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Stuck At A Job? The Golden Handcuffs Dilemma

Man sitting with his hands cuffed and a sentence that says: "Stuck In Your Job? The Golden Handcuffs Dilemma"

When talking about lifestyle design, purpose and fulfillment then inevitably the question of finances will appear in some way. It can either be your best ally in your journey or your worst enemy. In this post we will go over the most common hurdles and how to put finances on your side of the equation.

This is not a post telling you what to do and it is obviously not financial advice. But I believe that some people do it way better than others. This is how they do it. For the nuances of your specific situation please consult a professional.

Your Parents Were Right - Study STEM.

Damn, I said it. Don’t kill me. Here is the dilemma a lot of people face after high school: Study something boring that pays or study something you have passion about that guarantees you’ll be underemployed and underpaid your whole life, usually getting in debt in the process. At that point, parents heavily push you towards going into a STEM field that will guarantee food on your table. If you happen to like math and physics, then lucky you. For all others it will be an excruciating choice between stability and what you think you like. From working with people looking for a path however let me tell you this:

"Life is much easier for people that have soulless jobs that pay than for those that follow their passion, but can’t make ends meet."

If you hate your job, but make decent money then you have options. Options that will open-up the world to you. All you have to do is make smart decisions and take the opportunities in front of you. Through these blog posts we will show you how. But if you are chronically underpaid however that situation will shackle you with limited options. Guess where you want to end up? Now it doesn’t mean that you will necessarily live a happier life having more money, very far from it. I only said you had more options. The thing that does matter is what you do with these options.

When looking for a path, most people fall into three categories financially:

  1. They live paycheck to paycheck with low income

  2. They live paycheck to paycheck with high income

  3. They have good savings, but don’t know how to leverage them.

Let’s start by exploring all three possibilities.

Issue 1: Paycheck to Paycheck – Low Income

Time for a DISCLAIMER. I get it, the world fucking sucks these days. Rent in my area shot up about 30% since COVID hit, same thing for groceries. At the time of this writing, the CPI here in Canada is 8.1% for the month of June. And that's the official numbers that they are not scared of telling you and that result from some clever accounting.

It is becoming harder and harder just to survive for a lot of people and everything the government does will just make it worse as years go by. I don’t have a miracle solution for that. Unfortunately, it means that everything falls down to you as an individual, your drive and your willpower. It will require even more hardship and sacrifice than ever, but I don’t see any other way to get out of it.

Living paycheck to paycheck sucks, but the problem compounds if you also have a low income on top of it. If you have a low wage and have trouble making basic payments on your apartment and bills then beyond everything I else, figuring this out should be your first priority. Personal and career development does not matter to someone that is just trying to get by. Because fuck this economy, now you have to do everything in your power to:

  1. reduce your expenses AND

  2. find more income

Thanks captain obvious, easier said than done. For that specific reason there is a beautiful subreddit that exists: r/povertyfinance. It is a goldmine of information about very specific things that you can do depending on your individual situation.


After you have done everything that r/povertyfinance recommends. Chances are you will have to be hustling get out of that paycheck-to-paycheck hole. This will mean in all probability a second job, a gig job (Uber, food delivery), a side business, or anything that you can do in your spare time to rack in more dough. You will want to do this until you can take the next step.


If you are a low-income earner then chances are your skills are just not valuable in the job market. This has nothing to do with college education by the way. You can have a Ph.D in archaeology and still earn minimum wage in a library, without any better employment options, especially in this economy. So you need to build better skills to leverage them for better pay or a better job. Remember you have been hustling to afford to up-skill.

Don’t sheepishly go and try to learn to code like everything else. Find something that can be learned relatively quickly and that is in demand these days. Construction workers, electricians, machinists, welders, crane operators, fork-lift operators, truck drivers, aircraft engine mechanics, police academy, barber, etc. A lot of these skills can be acquired within a year or two doing night classes or certifications. Because they are in such demand they pay pretty well. Obviously do your own research specific to your location and situation.

The Promotion Hack.

Know how to get promoted at your job? This is the closest thing to a system I have seen.

  1. Learn to do your current job as best you can. Become the best in your team at it.

  2. Go to your manager and ask for more responsibility. Specifically ask him to delegate some of his tasks to you. Master them and become the best at it.

