The Epic Guide On How To Quit Your Day Job & Become A Digital Nomad

Davy Russell

On January 18, 2008, I quit my day job. I was 28 years old.

Less than three years later, I was living near the beach in Puerto Morelos, Mexico enjoying a digital nomad lifestyle.

Sure, I was scared when I gave my two weeks notice when I came back from Christmas break back in 2008.

I had tons of debt, just like anyone else. I had less than $4,000 in savings. I didn’t have ANY other sources of income to replace my paycheck.

I just quit my day job and prepared myself to do whatever it took to make a living doing what I love.

Escaping your day job to create a freedom lifestyle is a straightforward process that anybody can follow regardless of financial situation.

It all comes down to what you are willing to sacrifice temporarily in order to live the life you truly want.

Tracy on the beach.
What would YOU do with more time to do what you love? Here, Tracy enjoys the beach in Puerto Morelos, Mexico during the winter of 2010/2011 – a trip that would never have happened if we were stuck in jobs.

Imagine waking up on a Monday morning with a smile on your face and excitement about how you will spend the dayespecially during the hours of 9 AM to 5 PM.

How about taking a Thursday afternoon off – without having to ask permission – just so you can have an impromptu adventure with your family?

Do you ever wish that you could travel more? Or take more than 1-2 weeks each year for vacation?

Do you long for a richer, more fulfilled life doing what you love while spending more time having adventures with your family?

What if I told you that you could have all of this – this freedom lifestyle – right now? And you don’t have to be independently wealthy. You don’t have to have a trust fund. And you don’t need to wait until retirement (or win the lottery).

I promise – there is NO pitch in this article! 🙂

You can have this life much, MUCH sooner than you think is possible.

Being able to escape your 9-5 job is not a matter of financial readiness. It is a matter of mental readiness.

Are YOU ready to break free from your cubicle and live life on YOUR terms and YOUR schedule?

Step 1: Stop Thinking Like An Employee!

After being self employed for almost a decade, I’ve learned that the biggest obstacle that interferes with people being able to quit their job and live a more fulfilling life isn’t finances, or other obligations. It’s mindset.

Fear of uncertainty, worse-case-scenario thinking, attachment to things/status/relationships have a much stronger grip on people than things like debt and income (two fairly simple things to remedy).

The biggest reason why it took me 10 years to finally walk away from being an employee was not financial at all (and I DID NOT have a paycheck to replace my income at the time). It was mindset.

And once my mindset was in alignment with what I wanted out of life, I turned my “someday goal” into a “today reality”.

The biggest, and most likely only, thing preventing you from quitting your day job and making a living doing what you love is NOT a lack of financial resources or a dependency on a steady paycheck (even if you think you depend on that paycheck to pay bills).

Read the above paragraph again and pay attention to any resistance you have to what it says. These resistances are excuses that are holding you firm within the life you wish to change. *

Instead, what’s holding most people back is the FEAR OF UNCERTAINTY about leaving a steady paycheck and the DOUBT that they have it in them to generate a livable income AND have fun at the same time.

We’re taught early that what you love to do cannot, does not, and will not (ever) pay the bills.

We’re trained to think that in order to have a roof over our head or put food on the table, we must put on a tie, clock in, say “yes sir, yes ma’am”, and kiss corporate ass.

Sometime between your first job flipping burgers and your current stint pushing papers around the cubicle, you might have accepted your fate within the so-called “40-year plan” of working jobs you’d rather not with the hope of being able to retire in the distant future.

If you are just joining the workforce now, you’ll be lucky to afford retirement by age 75.

Most people who want to leave their day jobs get stuck in the WANTING phase and never progress toward the DOING phase.

They dream of storming into the boss’ office, saying the words “I quit!” and jetting off to a beach somewhere. And this remains a painful fantasy for the majority.

But not for you! Not anymore!

You are going to do something about your situation starting today!

The first step to leaving your day job and escaping the 9-5 rat race is to stop thinking like an employee!

An employee convinces him or herself that they are dependent on others for their income.

The employee believes that in order to succeed, they must always impress the boss.

They believe that working harder, faster, taking on more responsibility, and working more hours (weekends and bringing work home), is the surest way to get a raise or promotion.

Employees tolerate a 3% to 5% annual raise regardless of results generated. They accept that they won’t be compensated for job-related expenses such as attire and commuting time.

They accept two measly weeks per year for vacation. And if they get sick and can’t crawl into the office (which many do, anyway), then no vacation.

It is time to change your thinking.

Here are some affirmations to read out loud. Be sure to read them out loud! Pay attention to any resistance that you feel when you repeat these words.

“I am capable of generating an income for myself without having to take a day job, or rely on my employer for money.

This realization really hit me at the very last job I worked.

The company held monthly meetings where they talked about sales and revenue goals for the month, the quarter, and the year. The company provided a service-based product and was an outsourcing solution for large clients.

Because of this, they had to constantly work to find new business, which usually resulted in a contract that would last anywhere from 3-12 months.

You couldn’t look two or five years into the future and know exactly how much this company would make, but because of the efforts of the sales team, they were thriving month after month, year after year.

Most companies operate the same way. Without the efforts of a few sales people, and the quality of the product or service offered, the company would be out of business quickly.

