In 2024, I worked out 300 times, ran 587.4 miles (walked the last 13), lifted 1.4M lbs, wrote 9 essays, took 803 meetings, traveled 132 days, went on 14 dates with my wife, turned 30 and roasted a pig to celebrate, hosted 8 home cooked friend dinners, started 2 art projects and finished 1, and wrote 366 daily notes. I enjoyed a lot of time with family, especially my 4 year old nieces who recently moved out of state, and my cousins after an unexpected loss. I had a fulfilling, interesting, and healthy year with a lot of joy and connection (obviously) not captured here.

Partial summary of my 2024 data in Obsidian

There's a lot I didn't do well: my weekly and monthly planning was weak leading to unfocused learning and unfinished projects — not always bad, but not what I wanted. Moving the phone out of the bedroom didn't stick, leading to slow mornings. I wish I had written more and that I had read much more, although these habits improved significantly starting in September due to a substantial wager and collaboration with my friend Teddy Gold. I didn't solve a bothersome calf injury. Of course, I would have preferred to invest in even more great founders and build more awesome products.

In 2025, I'd like to be more judicious about zoom meetings and expand my written correspondence to make synchronous conversations more productive. I started tracking in-person vs zoom meetings with the objective of improving this ratio. I think 300 workouts is still a good objective, although I'll dial back running to make more room for flexibility and basketball. Breakfasts and morning fitness (runs, walks, padel, tennis) remain my favorite way to see friends and meet new people and I'd like to expand this habit. Due to the wager with Teddy, I believe I now have the processes in place to meet my writing and reading objectives. My wife and I also plan to host more in Brooklyn, ideally monthly, especially focused on our local community and marking a purposeful end to the work week.

Now, before I continue, my wife (and favorite editor) said I need to make sure people know that she thinks I’m fun, flexible, and relaxed in person. That may be hard to believe, but let’s dive in.

You have likely noticed that I take a particularly systematic approach to achieving my goals. Why? First, I think it's fun. I’ve always believed software should be malleable, personal, and bespoke to each user scenario. Second, it improves my outcomes and my capacity to handle more complicated obligations. Since my first system in 2018, I have significantly improved at setting and meeting goals. I have also improved at designing systems that are lightweight and bespoke to my routine — I throw systems out when my routine changes significantly due to a life change, new job, or new focus and tinker with a new one while adjusting to the change. Change is part of the point. Clearly, these systems must be in service of my goals and not the other way around.

I started an incredibly anal — my wife would lovingly say “psychotic” — version of this in 2018 to better understand how I was using my time as a programmer and learned a lot about my habits. At the time, the system was mostly observational and was easy to implement because nearly 80% of my time was spent with my hands on a keyboard, coding. This system revolved around tracking "pomodoros", 30 minute focused sprints, and daily actions (workout, cooking). Visually, it is a Google Sheet with 2080 entrees and an aggregated dataset comparing progress against goals.

Input section of my 2018 Pomodoro tracking system

There are 2063 more entries in this sheet

At the time, my work could cleanly be split into Fluid Framework, work on a side project (RIP CallBuzzy), studying, and volunteering — each of which required minimal context switching and was best done in dedicated time blocks. There was a lot I didn’t track (design, meetings, product planning, architecture, research, etc.), but my goal was primarily to focus my output on programming and understand my time management, so I was comfortable leaving out important, common activities.

Ultimately, my Pomodoro system was inefficient, encouraged low-value work, and led to minor burnout, but it was critical in helping me understand how I was using my time so I could improve my habits and focus and therefore make my work more efficient and sustainable. For instance, this system helped me identify that most of my productive work happened in 12 - 16+ hour binges and that I was unlikely to make use of less than 1.5 hours of time. I have worked hard on improving this, which has had huge benefits for sustainable long-term success, although I still find sprints to be fun when done safely. I also saw there was a classic gap between my ideal week and my real week — yes, I often worked out 4x a week, but I never worked out more and I often missed sessions. Most importantly, I significantly improved at creating and meeting goal aligned objectives.

I continued with my Pomodoro system for 3 years before stopping with the pandemic and the start of business school. During business school, my schedule was highly variable and extremely event and networking focused, so I split my processes into athletics (I ran a marathon tracked with Strava + Google Sheets and then started weightlifting again tracked with Strong), startups, and networking. I ended up building out a personal CRM in AirTable and some automations that helped me run 39 events with over 4,100 attendees while working, recruiting, and in school full time.

Kanban view of my school work, networking, and event planning Airtable

In 2022 I switched to Obsidian and in 2024 dialed in a system that fits well with my routines and goals in venture. Despite what you may be imagining, the current system is fairly lightweight and most of the work is basic planning, goal setting, scheduling, and notes, all of which are necessary for me to do my job at a high level. The year starts with a yearly reflection to myself, which is then translated into objectives (e.g., 300 workouts), outcomes (grow my newsletter to 100 readers), new processes (a weekly note is only complete with an empty inbox), and intentions (make conversations more purposeful).

To make this concrete, here’s how I break down the goals throughout the system.

Objectives: Numeric targets

Outcomes: Measurable results

Processes: System behaviors

Intentions: Qualitative Aims

Goals: Success criteria combining objectives, outcomes, processes and intentions across a period (e.g. a year)

System: The software, habits, and processes helping me to meet my goals

Each month, I (try to) plan out the big projects I need to find time for and how they'll relate objectives and outcomes. I also review how I'm doing against processes and intentions to see if I need to tweak anything. Each week, I do a more tactical review including getting to inbox zero, scheduling workouts, finalizing in-person meetings, and blocking off time for projects.

Most of the action happens in the daily note, which I create every morning. At the top of each note, I have a form for tracking my daily meetings, location, workouts, purposeful rest, and other habits. These are accumulated in a data analysis document, but are also easily exportable because the front matter is YAML, a format that is easily parsable using widely available python and javascript libraries. Of course, I also have standard templates for meeting with people and companies that flow into reminders to follow up, manage to dos, schedule meetings, and so forth.

My 2025 daily note template in Obsidian with mock data.
I naturally fill it out throughout the day as prep, notes, or reminders.

I estimate that I have spent 12 hours over the last two years building the structure of my Obsidian environment, with much of the automation created by prompting Claude to generate Python and Dataviewjs scripts.

I’m sharing these systems because many friends have been curious and some friends have similar, although typically less detailed workflows of their own. While any specific setup might not work for you, the core principles — designing and iterating on lightweight systems that work within your life, measuring meaningful goals and reaching them, and reflecting on process and outcomes — have helped me consistently expand what I can accomplish.

This is the first edition of what I plan to be an annual review, focusing future editions more on the year's learnings and system changes now that the historical context is established.