Slip Out of Golden Handcuffs without chopping your arms off

Ricky Tan
Side Hustle Survival Guide
7 min readMar 14, 2022

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What does the term “golden handcuffs” mean? How do you know if you’re trapped? Here’s how to get them off with zero pain.

Photo by Bermix Studio on Unsplash.

Psst. Read the original article on Side Hustle Survival Guide here.

Is your job too good to quit? Do you feel trapped before you’re 30? Do your dreams seem distant compared to how you felt in the past?

If so, you’re not alone. You have a great job, your co-workers love you, you have a nice apartment in the city, and you have friends you talk to and hang out with on a daily basis.

Life is good, but you can’t help but feel like something’s missing.

This isn’t where you saw yourself a few years ago. You wanted to start a business, work on your art, write a book, travel — just create something meaningful to you. But nowadays, the timing never seems right.

In this blog, I’ll explain what golden handcuffs are, how to spot them, and how to remove them gently.

Specifically:

  • What does the term “golden handcuffs” mean?
  • How do you know if you’re cuffed?
  • How do you break free from golden handcuffs?

What does the term “golden handcuffs” mean?

Golden handcuffs are incentives and benefits offered by an employer to encourage employees to stay at the company for a certain period of time.

Golden handcuffs can include (but not limited to):

  1. Vested employee stock options
  2. Free or discounted employee housing
  3. Company cars
  4. Guaranteed salary raises

Examples of time-boxed incentives and benefits (aka golden handcuffs)

For example, Microsoft and other tech companies use a popular golden shackle called vested stock options. Vested stock options are shares of company stock that are given to employees after a certain period of working at that company. They can be available to as early as entry-level employees. Typically, I’ve seen time periods of 6 months, 1 year, 3 years and 5 years.

Other companies might offer free or discounted housing for their employees. While it makes sense for companies like Hilton or Marriott to offer a 50% employee discount, tech companies like Facebook and Google are taking it a step further. “Company campuses” such as Facebookville are designed like college campuses for employees to develop their own communities.

Of course, there are the traditional perks like company cars to senior-level position holders and promised salary raises after a certain period of employment.

Time-boxed perks like these directly tamper with an employee’s lifestyle and earning potential. This is what makes golden handcuffs seem great — until you realize you’re trapped.

How do you know if you’re cuffed?

Here are some indicators that let you know if you’ve got golden handcuffs on:

  1. Increase in spending.
  2. You tell yourself you’ll change jobs after X years.
  3. You can’t make time for the people or things you love.

Spending way more than you used to?

Increased monthly spending is the first indicator you’re about to get cuffed. Now, does increasing spending mean you’re fully trapped? No. But it does make it harder to live without your new job if your spending increases for necessary expenses.

For example, moving to a better place or buying a new car that requires higher rent, mortgage or car payments makes it difficult to leave your job whenever you want — especially if it’s your only source of income.

Telling yourself you’ll quit after X years?

If you’re constantly telling yourself that you’ll quit after X number of years, you are likely handcuffed to your job. You’re just waiting for those cuffs to expire. This can happen as a result of the vesting period I described above, or because your employer has promised to help you repay financial obligations like student debt.

For example, you might have student loans like the other 46 million Americans who face a student loan debt. Average debt is $28,000 to $37,000 and, unfortunately, the average time to pay off student debt is 20–45 years. (The education system really needs to change in the US)!

But if you’re in this situation, all hope is not lost!

Staggering debt like this can make it seem like you need your current job. However, you can job-hop to earn a higher salary every 2–3 years. According to an article by Indeed.com, job-hopping is seen as a negative on your resume, but has become increasingly common in today’s work environment.

The only way you can become cuffed is if you start believing you need this particular job to repay your debts. The moment you decide you can’t leave your job at-will is the moment you know you’re trapped.

Can’t make time for people and things you love?

Finally, if you keep prioritizing your job over the things or people you love, you’ve got shackles on.

For example, you might be volunteering to work overtime or taking on more responsibility than what’s needed of you. These are not bad things, but if you’re doing them solely to stay in a good light with your boss and your coworkers, then this is unhealthy for your emotional well-being. You’ve become emotionally dependent on the external validation you receive from work — like a drug you’ve become addicted to.

This is the toughest trap by far to see, and it’s even harder to get out of.

From personal experience, there is a difference between passion for your work and doing a job because “that’s what you’re supposed to do”. This difference is very difficult to spot on your own. You might just be a workaholic or a very driven and goal-oriented person. But on the other hand, if you can’t answer why you’re so focused on your job, you should reevaluate.

How do you break free from golden handcuffs?

Here are 3 steps to remove those golden handcuffs gently:

  1. Do not increase your spending!
  2. Tell yourself you only have X years to pursue your dream.
  3. Always prioritize what you love most.

Benefits of keeping your spending the same

Short of starting a family, you should be living like a broke college student. I don’t care if you make a 6-figure income! Stick with what you could afford in college, repay debts as fast as you can, and invest the rest.

Why? Because changing your lifestyle to a more expensive one prematurely will bite you in the ass if you decide to change your career path. Trust me, it’s much harder to live with roommates in a tiny studio apartment again after living on your own in a beautiful apartment in the middle of a city.

By keeping your living expenses low, you’ll likely never need any one job. This gives you the freedom to explore other job options, experiment with diversified income streams and it gives you the power to negotiate confidently with employers.

Recognize time matters a lot more than money

Secondly, stop saying you’ll change jobs after X years! Start saying you only have X years to pursue that dream of yours.

Make no mistake, the clock is ticking on everything you want to accomplish. Someday, you might start a family, you might get too old, or you might lose the energy you once had. Timing will never be perfect, so that’s why you need to start sooner rather than later.

“Time is more valuable than money. You can get more money, but you cannot get more time.”

Jim Rohn

Once you account for opportunity cost in terms of time instead of money, you’ll realize it’s paramount to use your free time wisely.

Prioritize passion and use it as idea fuel

Lastly, always prioritize what you love most. If your job brings enough meaning and fulfillment beyond monetary gain that you love it, do that. Want to start a business? The first thing you do that day should be reserved for that, not your day job. If it’s your family and friends, then make time for them. Be stubborn about keeping that promise — no flaking allowed!

Although it takes more than passion to succeed, it’s the best fuel for any of your endeavors since it tends to produce the best result.

So I say use it.

Key Takeaways

If you have a friend who might have golden handcuffs on, share this article with them! And if you’ve enjoyed this blogpost, please consider subscribing!

  • Golden handcuffs are incentives and benefits offered by an employer to encourage employees to stay at the company for a certain period of time. These are things like vested employee stock options, free or discounted housing, company cars, guaranteed salary raises, or other timeboxed perks.
  • You know if you’re cuffed if you’ve increased spending after you’ve been hired, you constantly tell yourself you’ll change jobs after X years or you can’t seem to make time for the people and things you love.
  • You can remove “golden handcuffs” gently if you don’t increase your spending beyond what you could afford in college (before you have a family). Second, recognize that time is far more valuable than money since you can’t get more of it. Lastly, use passion to fuel all your pursuits as much as you can since it tends to deliver the best results.

Further Reading

Originally published at https://sidehustlesurvivalguide.com on March 14, 2022.

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Ricky Tan
Side Hustle Survival Guide

I'm a millennial trying to min/max a life I enjoy. I write about personal finance, self-improvement, and valuable life stories & experiences.