There’s absolutely no reason why you couldn’t take the reigns and provide your own service or sell your own product to your own clients and have complete control over your own income.

“I have valuable skills and knowledge that can be harnessed and packaged into money-making products and services.”

You probably definitely underestimate how valuable your knowledge and skills are.

If a company is willing to hire you for $15 per hour to do a job, rest assured you could make a lot more on your own (your salary is a portion of the profit the company makes off of your services).

Now you might only have worked simple paper-pushing day jobs and think you have no marketable skills that are worth more than $15/hr. Nonsense! The next part of this article will give you plenty of tips and ideas for rethinking your income strategy.

What you know, and what you can do well, are worth a lot more than your current company is willing to pay you for! I guarantee it!

“I will be far more successful on my own than I would be as a cog in a machine at a company.”

Employees don’t become rich. If you want to take full control of your income and really live the life of freedom you desire, you must leave your day job. There is no getting around this fact.

Without a dependence on your day job, you can take time off whenever you want.

You can travel and live anywhere in the world instead of spending an arm and a leg binge-traveling to some artificial resort. I recently spent 6 months wintering in the Yucatan. I couldn’t have done that if I was working a 9-5 job.

As an employee, you are at the mercy of your company. If they do poorly, your income could be shut off with little or no warning.

Your job can change from the one you signed up to do, to something else that isn’t at all what you want to do (or enjoy), and there’s not a thing you can do about it.

“I take full responsibility for what I currently have and for what I want to have.

Now is the time to stop giving your power away to your boss or “higher ups”. Instead, BE your own company and your own boss, even while you still work for others.

Instead of thinking of yourself as “just an employee”, think of yourself as a freelancer, a self-contained company of one – YOU – providing a service to the company you work for. This mental attitude is critical to hone when you are working for yourself.

Even if it’s just a mental game at first, thinking of yourself as company of one is an important step in segueing out of the 9-5 rat race.

Think of the company you work for as a client who has hired you to do a long-term, freelance job assignment.

When you want a raise, think of it as providing a quote for the services you provide (rather than permission for a few extra bucks to be thrown your way).

Manage your resources, including your financial resources, as if you were a company.

Instead of thinking of your income as just a paycheck you get from your boss, think of it as payment from a client based on your services.

Be ready to “fire” clients that will not or cannot pay a fair price for your services, knowledge, and skills.

“I recognize excuses for what they are – limiting beliefs.”

Instead of all the “yeah, buts…” that pop into your head when you think about quitting your day job, give equal weight to the positive “what ifs…” too.

Everybody is afraid of being homeless, broke, or bankrupt if they quit their day job. I was too.

But instead of dwelling on the possibility of these (very temporary) problems that probably won’t happen, give equal weight to positive outcomes for quitting your job – a higher income, the ability to work from anywhere in the world, more time with family, and to pursue your own interests, job and life satisfaction, better health.

Another major mental block that prevents employees from escaping their 9-5 day jobs is fear. Do you feel like staying put in your day job or quitting to pursue your dreams is a choice between freedom or security? What if you can have both?

What if quitting your job actually provided more security (and income) than your steady paycheck? I’ve found this to be true in my life!

“My day job is NOT a steady, secure source of income. I can generate a higher income without my job.”

And that brings me to our last affirmation. And I know this one sounds a bit negative, but it’s 100% true. Your job is NOT a steady, secure source of income.

You can be laid off (I was twice, and my wife was once.)

You can be fired.

Your company can shut down or relocate.

You could be forced to take a pay cut.

Your employee benefits could be cut.

You could become injured, sick, or disabled and unable to do your job.

So what then? Stop thinking about your job as the “safe, secure, and responsible” direction in your life.

Instead, take the reigns and direct your own life. Create your own income. Build a business that doesn’t require your butt in a cubicle in order to generate an income.

Step 2: Re-Think Your Income Strategy

Income is the number one thing that people worry about when faced with the desire to quit their day job. Truth is, there are a LOT of options for making an income without a job.

I recommend taking a two-prong approach. First, reduce your living expenses and get out of debt. Second, generate an alternate source of income.

Do both of these things at the same time.

Combining these two strategies teaches you better financial management while accelerating your goal of quitting your day job.

It is not hard to generate an income that will allow you to quit your day job and escape the 9-5 rat race.

You’ll start out small, with just a trickle of cash, but it’s up to you to grow it to the point where you can live on it for life.

When it comes to writing your own paycheck, you basically have two options: either provide a service or sell a product.

And then there’s a better, third option that I will also discuss in this article.

There are advantages and disadvantages to each income method. I’ll go over these below:

Income Option 1 – Make Money Providing a Service (ie: Freelance or Service Business)

The easiest way to generate a new (or additional) income is to cash in on a skill you already have and provide a service. I did this when I left my corporate day job back in January 2008.

Since my training was in film and video production, I invested in professional videography gear and moved to Chicago. I was then able to quickly make a living doing freelance videography work for a variety of production companies and corporate clients.

I did not get a job at a video production house. Instead, I hustled and found my own gigs.

The advantages of providing a service is that it is super-easy to set up. If you already have the skills, you simply need to market yourself.

Because I already had training in videography, as well as a good resume and demo reel, I was able to get work quickly.

I did have to move to a different state in order to position myself in a more lucrative market. I was willing to do whatever it took.

