How to Quit Your 9-5 Job in Six Months or Less

Are you dreaming of ditching your cubicle for greener pastures? You're not alone. The "Great Resignation" is real, and more people than ever are seeking alternatives to the traditional 9-to-5 grind.
By Cassie Smith - Financial Advisor
11 Min Read
How to quit your 9 to 5 job

Quitting 9 to 5 jobs has become a popular topic recently as people get drawn more to online opportunities. 

However, remember that walking away from your daily grind is also about crafting a life that aligns with your passions and values.

Let’s face it: change is scary. The steady paycheck and familiar routine of a day job can feel comforting, even if you’re miserable. 

But what if there’s something better waiting for you on the other side of that comfort zone?

In this guide, we’ll explore why people are leaving their 9-5 jobs. We will also dive into practical strategies for making your own great escape. 

Whether you dream of starting a business, embracing the freelance life, or finding a more flexible work arrangement, we’ve got you covered.

Why Do People Quit Their 9-5 Jobs?

The decision to leave a 9-to-5 job is often driven by a desire for more than just a paycheck. It’s about seeking fulfillment, flexibility, and the opportunity to shape one’s own career path. 

While the reasons vary from person to person, there are several common motivators that inspire people to make this significant change:

  • Craving more independence and control over their time
  • Seeking increased happiness and fulfillment in their work
  • Desiring location flexibility and the ability to work remotely
  • Pursuing better income potential and financial freedom
  • Feeling burnt out or creatively stifled in their current role
  • Wanting to explore passions or transition to a new career field

Whether driven by personal growth, financial aspirations, or a need for change, the decision to quit a 9-to-5 job is a significant step towards creating a more satisfying professional life. 

While it comes with challenges, many find the potential rewards well worth the leap.

4 Ways to Escape Your 9-5

Freelance writing

1. Start a Business

Entrepreneurship isn’t for the faint of heart, but it can be incredibly rewarding. 

Building your own business allows you to pursue your passions, set your own schedule, and potentially earn more than you would in a traditional job.

One popular option is starting an online business. Blogging, for example, offers a low-cost entry point — you can get started for less than $3 a month

The key is choosing a niche you’re passionate about. Whether it’s gardening, home decor, or personal finance, there’s an audience out there for your expertise.

Remember, success doesn’t happen overnight. Be prepared to put in long hours and face challenges along the way. 

But with persistence and the right strategy, you could build a thriving business that supports your desired lifestyle.

2. Do Freelancing

Freelancing offers the flexibility to work on your own terms while leveraging your existing skills. 

It’s a great way to transition out of a traditional job, as you can start building your client base while still employed.

Popular freelance options include writing, graphic design, web development, and digital marketing. Platforms like Upwork and Fiverr make it easier than ever to connect with potential clients.

You can also check out other freelancing opportunities in this comprehensive list of 97 high-paying side hustle ideas.

When I started my freelancing journey, I learned that client acquisition is also a very critical skill and needs some patience at times. 

According to Upwork, 60% of freelancers find work within their first week, but consistent marketing efforts are key to long-term success. 

Building a portfolio and reputation gradually makes finding clients easier over time.

3. Get a Remote Job

If you’re not quite ready to be your own boss, a remote job can offer a happy medium. 

You’ll still have the structure and stability of regular employment but with added flexibility in terms of location and, often, work hours.

Many companies are embracing remote work post-pandemic. Websites like FlexJobs and We Work Remotely specialize in remote job listings across various industries. 

Who knows? Your dream job might be just a click away — and you can do it from anywhere with a decent internet connection.

4. Try Investing

Investing isn’t a quick escape route, but it can be a path to financial freedom over time. 

Some people pursue strategies like the FIRE (Financial Independence, Retire Early) movement, aggressively saving and investing to retire well before the traditional age.

However, be cautious. Investing requires knowledge, patience, and, often, a significant amount of capital to start. It’s not a guaranteed path to riches, and there are risks involved. 

