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Many people love the idea of becoming their own boss and starting a business. Maybe you want to work on your own terms and have more control over your work. Launching your startup and walking away from your day job may be something you’ve always wanted to do. However, you aren’t sure whether or not it will yield significant returns.

We will cover 10 important questions you need to answer before quitting your 9-5 job to start a business. These questions will help you determine whether or not leaving is the right choice and ensure you avoid regret or failure.


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The most important question you need to ask yourself is why you want to leave your current job. So, why do you want to quit? Is it because you are unhappy? Is it because your boss is difficult to work with? Is it because you don’t like the treatment you’re getting around the workplace? Is it because no one values your opinion? Or maybe you just want to pursue your long-lost dream?

Know why you want to quit to avoid taking a step that you’ll regret later on when things don’t turn out the way you expected.

The best way to succeed and be happy with your decision is to quit for the right reasons. So, give it enough time. Explore different options before leaving. Especially if you aren’t sure if quitting is the right choice to make.

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For example, if you want to quit because you’ve always been set aside for that promotion you know you deserve, try to explore different options with your employer. Talk to your boss about the many times you’ve been overlooked for the promotion. Mention why you think you deserve to go to the next level and reference the impact some of your work has had on the company.

The goal is to try and find a way to navigate the issue without simply throwing in the towel and leaving your job. Especially if it is the only income source you depend on.

If you still want to quit after discussing with involved parties and after months of contemplation, answer the next question;


Knowing why you want to start a business is as important as understanding why you want to leave your job. So, why do you want to start a business? What’s motivating you? What’s your vision?

Do you want to start a business because you love the idea of becoming your own boss? Do you want more control over how, when, and where you work? Perhaps it’s about living your purpose?

Your reason for leaving your job to launch a startup should be tangible enough to keep you going despite failure and everything else you’ll encounter once you take the step.

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You need the right motivation so you won’t regret your decision and give up when things don’t work out as expected.

So, do you have a long-term vision? Where do you want the business to go? Where do you see yourself 10 – 15 years from now? And What steps will you take to ensure you get there? What happens when obstacles come? How will you overcome them? Do you have a business plan? And What steps will you take to achieve your goal?


Working for someone and being your own boss are two completely different things that require distinctive lifestyles. You have to start a new routine and adapt to it. You have to change the way you think and approach your professional life. You have to understand that many things will fall on your shoulders and require your time and attention. Your success or failure will depend solely on the steps you take, the choices you make, and your decisiveness.

So, when you know why you want to start a business and understand what you’ll be getting into, decide whether or not you’ll be happy running the business.

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Engaging in a business venture that makes you happy is important if you are to succeed. So, if you know you’ll be happier starting a business than working for someone, taking the risk may be wise. If it makes you happy and you know what you want to accomplish, then you can deal with the obstacles, uncertainties, failures, and setbacks that come with it.


Quitting your job for the right reasons and having a long-term vision are both important in ensuring business success. However, you have to leave at the right time to avoid failure and regrets down the line.

So, is it the right time to leave your job? Will you survive without an income source? If so, then for how long?

Do you have enough money to support yourself and fund your business during its early stages?

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What expenses do you cover? And will you be able to cover them if you quit your job and start building your business? Will you be able to pay the mortgage, bills, buy groceries, and take care of other responsibilities once you quit?

Answer these questions to make an informed decision that won’t leave you with regrets later on.


Every business requires 100 % commitment. Especially when you are starting. You have to wear different hats because your success depends on what you do as well as the decisions you make. You have to manage the business, market it, handle accounting, build your client base, deal with disgruntled customers, and ensure everything is running smoothly.

That can be too much to deal with. That’s why many startups fail. So, before leaving your job to launch your startup, ask yourself if you can handle all that. Do you have enough discipline to wear different hats? Do you have enough time to manage it? Are you disciplined enough to be your own boss?

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Maybe you are willing to oversee different aspects of the business. However, do you have enough time to do so? Can you manage to learn about marketing, lead generation, bookkeeping, and so forth while offering exceptional services to clients? Do you have enough time? Will you be able to work, learn and support yourself while building the business?


Another great question to ask is whether or not you have the resources you need to start and run a successful business. That is a great way to avoid failure, minimize frustrations, and ensure success. So, what sort of business do you want to start, and do you have the right resources? What do you need to launch and keep it afloat? Is it money, human capital, or both? Perhaps you want to be a solopreneur? But do you have enough time to learn everything you need about your industry and build the business?

If you need money to see it off the ground, do you have enough? Will you look for investors, business partners, or apply for a loan? If you choose to get a loan, can you afford to? What if things don’t turn out as expected and you incur losses? Will you be able to pay back the loan?

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If you want to be a solopreneur and have the capital but need to invest your time and energy into the business, can you afford to? Do you have the discipline and expertise you need to grow a successful business? If you have to invest in online courses, for example, can you complete the course and apply what you learn?

