Breaking Free from the Golden Handcuffs

Do you feel shackled to your job? Every time I hear someone say “if it wasn’t for the money, I wouldn’t be here” my heart sinks. Sure, every job is stressful. But it’s sad to see people working jobs they hate to afford a lifestyle that they think will make them happy. When in reality, they are miserable. So how do we break free from the golden handcuffs?

Money should give us a sense of freedom to do what we want with our lives. But it seems that the more money people make, the more their lifestyle inflates, and the result is they feel handcuffed to their jobs.

Here are lessons I learned from some of my friends’ experiences. Some of them choose to remain shackled to their stressful jobs. Others have created opportunity for choice. Then, I explore some of the common things that locks us and what I am doing as a key to break free from the golden handcuffs.

Lessons from Friends

Names and details may have been changed to protect their identities.

Friends Shackled to Their Jobs


Duke is married with two kids in college. He earns nearly $200K a year in an upper-level position for a major corporation, plus his wife’s salary. Duke was diagnosed with a terminal medical condition. Each day he contemplates leaving his position and spending the rest of his life doing something he loves.

Photo by Derek Thomson on Unsplash

But he and his family have grown accustomed to a certain lifestyle. Sure he has a big house in a gated community and luxury vehicles. But he also has a huge mortgage and car payments. He is also financing his kids’ educations. As much as he doesn’t want to stay at his job, Duke continues to go in each day. The thought of changing his lifestyle is too much for him. He has resolved himself to working at his current job for as long as his health allows.


Shopping, brunching, and travel make Luxe happy. She wears designer labels and orders apps and drinks along with every entrée. Luxe doesn’t mind paying for convenience. To afford this lifestyle, she works a lot of overtime. She realizes that she will be working for her entire life, but she chooses to exchange her life energy to live this lifestyle.

Friends Who Broke Free


Biff isn’t the type of guy who is happy with a desk job. He is young, single, and likes to have fun. But he did what he thought was right and took an entry-level office job. When offered $20K more for a supervisory position, he felt he couldn’t turn it down. But with more money came more stress. He was so miserable 40 hours a week that he spent his weekends doing extravagant things to forget his woes. Tickets to sporting events, weekend getaways, nightclubs and parties – every second of his time off was spent trying to forget the work day.

Photo by Sarthak Navjivan on Unsplash

The weekends were amazing, but Sunday nights he felt sick to his stomach thinking about returning to work the next day. The irony was, he was working the high-stress job to afford money to party on the weekends to forget the high-stress job.

After a few years he realized this lifestyle was making him sick. He left his job and pursued a lower-earning job that he loved outdoors.


Kiki is a secretary and mother of four. She loves her job. Her company is opening a new branch. Because they need strong employees at the new office along with the new hires, her boss offered her a raise to take the position. Kiki is feeling conflicted. One of the things she enjoys most about her job is the people with whom she works. If she moves to the new office, there’s a chance she won’t be happy there. She asked her boss if she can stay at her current location. He said she could, but her pay would also stay the same.

But Kiki has led a simple lifestyle. She keeps reminding herself that she doesn’t need the money. So she holds the power to decide whether the lure of more money is worth leaving a job she loves for the unknown.

Locks and Keys

Photo by Jason Blackeye on Unsplash

There are some common lifestyle factors that keep us shackled to our jobs. While some are of our own choosing (e.g., which house we buy), others  may be beyond our control (e.g., medical bills). Here are some things that keep us locked to our jobs and the key I am turning to break free of the golden handcuffs.

Monthly Bills

Lock: When people think of lifestyle inflation, the major purchases such as housing and vehicles come to mind. But small, recurring purchases can also have a major impact on our monthly bills.

Key: By minimizing my expenses for groceries, dining out, kids’ activities, and entertainment, I was able to put more money to debt repayment (i.e.,  buying back my freedom)

Related Article: Top Tips for Cutting Your Monthly Expenses

Student Loans

Lock: Some people believe they will be paying off student loans for 10 years or longer. This will certainly be true for those who defer payments, choose income-based repayment options, or participate in the public service loan forgiveness program (PSLFP).

