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How to Escape the 9 to 5 Grind FOREVER [Ultimate Guide]

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While being part of the 9-5 grind does have its pros, as years go by, more and more people grow to despise it with every fiber of their being.

I’m one of those people…

After having worked about a dozen diverse jobs during my 20s, I ended up hating almost all aspects of the 9 to 5 – from the stupidly inflexible working schedules and the pre-arranged bathroom breaks to the long commutes, workplace drama, and constantly having someone breathing down my neck.

If you can feel me, you’re in the right place.

In this article, I along with 10+ experts are going to take you by the hand and walk you through the process of escaping the 9 to 5 grind once and for all.

Let’s get started.

1. Define Your “F*ck Off Income”

The first step to ditching the 9-5 grind is to get specific on the amount of income needed to fully cover your monthly expenses without relying on the salary of a regular job.

Let’s call this “F*ck Off Income”.

For instance, if your expenses add up to around $2000/month, creating a F*ck Off Income of equal or higher value is going to be more than enough to quit the 9-5 rat race.

2. Build Alternate Income Steams

Once you’ve defined your F*ck Off Income it’s time to start building it up by cultivating one or more income streams.

For example, if your F*ck Off Income is $2000/month, you could create 5 income streams that generate $400/month each, or 10 income streams that bring in $200/month each, or just one stream that yields $2000/month by itself.

Whatever the case, such streams of income can be generated in 3 different ways:

  1. Freelancing
  2. Launching a business
  3. and Investing

Freelancing is the simplest, fastest, and most reliable path to generating an income but it’s not that scalable.

Launching a business involves tons of work upfront but is a scalable solution that offers the biggest income potential.

Investing requires very little effort but it carries a lot of risks and it could take many years until you start seeing any returns.

Regardless of which venture you choose to undertake, your monetization options are practically endless

For example, you could start investing in real estate…

Build a stream of income through real estate investing. That’s exactly how I escaped the 9-5 rat race on a household income of $100,000/year. Start educating yourself on the topic by listening to podcasts on your commute to and from work, use your lunch breaks to network, and spend at least one night per week interacting with like-minded investors. In 3-5 years, you’ll be able to punch your ticket to financial freedom and officially become a corporate dropout.

– Jay Helms, Founder, W2 Capitalist LLC

Or you could offer consulting services as a freelancer…

Explore the idea of becoming a consultant. No matter the industry and profession, it’s likely that there are companies out there looking for consultations from experts. The beauty of consulting is that you have complete control over your schedule and the projects you want to undertake. The only downside is the lack of benefits, paid leave, and health insurance.

 – Jen-Ai Notman, Founder at Eshe

Or you may launch an online business…

Start building an online business. It’ll take a couple of years before it generates a full-time income but you can work on it at your own pace during your free time and weekends. All the information you need to get started and succeed can be found on the internet for free.

– Angie Makljenovic, Owner, She Can Blog

Other hustle ideas that could potentially turn into viable income streams include but are not limited to:

  • Launching a brick-and-mortar business
  • Stock trading
  • Investing in cryptocurrency
  • Franchising
  • Becoming a social media influencer
  • & more

While leaping out of the 9 to 5 grind before even having an alternate source of income lined up might feel quite tempting, the worry of being unable to pay your bills could induce immense amounts of stress and pressure.

This could in turn cloud your judgment, drive bad decisions, increase your chances of failure, and maybe even force you to return to an unsatisfying 9-5 job a few months down the road.

To ensure that this doesn’t happen, start building up your F*ck Off Income on the side of your regular job.

This way, you’ll get to hang onto your steady salary, health insurance, and benefits until you’re 100% ready to commit to your side hustle full-time.

Yes, doing more work during the time you were supposed to unwind from all the hardships caused by your job is going to be frustrating and challenging.

However, the benefits of permanently ditching the 9-5 grind greatly outweigh the temporary frustrations of making some extra effort during your downtime.

Start hustling on the side of your job. The short-term loss of your nights and weekends will be replaced with the long-term perks of being your own boss. The transition to working for yourself once you’ve already landed a few clients, built up your portfolio, or developed your business will be much more seamless. This course of action mitigates most of the risks that could hold you back from escaping the 9-5 grind, particularly maintaining a steady source of income.

– Sam Hawrylack, Co-Founder, How To FIRE

4. Start a Passion Project

Cultivating a new source of income is no walk in the park, especially while spending the majority of your most productive hours working a job you hate…

That’s why it’s highly suggested that your side hustle revolves around an activity you’re interested in or even better passionate about.

Running a passion project alongside your job won’t feel so much like working but more like having fun, it’ll boost your energy, give you a sense of purpose and meaning, decrease your stress levels, maintain your motivation when the going gets tough, and increase your chances of success.

Plus, the whole point of leaving the 9-5 behind is to be more fulfilled in your work.

