pocket, wouldn’t everyone just always want to be out-of-the pocket?!

Later on, I flipped through some old journal entries looking for evidence of growth and evidence of risk in the last few years. And while I found plenty of personal development—navigating a breakup, buying a house, launching coffee brands and shuttering them, trying new management tactics, I realized there really wasn’t anything as risky like that first big jump from data scientist to bootstrapped startup founder. And consequentially, it was proven by the amount of agonizing I was journaling about for half a year before making that decision.

Can you manufacture yourself to be "out of the pocket”? Are we glorying the experience too much like the main character in Eat, Pray, Love?

Last quarter I gave myself a goal to launch a new product from 0 to 1. By June, I had iterated through enough customer interviews to know I wasn’t in love with anything. Back in-the-pocket I go? Instead on kind of a spur of the moment, I launched and AI course meant to teach data scientists how to become AI engineers. The goal was to actually build something in AI. The landing page went live. Customers signed up. And suddenly I was committed.

Being "in the pocket" is comfortable. It's snug. It means sleeping easy at night.

Being out-the-pocket? It’s doing crazy shit and then regretting it. I’m freaking out at how much work I have this week before I have to ship my course.

Are you in-the-pocket or out-of-the pocket right now?

Productivity Update 2025

“In the mornings I feel like my hourly rate is like $5000/hour and in the afternoons it’s not even $5 bucks”.

This was my friend telling me why we couldn’t go surfing in the morning. I was aghast. We were on a surf trip and the forecast said tomorrow morning would be firing. But he still couldn’t bring himself to go.

I understood because I discovered there really is something special about early mornings. Call it turning 30 or becoming an adult, but after waking up and readjusting myself into reality, I feel almost unstoppable. Any task I could obliterate it no questions asked. Whether it was locking down an hour of deep focus time or putting together a Ikea bed frame, nothing could stop my willpower.

After lunch however, there was little that I could actually get done once the carbs hit the stomach. My phone would naturally start drifting out of my pocket and into my hand. My focus timer would often get stopped as my gaze would move towards the bright notifications on my desktop.

I quickly realized that the afternoons, are essentially useless. And unless I exercise for 30+ minutes or take a nap, I’m not going to get anything done. Recently I’ve discovered you can take 2mg of nicotine gum, but that’s another story.

In a world of productivity hacking, I sometimes think about where I can apply constraints to myself so that discipline = freedom in my life.

If you don’t have a deep work routine in the mornings, I cry for you.

Things to Share

• A few months old but Scott Alexander’s The Colors of her Coat stand out to me as great philosophical interpretation of our pivotal point in AI. The production of paintings back in the renaissance period might be equivalent to creating large scales of art now like movies. I had never known anything about the insane work gone into creating Ultramarine blue. You can see the parallel in what might have taken hundreds of people twenty or thirty years ago to build a similar web app you can one-shot with AI today. It may not be even possible to fathom what will be increasingly easier to come in the next ten to twenty years.

• From Maybe Baby comes the unverified but perfectly intuitive psychological framework for why each person can be annoying in their own specific ways and why. Hint - we’re probably all self-sabotaging ourselves and the tricks to avoid it stem from how we can be more aware of these moments.

• From Jason Cohen at The Smart Bear comes Ruthless prioritization while the dog pees on the floor. This in many ways transcends business philosophy but also to productivity and life. Moments in our lives are unevenly distributed across a spectrum of importance and yet we get caught up in misallocating our time and attention to most of the times rather trivial problems. Why do I spend hours of my life getting mad at car rental companies?

• This clip from Louis CK was resurfaced to me by Frederik Gieschen’s article. Louis CK pays tribute to George Carlin and tells a compelling story of what it really takes to become great. What does it take to reinvent yourself or your act? Diving into emotions, finding his true words, throwing everything at the surface level away, and doing it his own way.