If you can’t wear different hats and need to work with other people, which route are you going to take? Will you get permanent employees or outsource some of the work?


Next, consider whether or not you have the required knowledge or skills to venture into that line of business. Answer key questions; “What sort of skills are required for this to be a success?” “What are my top skills?” “Do I know enough about this field to start a business?” And “Am I willing to acquire the necessary skills and constantly advance?”

The most effective way to start a business you’ll enjoy running years down the line is to start one that you have a lot of experience in. This is a great way to accelerate results and avoid failure.

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However, if you don’t have enough experience or history working in that certain field but feel strongly about it, you can still venture into it. You’ll have to be willing to learn, acquire new skills and take it one step at a time. The question is; do you have enough time to do so?


The next thing you want to think about is the market you want to cater to. So, is there market demand for your product or service? Are people buying or searching for what you intend to sell? If yes, then you may have a shot at success.

Once you realize there is market demand, answer the next equally important question; who is your customer? Who are you targeting? And who is likely to buy your product?

Know your potential customers to ensure you target the right people and avoid advertising to people who are not interested in what you are selling.

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The best way to identify your audience is to evaluate your product or service. So, understand what your product does, what sort of value it brings, and how it can impact people’s lives.

When you understand your product, you’ll know who to target.

Next, consider the competition and find out how you can make your offer stand apart. Answer key questions; who are you competing with? Who are your top competitors? What attracts people to their businesses? Can you compete with them? What’s unique about your product or service? And how will it get prospects to favor your business to the competition?


Starting a business is delightful and everyone gets excited about it during its early days. However, it’s what happens after the excitement is gone that truly matters. So, you have to make sure you can keep working on it even after the excitement is gone.

Always think long-term. Make sure you can keep the business going despite failure, losses, and other setbacks.

So, do you have a financial plan? How are you going to fund your startup? What sort of income source are you depending on?

If you were to quit your day job, will you be able to raise the money to take care of every expense you have and keep the business going?

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Will the business support itself or you are depending on other income sources? If you plan to use other revenue streams, how dependable are they? Will you be able to channel the money toward your startup whenever there’s a need? Will the funds be available?

Make sure you have enough money or dependable income sources to keep your business running. If you don’t, then you need to start one or two side hustles. That is because you don’t know how long it will take for you to establish your business and take it where you desire it to be. You don’t know what obstacles you’ll face along the way or what sort of losses you’ll incur.

That is why you have to be prepared for uncertainties and ensure you keep the business running despite what happens.


Lastly, consider other options that can serve you well before quitting your job. Answer important questions; “Is quitting my job to start a business the only option I have” “Why do I want to quit?”

If you want to quit because of your boss or unhappiness caused by your coworkers, consider other effective ways to deal with the situation. For example, approach your manager and talk about the treatment you are getting.

If you still want to start a business after answering all the above-mentioned questions, find out if it will work long-term. For example, will quitting your job serve you well in the long run? Do you have to quit to launch your business or you can keep your 9-5 job and launch your business on the side?

Launching your startup on the side and working on it during your free time, is one of the most effective ways to build a successful business and avoid regrets. Especially if you don’t have enough money or expertise to start and manage the business.

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It is a great way to avoid bankruptcy and ensure a safety net. If your business fails, you don’t have too much to worry about because you’ll still have a reliable income source. You can afford to keep working on the business without worrying about your daily expenses.

Leaving your job to venture into the unknown is everyone’s dream. However, it may be years before you succeed. So, don’t dive into it headfirst without reflecting on the above-mentioned questions. Consider the benefits of quitting your job and starting a business but focus on the drawbacks as well.

Your main concerns should be supporting yourself and everyone who depends on you, covering expenses, understanding why you want to quit, exhausting all your options, and knowing how you’ll fund the business.

Do enough research on the field you want to venture into and make sure you understand it before taking that important step. For example, what do you need to succeed? Who has made it in that industry and what can you learn from them? What sort of skills are required to venture into that business? Do you have the necessary skills or do you have to acquire them? If you have to pick up a new skill, do you have the time to do so? Are you disciplined enough to be your own boss? Are you willing to wear multiple hats and oversee everything since you are starting?

Do you want to run the business by yourself or hire employees? If you need to hire people, what’s the best way to go about it, and do you have the money to do so?

Access the market and identify the people you want to sell to. Study the competition and find out how you can stand apart and get potential customers to notice you. Understand your target audience to ensure you advertise offers they are interested in. The kind that will get them to favor you above the competition and turn them into brand ambassadors.

Determine if it’s the right time to leave. Can you support yourself and take care of other responsibilities once you quit? How long will you survive without your job? Do you have another reliable income source? And What happens if you incur losses along the way?

These are all questions you need to answer before leaving your job to start a business. So, consider them to ensure you make an informed decision and avoid failure.

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