Key: I refused to accept this fact. Every month when I saw the amount I was paying in interest, I got angry. I developed a plan to become debt-free. Instead of 10 years, I paid off my student loans within 3 years.

Credit Card Debt

Lock: People spend 12-18% more when using credit cards compared to buying with cash (that’s not including the interest). Rather than being used in an emergency to buy needs, many people have grown accustomed to financing their wants. Vacations, shopping, and dining out have become a large proportion of many people’s credit card debt. They buy now and work to pay it off later.

Key: While I do use credit cards, I track every cent I spent. Just like with cash, if I have a $100 budget for groceries, I shop with a calculator. If the tally comes to more than $100, something goes back on the shelf. By not charging more than I can afford, I pay off my bill in full every month.

Expensive Mortgages

Lock: A nice house or apartment is the ultimate status symbol. We all want to live in a safe and comfortable space, but many of us buy or rent a larger space than we really need.

Key: When buying a home, it was important that my monthly payment (including taxes and insurance) be <25% of my income. By not buying more house than I could afford, I have had extra to put toward my mortgage principle each month.

Currently, I am on track to pay off my 30 year mortgage in 7 years. With that expense removed from our budget, I would be able to survive on a minimum wage salary (not that I’d want to, but it’s nice to know I could).

Car Payments

Lock: Leasing is virtually resigning yourself to the idea that you will always have a car payment. Paying interest on a depreciating asset is equally insane. Yet so many people commit to paying $300 or more a month for years.

Key: One of the ways I was able to pay off my student loans and pay down my mortgage was by not having a vehicle payment. The car I drive is 15 years old. I plan to drive it for as long as possible. When it’s time to replace it, the next car will be purchased in full.

No Retirement Savings

Lock: If you save 15% of your income for retirement, how long will it take you to retire? 43 working years! (see Mr. Money Mustache’s The Shockingly Simple Math Behind Early Retirement)

Key: Sadly, many people work longer than they want (or physically should) due to lack of retirement savings. I am contributing up to the match in my employer-sponsored account and maxing out a Roth IRA. Once my mortgage is paid off, I plan to max out my employer-sponsored account as well.

The 2019 max for employer-sponsored accounts (e.g., 401k, 403b, TSP) is $19,000. Roth IRA max is $6,000 (plus another $6,000 for non-working spouse if filing jointly). So, after paying off my mortgage, by maxing out retirement I will contribute $31,000 a year.

Medical Bills

Lock: Even more heartbreaking is when people lose everything they have due to an illness in the family. This is honestly my biggest fear.

Key: There is little support available for middle class people. I do max out a Health Saving Account in hopes that this will provide some help when illness strikes. The 2019 maximum contribution is $3,500 for an individual and $6,000 for a family.

In addition to saving for medical expenses, I have also committed to living a healthier lifestyle. Eating a healthy, plant-centered diet, exercising daily, and reserving alcohol for special occasions will hopefully reduce the likelihood of most of the top causes of death in the USA that are due to lifestyle factors.

Related Article: Which Benefits Should I Sign Up For At Work

Kids’ Educations

Lock: Some people start saving for their kids’ educations from infancy. They even prioritize college savings funds over their own futures. I am of the mindset that there are options available for education. Although I don’t want my children to incur student loan debt, it is an option. Scholarships and starting at free two-year colleges are also options. But there is no one to whom I can turn in retirement.

Key: If I don’t take care of myself, no one else is going to. I have prioritized paying off my debt, saving for retirement, and putting money aside for inevitable medical costs. After these goals are met, then I may start to save for my kids’ educations. 

Final Thoughts

We all need money to survive. But after our needs are met, more money does not lead to greater happiness. I am fortunate to have a well-paying job. While I could use my income to buy a more luxurious lifestyle, instead I use it to buy my freedom.

Are you working for money or making your money work for you?

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