When was the last time I went to the gym? 

Did I get four hours of sleep last night or five? 

When was the last time I did bed time with the kids? 

Does my skin look kind of grey? 

Maybe I should just quit. But I really can’t, because my insurance is frankly superb and we have this trip to Tuscany coming up. Maybe if I just put my head down and work even harder, I will get promoted. And then I will have more control. And then I will get what I want. And then I will finally be able to relax.

This is the plight of the golden handcuffs. Or the hedonic treadmill. Or whatever language you want to use for that particular kind of stuckness where, technically, you are doing great.

And also, you are maybe not doing great at all.

Jon Hamm captures this beautifully in episode eight of season two of Your Friends and Neighbors, which, yes, I am featuring again in this newsletter because apparently this show has taken over a small but very active corner of my brain.

In the scene, he is talking to Liv, a woman he used to work with — and have relations with, as well, if we are being honest, which I always am in this forum — about the strange bargain people make with themselves when they are trying to get somewhere:

“I used to be where you are,” he tells her… ”there is a math that you do…calculus of compromise, right? What am I willing to do to get where I want to be? Now, of course, once I get there, I’ll stop doing the thing.  I’ll stop taking risks, because I will be there. Not here. The thing is, there is never ever there. There is no there. You are always just here.”

You are always just here. 

You are here prepping another slide deck. Here boarding another flight. Here sitting through another five-course client dinner. Here snoozing your alarm. Here missing bedtime. Here wondering if this is what success is supposed to feel like.

And for what?

That is the question we are going to ask in Goodbye Golden Handcuffs.

Not in an Eat, Pray, Love, move to Europe kind of way. Although…now that I’ve mentioned it…

Okay, back to business: This is not an anti-ambition group. I love ambition. I love people who want things. I want things!

But I also believe there comes a point when it is worth asking: What is this costing me? What am I protecting? What am I postponing? What am I pretending is fine? And what would success look like if I were the one defining it?

Goodbye Golden Handcuffs is a seven-part virtual group for people in high-octane careers who look successful from the outside but feel exhausted, stuck, or aware that there has to be more to life than this.

We will talk about ambition, money, identity, burnout, career shame, risk, purpose, meaning, and the complicated feeling of being both grateful for what you have and desperate for something to change.

This is not about leaving.

It is not about staying.

It is about being honest enough to know the difference.