If you’re considering this route, educate yourself thoroughly and consider consulting with a financial advisor.

How to Quit Your 9-5 in Six Months or Less

Paper with text quit 9 to 5 job

Step 1: Prepare Mentally

Quitting your job is as much a mental challenge as it is a practical one. You’ll need to shift your mindset from employee to entrepreneur (or freelancer, or remote worker — whatever your goal may be).

First, commit to taking action today. The “right time” never comes; you have to make it happen. 

Next, prepare for the mental whiplash of switching between your day job and your side hustle. It’s not easy, but it’s temporary.

Remember, this journey is a marathon, not a sprint. Stay focused on your end goal, even when things get tough. Your future self will thank you for pushing through the challenges.

Step 2: Research Your Interests

Now’s the time to get introspective. What really lights you up? What could you talk about for hours without getting bored? These are clues to your true passions.

Grab a pen and paper (yes, old school) and jot down everything that interests you. Cooking, travel, technology, parenting, business, motorcycles — nothing is off-limits. 

Don’t censor yourself; you’d be surprised what niches can become profitable.

If you’re struggling to identify your interests, try new things. Take a class, volunteer, or start a hobby. 

Pay attention to what energizes you and what feels like a chore. Your ideal path lies at the intersection of your skills, passions, and market demand.

Step 3: Act on Your Interests

It’s time to turn those interests into action. Start building your side hustle while still working your day job. This could mean:

  • Creating a blog or YouTube channel about your chosen topic
  • Offering freelance services in your area of expertise
  • Developing a product or service idea
  • Building an audience on social media

Check out our comprehensive list of high-paying side hustle ideas for more options

The key is to start small and be consistent. You don’t need to have it all figured out right away. Remember, even successful entrepreneurs started somewhere.

Step 4: Test–Hustle–Improvise–Repeat

Success rarely happens overnight. Be prepared to iterate and adjust your approach as you go. Here’s a cycle to follow:

  • Test different strategies and ideas
  • Hustle hard on what works
  • Improvise and improve your methods
  • Repeat the process

This cycle can be challenging, but it’s also where the magic happens. You’ll learn what resonates with your audience and what falls flat. Don’t be afraid to pivot if something isn’t working.

Use your free time wisely — evenings, weekends, lunch breaks. Every moment counts when you’re building your escape route. 

But don’t forget to take care of yourself, too. Burnout won’t help you reach your goals any faster.

Guidelines to Follow When Quitting Your 9-5 Job

1. Use Your Free Time

When juggling a full-time job and a budding side hustle, every minute counts. Those precious hours after work? They’re gold. Weekends? Even more valuable. 

It’s time to bid farewell to Netflix binges (for now) and embrace productive evenings and weekends.

Think of it this way: your free time is an investment in your future freedom. Use it wisely to build your skills, grow your side business, or learn about your new industry. 

Remember, you’re not just killing time — you’re building a bridge to your new life.

2. Get Your Taxes in Line

Taxes. Not the most exciting topic, but it’s crucial when you’re planning to quit your 9-to-5. 

As you transition to self-employment or a new business venture, your tax situation will change. Dramatically.

Don’t wait until April to figure it out. Connect with an accountant who specializes in small businesses or freelancers. 

They can guide you through the maze of quarterly estimated taxes, deductions, and record-keeping. 

Pro Tip: Start setting aside about 30% of your side hustle income for taxes. It might seem like a lot, but it’s better to be prepared than caught off guard come tax time.

3. Avoid Fatal Money Traps

Watch out for the sneaky “lifestyle inflation” phenomenon. It’s a common pitfall: as your income grows, so does your spending. 

Before you know it, you’re living paycheck to paycheck, even with a higher salary.

Another trap? “Keeping up with the Joneses.” Resist the urge to buy that flashy car or designer wardrobe just because your peers are doing it. 

Remember, your goal is financial freedom, not impressing others.