There wasn’t much of a learning curve to get up to speed on doing what I already knew professionally. You don’t need to be a marketing genius or a sales guru to get business.

If you can make friends with people and act professionally, you’ll do just fine in finding work as a freelancer – provided you put the effort into finding the work.

But you do have to show up, and 95% of the time spent freelancing your skills is in actually looking for work!

You can easily make money providing domestic services like housekeeping, babysitting, or dog walking.

Or you can cash in on your computer, photography, or writing skills. Everybody has at least one thing they can do well that people are willing to pay for.

A major disadvantage of a service-based income strategy, however, is that you are basically creating a job for yourself.

I say this is a disadvantage because your ability to earn money is directly tied to your ability (and availability) to work. If you are sick, injured, or want to take a vacation, you don’t get paid.

You are also reverting back to the employee mindset of trading time for money. This is a bad thing.

You’ll only make as much money as you have time to work. It’s a losing battle. Forget about taking spontaneous adventures on a Thursday, or working remotely, part time, from an exotic location abroad.

I recommend starting a service-based business only as a short-term strategy for leaving your day job.

Unless you are absolutely in love with what you are doing and see yourself doing that until the very day you die, I would look at ways of leveraging or diversifying your service business to where you no longer have to trade time for money.

Income Option 2 – Make Money Selling a Product

The second income option is to make money selling a product. Whether you create your own product or sell somebody else’s, this is the revenue generating option that either takes a ton of time (and perhaps money) to create the product and/or a knack for sales.

As with selling a service, you might find yourself trading time for money. If you have a store, a kiosk, or a food cart on a street corner, you’ll only get paid when you are physically present, keeping the shop. If you have others sell for you, commissions and wages will eat away at your profits.

The advantages of selling a product is that you can sell it online or sell to buyers who sell the product for you, but inevitably, you always end up trading time for money creating more product, finding buyers, managing inventory, managing customers, etc.

The business might become cost-prohibitive if the product costs a lot of money to develop or manufacture.

A large initial investment in a new product is extremely risky. If the product flops, you’re out a lot of money (and time).

So what about selling somebody else’s product?

The absolute worst way I can think of to try to earn a living is through a Multi-Level-Marketing (MLM) or Pyramid Scheme. These “businesses” require an upfront investment, regular subscription fees, a minimum monthly product purchase, and the requirement to sell both the pricey products and the business model to your friends, family, and anybody who will listen to you – and gullible enough to buy into the pipe dream these companies try to sell.

Of course, there are people who have the personality and connections (and friends/family with disposable income) to be successful at MLM programs.

However, these people are very few and far between. Most MLM’ers are barely making enough to make any change to their lifestyle, let along quit their day job.

Most people who give this option a shot give up within a year because they end up spending more money and investing more time each month than they get out of the business.

Believe me, I’ve been there! It’s no fun having a closet stocked with expensive products your friends and family can’t afford to keep buying from you, and knowing that in a few days, you will need to buy even more of that product to maintain your sales quota and stay “in business”.

Instead of making money with the business, you’re paying money to stay in business, and the “can’t-fail”, pyramid-shaped business plan you were pitched months ago has long lost its luster.

A Better Option – Sell Your Knowledge And Experience

The best option for generating a long-term revenue is found within your own head, and from your life experience.

In fact, this is the ONLY method I recommend unless you are desperate to leave your day job immediately, in which case you can do what I did – freelance your skills as a service business while you build a source of income online.

So what does “selling your knowledge and experience” really mean? Let me give you an example:

Tracy and I discovered green smoothies in 2007. We started drinking these smoothies in 2008. We both lost weight and felt great.

Because of our passion and the knowledge and experience we gained, we became experts on everything green smoothie related.

We launched a blog in 2009. Two years later, we were earning a comfortable, full-time income from that blog, and we have done so every year since 2012.

Our business is neither a service business, nor is it strictly a product business. We have no inventory.

Instead, we packaged our knowledge and experience into a downloadable program (e-books) that has helped thousands of people lose weight and improve their health with green smoothies and plant-based, whole foods.

In short, we turned our passion, knowledge, and experience into a passive income source that doesn’t require a butt in a chair to make a paycheck. Our website sells for us 24/7.

We have the freedom to live absolutely anywhere in the world we want as long as we have a reliable internet connection.

We make money on holidays, weekends, whether or not we are sitting at our desk.

This is the business model that I recommend.

Find something that you are deeply passionate about, and turn your knowledge and life experience into an income-generating blog or website.

The advantages of creating a website that generates income online are many. For one thing, your website earns income whether you are actively working on it or not. It’s true – you can make money while you sleep!

The order and delivery process is 100% automated, and your website can attract potential customers and clients 24/7.

There’s nothing to ship and no inventory to track. The customers get what they paid for immediately, and I get paid before I even roll out of bed in the morning.

I get paid whether I work that day or not. This is impossible with a job or a service-based business.

The other great advantage of an income-generating website is that you have a global reach – not just your friends, family and local community that you are limited to with a work-at-home, MLM “business”.

With a website, you can create information products for little or no money up front and sell them for almost pure profit. (No more closet stocked with inventory that won’t sell.)

You can even launch a website and make an income without having an information product (like an e-book) to sell. Until you develop your own information products, you can sell other peoples products as an affiliate and earn commissions on those sales – provided these products are a good fit for your readers.

