16 Vital Questions To Ask Before You Quit Your Job To Be Self Employed

How many times have you heard people say the only way to become financially independent is by becoming your own boss? 

I am strong believer of entrepreneurship, but I do not subscribe to the often believed misconception (that 9-5 jobs can't make a man financially free). Self-employment is good but not a guarantee for financial freedom. As a matter of fact, there are throngs of wealthy people in our neighbourhood that never had any business to their names, they got to that height through 9-5 jobs. Now, don't get me wrong - being wealthy and financial freedom are two different things. Both can come from either self employment or salary - depending on your adherence to some universal principles.

Questions To Ask Before You Quit Your Job


Also Read: Top 6 Employability Skills In Shortage Among Nigerian Graduates 

Entrepreneurship can either make or mar you... We are all not cut out for self-employment, some of us will do better as employees. Frankly, it is not easy to know which path better suits you but there are pointers you might want to look out for...

Most people have ventured into the path of self-employment and got stuck at the base... with nothing to show for it. For these people, the romantic vision of being your own boss has faded away and now they're regretting. You need not learn from your own mistake when there are thousands of scenarios you could learn from.

You might want to answer the following vital questions (as suggested by experts) before you plunge to the other side.

1. Do I have to quit now? 
The first question you should ask yourself is if you have to quit right now. If you’re just getting started you’re almost always better off keeping your job and working on your business during nights and weekends.

My friend Scotty Nelson created the multimillion dollar brand “On The Mat” while working his day job.

2. How much money is needed to start the business?
This might be the most important question to ask yourself before you quit your job. You have to factor in not just the start up costs (offices, insurance, websites), but also the ongoing costs of salaries for employees, advertising and other unexpected fees and costs.

In my experience everything always ends up being about 25-30% more than you expect it to be starting out, so I recommend factoring a 25-30% cushion just in case.
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3. What do I like about the job?
Can you think of a few things you actually like about your job right now? Is it building relationships with clients or even the benefits package available to you? Be honest and thoughtful here. Try making a pro/con list to see the bigger picture. Answering this question truthfully is quite important, as these will be the qualities you want to replicate in your next venture.

4. What do I dislike about the job?
Figuring out what you like about a position might be daunting, but if asked you probably could fire off about 10 things you can’t stand about your role. That’s the easy part. The harder task comes with figuring out how you’ll take both your likes and dislikes and morph them into a stable career. Many people skip over this step, looking to get to the next position immediately. But without a few clearly defined long-term goals, you’ll just aimlessly wander from position to position with no target in sight.

5. What’s my game plan for the future?
No, this question is not too obvious. Often in a blind haze, many job searchers forget to actually outline a plan of attack for the future. Maybe you have a solid business plan drafted for your new venture or have already solidified a few contacts in your desired field. If you’re lucky, there’s another position waiting for you should you muster the guts to resign. Either way, a solid game plan moving forward makes everything manageable during such a tumultuous time.
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6. What Besides the Paycheck Are You Giving Up?
Whether you're moving on to another opportunity or just can't stand one more day, take a moment to consider the intangibles. What else does this particular job provide? Training in a growing field? Connections to other professionals? Or little joyful things? ...Maybe you have enough in savings to cover your bare-bones expenses, but have you thought about what happens when the cat has a dental problem?

7. Does This Job Make the Life You Love Doable?
I actually know someone who works in the circus. Really. She's an elephant trainer. And she's going to have great stories to tell when she's an old lady. Do you want to run away with the circus? Maybe. Do you have a life that allows for constant travel and lots of spandex? Or, come to think of it, do you need a job that allows for flextime so you can operate a gymnastics-practice car pool (aka your unpaid position as the patron of future circus performers)?

8. Can You Be a Nighttime Baker for a While?
Before making a big career change, consider what kind of apprenticeship you might be able to engage in without leaving behind that sweet, sweet paycheck. Careerosity, a website dedicated to helping people navigate career change, recently interviewed product manager Emily Johnson, who left behind her freelance writer career. How did she decide to take the leap from writing to being a product manager at a tech company? As she put it: "If you're interested in trying it, I'd recommend starting a mini business of your own. Most of the product managers I know sold pizza on the corner in college, or made jewelry to sell on Etsy, or started a website. These mini businesses failed in many cases, or made just a bit of extra spending money, but thinking about your market, your product, and your delivery will teach you most of what you need to know for a regular product manager job." In other words, if you think you want to be a product manager (or whatever it is you're thinking of), try it out on the side first. Just to make sure.
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9. Am I doing this for the right reasons?
"It's not cool to do a start-up. It's painful. CEO on your business card is a massive responsibility, not something fun to pass out at a cocktail party," says Sam Rosen, CEO and founder of MakeSpace, a New York City-based storage company that launched in 2013.

