What to Consider Before Freelancing


Freelancing. It’s an industry shift rapidly becoming a driving force in the business world. According to The Wall Street Journal, one in every three U.S. workers is a freelancer and by 2020, 40% of Americans will be freelancers, according to Business Insider.

person-801823_1920Why are so many professionals leaving the stability and familiarity of a traditional job and venturing out into the exciting but uncertain world of working for themselves? The answer is in the question. Who doesn’t want to be their own boss, able to handpick their clients, workload, and scheduling? It’s a notion most professionals would admit to dreaming about at some point in their career. At 4word, we have freelancers in our network utilizing their skills from different corners of the country.

If a freelancing career is luring you away from your desk job, it might be time to do some “career soul searching” before making a drastic job change. While freelancing can be a profitable and enjoyable career move, it is not without its risks, unique needs, and requirements.

Below are three questions to ask yourself as you contemplate leaving a corporate office and setting up shop at home.

Are you good with people?

This might seem like a strange character trait to consider when preparing to embark on a solo career, but being a personable freelancer with the ability to network is vital to whether or not you will survive your first year of working for yourself.

At a traditional job, clients are typically brought into your company’s fold, either of their own Screen Shot 2015-05-18 at 9.28.28 AMvolition or through a sales team. Projects are brought to you and you take the reins from there. When you’re freelancing, not only do you have to facilitate any and all projects, but you must also go out and seek clients willing to give you those projects.

There are many ways to build your client base. You might have some Facebook friends who either run or work at companies interested in contracting out some upcoming projects. (One of our writers at 4word connected with us through a friend on Facebook!) A couple of your loyal clients at your current job may be so happy with you and the work you’ve done for them, they’ll continue to use you even after you’ve gone out on your own. Supply your information to local staffing agencies and let them know you are interested in freelance or contract work.

Another way to get work? Connect with other freelancers. This may seem counterintuitive, but freelancers are an increasingly tight group of professionals who will usually not hesitate to pass along work when they’re overloaded or just not interested. The more fellow freelancers you network with, the more potential doors you’re setting up for yourself. Be sure to return the favor of passing along gigs, and you’ll soon have a teeming web of job opportunities.

Are you good with numbers?

Another plus to keeping a traditional corporate job? The in-house accounting and payroll departments. When was the last time you had to calculate the percentage of federal and state taxes to remove from your paycheck? When was the last time you had to meticulously list Screen Shot 2015-05-04 at 10.32.11 AMdozens upon dozens of itemized deductions on your taxes? Chances are, you’ve never had to worry about anything beyond filling out a W-2 and making sure you receive the correct tax papers at the end of January.

Freelancers not only take on the boss and creative roles, but they also shoulder the responsibilities of handling all financial duties necessary to keep their business afloat. Khaleelah Jones with Career Contessa shares insightful tips for how to budget without fear as a freelancer. Glory Edim with Freelancers Union also compiled a list of 10 must-have apps for freelancers that will help keep you organized, from timesheets to to-do list.

Getting handed the financial keys to your business can be a scary thing, but it’s not a role you should shy away from if you truly want to freelance. With discipline and organization, you can get (and keep) your financial ducks in a row, and before you know it, you’ll be creating top-notch client contracts in your sleep. (OK, not really, but you know what I mean.)

Are you good with schedules?

Nothing is worse than a freelancer unable to stick to a schedule. Not only will your clients get frustrated (and likely take their business elsewhere) but you’ll also grow to hate your newfound career. If you aren’t at least moderately skilled at creating and sticking to project timelines, freelancing is not for you. In a traditional office environment, you might have one or two co-workers that are willing to “do you a favor” and pick up your slack when you get behind. In freelancing, it’s all on you.

Screen Shot 2015-07-24 at 6.53.24 PMEven the most detail-oriented people in the world will reach a point in their workload where they find themselves overbooked and overwhelmed. What are some practical and easy way to stay organized? Pick a project management tool you like and stick with it. From Asana to BaseCamp to Liquid Planner, there are many online project management services designed to keep you and your many client schedules in sync. Many of these services also offer mobile apps to keep you organized on the go!

At 4word, a good portion of our team is comprised of freelancers, so it is vital that we all stay on the same schedule and everyone is up to speed on the progress of projects and promotions. In order to do this, we have had to come together as a team and meld a few programs and tools to create our team’s ideal project management process. It took some trial and error, but in the end, we were all very glad we’d put in the elbow grease!

Once you land on a project management tool you like, invest the time needed to get entirely situated in it and then develop a system to keep everything updated and moving forward. You won’t regret it!


As we tell prospective freelancers that come into the 4word network, freelancing can be an incredibly rewarding and profitable career, but it is one that takes hard work and determination to be successful. If you feel like you’re up to the task, congratulations and good luck! If you are on the fence about whether or not you’re cut out to go out on your own, try taking on a few side gigs you can manage on your own time, while keeping your full-time traditional job, to give you a taste of the freelance life without a full commitment.


If you’re currently working as a freelancer (full or part time), how did you make the jump from traditional job to working for yourself? What additional tips would you give someone interested in pursuing a career in freelance? Leave a comment below with your tips!


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*This article was originally posted by Diane Paddison on LinkedIn.