Breaking Golden Handcuffs
Mental jiujitsu to make the decision of breaking it easier
A year and a half ago, I worked at a trading firm and was surrounded by conversations about TC (total compensation) and rumors on what the next bonus looked like.
Despite having minimal lifestyle inflation from university when I had no income, I found myself grappling with greed and desire for more money while feeling trapped in Golden Handcuffs.
You can find my deliberations at the time here: Golden Handcuffs (sorry for the big wall of text!).
In the current landscape of rising AI valuations and prevailing news in tech, I find myself in a similar situation as before.
Except this time, it’s much more pronounced.
In the past, I lamented about being held in golden handcuffs.
Knowing that I wanted to pursue something else while being heavily rewarded in what did not interest me felt like a luxurious prison.
Even though I held the keys for my escape, I hemmed and hawed about opening my own cell, tortured by the weight of losing what gave me so much comfort: a healthy work environment, status in an exclusive industry, and guaranteed net worth accumulation and liquid cashflow.
Now, I see golden handcuffs as a test rather than a prison.
I am a strong believer that one cannot call oneself authentic and courageous without being tested otherwise.
The decisions surrounding golden handcuffs serve as evidence for authenticity and courage due to their nature of having very rewarding and tangible opportunity costs in selecting for what is authentic and courageous.
There are 2 paths when I project my possible lives based on any given decision revolving around golden handcuffs.
One path is of certain gold. My net worth reliably increases over early adulthood to compound significantly later in life. Buying property becomes more of a question on “when” versus “if”. Rich experiences from travel and time spent with friends will be plenty.
The other path is of an authentic yet uncertain future. I cannot come close to accurately predicting how much money I’ll have, what home I’ll afford (if any), and what experiences I’ll accumulate.
If I am to believe myself as an authentic person, I will have to provide evidence of it by choosing the path that leads to a more authentic life, regardless of its downsides and the opportunity costs of other more rewarding paths.
In fact, the more attractive the alternatives are, the stronger the temptation to divert from my true path- and thus the greater evidence that I am indeed authentic.
The shininess of alternatives also gives weight as evidence of courage as well.
Best defined by Jocko Willink, courage is not acting while being fearless, but quite the contrary.
It’s acting while being fearful.
In the context of golden handcuffs, the fear of losing certainty and the other attractive possible opportunities makes the decision of breaking out of them as evidence towards courage.
The greater the fear, the greater the evidence towards courage.
Making a decision to break Golden Handcuffs, becomes less so about pain avoidance, but now reframed as pain acceptance and tolerance.
It’s another piece of evidence of I am who I believe I am.


