New Schedule for Productivity

Great week here in Puerto Rico.  My friend Ian, from my olden days of equity options trading in Chicago, visited for half of the week.  It’s crazy that I’ve been out of that business for almost a decade now. He was one of my main mentors at Third Millennium Trading, allowing me to use his name (he was one of the very few successful traders left at that point) to give me enough credibility to be allowed to start trading.  Before that I was an assistant for 1.5 years, with no hope in sight of being able to escape that position. Some combination of me planning to quit/Ian’s reputation/my friend Jeff pressing our bosses to give me a chance was the difference between me never having a career in the trading business.


It was very cool to openly talk about our trading strategies, what we did right, and what we did wrong back then.  When we worked together we were friends/co-workers, but it was a very competitive environment. We both benefited a lot from sharing information, but at some point the traders at the company started mostly trading the same stocks, and each option I traded was one someone else wasn’t getting.  It was probably the thing I hated the most about the business; telling half-truths or perhaps even lying. We were all paid on a personal profit-percentage basis, which was good for personal motivation, but teamwork suffered when you’re playing in the same game everyday.


All of these years later our strategies in options trading are no longer relevant, and it was fun to talk about some of our best and worst trades.  The downside is it was a long time ago, so a lot of my trading memories are hazy recollections. In trading/poker/gambling you make money in the long-run if you have positive expected value aka edge.  Things happened so fast over those years, and we all did really well, but to this day it’s hard to precisely figure out what our edge was over the big established companies and other traders. Definitely was fun to get nostalgic about such a formative period of my life, and take a stab at answering that question.


Sunday I went on a hike in the middle of Puerto Rico that was as enjoyable as life can get.  An eclectic mix of around 40 people in our hiking group, the majority of which are extremely nice people, all exploring this beautiful island.  Light rock climbing, waterfalls, jumping into a pristine river, and having great conversations for a full day. All it cost was some gas money, but even that was refused as a nice couple drove Johanna and I from San Juan.  There are a few times a year when I get a glimpse of a perfect day.  I then go back to trying to artificially create an even better one, usually via spending money, but it’s never close.


On the lifestyle front I’m cracking the whip on myself!  I felt like the previous few weeks have been me dragging myself into a deeper pool of procrastination and bad habits.  My plan was to develop a “perfect work-day schedule” that I can look at so I don’t have to think about what to do/when to eat/etc.  It seems so simple, but I get my head wrapped up in whatever I’m thinking about (crypto research, writing, training, etc.) at one moment, take some massive long distraction breaks, and then my day can go off in any number of inconsequential directions.  It’s been very freeing to just follow my schedule, even as I am a bit behind today.  In case this is of any help my rough, rough draft (work in progress) is something like the following:


6:30 am wake up, check the crypto markets and make any adjustments as necessary.  Get ready and commute to gym

7:30-9:00 Do my functional bodybuilding workout, come back home.

9-10: Shower, eat, meditate

10-11: Work on a blog post or usually fiction

11-12: Work on outlines of future writing, or more writing

12-1: Studying writing


1-1:20: Movement Vault wod of the day (mobility work)

1:20-2:  Eat lunch, light walk

2-4pm: Crypto research and programming

4-5: Return texts, phone calls, emails

5-6: Read for fun

6-6:30:  Have a “meeting” with my girlfriend about her art business or our travel show/do some Spanish lessons.

6:30: Eat dinner together, and then movies/TV/ go out and be social/Spanish lesson

10 pm: Final check on my trading and make adjustments if necessary, and in bed reading reading.

10:30 pm: Lights out


This is just for Monday-Friday, and one day on the weekend has to be a massive meal prep day to make this work.  We did that Saturday (paleo meal on the stove, instant pot, and oven at the same time) and it’s amazing to just re-heat quality food when it’s time to eat.  I also imagine on Wednesday I might put in a chunk of time for more personal errands when necessary. The other key is that I’m working from home, so eating and working involves 0 commute.  If I go back to co-working it will take a bit more prep, but not too much.

It will be interesting to see how this evolves, and what version of this (I really hope!) I end up sticking to when I’m not traveling.  In the meantime it’s getting close to my scheduled study time, so will finish this out. Thursday I’m going to Medellin, Colombia for almost a week, so looking forward to updating you with some highlights from there.  I’ll leave you with a few pics from the hike.


2 Replies to “New Schedule for Productivity”

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