If you ever worry what it will look like when your kids take over your life, this is it: lunch at my investor’s favorite restaurant to discuss my son’s cello lessons. Me getting there two hours early because one son has an orthodontist appointment and one son has a cello lesson and my husband is taking cows to market, so even in a family with two cars and a nanny and a driver, there is no way for me to get to my meeting on time unless I’m two hours early. Read more

Many of you have asked what happened with Kate. In case you don’t remember, Kate was a homeless teen I found myself coaching in Florida. When I realized she was homeless I bought her a plane ticket to come to my house. We made our guest room into her room. I bought her all new clothes, and I told my sons to stop asking how long Kate is staying for. I told them, “This is her home. It’s the only home she has. She leaves when she wants and comes home when she needs to. Just like you guys will do when you’re older.” Read more

Reinvention is part of being human. The nature of our lives is that we learn more and collect new ideas and that makes us want to do new and different things with our lives. But we often never actually make that transition.

The problem is that we are hard-wired to think about the present. Even people who are great at planning get tangled up in daily details because, after all, this is how humans stayed alive as they evolved: never taking their eye completely away from their immediate needs. Read more

After three days of silence on the cause of death for Dave Goldberg, the New York Times has changed their story in the span of seven hours, some mysterious source said collapsed while exercising. Then a leak to the Associated Press said head trauma. If we were in an Agatha Christie mystery, I’d say heart attack. Read more

First of all, let me say that I feel really bad for everyone who is losing Dave Goldberg in their life. I feel bad that he will not get to see his two kids grow up. His death is very sad. I have not had a spouse die or a parent die and I’m sure the experience is more awful than I could even imagine. Read more

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INTJs are only 2% of the world’s population, and female INTJs are the most rare of all types. However, the most common type on this blog among women is INTJ, which is statistically amazing.  Maybe every female INTJ in the whole world reads this blog. And almost all the super high-level men I coach are INTJs (Mr. Famous is an INTJ.)

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This story begins at 3am in the Orrington Hotel when I am answering emails. I woke up in the middle of the night to my son vomiting on the bed, which we are sharing, and now smells faintly of chewed up room service fruit plate. Read more

Many of the coaching sessions I do center around a single question: is it time to switch careers? What I’ve found is that in most cases, the answer is no, it is not time to switch careers.

Here’s why: We are absolutely terrible at predicting what we will like to do in our careers, and we overestimate how much we’ll like a new career. Read more

If you want to understand Generation Z (born in the 200o’s), take a look at Pope Francis. He is not just a new pope. He is revolutionizing the Vatican in a way that Generation Z is likely to revolutionize secular institutions. For those of you who are not following Pope Francis, you should. He is so cool he makes me want to give money to the Catholic church. He is a Gen Z mascot. Read more

Most of the time on this blog I focus on bursting bubbles. I deliver bad news about finding a spouse, choosing a career and earning money. But the thing that really keeps me going as a career adviser is the good news. Read more

© 2023 Penelope Trunk