Introduction

As I write this, I am nearing the completion of the first three months of my retirement, July to September 2025. In the world of business and startups, this is, of course, the end of a quarter, and it is normal to review how things went during the past quarter, examine what went wrong and what went right, and adjust the plan for the next quarter. Often, these review and planning sessions were conducted in so-called “Quarterly Business Review” meetings, commonly abbreviated as “QBRs”.

I’ve applied that same approach to optimizing my retirement life. I have a particular set of goals and strategies for my retirement, and to achieve those goals, it’s essential to review and course-correct as necessary, just like running a startup. So this past weekend, I spent a significant amount of time (most of Saturday and Sunday) going through my data and goals. Here, I found the use of AI tools like ChatGPT and Gemini super helpful.

As I came out of the weekend, my approach to optimizing my life was sufficiently different — a nice way to say that I know I’m a weirdo! 😀 — that this might be interesting and helpful to others.

So I’m posting my approach here.

Process Overview

Data: Data is everything, and I like to have all the data organized together on the computer. By storing this information in files, you can utilize tools such as spreadsheets and AI to analyze it. These files include storing your goals and strategies (which you should be writing down anyway, for other reasons) in .txt files, which are essential if you choose to use AI tools like ChatGPT or Gemini.

Tools: Excel for basic analysis (I’m still most comfortable in Excel, although I’m trying to get more comfortable with Google Sheets and Numbers, with limited success), Soulver for more free-form calculations, and Google Gemini for AI-assisted analysis, brainstorming and discussions (I’m in the process of migrating from OpenAI’s ChatGPT to Google’s Gemini, which I’ve found more capable for my particular use cases). I take a lot of notes (using Vim, of course!), journal high-level plans and results (using DayOne), and manage my tasks (using Things).

My QBR Process: Once I’ve got everything gathered together, I sit down in front of the computer and go through the various areas of my life. These areas include Health, Money, and Goals, which I’ll cover at a high level below.

Health

I’m going to focus on my progress here, so I won’t dive into specifics about what I’m doing to optimize my health. I am heavily influenced by Peter Attia’s science-based principles for optimizing longevity and healthspan, which he has well-documented in his book, “Outlive: Longer, Stronger, Healthier.” In summary, I have health goals in the pillars of diet, exercise, sleep, and mental health.

In terms of data and tracking progress, I have PDFs of all my blood work, ultrasounds, and other medical records. I have written out my exercise routine, my family’s health history, my prescriptions and supplements, and even my current assessment of my mental health and social support system.

I use Excel to track high-level trends, utilizing AI to extract data from unstructured documents whenever possible. (AI is really good at pulling out tables from blood work PDFs, for example, and charting them.) I upload all the documents to Gemini within a Gem I’ve created for my health (in ChatGPT, I used to do this using a custom GPT), along with instructions that reference Peter Attia’s approach and my high-level health goals. Then, I discuss my progress with the AI to analyze both the positive and negative aspects and identify areas for improvement.

Money

What is the goal of money? To optimize the financial section of my life, I am influenced by Bill Perkins’ excellent book, “Die with Zero.” I really resonated with this book when I read it a few years ago. I realize that not everyone is in the same privileged position as I am. However, as a recovering workaholic, I am deeply aware that without mindful planning, the money I have worked so hard to accumulate over my years of work will not be able to do as much good as it could. And that would really be unfortunate. The goal of money is to help you provide for and care for friends and family when they need help the most, and to pay for the experiences that you can enjoy while you can. Many of my financial goals are related to helping those I care about and traveling to specific places in the world, which I can do while I’m able.

I have banking records and so-called “wealth plans” that have resulted from my meetings with retirement planners and accountants. I have also documented my financial goals, including things I want to buy, people I want to help, my significant recurring costs, places I want to travel to (and when), and my high-level budget (which I brainstorm in Soulver and can export as a PDF).

I upload all this data to Gemini as a custom Gem, along with instructions related to my high-level retirement and goals around money. And, just like health, I have a discussion with AI about how things look. Am I spending too much, and will I start to encroach upon my self-declared safety buffer? Equally important, am I spending too little? Should I travel more or more aggressively, while I have the health to do so?

Goals

I find AI really good at brainstorming and providing “second opinions”. Having a separate session focused on high-level life goals, once a quarter, is incredibly useful to round everything out. I have specific goals around happiness, family, and even how I’d like to die. Going through these heavy but essential topics with an AI that is no longer sterile but is now empathetic, creative, and engaged — well, I find that helpful and even therapeutic.

Summary

As I engage in these AI conversations and brainstorm sessions, I inevitably come up with ideas, changes to my strategy, and tasks that I need to take action on. As these come up, I write them down. I update strategy documents, so I’ll have them ready to go for my next quarter’s QBR. I write down actions and concrete next steps or projects in my to-do app. I document high-level shifts and their reasoning in my journal, so I remember the rationale behind them.

I hope someone finds this useful or interesting. At the very least, it helps exemplify that the data-driven approach I applied at work is something that is actually helping me with retirement. I want to succeed at retirement. Like life, I only get one shot at this! So I’m going to use all my experience here to optimize it to the fullest.

Have an excellent Q4, everyone!