In the Valley, we have the term "golden handcuffs." I first heard it over a decade ago, during a wave of acquisitions of small tech companies by big tech companies, many times what they call an acqui-hire (acquiring small companies for their exceptional talent). These people didn't hit the immediate jackpot but they would vest (typically over 4 years) and bide their time as their generous stock option packages would pay off. They would, as they say, vest in peace.

It would sometimes be characterized by people who would go easy on their job and cruise. You would see some leave early -- leaving money on the table -- because they already made their life changing money and they didn't want to wait. Maybe they were not mentally challenged and sought more, maybe they wanted to leave the corporate life early and not waste their years away.

During my time here, I've seen many versions of this post. Maybe it's in tech, similar to above, sitting on high compensation where they've reached their number but they're debating the move to more. Or it's a person who has a business that's been successful but still requires their attention to some degree, and they're debating whether it's worth putting in the time to making more.

As someone in this position, I've been thinking about a lot. Those of us who feel like we're on the cusp and the difficulty in deciding direction. At what point is more just more and not a meaningful difference? What tradeoffs am I making, especially against Father Time?

La Dolce Vita

In Scorcese's 1990 hit Goodfellas, a few mafia bosses are doing time in prison. However, they've got it good since they have everyone on payroll, and the scene shows them with their own private area, cooking gourmet meals of veal and pasta, drinking red and white wines. They've got it posh, but posh for a prison, doing their time.

https://www.youtube.com/watch?v=rQV6CijIzrc

One option to doing time that's often suggested here is "doing the time" but making the experience more fun and palatable. Take up a hobby on the side. Pare back the hours as much as you can. Delegate as much as you can to someone else. But, at the end of the day as responsibilities fall to you, you're still doing time and not living la dolce vita on the outside.

Zihuatanejo

In the 1994 hit Shawshank Redemption, Andy Dufresne is doing life in prison. There, he makes a good friend Red, who's much older and a seasoned veteran of the prison system. In miraculous fashion, Dufresne escapes prison after 19 years. Meanwhile, his friend, Red, is finally paroled after doing 40 years, entering as a young man and leaving as an old one.

https://www.youtube.com/watch?v=dpjB6b9OZYI

Red has a difficult time adjusting to time on the outside. He's lived the majority of his life in prison and that becomes his whole identity. He narrates this fear accordingly:

"There's a harsh truth to face. No way I'm gonna make it out the outside.

All I do anymore is to think of ways to break my parole, so maybe they'd send me back.

...

All I want is to be back where things make sense..."

The one thing that kept Red alive was a promise his made to Andy to meet him on a Mexican beach in Zihuatanejo if he ever got out.

I wonder how much those who work all their lives build an identity around those handcuffs. We make it a core focus of our lives to make money such that that becomes our identity. We become institutionalized in a system where we seek financial freedom and when we reach it, we face problems adjusting to the other side. We seek to be Andy, who we see finds an inner peace, absolved of his sins, living a simple life with his fishing boat.

It comes down to a simple choice

Here end my exploration of golden handcuffs, breaking down what it manes and why we struggle with this choice. If this resonates with people, I have the making of a part 2 somewhere in my head.

The day before Andy breaks out of prison, he talks to Red about what he'd do if he were free. Red thinks this kind of talk is dangerous talk as it would drive a man crazy to think about freedom while locked up in prison. Andy then says,

"I guess it comes down to a simple choice, really. Get busy livin' or get busy dyin'."