Identify that one thing you enjoy doing the most and find a way to monetize it. Devote all of yourself to that course, stay consistent, and never stop taking action.

– Daniel Roberts, CEO, ThinkImpact

Get clear on your Zone of Genius/Ikigai; the work where time stands still. Then, figure out how to turn that into a career.

– Jeff Harry, Rediscover Your Play

Tons of successful entrepreneurs kickstarted their journey this exact same way – by investing parts of their free time and energy in a passion project on the side of their full-time jobs.

If you’re not quite sure what you’re passionate about, answering the following questions might help you gain some clarity.

  • What is that which you can’t wait to do during your days?
  • Is there any specific activity that makes you lose track of time?
  • Where is the bulk of your free time spent?
  • Is there anything that pisses you off if you’re unable to do it?

Furthermore, consulting with a career or life coach along with utilizing assessments such as StrengthsFinder 2.0, Myers-Briggs, DISCAssessment, and/or Strong Interest Inventory could help you uncover your passion as well as gain clarity regarding career paths that align with it.

Whatever your passion turns out to be, I’m 99.9% sure that it could be monetized in some way or another…

Guaranteed: Whatever you like to do for fun, someone is getting paid to do it. Just share your love for your passion, and slowly but surely, you can build an income from it. I used to work in a windowless office for ten years. Once I took the leap I started working from the beaches of the Australian Sunshine Coast and Bali. It may start slow, but if you love what you do it won’t feel like working.

– Dr. Jeremy Britton, CFO,

Nonetheless, before launching your passion project, it’s highly suggested that you conduct some research to ensure whether it could potentially generate a solid profit.

  • Are there other successful people and/or businesses in that same industry?
  • Are there bloggers, YouTubers, and/or influencers talking about the subject? Do they seem to have a healthy amount of followers, readers, viewers, and/or subscribers?

If so, your idea is probably viable and in-demand…

If not, maybe you should reconsider.

5. Set Up an “I’m Out” Fund

Life is unpredictable…

No matter how perfectly you’ve planned your way out of the 9 to 5 or how well your money-making projects perform, you could still come face to face with unforeseen financial emergencies.

Maybe it’s a health issue, or damages from a natural disaster, or an unexpected nosedive of your side hustle’s revenue due to a pandemic outbreak (been there).

Whatever the case, if you ditch the 9 to 5 grind before properly prepping your finances and you find yourself in dire need of money, you could easily end up back to a regular job you hate in the blink of an eye.

To prevent this from happening, make sure to set aside at least 6 months’ worth of expenses before leaping into the unknown.

The more, the better…

Having a substantial financial cushion will enable you to confidently deal with potential urgent financial setbacks without compromising your action plan along with everything you’ve worked so hard for up to that point.

6. Eliminate Unnecessary Expenses

A course of action that could greatly speed up your exit from the 9 to 5 grind is cutting back on unnecessary expenses.

First, with fewer expenses to cover, your savings will stack up much faster and last a lot longer. Also, the more you lessen your expenses, the sooner you’ll be able to reach your F*ck Off Income.

Moreover, living below your means offers a plethora of benefits, such as:

  • More financial stability, security, and freedom
  • Less stress & anxiety
  • Debt-free living
  • No more keeping up with the Joneses
  • Better prepared for financial emergencies
  • Willingness to pursue more fulfilling professions that pay less

It sounds trite, but detaching yourself from material possessions and learning to live with less reduces your need for income, which opens up a wide range of employment options that could be far more fulfilling even if they’re lower-paying and less stable.

– Sebastian Schaeffer, CTO/Co-Founder,

While reducing your expenses isn’t mandatory to escape the 9-5, reflect upon what would make you happier – spending all your money on crap you probably don’t even need or ditching the 9-5 rat race in half the time?

If you pick the latter, then it’s time for some drastic changes.

Start by cutting down binge shopping, ordering takeout daily, partying every weekend, using your car for short distances, and paid subscriptions you could live without (e.g. gym, TV packages, online services, etc).

Furthermore, consider downgrading your lifestyle as much as you possibly can (e.g. moving to a smaller apartment/house, getting a car that consumes less gas, etc).

Small sacrifices for a short period could eventually have a huge impact on the quality of your professional and overall life.

Drastically lower your cost of living. You could buy a duplex, live in half, and rent the other half. You could also start growing food and vegetables in your yard. Once you’ll no longer have to pay for rent, mortgage, or food, you’ll become much less reliant on the salary of a 9 to 5 job. Now, create a small source of income to cover the rest of your expenses and you won’t need to work another regular job again.

– Stacy Caprio, Founder, Her.CEO

7. Fine-Tune Your Expectations

People tend to envision the escape from the 9-5 as a golden ticket to ultimate freedom, absolute fulfillment, zero work-related stress, and minimal financial worries.