But please – don’t get suckered into “easy money schemes” on the Internet. There is no such thing. Build a real (blogging) business that provides value to a group of people who will gladly pay for your knowledge, experience, and solutions.

My personal experience is that the absolute best way to earn a living AND live the life you want is to earn a living online with your own website.

Create Multiple Streams Of Revenue

A critically important action for getting ready to leave your day job and escaping the 9-5 rat race is to create multiple streams of income. Preferably, these multiple streams of income will be through online sources.

Now I realize that “multiple streams of income” is a buzzword that is usually followed by a glitzy pitch to pay $99 or more to buy into a can’t fail online “cash machine”. I assure you, this article contains no such pitch.

An important break from “employee mentality” that keeps you trapped in a cubicle is to understand the necessity of multiple income streams.

Employees accept and tolerate just one income stream – their paycheck.

Unfortunately, that one income stream can be cut off in an instant when the boss or company no longer needs (or wants) you around. And many employees think quitting their day job to work for themselves is risky!

So what happens when your only source of income is taken away from you? With the current economic climate, too many people have recently found out! Don’t be one of them.

Whether you are employed, currently self employed, or want to be, find ways to diversify your income sources.

As I mentioned above, earning an income online with your own website is THE best way to escape your cubicle, and build a lasting business.

How do you create multiple streams of income with a website or blog?

Well, you can create multiple websites over time. Of course, this may become difficult to manage as a popular, high-traffic blog can take a lot of effort to create.

A better idea is to create one website and place carefully selected affiliate ads for products that are specifically targeted to your readers – that’s income stream #1.

Then you can place some paid advertising on your website (income stream #2).

Eventually, create your own information product to sell such as an e-book, audio, or video product (income stream #3).

And don’t just rely on one or two products to promote or sell on your website. Cycle through different products to solve different problems that your readers have.

Also, if one product falls in popularity, or flops completely, you have others that can take its place.

As you build more and more content and your readership grows, consider creating a premium, subscription-based service where readers can get “inside tips” or special content (revenue stream #4).

Create a mailing list and send a newsletter with targeted affiliate product promos or pitch your own products for income stream #5.

Do sponsored blog posts for income stream #6.

Utilize Amazon Kindle Direct Publishing and other e-book marketplaces for income stream #7.

The list could go on an on, including hosting local workshops, teaching classes, speaking events, publishing deals (our work on Incredible Smoothies got us a publishing deal), and providing online teleconferences for your niche or industry – all of which can generate additional revenue streams.

In the same way that traffic to a blog comes from multiple sources (search engines, social media, links from other pages, and e-mail newsletters, to name a few), it’s critical to open up multiple paths for money to flow to you.

So how do you create multiple streams of income in a freelancing business?

Okay, so let’s say that you are currently employed and plan to do freelance photography as your second income stream.

You can create a third income stream by posting some of your images on stock photography websites where people pay to download and use your images.

You can do fine art photography and sell prints.

You can publish a blog on photography tips and promote relevant affiliate products or create an e-book or video product on how to take better wedding portraits.

You see there are lots of things you can do simultaneously that could bring in multiple streams of income, no matter what you do for a living.

With multiple streams of income, you have options. You are flexible and in control. If one income stream dries up or under-performs, you’re not suddenly cut off from your only source of money. You can fall back on other streams of income, or create new ones.

Maybe your photography blog and e-books are bringing in the same or more money than your wedding photography business. Maybe you want to take the next year off and do some travel photography. Creating multiple streams of income opens doors, and lessens the financial stress of self employment.

Do you know a lot about a particular topic but don’t want to manage a website about that topic? Write an e-book and then set up an affiliate service where people sell it for you.

Become the next YouTube star.

The Internet is full of opportunities like this!

Look at other areas of your life where you can easily create an additional income stream. Keep in mind that EASILY is the key word here.

Two or three income streams might take up most of your time; the rest should be income streams leveraged off the first two that could stand on their own if they had to.

You don’t want to work 100 plus hours each week juggling a hundred things that earn you pennies.

For example, generating content for our website is a full time job for my wife and I. But our mini e-books sold in the Kindle and Nook stores took less than an hour each to create and we spend absolutely no time promoting them. It’s easy, effortless money.

Just one of these 30-page mini e-books took us about an hour to create and has earned us thousands of dollars in just a few months.

A photography blog or selling stock photos might not take much of your time or earn you as much as your freelance photography business, but if something should happen where you can’t go out and shoot, you at least have other things in place that you can tap into and develop if you had to.

I once heard about a plumber who leveraged his skills into an online business. He set up a website and charges an hourly rate to provide expert advice to people working on a DIY home improvement project.

And even while DIY homeowners are trying to save a buck by doing the repair themselves, they know that it’s a great deal to pay $99 for expert advice than it is to get a contractor out to their home, or to do the repair incorrectly.

If you are a skilled laborer and not sure that making an income online is possible, consider creating informative DIY how-to manuals for simple household repairs, then selling them as illustrated e-books or videos.

This is exactly how you make money from your skills without having to be physically present in order to make money.