Instead, funnel that extra cash into your escape fund. Consider opening a high-yield savings account. 

CIT Bank, for instance, offers a Savings Builder account with a 2.20% APY—much better than the national average of 0.09%.

4. Build Up Your Emergency Fund

An emergency fund isn’t just a good idea — it’s your financial safety net. Aim to save at least 3 to 6 months of living expenses before you quit your job. 

This cushion will give you peace of mind and breathing room as you transition to your new venture. In fact, this task is also one of the ways to achieve financial freedom faster.

I learned this lesson the hard way. When I first quit my job, I had barely a month’s expenses saved. Then, my car broke down, and I faced a hefty repair bill. 

The stress of that situation was intense. Don’t put yourself in that position. Build that emergency future fund, and you will be thankful.

Pro Tip: Automate your savings. Set up a recurring transfer from your checking account to your emergency fund for each payday. You can’t spend what you don’t see!

5. Be Consistent

Consistency is the secret sauce of success. It’s not about making huge leaps every day — it’s about taking small steps forward — consistently! 

Whether you’re building a blog, freelancing, or starting a business, show up every day, especially when you don’t feel like it.

Remember, motivation gets you started, but habit keeps you going. Make your side hustle a non-negotiable part of your routine. It might be tough at first, but soon it’ll become second nature.

6. Enlist Your Loved Ones

Quitting your job isn’t just about you — it affects your family, too. Have open, honest conversations with your partner, kids, or anyone else who relies on you financially. 

Get their buy-in and support early in the process.

Here’s a script to start the conversation: 

“I’m thinking of going full-time with this business. I know it might be risky, but I’m working on a plan so we’ll be comfortable. I want to know what you think — would you be OK with this?”

Remember, your loved ones can be your biggest cheerleaders and support system during this transition. Keep them in the loop.

7. Treat Yourself as Running a Real Business

Even if you’re just starting out, adopt a business owner mindset. This means:

  • Opening a separate business checking account
  • Tracking all income and expenses meticulously
  • Setting aside money for taxes (remember that 30% rule?)
  • Creating a business plan and setting clear goals
  • Investing in your skills and education

Pro Tip: Consider getting a business debit or credit card. It can help you keep business expenses separate and may offer rewards tailored to business spending.

8. Plan for Retirement

Just because you’re leaving your 9-to-5 doesn’t mean you should forget about retirement. In fact, it’s more important than ever to take charge of your future financial security.

Look into opening a Solo 401(k) or SEP IRA. These retirement accounts are designed for self-employed individuals and small business owners. 

They often allow for higher contribution limits than traditional IRAs, helping you catch up if you’re behind on savings.

Remember: You’ll need to replace any employer match you’re currently receiving. Factor this into your financial planning as you prepare to quit your job.

Final Thoughts

Quitting your 9-to-5 is a big step, but with careful planning and dedication, it’s absolutely achievable. Remember, this journey is a marathon, not a sprint. 

Be patient with yourself, stay focused on your goals, and don’t be afraid to adjust your plans as you go. Your path to freedom might not be easy, but it will be worth it. 

Imagine waking up excited about your work, having control over your time, and building something that truly matters to you. That’s the power of escaping your daily grind.

So, are you ready to take the leap? Let us know how you feel about quitting your 9-to-5 job, what you can do to prepare for it, and what questions you may have about this topic in the comments below!

Share This Article
By Cassie Smith Financial Advisor
Follow:
Hey there! I'm Cassie Smith, the founder of Love to Finance. With a bachelor's degree in finance, I share insights and tips on personal finance, frugal living, budgeting, and other financial advice that can make a difference through this blog. My aim is to make finance approachable and fun for everyone. Outside of the blog, you'll find me hiking with my rescue dogs, Lucy and Frankie, enjoying the simplicity and beauty of nature.
Leave a comment

Leave a Reply

Your email address will not be published. Required fields are marked *