"And if you're thinking this is a get-rich-quick scheme, know that the average start-up takes 10 to 12 years to see a liquidity event."

"Most businesses fail, and yours is unlikely to be the exception, so make sure that the work is itself rewarding and interesting," says Naval Ravikant, the founder of AngelList, a social network for founders, investors and job seekers. "Also longevity is important, and you're unlikely to sustain something through long and hard times unless you love the process."
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10. How disciplined are you? If you want to work for yourself, you need to be able to self-motivate. This is particularly important at the beginning when you’re just ramping up and don’t have clients or customer demands to meet. You need to be able to put in long hours in order to set up your website, marketing, blog, and more – and you’ll need to be able to put your nose to the grindstone even when there’s no boss to set your schedule.

11. Can you sacrifice a steady lifestyle? Ask yourself how important are the following things to you right now at your stage in life: a steady paycheck, 4-weeks paid vacation, employer-paid health insurance? Most entrepreneurs will need to forgo such perks for the first few years of their business. You’ll need to be able to handle the uncertainty and lean times…both financially and mentally.
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12. How Much Should You Save?
If you have no other sources of income to pay the bills after you quit your job, how long would your savings last? Do you feel comfortable giving yourself three months to get your new freelancing career off the ground? Or is six months a more reasonable timeline? Obviously the more money you save up, the less risky your leap into freelancing will be. There are additional factors that need to be accounted for too, like whether or not you're the breadwinner for your family. It's likely you'll have to pay for your own health insurance, taxes, and fund your own retirement account. All of these things need to be calculated before you can accurately estimate how much money you should save. Most experts suggest that you keep at least three to six months' worth of expenses in a separate savings account to cover any emergencies or losses of income (some even suggest as much as twelve months' worth). As a freelancer you might as well double this amount to account for the added risk of being self-employed.
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13. What’s the Worst That Could Happen? This little question can and should be asked the moment any indecision strikes. Should I move cities? Should I go for that job? Should I order another martini? We often put false expectations, pressure and weight on our decisions and assign impact to their outcomes in ways that stretch far beyond their actual capacity. I had to remind myself, repeatedly, that the worst-case scenario wasn’t that bad at all. If my startup failed, and if I couldn’t get enough clients to pay the bills, I’d just get another job.

14. How Will I Keep Growing?
Going boss-less is a strange thing. Suddenly you’re in charge of it all. You’re your own lifeboss. This has some obvious perks, but what about the good side of bosses? The side that pushes you to dream bigger? To hold yourself accountable to exceptional standards? And to teach you new skills and perspectives?

Luckily, there’s one easy solve: mentors. I often feel like the luckiest person in the world when I think about the mentors I have around me. Each teaches me something different, each I respect more than anything, and each betters and emboldens my thinking. So, If you’re off to pursue your own thing, get some mentors.
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15. Are you able to listen without judging or evaluating? When you start your own business, you must develop your listening skills to a level beyond what you ever thought was possible. You have to listen to your customers and prospects so closely you can even hear what they don’t say. You need a level of understanding of your customers that you can’t get unless you listen to every word they say and understand their needs and aspirations better than they do.

16. Are you cool with failure? The media loves failure. They love to see businesses, celebrities and entrepreneurs fall on their face because it makes great news. They’ve convinced us that “failure” is a big, catastrophic event and (worst of all) the end. It’s not. Failing is just part of the process. It’s just another step toward success. The important thing is to never believe that failure is the end. Just get back up and keep going.
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Chukwu Emmanuel

I am so passionate about helping people improve their lives... I research, cultivate, curate and share highly valuable and relevant contents from reputable websites to help you reach your full potential without scouring through the internet.

2 Comments

  1. Keep this going please, great job!

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  2. These are very important questions. I definitely agree that you don't have to quit your job to become financially successful. There are so many ways to make money without having to be the boss.

    Through the years of building my business, I've held on to freelance and part-time jobs to keep my basic needs met. One of the things that helped me realize I am better suited for self-employment was recognizing that I have always performed my job duties as though I was the head of the company. I realized that it wasn't enough for me to even be a manager, because there'd still be someone to answer to, someone else telling me how to do my job.

    Coming into work everyday like I owned the business was how I knew I could run my own business. I also realized that self-employment is not about making lots of money, but about having control over my time. I work when and how I want to, and that means so much more to me than money.

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