  3. Make a deal with your boss that you will keep learning how to do his job so that he can do the same to his own boss.

  4. When the time for promotion comes, your boss will be promoted higher and who do you think is in the best position to replace him? You already know how to do his job blindfolded.

  5. And even if you don’t get promoted, you can leverage your new skills in your salary renegotiation.

  6. Warning: If you have a shitty boss, your work ethic will be threatening to him/her. Use your judgement not to get fired. If you think you can’t do this where you are then sometimes it’s easier to find a better boss.

Jump-starting your life.

Finally, some people have just been dealt a shit hand at the start of life: abuse, unstable family, severe poverty, no opportunity for education, mental illness, disability, war, etc. So, if you want to speed-up this whole process of increasing your income there are two ways that you can jump-start your life. There may be others, but these are the ones I know of.

Do jobs no one wants to. You know the kind I am talking about, where you come home every night smelling like (real) shit from the sewer work, or living for 6 months on an oil rig or in the deep north, or running 20 miles per day behind a garbage collection truck. These are hard jobs. But they have the benefit of compensating you more. All depends how much you can tolerate.

The military. One such job that no one wants is the military. Assuming that you live in a NATO country, or any other country where service has a reasonably low chance of killing you then the military is actually an amazing opportunity. They pay and train you at the same time and you don’t have to be a frontline soldier. There are so many technical trades in the military that after your first 4 or 5 year contract you can come out of it significantly richer, highly skilled and without ever seeing combat.

They will also pay for your higher education if you stand out. If you are in the United-States or Canada you can have all the advantages of the regular force, but little of the downsides by joining the reserves. It’s the same training and almost the same pay. It’s honestly a no brainer if you are looking for a shortcut in life. You can accomplish in 5 years what will take you twice or three times as long being out there hustling in the civilian world. If you want accurate information, find a vet and talk to him about it. Don’t blindly trust a recruiter. Talk to someone that has been in the system AND ALWAYS GET MORE THAN ONE OPINION.

Conspiracy Theory meme with text: "Me trying to explain how the army is the best option to a highschool senior"

Issue 2: Paycheck to Paycheck – High Income

If you have decent income, but still live paycheck to paycheck you have much more of a first-world problem. You might feel stuck at your job because you need the money, but most of that is of your own doing. This is the golden handcuffs dilemma, so let’s get into reducing expenses.

Deal With Your Debts.

The first reason most young professionals live paycheck to paycheck is bad debt. This means either student loans, credit lines or credit card debt. If that is your case you need to start paying that shit down as fast as humanly possible. The interest payments alone in this can cripple your life for the next 20 years if you are not careful. Take a look at the previous low-income section and hustle away. Bad debt like this is what poisons your ability to get on with life and make independent choices. I can’t stress how important it is to get over this.

Choose The Right Housing.

Housing is tricky. It is an extremely personal choice on where you decide to live and how much you want to pay. Each individual has preferences whether it’s better to live in a house, a condo or an apartment as well as the specific location for it. This is the section that you should most discuss with your actual financial advisor, but I will just leave a couple of points.

First, we live in a cult of homeownership. With the maintenance costs, realtor costs, welcome taxes, yearly taxes, I believe the math of buying a house doesn't add up anymore. Home ownership is about your personal well-being, but no longer a valid investment as the opportunity cost is just too big. If your reasons are purely financial, I don't see anything wrong with renting. One of those days I will post a complete budget comparison between the two.

Yet 2020 and 2021 have seen insane housing buying frenzies and now the rates are rising and prices are falling. I'm not sure this is a great market to be in. Remember that this post is not financial advice so your mileage may vary. I'm just pointing out that there are alternatives out there. For the sake of the argument, I will leave this below:

Graph of the Canadian vs American housing prices adjusted for disposable income
American vs Canadian Housing Prices

Manage Transportation Costs

Ah, car loans. The bane of every financial success plan. A car is not an investment. An investment is something that makes you money in return. A car is something that loses a third of its value in the first year. German sedans and sports cars are luxuries you can’t afford if you live paycheck to paycheck and it’s the first thing that should go from your lifestyle because they cripple your ability to make good life choices when you have to pay a significant amount of your paycheck every month. Downgrade and buy used. Get the best deal you can on a decent, low-cost used car with average mileage and drive it into the ground. The only exception I can see here is if you job depends on you driving luxury because it’s important to your image. Even then find the cleanest used vehicle you can and save yourself a few (thousand) bucks.

