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Should I Quit My Job? 9 Questions To Answer First

Should I Quit My Job? 9 Questions To Answer First

“Follow your passion”, “Quit your job and start your business”, “Make a profession of what you love doing”. Have you heard such advice or read similar inspirational articles on the internet? I am sure you have.

You might have even considered going down the same path after listening to such success stories. But, how practical is it to quit your job and follow your passion in real life? You might asked yourself many times, “Should I quit my job and pursue my dream?” But, have you thought the decision through?

Should I quit my job

Any story of rags to riches gets media coverage but the tales of failure go unnoticed. Here are honest statistics that shed some light on the chances of success in reality. 9 out of ten businesses fail within the first 5 years. Less than 2% of actors earn enough to make a living. About 77% of artists make less than 10,000 $ a year.

If you dig into such numbers, you will realize the harsh reality of following your passion. But does that mean you should not pursue your dream? Of course not. Quitting your job to chase your goal isn’t bad advice if you time it right and put in enough effort to prepare yourself.

Unfortunately, most people think they can type their resignation letter out of the blue, and make all the money and fame. But such hasty decisions often lead to disastrous consequences and failures. The occasional story that makes it big gets all the limelight, creating a false illusion that anyone following the same route will achieve the same results.

I do not intend to discourage you from following your dream. The purpose of this article is to make sure you remain realistic instead of merely being optimistic.

If you plan to quit your job to pursue your passion, here are 9 questions to ask yourself before you take the plunge.

9 questions to ask yourself before quitting your job

1. Can I manage my expenses for X months?

No money

The central problem when you do not have a job is managing your expenses. Your savings will burn faster than you expect.

Depending on your goal, the time required to earn an income can vary. For example, opening a departme

ntal retail store brings in cash faster than a career as a singer. If you are building a software product without any monetization model, you’ll need even longer unless you have funding to draw a salary.

“How long should I stock up funds for?” you ask. I cannot suggest a universal benchmark due to the diversity of factors that influence each goal. Before even asking yourself, “Should I quit my job?”, at the very least, you need to have enough money to handle expenses for 6 months.

Related article: How to prepare a budget for your startup

2. Am I prepared for emergencies?

Emergency rescue

Managing your expenses isn’t only about putting together an excel sheet with the rent you pay and the groceries you’ll need. You’ll stumble upon unexpected expenditure one way or another.

What if your car breaks down? What if you fall sick and need to be admitted to a hospital? What if you need to travel to attend to an ailing family member?

Emergencies will occur, and practical people have themselves covered. You need to have all the necessary insurances in place along with an emergency fund when the unexpected happens.

3. Am I trying to escape current circumstances or genuinely attempting to chase my goal?

Running from reality

When you hate your job, your manager, or both, you might feel like pursuing a long-forgotten goal. You feel like typing your resignation letter right away because you suddenly feel the motivation to chase your dream. But such desire is usually triggered by your frustration than passion.

When you plan to quit your job, ask yourself what your “why” behind the decision is. Are you trying to accomplish your goals or simply trying to escape reality?

Related article: Are you chasing your real goals?

4. Do I have the necessary skills to achieve my goals?


To pursue your long term goal, you’ll need basic skills to begin with. You can start from ground zero, but you’ll end up paying the price in terms of time and money.

When I began my journey into entrepreneurship, I believed I had all the necessary skills to build a billion-dollar enterprise. After I placed my feet in the water, I realized I lacked even the fundamental operational and leadership skills. Had I put effort into learning some tricks of the trade, I would have avoided many of the mistakes that I committed.

Likewise, many people assume that they possess the necessary skills already. A first-time entrepreneur thinks he can put Jeff Bezos to shame, a new writer assumes he can become the next Stephen King, and an upcoming actor believes he can rise to the fame of Brad Pitt.

