12 Questions To Ask Yourself Before Leaving Your Day Job To Start Freelancing

Past few years have been an incredibly profitable time for freelancers. Some freelancers are now making a lot of money these days that they make my $5,000 a month earning look like nothing.

It’s understandable why these stories would make everyone want to suddenly quit their day jobs to become freelancers. Buy what they all forget is to realize how much of a risk they take when they try to start a freelance career without a proper plan.

So, before you go and quit your job to become a full-time freelancer, take a moment to ask yourself these questions, just to make sure you’re ready for the long ride ahead.

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#1 Is Freelancing The Right Career Path For Me?

Do you love getting a steady paycheck at the end of every month? Do you wish you can work less at the office? And do you like hanging out with your office buddies at the water cooler or grabbing drinks at the bar every Friday night?

Then freelancing might not be the best career path for you.

Yes, freelancers do have more freedom to choose only the jobs that they are most comfortable with and do work that they truly enjoy doing. But, in return, you have to work more hours to make ends meet.

Freelancing also includes giving up on certain luxuries, like partying with friends or taking weekends off.

Simply put, freelancing is the ideal career path for introverts (like me).

You’ll have to be willing to make some changes in your life to survive a freelance career.

#2 Am I Ready To Leave My Comfort Zone?

Becoming a freelancer is like running your own business. You will be finding work, managing projects, and dealing with clients all by yourself.

You will also have to work unusual hours because your online clients have different time-zones. And you will have to deliver your work on time in order to get paid.

Are you ready to take in on all that responsibility? Are you willing to push yourself to the limits to achieve success as a freelancer?

#3 Is It Safe For Me To Quit My Day Job?

Freelancing does not come with a steady income. You’ll never know how much you’re going to make next month and you’ll often find yourself struggling to find clients as well.

Pause for a moment to think about what kind of a risk you’re taking by quitting your day job and who you’re putting in danger with your decision.

For example, if you’re a family man, you might want to think about your children. Will you be able to provide for your family as a freelancer?

This doesn’t mean you have to keep working at a demeaning job. Just come up with a better plan. Try to save up some funds and make sure you have a few clients to work with before quitting your day job.

#4 Can I Afford To Work From Home?

Having a fast computer, a speedy internet connection, and an isolated office space at home to peacefully do your work are only the basics you need to start working from home.

You will also need to think about your finances.

Don’t expect to make any money in your first couple of months as a freelancer. You still have a lot of figuring out to do and it will take some time for you to find long-term clients.

Do have enough money saved up to pay your bills during that period?

#5 Do I Have A Marketable Skill?

Similar to applying for a regular job, freelancing also needs a valid skill to turn your experience into money.

Even a simple freelance data entry job requires knowledge of working with certain software. And you will go out of business within a short time if you don’t have a marketable skill to promote your freelance services.

Whatever skill you choose to be an expert in, make sure that you can make money with it. Do some research to see if your skill has enough demand in the freelancing market.


For example, you can go over to UpWork website and search Jobs with a keyword related to your skill and see how many jobs are available under that category.

#6 Do I Have Enough Experience?

If you’ve worked at your day job for several years and managed to collect a lot of experience in your field, it will help you greatly to stand out as an expert when it comes to marketing your skills and freelancing services.

Otherwise, you’ll have a tough time getting clients.

There are no internships available in freelancing. If you don’t have any experience, take some time to earn it and learn everything you can about the skills you already have.

#7 Will I Be Able Make Enough Money As A Freelancer?

If you’re willing to work hard enough, you will be able to double, or even triple, your day job’s salary as a freelancer. But, just to be safe, do a research to find out how much freelancers with your skills are actually making.


For example, you can visit Quora and search for a term like “how much do freelance designers make” and find information from other freelancers on what kind of money they’re making.

Now, grab a calculator and plan a budget to figure out how much money you need to pay for food, bills, kids, and Netflix. Is your estimated freelance earnings enough to cover those costs?

#8 How Am I Going To Find Clients?

Decide whether you’re going to work online or locally.

Some freelancers prefer to work for their employer under freelance contracts even after quitting their job. Obviously, it depends on how you leave things with your boss.

Although, most freelancers find it easier to look for work through freelance platforms such as UpWork and Freelancer. Of course, it’s easier said than done.

These freelance platforms consist of millions of freelancers from around the world who offer their services at cheap prices. You shouldn’t lower your expertise and services to their level.



So, figure out how you’re going to promote your services. Are you going to find local clients, use online platforms, or be more independent by using tools like Twitter, Reddit, and LinkedIn to find clients?

#9 Do I Know How To Handle Clients?

A skill even some of the so-called expert freelancers lack is the ability to communicate properly with their clients.

Communication is the key to winning clients, understanding their needs, delivering quality work, and establishing long-term relationships. Without this one skill, you will have a hard time landing jobs online.

Learn how to write great emails and learn how to write great project pitches on freelance sites. And, more importantly, make sure you develop the necessary mindset to stay calm when receiving criticism from clients and when things get rough.

#10 Should I Charge Per Project Or By The Hour?

Planning out how you’re going to charge for your services is another dilemma most new freelancers face early in their career. Make a choice depending on your skills and the amount of experience you offer through your service.

For example, there are freelance coders who make $1,000 an hour, but that doesn’t mean you can charge the same amount. It depends on the quality of your work and how quickly you can finish a project.

I myself prefer to charge by the project. It gives me the freedom to work at my own pace and get things done without having to rush through my work. And also, it’s more profitable that way.

#11 Am I Good At Multitasking?

Multitasking is the one thing that most people ask you to avoid if you want to become successful. But, not in freelancing.

As a freelancer, you’ll be working with multiple clients and multiple projects at a time. You will be managing the finances, generating invoices, and finding more work on your own. That’s on top of all the regular stuff you have to do at home.

It goes without saying, multitaskers have a better chance at making more money as freelancers.

#12 Do I Have A Plan B?

What if I fail as a freelancer? Can I go back to my day job again?

Stop right there! Don’t even think about developing a plan B.

Freelancing works best when you go all-in with everything you’ve got. That way you’ll work harder to achieve your goals because it’s the only option you’ve got.

Don’t even think about starting this career with an exit strategy.

You will fail, you will get into trouble, you will get lost, but, just like Thomas Edison, you will also find success, eventually. Until then, just keep moving forward.