Step 3: Make It Happen – How To Quit Your Job Before You Have Replaced Your Paycheck

In January 2008, I quit my day job. I didn’t win the lottery. I didn’t get investors or any financial windfall. My fledgling freelance videography business had zero income. ZERO $$$! I had less than $4,000 in total assets, and no prospects for clients.

In short, I quit my day job before I had an income to replace it.

From all accounts, I was not ready to quit my day job back in 2008. But I did. Was it irresponsible and reckless? Perhaps, but it was a necessary step to successfully leaving my day job for good. (In January 2017, I will have been self employed for 9 years!)

For ten years, I had tried unsuccessfully to quit my day job and become self employed. It wasn’t until I pulled the complacency of a “steady paycheck” out from under me until I finally got the fire to live my life on my own terms. It was the most rewarding experience! And it was a little terrifying, too.

Moving from absolute reliance on my paycheck to confidently leaving my cubicle behind for good felt daunting. It felt impossible.

However, there are a few solid strategies that I used to free myself from my day job long before I had a replacement income. I used these four key strategies to quit my day job, start up a freelance videography business, then build a blog with my wife that started earning us a six-figure income in just over two years.

Strategy #1: Reduce Expenses

The first thing I did was to take a ruthless look at my monthly expenses, and cut as many as I could. Yes, that meant that I lived on a very strict budget.

For Tracy and I, that meant canceling cable TV, and sticking with a basic cellphone, foregoing the sexy new iPhones everyone else carried with them at the time.

We also moved to a smaller place with cheaper rent, and relied on public transportation. We stopped eating out at restaurants and got furniture and other household essentials from Craigslist when needed.

For 13 months, Tracy and I lived in a studio apartment, living on just over $30,000 – for the year. But we also had lots of time to work on our online business, and in the very next year, our annual income jumped to $121,000! (When was the last time you received a $91,000 pay increase?)

It was SO worth the sacrifice! After 13 months of sharing a cramped studio apartment (with the occasional cockroach) and not spending any money, we moved into a spacious apartment home, got our sexy iPhones, and caught up to the rest of our friends – but we also had no debt, and we didn’t have to spend 40+ hours per week at a job we hated in order to enjoy these things.

One year later (2013), we upgraded our lifestyle again with a new car and a 4-bedroom house (that we rented). Now we own our own home.

Remember that the goal is not to live an austere life for the rest of your life. You are simply reducing your expenses temporarily, in order to also reduce your income requirements so that you have more time to work on your business.

Once you no longer need to rely on a day job to buy the things you need and want in life, you can acquire these luxuries (larger house, top-of-the-line gadgets, 1000+ channels of cable TV, etc…) You will enjoy these things more when you don’t have to spend so much time doing what you hate in order to get them.

Can You Live On One Income?

If you live in a multi-income household (i.e.: both you and your spouse work full time), it might be possible to live on just one income.

I know it sounds impossible at first, but if you fully embrace strategy #1 and ruthlessly eliminate non-essential expenses, and you follow the other strategies in this guide, you might find that you can squeeze by on just one income for a year or two while one of you works full time on the new business.

If not, perhaps you are just a little short on living expenses from one income, but you can make sufficient money by working part time – preferably with a freelance side business or a job.

The goal is to free up your time so that you have more of it to work on your business. If you have your partner’s support, then consider a temporary lifestyle “downgrade” while you work toward living better in the future.

Strategy #2: Tackle Your Debt

In early 2009, before we launched our online business, we were drowning in debt. It was smack dab in the middle of the big economic recession. Friends were being laid off from their jobs, and one day, my wife got her pink slip too.

There was no way we could both live off of my freelance videography income, which also took a hit due to the recession. In fact, her unemployment combined with my unreliable videography income wasn’t even enough to cover our basic expenses.

For years, our debt was holding us back. We were determined to pay it all off, but Tracy’s layoff was the straw that broke the camels back. We simply couldn’t afford debt payments anymore. We were beyond being able to dig ourselves out of the pit of debt we had gotten ourselves into.

So we looked into various options for getting out of debt (I will outline them below) because we desperately needed help and despite our best efforts, we weren’t able to dig ourselves out of that hole.

When you need to get out of your day job, you absolutely must reduce your expenses. However, hundreds or even thousands of dollars in debt payments each month will hold you back indefinitely. It could take decades to pay off all your debts, and you’ll be walking a financial tightrope the whole time. You can’t focus on improving your life, your circumstances, or creating abundance, when you are shackled by stressful debt.

You have five main options for tackling your debt. They are:

1) Pay Your Debts Off Over Time: Suck it up and pay your debts off over time by yourself.

However, if your income is low, and your debt is massive, you may never be able to pay it off – especially if you consistently add to your debt.

If your debt is growing month over month, I would suggest looking at the other options outlined in this guide.However, if you are determined to pay off everything that you owe, then pay the minimum payments on all of your credit cards and other debts until you have built up a significant savings account – at least $1000 to cover a car repair, sick pet, or emergency trip.

Once you have saved up enough money to weather an unexpected financial setback or two, then work on paying off the highest interest debt first.

2) Beg Your Lenders For Better Repayment Terms: Option 2 is to call up each of your lenders and beg them to give you better repayment terms, such as lowering your interest rate. And let me tell you, it’s often futile to do this.

Getting them to lower your monthly payment is a bad idea, too. You’ll only lengthen the amount of time (by years!) that you will be in debt, and you’ll pay even more in interest.