Any goal you’re pursuing requires skills in that specific area. You do not need to know every last detail, but starting with ignorance and overconfidence is a terrible idea. If you spend time improving your skills before you quit your job, you’ll avoid many costly errors down the road.

Related article: How to learn the skills to start your business

5. Have I done my research?


Do you know enough about the goal you’re chasing? Are you aware of the top 3 things necessary to achieve your goal? Do you know the success rate of people in the same profession?

You don’t always have to step into a field that has a high chance of success. You can take your chances by trusting your hard work, persistence, and skills. But, if you do not know how often people succeed or fail at the goal you’re trying to chase, you have not spent enough time understanding the market.

Ignorance is not always bliss. There is only a thin line between a calculated risk and a blind assumption. If you do not know which side you’re on, you’re not making a thoughtful decision.

6. Have I spoken to others who have done it before?

The best way to know the reality of your upcoming journey is to speak to someone who has attempted it before. When you’re trying to chase your dream, you can easily get blinded by passion due to confirmation bias and fail to look at facts.

When you have a conversation with a like-minded person with experience, you’ll know both sides of the story. Any over-optimistic expectations will strike a balance with reality.

If you don’t know such a person, you can use social media platforms like LinkedIn, Facebook, Quora, and Instagram to get in touch with similar individuals.

7. Am I prepared to wait longer than expected?

Wait longer stress

When I had the idea of starting my first business, I assumed we’d grow rapidly in a year or two. In reality, at the end of the first couple of years, we were struggling to pay bills and make ends meet.

Your optimism urges you to believe that you’ll achieve success in the shortest possible time frame. But, the real journey takes much longer. When you have to wait for a prolonged duration to achieve your result, all your other plans fall all over the place. To cite the most critical problem, you might run out of money to manage your expenses.

Before quitting your job, ask yourself what would you do if you’re making progress towards your goal but not at the expected pace?

  • Will you make other arrangements for expenses?
  • Will you stop your efforts and find another job?
  • Will you work part-time? Is that even a good idea?

If you do not prepare for such situations, you run into the risk of being in a soup when it occurs in reality. Anticipating different possibilities makes the circumstances much easier to handle.

8. Am I willing to pay the price?

When I say “price”, I am not talking about money. If you have to quit your job and pursue your goal, you’ll need to make sacrifices.

  • Are you willing to move to a different city if required?
  • Can you stay away from your family and loved ones?
  • Will you adjust to a frugal lifestyle where you can no longer buy the shoes you like or dine at your favorite restaurant?
  • How will your family accept the change in day to day life? Have you spoken to them about it?

Unless you have deep pockets, you cannot achieve your goal without giving up a portion of your time, money, and comfort level. Even if you think you can compromise, the real experience won’t be as easy as you expected.

9. Can I handle failure?


Every person with the big dream envisions the highest success that can be achieved. An entrepreneur assumes he will make billions, a writer visualizes himself hitting the New York Times bestseller list, and an actor dreams about stepping on stage to receive an Oscar.

Sure, such dreams motivate you to put your best foot forward. But, are you prepared to handle failure? What if all your effort goes down the drain? What if you lose a lot more than what you assumed you’d gain? What if the time, energy, and money you spend results in absolutely nothing but experience?

Preparing for such questions isn’t a sign of pessimism. It helps you look at all the pros and cons to make an informed decision.


You might want to get out of your current job because you’re not enjoying it. You believe that quitting your job and pursuing your dream will be a fascinating journey. Yes, you’re right about the excitement, but if you assume you will go through a rosy path, you’re mistaken.

The effort of chasing your dreams can be much harder than the job you hate when compared on a different scale. So, blindly deciding to take the plunge can lead to outcomes you never expected. When you’re dreamy enough to look at the brighter side, be rational enough to look at the darker side too.

If you believe you have thought through all the 9 questions above, taking a leap of faith is a great idea. If not, have the patience to put in the effort side by side along with your full-time job.

Do not aim to chase your goals fast. Aim to chase them right.

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