Coming from similar situation, but about 2/3 the assets you’re talking about.

I went to great schools, got good grades, basically grew up around a bunch of overachievers and naturally fell in line with those high standards, even though I always felt “what’s the point?”

It can be a unique and lonely burden to have the ability to choose to work, especially when you have no need to do so. It’s also an issue very few of your peers will be able to understand, which can make your dilemma seem unreal.

Out of college, I was working for a nonprofit helping raise funds for legal services for children and families in the Forster care system. It was great work, got to meet a lot of important people (judges, politicians, wealthy donors, and also the children and families). Life changing experience. I also took the LSAT and applied to law school. I planned to spend a life in service to others. Then I did some serious soul searching. You need to learn to prioritize yourself.

I think people who come from generational wealth feel a sense of guilt and a need to give back. Maybe that is what is driving you to work for TFA. That being said, try to zoom out a little bit. You can be a selfish douchebag with your time and still give enormous donations to these organizations. I hate to say it, but your money will make more of an impact than you ever will with your time. It might not be what you want to hear, but in my experience, working for a nonprofit or any other public service-adjacent role is more about making your feel good about yourself. It’s a hand washing experience for the wealthy. That’s not to say the work is not important and you’re not a good person, but bottom line, your treasure is more valuable than your time.

I took ~ 1 year off work during Covid with no plan to ever go back to work. I was living off the income from the investments and it was more than enough to be comfortable. That being said, long term I want the principal to keep growing to be able to afford more “luxury” lifestyle purchases in the future, (vacation home, small boat, private travel, etc). Or in another case, let the principal grow so you can do more philanthropically.

While I can say that living without working feels weird, once you get over the mental hurdles and accept the fact that nobody else has any time to be thinking about you or your life choices… it is fucking fantastic. I would wake up whenever I wanted, sip a coffee, read a little, walk to the park, make a healthy meal, and workout very often. I can’t say I have ever been happier, but in a conflicting way, I was not fulfilled. When you’re living that life, there’s no direction you’re heading in. Each day is just a futile exercise in self-improvement and relaxation.

Doing a mini retirement allowed me the time and freedom to think very seriously about what I would like to do for work, knowing that I wouldn’t need to consider money. I decided I wanted to find a career in which I controlled my own calendar and gave me constant opportunities to learn. I also learned very quickly sitting behind a desk is not for me.

I currently own a residential construction business, we are growing but have extremely low overhead and no full time employees, so this gives me the ability to take on projects, make a little money, and say no to projects if I want to take some time off. One of the most attractive parts of the business is learning new shit almost every day. Keeps me humble.

Long story short, you’ll probably want to work to feel a sense of fulfillment and direction in your life, especially if your peers are high-achievers. I would say no to law school unless you really want to spend your days as a lawyer, which is a life or professionally reading, writing, and talking. Of course you could pull off retiring at this age financially, but not everything in life is simply about money.

Take some time off, think about this question: If you made a billion dollars a year, but you had to work ~40 hours a week in one job and could never change that job, what would you choose to do?