10 Burning Questions to Answer Before Quitting a Job

questions to answer before quitting a job

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You want to hammer down your job.

Sitting on that nice, comfortable Office Chair is no less than sitting on a gas stove. Isn’t it?

Deadlines, targets, promotions, politics…

There is so much that burns you every day. You feel grilled under that never ending pressure, just for the sake of a tiny paycheck.

You don’t get enough time to breathe.

Suddenly, the job decision starts to seem like a huge mistake. You lack time, freedom, money and the most talked one,

Peace Of Mind.

The feeling to get out of the job and follow a passion gets stronger, day by day. You start thinking about it, craving about it but never able to do it.

You want to carve financial freedom. You want to spend quality time with your family and friends.

But, it remains a dream because you are bound to run day and night, burn midnight oil to get the maximum throughput out of your job.

You keep on pondering all day, “I will follow my passion, make huge money and the whole life will be as awesome as a beach party”.

Do you think it’s a piece of cake?

It is NOT. You haven’t gone through a reality check.

What if you have a 20- point check list before you leave your job, to get the real taste of your entrepreneurial journey before it begins?

If you are in doubt, it will remain only till this sentence you are reading.

Are you ready to face your challenges?

Here are 10 Burning Questions to Answer before quitting a Job


#1: Are you just trying to escape your Current Boss?

99.99% people hate their boss. It’s a fact. Does that qualify them for entrepreneurship?


If all the dilemma is because of a super annoying boss, it’s better you re-consider your decision. If you want to follow your heart, I am with you.

But, if the realization is because of your boss who is a pain in your neck, you should focus on a workaround; rather than quitting the job in seconds. You are more likely to quit under pressure, once you leave your job.

So, if you have this issue, try talking to your boss or fix it by finding another job as it’s just a reflex of your current situation.


#2: Is quitting really going to help you? 

The only thing in your mind is to quit.


You have no idea about the next course of action. You think getting away from the current situation is the right thing to do, just because it will spare you from the routine office frustrations.

After quitting, you don’t have to worry about deadlines. No more complex reports. No more teasing by the senior management. No more clueless meetings.


Do you have any business idea in mind, that could compensate your day job?

Forget about the dollars raining, do you know how to monetize your own work?

If the answers are NO to the above two questions, quitting your day job is just going to add to your misery. It is never a good idea to be pathless.

You don’t have to answer me, but you should be able to answer this question to yourself.

Whenever you ask this question to yourself, make sure the reply is definite. It shouldn’t be this one in any case,

“I haven’t decided yet.”

“I will decide later, once I get rid of this job.”

Fire this question to yourself, right now. Once you get a precise answer, you are free to quit. Answering this question will ensure that quitting the job will really help, and you won’t be stumbling in the dark.

Your passion should meet a business need. There should be enough people looking for it, if you want to earn money from it.

In short, your idea should be financially viable. Else, there is no point suffering by leaving your job.


#3: Are You ready to get grilled by your family?

The 9-5 isn’t meant for you. You and I know this.


But, Is your family going to acknowledge your entrepreneurial spirit?

Will they support you from the beginning to the end?

I am not saying family support is mandatory for your entrepreneurial career. But,

There would be a lot of strain on your relationships. Things won’t flow easily. Your parents, spouse, friends are going to give you a very tough time.

You will see them worried about you, sometimes complaining and furious as well. You will face the pressure to go back to the usual 9-5, every time you fail or even struggle to achieve the desired results.

Actually, it’s not their fault. Our conditioning has taught us to go for a 9-5 and depend on a monthly salary, because that is a less risky option. Even if you aren’t happy at job, your salary won’t be unhappy with you at the end of the month.


So, you should be ready to cope up with these grilling emotions. They shouldn’t impact you if you have the real entrepreneur in you.

I am not asking you to be insensitive towards your family. I am asking you to respect their opinion, unshaken towards your dreams at the same time.

So, if you can conserve your relations well instead of all strains; You are free to quit your job for entrepreneurship.

Start when you are young. Entrepreneurship is incomplete without making mistakes and rectifying them. It’s the only thing you need.

If you are starting late and have a family to feed, make sure you have a contingency fund for them. In no case they should suffer, because of your decisions.


#4: Are you imitating or emulating someone’s success?

This is what I call the “Passion Test.”

In every day discussions, we talk about people who adopted a certain business idea or model and succeeded well in their lives.

Our immediate response is,

“If they could, I can do it as well.”

Of course, You can.

But, The story is a bit different here.

You are not emulating. Its mere imitation. The idea doesn’t seem to make any sense to you. You have no interest. It isn’t igniting your passion or you have no zeal to achieve it.

Actually, you wanna do it just because it yields more money. XYZ person is a millionaire by doing this, I will also become the same.

This is what you think.

So, You failed the “Passion Test.”

For example, I am writing because I love to. It helps to keep my senses alive and I really enjoy doing it.

Now, if I try to imitate Leo Babauta, Marc and Angel,  or Henrik Edberg  who are the best in the business, would I be able to succeed?


If you want to succeed, you should have the requisite passion to qualify for success. Imitation won’t lead you anywhere.

So, before you leave your job for a business idea; make sure you emulate and not imitate.


#5: Are You aware money won’t fall Overnight?

You want to be an entrepreneur because of one primary reason.

