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Time to Quit? Questions to Ask Before Quitting Your 9-to-5 and Becoming Your Own Boss

Time to Quit? Questions to Ask Before Quitting Your 9-to-5 and Becoming Your Own Boss

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Black entrepreneurship is a progressive movement. With around 3.5 million Black-owned businesses in the United States, Black people are confidently making their mark in the business world. 

Yet entrepreneurship isn’t an easy road. Of course, there is the allure of being your boss, setting your own hours, and working on things you are passionate about. Yet owning your own business means considering the risks, cultivating a specific mindset, and relentlessly pursuing your dreams.

Do you have what it takes?

When evaluating whether entrepreneurship is a reality or a daydream, here are some things to consider. 

Choosing entrepreneurship over a 9-to-5

You may be thinking of quitting your job because whenever you clock in, you feel like a piece of your soul dies. While strongly disliking your job seems like reason enough to leave, there are a few things you should consider before putting in your two weeks’ notice. 

LinkedIn career expert Andrew McCaskill wrote to Black Girl Nerds via email and explained that many Black professionals are walking away from traditional employment for various reasons. “Many are driven by a desire to focus on something they’re passionate about,” says McCaskill.

“Others seek more flexibility and work-life balance. Ultimately, many seek fulfillment in their work,” McCaskill comments. “For many, entrepreneurship isn’t just about leaving a job; it’s about taking charge of their future and building something that aligns with their values and goals.”

If the above reasons resonate with you, keep reading to understand whether leaving your job should be your next career move.

Six questions to ask before quitting your 9-to-5

A golden rule of employment is only to quit once you have another job lined up. However, if you’re considering entrepreneurship, your transition will look different. Let’s review the essential things you need to consider before quitting your job.

How do you feel about uncertainty and taking calculated risks?

I know firsthand that being an entrepreneur means getting comfortable with being uncomfortable. Why? Entrepreneurship isn’t a clear path. It’s like driving in Mario Kart; the road is smooth for a moment, and suddenly, an obstacle crashes into you.

Things won’t always go according to plan. There will be unforeseen complications, and you will have to take calculated risks. However, if, theoretically, you feel confident walking off the cliff knowing that you can build your parachute on the way down, you’ll be fine. 

Do I need to change my work environment or my work style?

You might be unsatisfied with your work because of the people you work with or your environment. If so, consider a few things before quitting.

First, speak to a manager or the head of the company about switching teams or offices. This could help lift your morale. 

Second, consider staying in a 9-to-5 job but working with a different company that better aligns with your values. 

Lastly, if these changes don’t make a difference, entrepreneurship may be calling you.

Do I have the financial means to sustain myself during this transition?

You’ve probably read stories of entrepreneurs quitting their jobs and making millions with their businesses. Those stories sometimes leave out how long it takes for that entrepreneur to gain wealth.

Entrepreneurship usually means starting from scratch. You have an idea, a business plan, and some savings. So, before quitting your job, ensure you have enough to sustain yourself as your business slowly generates money.

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What skills do I need to improve on or learn to help me better navigate entrepreneurship?

A crucial question to ask yourself is what skills you lack that you may need to run your business. This question is essential if you are used to working on a team or are only accustomed to handling specific tasks. 

According to McCaskill, every entrepreneur needs to have a few key skills. One of them is networking. “Building and sustaining valuable relationships can open doors to opportunities and support when you need it most.”

Another crucial skill is adapting to current trends and technological advancements like AI. If your palms sweat thinking about how fast the business world moves, you don’t have to stress too much. You can access many resources to learn skills, such as LinkedIn LearningCourse, HubSpot Academy, and more.

What is my plan B?

Having a backup plan will prevent you from pulling your hair out and losing sleep trying to keep your business afloat. A plan B can take any form that works for you, but it’s ultimately a way to either save your business or sustain your livelihood. 

A strong plan B can involve unique ways to generate revenue, reach out to potential investors, or have ways to cut costs.

Your plan B can even be returning to your 9-to-5 for a short time just until you can get back on your feet.   

What do I want my life to look like?

When entrepreneurs first start out, many focus solely on how they want their business to run. In addition to this, it’s essential to know how you want your life to be.

I know firsthand that it’s easy to sit behind my computer and get sucked into work. I remind myself daily that I became an entrepreneur to live on my terms and have a work-life balance. 

If you’re serious about entrepreneurship, take some time to consider the type of lifestyle you desire.

How will I recover if entrepreneurship doesn’t work out?

Starting your own business means there’s a chance you might fail. “If your first try at entrepreneurship doesn’t work out, it’s important to remember that failure is often a part of the journey, not the end of it,” advises McCaskill. “The key is to approach failure as a learning experience and take stock of what worked and what didn’t.”

Remember, if entrepreneurship were that easy, everyone would be their own boss. Starting and failing is only half the battle. The other half is learning from your mistakes and trying repeatedly until you find what works for you. 

The two greatest things about entrepreneurship are taking an idea, making it a reality, and using your unique talents to help people. If creating your own business is something you feel ready and prepared to do, then go for it. Remember that you can start building your business on the side while you work your 9-to-5. Then, once you feel confident, take that leap of faith. 


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