3) Debt Consolidation: Basically, you call up one of these non-profit debt consolidation services and they work with credit card companies and other lenders on your behalf to negotiate lower interest rates, lower monthly payments, and a definite end date for your debt.

Typically, you’re in debt consolidation for anywhere from 3-5 years, depending on how much you owe and how much you can afford to pay each month.

The benefit of this is that you will have an exact due date for being debt-free. The bad new is that your credit history will still take a hit, you won’t have access to any credit cards or lines of credit (which may or may not be a good thing), and the biggest drawback is that you’ll still be saddled with hefty monthly debt payments for up to five years!

4) Debt Resettlement: This is not for the faint of heart or non-confrontational types. Essentially, you stop making all debt payments for up to six months. By that time, your account has been sent to collections and you are now working with a collection agency, and not your original lender.

You can then attempt to negotiate a repayment plan, and if you are a rock star negotiator, you might be able to get out of debt much quicker than debt consolidation, and end up paying less money over time.

Here’s why this can be effective: Debt collection agencies buy up bad debt for pennies on the dollar, so they still make a profit if you are willing to pay a portion of what you owe. Your original lender has already written off the debt.

However, debt collectors are profit-driven, so they will try to intimidate you to pay the full amount. It’s their job to squeeze you for all they can. But at some point, it’s worth their while to settle. If you are not a rockstar negotiator, you can work with a debt settlement company, though many of these companies are not necessarily on the “up and up”.

In my opinion, if you’re at the point of debt resettlement, you might actually be better off going with bankruptcy instead as it’s quicker, and you’ll recover quicker (both credit score and financially).

5) Personal Bankruptcy (Chapter 7 or 11): Yes, it sounds devastating, but it really isn’t that bad. Bankruptcy is quick and straightforward.

You simply call up a reputable bankruptcy law firm. You provide them with all of your financial details, and information on your assets. Your lawyer then determines which type of bankruptcy you qualify for.

Chapter 11 is essentially debt consolidation. You and your creditors agree to a monthly payment plan, and you make payments (typically 3-5 years) until you are debt-free.

Chapter 7 is the “better” form of bankruptcy. This is complete dissolution of debt. With Chapter 7, all of your debts are absolved (with some exceptions, such as student loans), and within 2-3 months, you are 100% debt-free.

In most cases, you will keep your car, and no, you will not be forced to auction off all of your possessions. While a bankruptcy stays on your credit report for 10 years, you can get a platinum cash-back or rewards credit card with 0% introductory APR the very day your bankruptcy is official. You can easily get a car loan in a few years (no shady deals – a straight up car loan), and you can qualify for the same mortgage rate as somebody without a bankruptcy in as little as 5 years.

The key is to rebuild your credit immediately after bankruptcy. Take the credit card offer, but then pay the thing off every month!

None of the above options for getting out of debt are necessarily pain-free. But you need to do what it takes to get out of debt ASAP, be it debt consolidation or filing for bankruptcy. You need to start living your life again, with much less stress, so that you can work on living the life you want.

The important thing after tackling your debt, regardless of which strategy you use, is to learn your lesson and never repeat your bad-debt history.

While you are going through the process of getting out of debt, learn financial strategies, live according to a budget (and stick to it), and be sure to rebuild your credit with a new credit card and other line of credit or small loan. But be sure to carefully manage these so that you don’t end up back where you started, with zero options for getting out of debt the second time.

If you can settle your debt or pay it off quickly, do so. If not, talk to a bankruptcy attorney and set yourself free.

Quick Disclaimer: Discuss your unique situation with a financial expert or attorney, as laws change, or may be different in your area. When going through any sort of debt-elimination, keep your 5-year plan in mind.

Strategy #3: Start A Freelance Business

Another strategy for leaving your day job before you are ready is to monetize your skills and start up a freelance business. Six months after I quit my day job in January 2008, I was making a full time income as a freelance videographer. (It really only took me two months after I moved to a city that had enough freelance work for me – more on that in Strategy #4).

If you have a valuable skill, then work your way toward living off the income of freelancing that skill.

Shortly after I quit my day job, I sought out freelance videography gigs. I had two years of film school experience under my belt, and five total years of film and video production experience. I had just purchased the bare essentials for equipment (prosumer camcorder, shotgun microphone, video light, tripod) – all of it used on eBay.

Perhaps your skill is graphic design, or social media, or carpentry. It doesn’t matter. Just find a way – any way – to get paid for doing what you are good at.

A freelance business has a couple big drawbacks, however. For once, you only get paid while you work (no paid vacations or sick days). So I recommend looking for ways to leverage your freedom as a freelancer to diversify your income. It’s better if you are not 100% reliant on one source of income – such as your freelance business (or day job).

For me, freelance videography was an excellent solution. I charged anywhere from $400-$500 for a day of shooting. That meant that I didn’t need to work every day. Just a couple gigs per week was all it took to replace my salary. That left anywhere from 4-5 days (sometimes I worked a half/day gig), where I could devote the entire day to writing content and building traffic for our fledgling blog that now earns us a six-figure income.

Also, I avoided taking on editing work (as long as I could afford to say no to it). Shooting is a one day job, and that’s it. Editing what I shot, however, made more money, but it also meant that I had no time to work on my online business.

