What Are You Optimizing For?

Holiday week threw me off, I thought today was Wednesday 🙃

That question—what are you optimizing for?—has quietly shaped everything from my training schedule to how I engage with social plans and evaluate professional opportunities. In this issue, I share three recent reflections: the surprising power of AI-assisted planning for a 100-mile ride, a look at how creative work is changing inside tech giants, and a behavioral deep-dive into why FOMO still strikes, even when you’re living your dream. Each entry is a window into how we make better choices when we design with clarity.

🏔️ The Personal Growth Lab 🏔️

Takeaway: Even in something as physical as training for a race, the right combination of reasoning models and personal context can produce systems that are smarter, faster, and surprisingly human.

After completing an Ironman 70.3 last year, I saw firsthand the value of having a goal to train for. It made self-control easier and gave my daily routines more purpose. This year, I signed up for a 100-mile charity ride called the Obliteride (supporting Fred Hutch Cancer Center). With a few months to prepare, I wanted to approach my training with intention, this time using generative AI to help build the plan.

Here’s what that looked like:

First, I wanted to understand the factors that would most influence my race performance. Sure, fitness and bike quality matter. But what about sub-factors like flexibility, weight, cardiovascular health, or the specific terrain? I turned to ChatGPT-4o to help me craft a detailed research prompt for OpenAI’s o3 model. Within ten minutes, o3 generated a breakdown of all relevant variables and ranked their importance.

Next, I asked o3 to design a 10-week training plan grounded in the research. Then, I layered in the personal data from my fitness trackers, heart rate, VO2 max, sleep patterns, and had the model build out a custom milestone tracker. I even asked 4o to generate simple visualizations to pair with each training phase.

In 30 minutes, I had a fully tailored, research-backed plan that in the past would’ve taken a coach weeks to create.

AI Workflow Recap:

4o – Wrote targeted prompt for o3

o3 – Conducted deep research on performance variables

o3 – Built 10-week training plan

o3 – Created a metric-driven milestone system

4o – Generated visuals to accompany the training plan

⏰ Timely Insights ⏰

Takeaway: The future of work won’t just reward those who learn new tools, it will reward those who can mourn and move beyond what those tools replace.

During the Industrial Revolution, the assembly line transformed how goods were produced, but also wiped out many crafts. Jobs didn’t disappear; they were redefined. As work became more routine, it gave rise to new hierarchies and management norms that still shape our workplaces today.

A recent New York Times piece examines a potential echo of that transformation. It profiles Amazon engineers whose once-creative roles have shifted toward quality control as AI systems solve more and more of their problems. What remains is high-volume, repetitive work, technically advanced, but stripped of the improvisation that once made it fun.

We don’t know yet whether this marks a new automation cycle. But it’s a powerful reminder: adapting to technology isn’t just about learning new tools. It’s about acknowledging the emotional and identity-based shifts that come with the change. Grieving what’s lost is often part of moving forward.

🗺️ Behavioral Blueprints 🗺️

Takeaway: FOMO is a signal, often not of what you want, but of how much your identity is tied to being seen. When that’s the case, curiosity beats comparison every time.

I recently returned from several weeks of travel. While it was a great adventure, I noticed something surprising: every time a party invite or group chat pinged my phone, a wave of FOMO hit. Even surrounded by beauty and novelty, it felt like I was missing something “back home.”

It got me thinking: FOMO isn’t about real opportunity, it’s about perception.

Scientifically, FOMO is the anxiety that you’re missing out on a rewarding experience. But more often than not, this anxiety is driven by external validation, being seen at the event, sharing the moment on Instagram, reinforcing your identity as “someone who was there.” Rarely is the fear grounded in an actual belief that this event will be more fulfilling than what you’re currently doing.

That’s why the FOMO tactics used by companies, like travel sites saying “8 people just booked!” or ticket sellers shouting “Only a few seats left!”, can feel manipulative. They rely on social proof and urgency, not substance. And yet, when FOMO comes from real cultural moments (a viral concert, a once-in-a-lifetime experience), it can hit hard. The trick is knowing whether your desire to be there is rooted in true joy or the chance to say you were.

After reflecting, I realized: I didn’t regret missing a single event I saw in those chats. I was already living a story worth telling. FOMO faded as perspective returned.