It yields big money than the usual 9-5. Right??

The problem is,

You wan’t to get rich overnight and that is just not possible. You are fascinated by the money, but aren’t aware how it is coming.

To be very clear, entrepreneurship is no “get rich quick” scheme. It takes a lot of sincerity, patience and devotion.

You can’t expect results in a week or two. Not even a month or two. It would take time to flourish. If you ask about time, it is dependent upon your efforts and the ability to recover from mistakes.

In the starting days, you have to keep money aside and just work your ass off.

So, if you think quitting your job and starting a venture would make you Steve Jobs; please keep your job.


#6: Do You have enough discipline to Rule Yourself?

You get late for office and still able to get away.


You goof up meetings and reports and get away with a bit of admonishing.

Even better.

But, You know what??

Once you quit your job, this attitude is going to doom you. You lack discipline.

At office, you work around 60 hours a week with two weekends for merry making.

What if you have to work for 90+ hours a week, sometimes without week offs?

Ask yourself, if you could sustain this enormous pressure. Consider it as the cost of working for your dreams.

You won’t be able to fool around because you will incur huge losses if you do that.

So, make sure if you have the ability to work 80-90 hours a week for your goals.

If even a corner of your mind wavers, leaving your job is not the option for you.


#7: Do You have the guts to let go Jealousy?

You want to build a thriving business, but you know that you have to let go that monthly paycheck.

A successful business takes time to propel and won’t skyrocket in a day. I hope you are well aware.


Can you feel OK when you see your old colleagues getting promotions and salary hikes??

You would say, “They are frustrated and they don’t have a life.”

But just saying and not feeling won’t help.

Just ask this heart pinching question to yourself,

You will see your colleagues growing professionally, in terms of money, recognition and respect. It might be possible your business will grow at a snail’s pace.

Will you be able to get off that Jealousy factor?

If your mind really says YES, quitting your job for a business is what you are made for.

Never allow jealousy to creep in front of your dreams. If you want to do something different, act different and that’s not easy. It won’t be a joy ride.

But, once you pave your path; you will feel proud of your decision.


#8: Can You Start Over again if you fail?

You will make mistakes in the beginning. Every newbie does. Then, you have to identify and rectify them in order to follow your dreams.

The above statement is idealization, the reality is totally opposite.

When people make mistakes, they think its not working and eventually quit. I know its hard for you to  accept, but truth remains the same.

You don’t have to sink under pressure. Whenever a strategy isn’t working, you should be able to troubleshoot the root cause instead of victimizing yourself.

For example, You are writing a blog and want it to flourish as a community business. But neither you are getting traffic, nor subscribers.

Money is still an alien.

Something is going wrong and you know that, but

Will you take a step to identify the cause or continue crying over the situation like an infant crying for milk?

Accept it now. There will be mistakes. There will be frustrated moments when you will feel like quitting or regret leaving your job.

If you have the skills to start over, even after having the worst experiences while chasing your dreams, entrepreneurship is for you.

But, if you tend to break down very easily or sink under some random advice; then its sinful to even think about quitting your job.


#9: Do you have the two M plans

Monetization and Mitigation- The two M plans I am talking about.

You want to start a business, but don’t have a monetization plan. You are preparing for failure.

In case your plans won’t work first hand, you don’t have a mitigation plan either. Now, you are preparing for a disaster.

The first motive of a business is to make money, to earn a living out of it. Forget about authority and freedom. All secondary.

Before even thinking of quitting your job, there should be a step by step strategy about the income streams you are going to have.

Make a list of all the possible ways you can make money from. Once you are finished with that, prepare yourself for the worst.

What if all income streams fail or the plan is not working at the moment?

I am not asking you to quit. But, what do you do when you are injured?

Take medicines and recover. Right??

You get it right. Prepare a recovery plan now. How will you recover if nothing is working for you?

Once you have the two M’s ready, think about quitting your day job.


#10: Can you let go blame game and experiment?

You start a business. It’s a natural tendency to take business advice. Right??

Sometimes, they prove to be really good and most of the times; they truly suck.


You own the business. Remember??

You are answerable for your actions. The profit is yours. so is loss.

If any advice backfires, you shouldn’t be wasting any time playing blame game. It is the biggest time spoiler.

Instead, go and experiment. Nobody can tell you what works and what doesn’t.

Once you experiment, the picture will be a lot more clear.

So, don’t blame anybody for your mistakes and failures. Learn to be accountable.



Following your passion isn’t a crime. But, you should be able to see both sides of the coin before taking a decision. The very much lucrative life of entrepreneurs often tell a different story. It’s just that, you lack observation. 

You want to gain customers, but talk very arrogantly at workplace. You tend to lose your patience in seconds.

How can you expect to be a good entrepreneur?

If you can’t love your job, its fine, but there is no harm in acquiring the basic skills. I am talking about soft skills. Develop these skills at your job. It will definitely help you in starting out as an entrepreneur.

Once you find an answer to all of the listed questions, you will find yourself in a better position to leave your job gracefully and follow your dreams to the fullest?


It’s Your Turn know,

Do you have some more burning questions to ask before leaving your job?

What’s your biggest pain in making the decision? What one question stops you every time?

Share your pains in the comments. We will find out a way for all.

Keep up the passion in yourself.

Talk Soon,

Harsh Tripathy





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