@VSH – yep, life can be complicated. And while I recognize that a billionaire could hire someone to manage all their household staff, I feel like stuff still winds up with you. Like someone’s going to wind up asking you if that third vacation house should have blue or green paint, and the staff manager will want to go on vacation and…

Re: school choice- I appreciate both of your default to preserve family well-being by making things easier re: logistics. For Sarah this comes at a cost (us too). In our area (Baltimore), there is a strong private school culture. Many families have children at different schools due to fit. It makes life unnecessarily complicated.

Re: thought experiment on outsourcing- nailed it with the issue being logistics, not money. Many times I find myself struggling and wonder how I could use money to solve some of the pain points. However all of my solutions involve having other people help me do things (driving kids around, cook, grocery shop). I end up not making this happen because managing a small team of people in my house is too complicated. The one thing that has helped a lot is carpooling with other families. My 9yo daughter is a competitive swimmer and we live 10min away from her pool. We carpool with another family. It’s free and has deepened our connection to the other family. We get and provide help with transport to dropoff birthday parties and sometimes just say no to things if it will be too exhausting to get there.

Another aspect of this is just accepting that choosing a full life means that life is not easy. A lesson that I try to teach my kids is that challenge and difficulty are good for the soul. Sometimes need to be reminded of that.