While the perks of not being shackled to a regular job are indeed indescribably amazing, unfortunately, it’s not all rainbows and butterflies…

For instance, being your own boss usually involves much more work and dedication than a regular job at least until your income-generating project(s) start gaining some significant traction.

Although being self-employed has its own freedoms be prepared to work longer hours than your typical day job, including on weekends and holidays.

– Vanessa Perry, Owner of Impeccable Credit Services

Also, regardless of whether you attempt to monetize something you’re passionate about, chances are that you’ll still find yourself regularly immersed in tasks you don’t really enjoy.

For example, you might have a passion for shooting YouTube videos but hate the process of editing them. Or you might love practicing Yoga but hate marketing your studio.

Furthermore, being free of the 9-5 rat race doesn’t really mean that you get to do whatever you want, whenever and however you want…

You could, but if you fail to maintain a steady daily working schedule, you might find yourself back in a regular job before you even know it.

Moreover, all kinds of ventures suffer economic downturns at some point, especially during their early stages. This could trigger occasional financial stress and worries.

Being so-called ‘free’ and no longer working for someone else can sound amazing and at some level it really is. However, it’s important to understand that the life of an entrepreneur or freelancer is not any easier. There are times, especially early in your business, when you might not know when and from where your next income will come, and this can be a source of great stress. 

– Darrell Rosenstein, Founder, The Rosenstein Group

Having said all that, setting your expectations straight regarding what life outside the 9-5 looks like could save you tons of frustration and disappointment that could drive you to give up and fail.

8. Go Part-Time

Escaping the 9 to 5 grind doesn’t happen overnight…

Most of the time, the process of prepping the ground for such an exit involves significant amounts of effort on the side of your full-time job over a few months to maybe even a couple of years.

That’s depressing and discouraging, at the very least.

Nonetheless, something that could turn the whole situation much more tolerable is going part-time…

Cutting your working hours in half comes with a plethora of benefits, such as:

  • Lots of extra time & energy to invest in building your F*ck Off Income
  • Less stress & anxiety
  • Fewer duties & work-related responsibilities
  • More freedom & flexibility
  • More time to devote to resting and doing things you love
  • You might even start liking your job

Also, going part-time will make you feel that you’re with one foot outside the door.

This will enable you to jump out of the 9-5 with much less hesitation, once you’re ready.

And all that without sacrificing the steady paycheck and security of your current job.

However, be aware that to make ends meet as a part-time employee you’ll have no option but to minimize your expenses and downgrade your lifestyle as much as possible.

9. Make the Leap

Once you’ve laid the proper groundwork for your exit from the 9 to 5 grind, you’ll reach a tipping point where the paycheck of your regular job will start feeling like a dead weight holding you back from further improving your life.

That’s when you make the leap!

Chances are that you’ll still have doubts, even if everything has fallen right into the perfect place.

This is absolutely normal…

Truth is that no matter what you do the moment that you’ll feel 100% ready to ditch the 9-5 grind will probably never come.

Having said that, if your finances are in order and your side hustle(s) seem to be on a promising trajectory, have faith in yourself and make the leap sooner rather than later.

“When will I know I’m ready? You won’t… It’s a leap of faith…”

– Spider-Man: Into the Spider-Verse

The longer you stick it out in a career path you hate, the more you’ll grow to regret it.

BE BRAVE… I escaped the 9-5 rat race fourteen years ago to become a freelance writer and have never looked back! I wish I’d done it sooner. So many people remain stuck in jobs they hate out of fear and insecurity. Having the courage to step out of the “usual lane” is how career fulfillment is born.

– Rigel Celeste, Online Writing Coach,

I used to dread going to work. I was living for the weekend. I wanted to quit my job to travel the world but I let my fears dictate my life. I regret not following my dreams sooner. Life is too short to not be doing what you love. 

– Kimberly Pong, Founder, Come Along With Pong


Escaping the 9-5 rat race is no piece of cake…

It’ll probably take twice as long as you’d hoped, cost exceedingly more than you’d planned, and be more challenging than anything you’ve ever tried.

– Lori Cheek, Founder & CEO at Cheek’d

On top of that, leaving its perceived stability and security to head off the beaten path into completely uncharted territories is horrifying.

However, once you’re out, you’ll realize that the freedom and flexibility you’ve gained are absolutely worth all the trouble.

Hell, chances are that you’ll regret not breaking free sooner.

And even if all your plans fall apart (sometimes sh*t happens), having put in some effort towards improving your situation is going to be much more fulfilling than wondering “what if”.

Worst case scenario, you temporarily return to a regular job until you’ve regained the strength for yet another, hopefully, more successful leap out of the 9 to 5.

Written by:

Harry is the founder and creative director of Dear Boss I Quit. His mission is to inspire and help as many people as possible escape the 9-5 grind forever by building a passive income online just like he accomplished a few years back.

You can read more about Harry’s story right here.

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