Rob Brooks

One big realization of 2 decades of working: Even if it’s simply perspective, the belief one has agency/control over their situation is the key to happiness. I had W2 jobs on the buyside with literal 7 figure guarantees. However the inability to control positioning sizing or size of my sectors exposure drove me to levels of insane frustration. Or seeing other parts of the book implode offsetting 8 figures of p@l contribution in my coverage drove me nuts. Some of my highest earning years were my most unhappy professionally. Some of my best income years were better as an analyst than when I was a portfolio manager, but having 100 pct control of the book as portfolio manager meant my happiness was much higher even in the years my income was lower than some of my analyst income years. As a junior banker, it was more doing nothing all day only to get staffed on a bake-off on a Thursday evening at 5pm that would ruin the next 4 weekends in a row. The lack of control was brutal. I bring this up as more of my conversations with friends or strangers looking for advice lately have centered around this idea of agency/control. Recently it is high earning W2s frustrated with pointless meetings, the inability to get promoted until someone dies or retires, or the existential concern that the AI justified job cuts will eventually hit them. I always warn people that in small business ownership, the idea of control is over-stated with employees sometimes not showing up, customers paying late or not at all, and vendors or freight companies making mistakes. That said, this path has been working for me. Most are better off just finding another W2 (I know easier said than done in this job market.) My business has been negatively impacted by tariffs and now oil prices driving up resin prices. I can only adjust and adapt. We will be okay. I wish someone had told me in my early 20s when I was starting my career that choosing path where I could have more autonomy and agency in my 40s would be more important than maximizing income in my 20s and 30s. I’m fortunate that things have worked out in life and I’ve been blessed with more than I deserve with a wonderful family, but I do think alot of super smart W2s in high income paths should think about reverse engineering what a good life looks like for them at 40 earlier over maximizing near term compensation (I get a lot of inbounds on what is fair pay in hedge funds even though I’m more than 3 years removed from the industry while the industry has gone bonkers with respect to comp).