5 Questions to Ask Yourself Before Quitting Your Job to Become a Freelancer

By Crystal Simmons

Photo by Unsplash, CC0 1.0

So here we are. You’ve decided to quit your boring 9-5 job at the office in favour of becoming a freelancer of some sort. Whether you’re going into the writing field, consulting, legal, or whatever it may be – there are tons of questions you should ask yourself before you hand in that resignation letter.

The first question you should ask yourself before you do anything is why are you becoming a freelancer in the first place? Out of all the things you can do, you’ve chosen freelancing. You might want more flexibility in your work-life balance or the ability to be your own boss.

Whatever your reasoning, make sure that is solid in your mind first. That will give you a good base to move forward on as you start your business. Next, move on to these five questions to ask yourself before you quit your job.

1. Can You Handle the Loneliness of Working from Home?

Any freelancer will tell you that one of the hardest parts of becoming a freelancer is the loneliness that potentially accompanies it. Of course, you still have your friends and family to lean back on. But working from home or in a coffee shop where you don’t know anyone has a distinctively different feeling from working in an office where you have colleagues that you know sitting a desk away.

Be sure that you’re ready to handle the loneliness that comes with being by yourself for big parts of your day. To mitigate this, you can inquire about moving into a start-up space where you can collaborate with other small business owners and freelancers.

2. Can You Handle Creating Your Own Schedule and Sticking to It?

One of the hardest parts of being a freelancer is creating your own work schedule and actually sticking to it. It can be pretty hard when you don’t have a boss telling you to get to work on time or to leave work at a certain time. So, you’ve got to be prepared to make yourself get out of that comfy bed in the morning and get to work. And you need to be able to tell yourself when it’s time to stop working. Your personal time is important too!

3. Are You Organized Enough to Plan Ahead Months in Advance?

Organization is the key to big success in the freelancer world. No matter how good of a job you do with your clients, if you’re not prepared and organized for the next few months of your freelancing life, things can get ugly really quickly.

Be sure to know what clients you’re going to keep for the time being and which projects you’re going to take on in the next couple of months. You’ll want to be fully aware of when your clients won’t need your assistance anymore and when you should have other clients come in to fill their shoes.

4. Are You Comfortable Being Your Own Boss?

You’re a freelancer and that means you have no bosses. No one telling you how to do things or when to go to work. Are you comfortable keeping yourself accountable to get all of your work done?

That’s a big question you should ask yourself because it’s pretty easy to put off work one day in favour of getting brunch with your friends.

5. Do You Have Enough Savings for A Rainy Day or Two?

Freelancing is a notoriously financially unstable profession at the beginning. You’ll want to make sure that you have enough savings before you quit your job to be able to survive a rainy day or two. And once you’re actually freelancing, you should be comfortable with saving a good bit of your money for even more rainy days to come, rather than spending it all on fancy vacations.

A lot of people may think that freelancing is an easier profession to go into than a 9-5 job in the office. However, that’s not true at all. Freelancing is incredibly difficult for the reasons outlined above and so many more. Make sure you know the answers to all of these questions before you quit your job and head out into the big, wide freelancing world.

  Back to Candidate blogs