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7 Questions to Ask Yourself Before Entering a Freelance Career

Posted on March 8, 2017 by Franco Alvarez


You may have your own reasons for thinking of going freelance, but chances are, it’s about the autonomy, control, and flexibility. People choose to go freelance because they want to work the way they want to, and have the control over what they do. Freelancers are happy to escape micromanaging bosses, traditional office politics, and a rigid 9-to-5 day job.

If you’re interested in quitting your office job to do freelance work, you need to know that it’s more than being your own boss, having your own schedule, and working from a shared office. Here are seven questions to ask yourself before you enter a freelance career.

1. Do you have a freelance-able skill?

Before going out on your own, you have to know first if you have the skills that are in demand in the freelance market. Whereas just a majority of professions has the potential for freelance work, some industries have more opportunities available.

In 2015, popular freelance website, Upwork, revealed that the most in-demand skills include programming/development, graphic design, data entry, content writing, internet research, and virtual assistance.

2. Are you responsible enough?

Freelancing full-time means you are your own boss. You no longer have a supervisor around to monitor how much work you’ve done.

To become a successful freelancer, you need to have a high sense of responsibility and a strong work ethic. Otherwise, you’ll end up scrolling through your Facebook news feed or binge-watching a TV series without getting enough work done, and clients will see the effect in the work you deliver.

3. Can you create your work schedule?

You need to create a work schedule that differentiates work and play. It’s true that freelancing gives you the flexibility when to do your work, but many seasoned freelancers recommend having a consistent schedule that can work for you and your potential clients.

For example, if you foresee that a majority of your clients will be based in a different time zone, you should have at least a few work hours a day that overlaps with theirs so they can get fast responses when they contact you. You also need to consider building a schedule around other responsibilities you may have.

4. How do you feel about working from home, cafés, or a shared office?

Freelancers have a lot of freedom on where to do their work. A large proportion of freelancers works from home, though, because this is the most practical choice. Working from home is also the perfect alternative for individuals with other commitments such as household errands and kids.

When in need of a more social environment, freelancers often go to a coffee shop or a shared office. Staying at coffee shops are often laced with light conversations with staff or a fellow customer, which may be ideal for some in terms of getting some form of social interaction without getting too distracted.

On the other hand, coworking spaces are excellent when you miss the hustle and bustle of a traditional office—without having to deal with politics or fitting into a work persona.

5. Are you introverted or extroverted?

As a freelancer, you will mostly be working alone. If you are an extrovert, you need to contemplate whether or not you will be satisfied in working by yourself.

On the other hand, while working alone may favor introverted freelancers, they may need to put in effort in something that may come naturally to extroverts—networking.

Whatever your personality may be, it’s important for freelancers to be proactive in social networking activities such as meetups with freelancers, volunteering in the community, or even just renting a coworking space.

6. How are your sales and marketing skills?

No matter how good you are at the freelance job you want to pursue, you will hardly find any work if you don’t know how to sell skills.

The ability to effectively market your products and/or services is essential in starting a freelance career. Whether it’s being able to find the best freelance platforms to create an account for, personally sending messages to people regarding your service, creating a portfolio, or putting up a website, you are the only one who knows how you can properly market yourself.

Moreover, if the work that you get is on a project basis, you need to find new clients months before your current projects end. From marketing to closing a deal and launching projects—all of these take time, so you need to have sales targets and plan accordingly.

7. How are your project management and administration skills?

You are your own project manager, accountant, customer relationship manager, secretary, and more. Fortunately, there are many apps and tools to help you get these roles done properly.

For project management, some popular options are Basecamp, Zoho, and Todoist. For accounting, time tracking, and invoicing, spreadsheets, and word processors can be used, but good alternatives are Harvest and Freshbooks.

You will need to spend time in finding the right tools so you can be more efficient in doing admin work that you likely did not have to do as an employee.


While there are many things to consider before going out on your own, the rewards are always worth it. You can take a break when you want to, work extra hours when needed, spend more time with friends and family, avoid the stress of commuting, and much more.

The secret to being a successful full-time freelancer is to think of it as running your own company. It’s more than just being a contractor, but being the CEO of a small business.

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Franco Alvarez

Franco has always had a passion for entrepreneurship. Even at a very young age, he would constantly find an opportunity to make a little cash on the side. May it be selling women’s bracelets made out of safety pins and cheap stones or writing research papers for his rich classmates who didn’t want to study, he took advantage of each chance he got. Now, as a father of three and a full-time entrepreneur, he believes that there is always an opportunity to be of service to your fellow businessman. All you need to have is the right intention, and the proper skill set to be of help to others. In his downtime, he and his wife find new things to distract their kids with.