Strategy #4: Flee The State (Or The Country)

The final strategy I will talk about is a bit more drastic. This involves moving, either to a different city, state, or even country.

I used this strategy twice. The first time was four months after I left my day job in 2008. I was living in a small town in Vermont, and rapidly running out of money. Vermont is not a good state to live in if you want to be a freelance videographer and eat dinner every night with a roof over your head.

So Tracy and I packed up our stuff and moved to Chicago. Chicago was a much larger market for video work, and the cost of living is much less than pretty much everywhere in New England. The Chicago video production market was also much easier to break into than much more crowded and competitive markets in New York and Los Angeles.

Moving to Chicago meant that I could reduce expenses, live frugally but comfortably, and have ample opportunity to score freelance videography gigs.

Just two months after our move, I was making a full time income as a freelance videographer. I found all of my gigs on Craigslist. Tracy quickly found a new job, since at the time, there were a lot of job opportunities in the city.

The second time we used this strategy was late 2010, after Tracy had been laid off from her job and her unemployment was running out. Despite a six-month job search, she was coming up empty-handed. This was right in the midst of the economic downturn.

We were rapidly approaching the fall and winter slow period for my videography business. We were months away from having no income (or very little income), and no end in sight until the next spring.

So we decided to sell everything we owned (yes, even my videography gear), and move to the Yucatan Peninsula in Mexico where we could live off our savings that we created from our sold possessions. While there, we would devote our lives to turning our little green smoothie blog into a business that could support us.

In Mexico, we were able to live comfortably on less than $1300 per month, and we had all the time in the world to build our online business.

We were only making about $350 per month in total income from our blog when we boarded the plane to Mexico, but three months later, we were making almost $2,000 per month from it, and no longer living on savings.

After six months of living in Mexico (and working our tails off on our blog), we were able to afford to return to Chicago and live frugally (we lived in a studio apartment, although we could have lived in a much larger house if we stayed in Mexico) for another year while we built our income to the six figure range – just eight months later.

Moving out of state, or even out of the country, can feel drastic. It is. But sometimes it’s a solid strategy for being able to quit your job sooner rather than later (later almost always means never).

And you don’t have to consider it a permanent relocation. Anywhere from six months to a year might be enough time to give yourself a chance take your blog from hobby to business, while having an awesome cultural experience that will forever change your life (in the best way).

And if you make a living with a blog like Tracy and I do, you can live absolutely anywhere in the world you want!

Step 4: Quit! (When To Quit Your Day Job)

When to quit your day job is THE major, nerve-wracking decision that you have to make when getting ready to escape the 9-5 rat race. When is the right time to strike out on your own and leave the safety of your steady paycheck?

Well, different people will tell you different things. Most will discourage you from quitting your day job.

Others might advise that you keep doing your side business on the side until it makes as much if not more than your current job.

I once read a recommendation that one should not quit their day job until they have one year worth of living expenses in the bank, and are completely debt-free.

On the surface, these recommendations sound reasonable and “safe”. However, these recommendations are the ones made by people who currently work a day job and will likely never quit their job or do anything risky in their lives.

I think all of these recommendations for when to quit your day job are terrible and will leave you trapped in your day job forever. At the very least, they are an excuse for why you are too afraid to quit and go out on your own.

Seriously, how long do you think it would take you to save 12 months worth of living expenses AND pay off all of your debts?

For most people, it’s not likely to happen anytime soon. It’s not likely to happen in ten years or twenty years…or ever!

If I followed any of the above suggestions, I would have written this blog post from a cubicle in an office building rather than a cabana in the Caribbean! [Editor’s note: I originally wrote this 4-part series while I was living in Puerto Morelos, Mexico in November 2010.]

When you quit your day job is up to you. Just know, however, that there will never be a “right time” to quit your day job.

There will always be unknowns and uncertainties. There is never a right time to walk away from a paycheck or any significant source of income.

However, you can’t wait until absolutely every aspect of your life is in order before you fire your boss or you’ll work at a job until the day you die (or until your boss fires you).

You may never feel ready to quit; you just have to do it!

I wasn’t ready to quit my job, but I knew that I wasn’t ready to sit in my cubicle forever.

I was scared when I walked out of the door to the building where I worked for the last time. But I was also excited.

Removing the comfort and complacency of automatically receiving a paycheck every other week was both liberating and motivating.

I can’t stress this enough. A steady paycheck acts like a pacifier for your dreams. It gives you the illusion of safety. It kills your motivation.

It provides a reason to avoid risk, to avoid taking chances, to recoil from the unknown.

Your steady paycheck is keeping you from making a living doing what you love!

Get out from its spell, and you will soon realize that you have it in you to write your own paycheck.

The joy and excitement of actually living my life the way I wanted to far out weighed the fear and anxiety of wondering where my next paycheck would come from.

And because I was willing to do whatever it took to make money on my own terms (relocate, reduce expenses, watch less TV, and go get work), I found it easy to earn a paycheck without a day job.

Have confidence in yourself and embrace uncertainty fully and do what you love. The money will follow.

So when do I recommend quitting your day job?

There’s no one-size-fits-all answer to this question.

I left my day job back in January of 2008 with a ton of debt and only four months of extremely frugal living expenses saved up.