Eat Right

Here is a category where nature has blessed us with a money saving opportunity. You know what food costs the most per calorie? Take-out. In North America it is also the unhealthiest way you can eat. The second most expensive food per calorie? Processed foods. That means chips, chocolate bars, frozen chicken nuggets, packaged cereal, sugar-filled juices. You know what’s cheap? Vegetables, rice, potatoes and meat. Meat can be obviously expensive so look for specials in cheap supermarkets and stock-up when an entire chicken is cheaper than a bag of chips. Do yourself a favor, learn to cook at home, eat healthy and your wallet will thank you for it.


The amount of people I see with 1000$ phones and 100$/month phone plans is astounding. You can buy a perfectly good new smart-phone for as low as 300$. Much less for a used one. Bring your own phone (BYOP) plans are much cheaper than leasing your phone and have all the data you will ever need. Never lease a phone. Buy one and it keep your as long as you can. The same can be said for home internet plans. A lot of people get sold on plans they never use at full capacity. Consult someone knowledgeable that you trust on what you actually need and you can possibly cut your payments in half. Also try to save power whenever you can by reducing the AC, lowering heating in the winter, change light bulbs for LEDs, etc. It’s also good for the planet.


Or also knows as the biggest money sink ever, especially if you are young. You don’t have to stop partying. You just have to quit drinking (or doing drugs). That alone saves me over 4000$ a year and I go out, a lot.

Buying useless shit.

Do you really need that 23rd pair of shoes? Or a new GPU to keep playing Minecraft? Or a 300$ for a new led kit for your pimped-out Subaru (which you bought used anyway, remember?) A lot of people spend money to feel better about themselves or their lives. If your life sucks, or is stressful, or not quite the way you want it then go spend that money in a way that will change that, not just make you feel better for three days. The sooner you quit doing that the more freedom you will have. Also, most of the stuff you buy either had to be maintained, cleaned or put away, putting more strain on your time and wallet as it is. That’s how most of the stuff you own will end up owning you. Simplicity and minimalism are great.


Luxuries are another tricky subject. On one hand if you can’t afford them or they put too much strain on your wallet you should cut them out like everything else on this list. On the other hand, small and simple luxuries that are affordable should absolutely be maintained if they are essential to your wellbeing. There is nothing wrong with having sushi once in a while or buying an expensive bottle of wine for date night. These are the moments that you should focus more of your money on and it makes your life way more meaningful than a new car, new shoes or binge drinking. You have to find the particular balance that works for you.

Don’t tell me how to run my life.

Along with “go fuck yourself” this is probably the most common reaction I imagine the readers thinking when I speak or write about lifestyle reduction. I get it, it’s not easy going back to a student lifestyle after you’ve been swimming in cash you could (or already did) spend. But really it comes down to a simple choice:

  • Keep living the life you are currently living; or

  • Make some changes that will make give you more options and potentially make you happier. My guess is since you find yourself on this blog you have at least some interest in this option.

Robert Downy Junior Meme with Text: Don't tell me how to run my life"

Issue 3: Not Knowing What To Do With Money.

What it means to have financial freedom differs from person to person, but for the sake of the argument in this post it is loosely defined as:

  1. An emergency fund for at least 6 months of minimal expenses AND;

  2. A savings or investment account able to finance at least a year of your current lifestyle. AND;

  3. A positive savings rate. Meaning that you spend less than you earn. The specific number here is up to the individual, but I recommend savings ranging from 10 to 75% of your net income. You obviously want to save as much as possible and not just do the minimal 10% if you can afford it. OR;

  4. No significant debt or liabilities that prevent these points from happening.

In terms of finding a path this is the situation you want to be in. I could estimate that at least 50% of the misery people feel at their work is because they are financially shackled to their work and do not have the options of just quitting. Not saying that they would quit given the option, but at least having the option is hugely beneficial to your mental stability. The other 50% misery comes from making all this money and having no clue what to do with it, being uninspired and feeling all you do in life is working for the said money. If you find yourself in this situation, you can leverage your finances and pay for experiences to find a new path faster. Let’s take a look at your options.

