My son’s personality type is ISFJ. I’m an ENTJ. We’ve always worked well together: I could see where to climb, and he could see how to do it. I offended people, and he smoothed things over. At first his people-pleasing, detail-oriented nature made me think I was failing as a parent. Then I worried that we were such a good team that we’d become codependent.

Now that he’s in college, he doesn’t trust my plans. He relies on advice from friends at school who are obsessed with positioning themselves well for an AI-infused workforce. Read more

My to-do list when the kids were home was divided into A’s, B’s and C’s. The A’s were emergencies — like ordering a SpongeBob cake. The B’s were waiting to become emergencies, like seeing if swimsuits still fit. The C’s were things I couldn’t admit I wasn’t doing. It was like my off-site storage for wishes.

Once both kids were in college I did what everyone does with off-site storage: ignore it. But after a year, I took a peek. And this jumped out at me: attack people who think there’s virtue in conscientiousness. I felt an urgent need to do this because people think I would have more money saved—any money saved—if I were more conscientious. But I know the truth: conscientiousness has no impact on success except being a gateway drug to perfectionism. Read more

My oldest kid is looking for internships.

For those of you who have not had a kid call you hysterical because their life is over, let me tell you that all the good summer internships are given away in June of the summer before. Read more

When my kids lived with me I felt like I had no control over when I could write, so I had to find happiness in helping my kids meet their goals. With both of them in college, I don’t set their goals anymore. So I’m trying to train myself to be happy when I write since that’s what I can control.

Meanwhile, I try to be an encouraging listener because I read that the thing that most influences college success (after the super-influencer: money) is parental encouragement in the student’s ability. Read more

This is a picture of indomitable me: Look at the Cartier watch. I bought it with the stock sale from my first startup. It felt like money was falling from the sky, so ten grand for a watch was nothing. We walked through Central Park every day to get to the top nursery school for autistic kids in NYC. I got him the best speech therapist, the best occupational therapist, and I was networking to find out what was next. Read more