I had to move from Vermont to Chicago (which ate up one month’s worth of living expenses that I had in savings), but I was able to live on my freelance videography income for the next three years without needing a day job, skipping rent, or going hungry.

Tracy had it easy. She never had to make the decision because she was laid off in early 2010.

In a way, getting fired or laid off is wonderful because you’re forced to sink or swim, and you don’t have the “luxury” of clinging to fears and anxieties that will keep you trapped in your cubicle.

Without the pacification of a steady paycheck, you are free to use your own powers and skills to generate your own income.

Here are some suggestions for when the time is right to leave your job immediately:

  • When you look yourself in the mirror and ask if you are truly happy. If the answer is “no”, quit that day.
  • The day that you would rather pick up a shovel and do hard, physical labor in 90+ degree heat than sit in your cubicle for one more minute (or answer one more phone call).
  • You have a marketable skill that you can cash in on, or that you are willing to make whatever sacrifices or changes needed to be able to cash in on. (For me, that meant moving from Vermont to Chicago so I could get videography work in a larger market that would support my income requirements.)
  • You have a website or two, and you have a mentor, either a person or a program (NOT a get-rich-quick online cash-machine “business opportunity”) guiding you through the steps necessary to make it work AND you have at least six months or so of living expenses in the bank (or less if you’re like me and you are ready to sink or swim).

I’d consider any of the above as good positions to quit your job regardless of any “I can’t because…” lifestyle circumstance you might dream up (they are all just excuses for not facing your fear of uncertainty).

But ultimately, it’s up to you and how much risk you are willing to tolerate.

I quit my day job in 2008 without much of a safety net and made the necessary (and rapid) lifestyle changes that were necessary to make a full time income from freelance videography.

Tracy was forced into unemployment when she was laid off.

We both eventually made the decision to focus our full time efforts on the website that eventually turned into a major source of income for us (and continues to do so).

I was never “financially ready” to leave my day job.

Tracy was never financially ready to get laid off.

We made ourselves financially ready to spend six months in the Yucatan to make our website profitable by selling almost everything we had, and living where we could be comfortable on just $1300 per month.

Trust me, if you are willing to do whatever it takes to live the life you truly want, and you are willing to embrace uncertainty, the payoff is much greater than any initial discomfort you might face in the beginning.

Potential financial hardship, or a brief lifestyle downgrade, is a very small price to pay for having the rest of your life to live the way you want to!

For the first time in my life, I can wake up on a Monday morning with a smile on my face and an eagerness to start the day. I don’t worry about money anymore.

You can say that “I was lucky” or that “not everyone would have come out on top like I did”. And to that I say “rubbish”!

There is no luck involved with being able to quit your day job and escaping the 9-5 rat race. It’s all up to you. It’s all within your power.


I wish that there was a magic button that would allow you to quit your day job right now and start doing what you love every day, and get paid for it starting tomorrow.

Sadly, there isn’t. So you have to make some decisions, some of them difficult, and prioritize working toward your future success above keeping up with your friends and neighbors lifestyles.

I utilized all of the strategies in this guide from one time to another, and I would not have included them if they weren’t strategies I’ve used myself.

Ultimately, you must blaze your own path toward entrepreneurship. However, you can see that you don’t HAVE to be stuck in your day job forever. You don’t have to delay your dreams. You can start living your life today!

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Magick Monday

13 thoughts on “The Epic Guide On How To Quit Your Day Job & Become A Digital Nomad”

    1. Thanks for sharing and I really enjoyed reading the info on smoothies and i hope to be able to quit my day job someday in the future while doing something that i love..I am all for learning more about health and healthy ways of living so maybe I could sell some health products as i do believe that people are on a search for products that are going to greatly enhance their overall health…You guys are really inspiring and I can see that you have a genuine desire for people to succeed. Wishing you all the best in health and happiness 🙂

    1. I do, though not at the time I quit my job. Having kids, however, is not an excuse for why you can’t be an entrepreneur.

  1. Thank you very much for advice. Anyway, i quit my job today and find this blog. And I prepared for my retirement since 2 months ago.

  2. Inspiring story! After a year and half of planning (and research about entrepreneur work) to leave 20+ years of university employment, I am leaving my job on June 29th. I am excited to begin work as a writer/blogger.

  3. Thanks for sharing both your smoothie tips and your story of the journey of quitting your day job. For years I’ve been trying to figure that out while being a single mom, finding balance to be able to take small risks, while trying out opportunities, and yes wasting money after seeing that some things took more of my time than expected. I guess I also haven’t figured out what my true passion is as of yet, but right now am thinking of trying out the inevitable Amazon FBA opportunity without breaking my bank. I do have to say taking risks such as yours is much sweeter when you work as team and your (if you have one) mate is on the same game plan.

  4. Great article. I’m trying to do exactly what you wrote about. The link to the masterclass is down, is there a way to access it?

    Thanks in advance!

  5. Thank you so much for your advice. You have opened my mind even more to being an entrepreneur in which I have been thinking about a while now. Just have to at some point of time step out on faith with fingers crossed the whole way right 😀 .

  6. Thanks Davy for the inspiration! Very helpful insights, such an eye-opener, thought-provoking, and confidence booster…I’m now more inspired to take that leap of faith. More power to you. Take care.😊

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