Long Term Time off.

When you get to a point where you don’t have to worry about your finances for some time if you quit, a lot of people make that choice and willingly take time off. From a couple of months to a couple of years. Or they secretly wish they had the guts to and look up with envy to those that actually do. The reason for this choice is simple. If you have been working in a draining job for some time you are spent and exhausted. Take it too far and you have people on burnouts. A week of vacation here and there doesn’t cut it anymore and you absolutely have to take some time to yourself. Especially if you come home drained with no more energy to do anything to fun or productive for yourself. This is your chance to get some self-care, restore balance to your life and spend time doing all the things you couldn’t do on a tight schedule around work. Things like training, eating well, catching up on sleep, visiting friends and family, finishing a couple of books and get back into your hobbies. This also leaves you time for:

New experiences.

With some decent time off and financial wiggle room you can afford to do the things that you always wanted to, but never dared say out loud. Things like travel, van or boat life, volunteer for a cause close to your heart, do all the things you have a passion for but don’t pay, etc. New experiences generally mean something that will nourish your soul. Trying a new flavor of chicken wings is nice and all, but has a lower probability of making a profound impact on your life. To learn more about how to get the most out of new experiences take a look at How to Find Your Path.

Reduced Hours.

A slightly easier option than long term time off is reducing your hours. I hear the following story a lot: Person has enough savings to cover years of expenses or even retire. They don't need the job they have anymore, instead of quitting they leverage the boss to either reduce their workload or change their role. They start working 3-4 days per week for 60-80% of the pay and their stress levels drops through the floor. It's up to you to figure out whether this is realistic for you. Some bosses will be inflexible, others may be very flexible and you don't even need to be that well off to ask for reduced hours. Either way, having lots of savings opens up your employment options because you know that you can easily find another job or better yet, you don't even need one for the next year. The benefits are the same where you have more energy and time for yourself and new experiences.

New skills or education.

Financial freedom brings great opportunities for personal development. Most of the top quality certifications out there can be on the expensive side, but would maybe open the doors for a potential promotion. On the other hand, you can get into actual personal development that has nothing to do with work. Pay for dance classes, sky diving classes, flying lessons, diving instruction or whatever else fancies you. Learning and investing in yourself is probably the best way to spend your money.

Hiring mentors.

Along with new experiences, this is probably the category in which each dollar you spend will go the furthest. Sometimes we are lucky to find a quality mentor in our immediate surroundings that will gladly take us under their wing for free. However, this doesn’t always happen. Especially if the skills or experiences you want to build are so far out of your comfort zone that no one you know can guide you through them, then you are best suited to find a mentor you can pay for. This can literally be the difference between wasting months and years on an experience and making it the best moments of your life. Typical cases in which you want to find a mentor:

  1. Starting a business

  2. Building new soft or hard skills

  3. Help with your relationships or social skills

Hiring Coaches.

The same goes for coaches. Coaches are different from mentors as they don’t provide the same services. Coaches are very good at helping you find clarity and perspective so that you make your decisions with confidence. While a mentor usually tells you what to do based on his perspective, a coach helps you become more independent by giving you the tools to build your own. Sometimes you can find a good coach and mentor in the same person, but you have to vet the candidates very carefully. Here is what a coach does really.

Financial Planning 101

When asking why most people don’t quit their miserable jobs they usually say because they need the money. Then when I ask, “ok so how much do you need?” I get blank stares in return because people have no clue. If you had a very specific plan in mind where you need to reach X amount within Y years in order to do something specific with it like pay off your debt, mortgage or else, then yes, you are stuck at your job because you need the money. But if you don’t have a financial plan in place then it is not money that is keeping you at your job. It is the fear of running out of it. The former is factual, the latter can be dealt with without making an extra cent by understanding how much you truly need.

This is no way to live. If you do not know how much you actually need, you risk working years or even decades longer than you need to accomplish your goals all because of the “what if I don’t have enough” feeling. This is why financial planning exists. To make an actual financial plan speak to your financial planner, financial advisor or at least someone that you trust that knows what he’s talking about. Not some random dude on the internet. Here however, is the general rundown of what a robust financial plan should include:

  1. How much do you have? For some this totals the money in their current bank account and this is relatively simple. But less so for others that have 401k, pensions, retirement funds, etc. If you are married or at least counting on a partner’s financial contribution to your family then this will also include everything you have in joint accounts and the relevant stuff in your partner’s name.

  2. How much do you need right now? How much do you spend per month on average? Split that into categories: Housing, utilities, food, transportation, going out, buying stuff, business and school expenses, etc. Find out the average number for each month. This is your budget. Knowing this number allows you to project your financial needs into the future.

  3. How much do you ***really*** need right now? Now take your numbers in Part number 2 and strip all the stuff that is not related to you surviving. Keep the housing and utility costs, food and transportation to work. Basically, how much do you need to not starve and keep making an income? This is your minimal survival budget and the money you need not to starve. This is the number you need to create your safety net.

  4. How much do you need in the future? What are you trying to achieve with that money? Here are the most common important questions that you need to answer.

    1. How much do you need to cover your present debts (Student, mortgage, car-loan)?

    2. How much do you need to cover your planned debts (Buying a house in the future)?

    3. What is the lifestyle that you want to build for yourself? (More houses, cars, travels, experiences, etc) How much is the lump-sum entry cost and how much is that going to cost you to maintain per year? Any relevant debts to add to point b?

    4. When do you want to retire? Or how many years do you have left to achieve those goals listed above? Take note that the earlier you decide to retire, the more pressure you will have on your finances because you’ll have less years to accomplish your goals.

  5. How and when will you earn that money? What are your projected earnings until you retire? Create multiple scenarios. Imagine yourself working until retirement and earning a low, medium or high estimated income. How much do you estimate you can earn per year in each different scenario? What does that mean for your retirement plan? How will you go about making it happen?

  6. Putting everything together. Play with this formula until your lifestyle expectations match your projected income and both side of the equation balance out. Once you do this becomes your financial plan. This is just as valid for individuals as it is for families. The principles remain exactly the same.

Piglet savings bank with stacks of coins on the desk with text that says: "It is not money that is keeping you at your job. It is fear."

As the saying goes, no plan survives first contact with the enemy. In the same way, life will get in the way of your financial plan and you will have to rework it from time to time. This is normal. The benefits of having a plan however are HUGE. It gives you direction and clarity as to what kind of financial situation is acceptable for you and which is not. You will be able to make the right career and lifestyle decisions based on your specific needs and not what others expect of you.

As you create your plan you will also see, on paper in front of you all the opportunities you didn’t think you had. It’s at this point that people realize that maybe they already have enough to quit their jobs and start businesses without worrying too hard. Or sell their house and go travelling for five years. But you wouldn’t have discovered any of it if you hadn’t put it all on paper in front of you. You would still be living in fear of quitting because “you think you need the money”.

A Lot Of The Good Thing In Life Are Free.

No matter your financial situation, a lot of the stuff you can do to push your comfort zone and explore are free or cost very little. A couple of examples:

  1. Subsidized training programs for skills in severe shortage in an industry

  2. Youtube tutorials where you can get much of the same knowledge as in college or university.

  3. Physical training and getting into shape.

  4. Local travel, hiking, long distance bike rides, etc.

  5. Volunteering.

  6. Socializing and working on your soft skills.

  7. Personal development. A personalized mentor will of course cost you a lot, but 90% of the resources out there are below 20$.

More Free Resources

This is probably the longest post in the series. But there is just too much to cover. To help you further here are the resources I recommend you check out.

  1. The richest man in Babylon. A great book that distills financial lessons into stories. It’s basically free for the kindle edition.

  2. r/personalfinance The general thread for anything related to finances.

  3. r/povertyfinance A gold mine of information and life hacks for people in precarious financial situations.

  4. r/financialindependence For those that want to save lots and retire fast.

How We Can Help

Not sure where to start? Take a look at our coaching program to see how we can help.. Schedule your orientation session today to get your bearings! We also offer free two-hour orientation sessions to any new comers. All you have to do is book yourself a time-slot here:

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