Making the Big Decision to Work Freelance: An In-Depth Look at What to Consider

Updated on April 12, 2018
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I'm a work-from-home freelancer & entrepreneur. I own both my own writing and balloon businesses.

I covered my thoughts on what some big steps to going freelance are, but I haven't talked about what goes into making the decision to go freelance in the first place. There is a lot that you have to take into consideration before you make the choice to go freelance.

While it may seem like freelancing will solve all your problems—and for the right kind of person, it certainly can—it comes with a lot of risks and responsibilities that other careers don't. That's why I've decided to talk about that (and more) as I've experienced it. These are some of the most important things to consider when deciding if a freelance career is right for you.

Responsibilities and Risks

Freelancing isn't sexy. It has a lot of appeal and works out great for some people because you get to take charge. But at the end of the day, that means that everything falls on your shoulders. Win or lose, it's all on you. While that by itself could be enough to deter some, it's not the only thing I'll be talking about. Here are a few things you need to think about before going freelance:

  • Insurance is a big turn off for a lot of folks. You don't get health, dental, or vision insurance when you work freelance. Those are things you have to pay for yourself. If you qualify for state benefits, this might be okay, but as you earn more, you will likely disqualify yourself from those benefits. While some states offer pretty decently priced insurance that you can buy yourself, other states - like Texas - can be a little pricey. With recent tax laws that say you must carry insurance or suffer huge fines, this can be a big issue. Be sure you read up on and understand exactly how much you'll be paying either way before you make the jump to freelance.
  • Vacations aren't a thing of the past, they just work a little differently. You don't get 2 weeks paid vacation unless you work extra hard and save up for it. The good news is, you get to set your own schedule and don't have to worry about clearing vacation time with your boss. If you work directly with your clients (rather than through a firm), you may have to let them know that you'll be unavailable. But when you're freelance, vacations truly are the fruits of your effort rather than a token of time spent at work.
  • Money is going to be all yours to handle. Whether you're collecting it or spending it. But that entails a lot more than you might think. You'll be in charge of ensuring you get paid. It doesn't happen often, but there are clients out there that are going to agree to a price or time frame, then change it when the bill comes due. You'll have to save up for vacations, upgrades, repairs, insurance, bills, everything. You'll be responsible for fixing any billing issues, and for making your payment system easy to use. Not all freelance careers require this level of detail to money, but you will need to be prepared to handle every facet of money.
  • Taxes are all on you. From reporting your income to paying taxes at the end of the year, you're completely in charge of keeping up with what you owe, reporting it, and paying it. Some freelancers choose to donate their time, services, products, or even old equipment to help offset how much they owe at the end of the year. Keeping track of things like your mileage will also help to offset what you owe. I know I've said it before, but I can't stress it enough: Study up on tax laws as they apply to you.
  • You have to schedule everything. This means you have to balance personal time, family time, date time, work time, due dates, vacations, payment schedules, everything. Everything. If you aren't good with scheduling, time management, and organization, get good. It doesn't have to be a dazzling, professional layout that anyone could use. It has to make sense to you and work for you.

You will essentially have to plan for and undertake all of the issues that conventional employment does for you.

Talk to Your Partner

Even working a 9-5 you probably talk to your partner about any big changes. Because going freelance comes with so many risks and such great responsibilities, talking to your partner is a must.

My husband and I have been entrepreneurial since we were kids, and so when we got together and talked about our love of creating our own businesses and doing freelance work, it wasn't an issue. Though we've both worked conventional jobs, we always kept going back to freelance work or trying out our own businesses.
However, we also have 3 small kids. So when we made our most recent commitment to freelance work, we had a serious talk. We worked together to come up with schedules and monetary amounts that would work for us.

Your partner may not be as understanding. Or they may be completely on board but not really understand the huge risks that come with it. Make sure that your partner is not just on board, but understands and fully supports you. Your partner's support is pretty much mandatory, as it will help avoid a lot of fighting, help get you through the bad patches, and help you figure out anything that might have you stumped.

Divide Your Time Wisely

I've talked about the importance of scheduling before. But you won't just have to schedule your work time. It's easy - especially when you're just getting started - to work all the time. Here are some tips for balancing out your schedule:

  • Find a work schedule that works for you. Typically, I work six hours a day, five days a week. But watching three small kids while working for six hours straight doesn't work for me. So I work three hours in the morning and three hours at night. When work hours are over, they're over.
  • Make one-on-one time for your partner. If you try to lump everything into work time and family time, you'll find that you and your partner tend to have more arguments and a bigger rift between you. Even if it's cheap, have dates. Give updates on how things are going. Talk about your hopes, goals, and dreams (both of yours!) Have fun.
  • Make time for your family. Between school, work, and making time for your spouse, your kiddos may feel a little left out. Spending time together as a family can help them feel included, loved, and well-cared-for, even if it's only a couple of hours a day. And just like with your work schedule, this can be broken up throughout the day.
  • Take some time out for yourself. I'm an extrovert, so I don't require too much alone time to get myself together. Usually, an hour in the shower gives me plenty of time to recharge and plan out my week. My husband, on the other hand, is an introvert and needs a few hours a day to get everything planned and feel happy and relaxed. Take care of yourself so that you feel refreshed and ready to tackle the rest.

Try Out Several Avenues

In a future article, I'll be talking about some of the platforms I recommend to get started freelancing in a few fields - so please take what I say here with a grain of salt.
When I was first getting started with freelancing writing platforms, I tried out iWriter. It was better than what I had been doing, but after a few months, I hated it. I actively quit working, and it put a huge damper on my confidence to work freelance. In fact, I took a couple of years off to give 9-5 another try.

When I came back to freelance writing, I tried a few platforms. I found a couple that I really loved and have stuck with them. I still try out new ones as I find them. This is important because not only does it give you variety if something goes wrong on one platform, it also allows you to do the work you want with little worry.

Just because one platform doesn't work doesn't mean you should give up. It means you need to find a platform that works for you.

Decide Whether to Rent or Make Space

This can be a tough decision, especially if finances are already tight. Sometimes neither is an option. But whether it's setting boundaries with your spouse and kids (don't bother me while I'm in my office), allowing you to free yourself from distractions, or keeping your products safe and organized, you'll find that having a space to work in is important.

  • If you have the space in your home, consider making a small office. This can include converting corners and closets into offices or even dedicating a garage or spare room into one.
  • If you can come up with or already have the cash, you can rent everything from a storage unit to a shared office space to use as an office.
  • If you'd rather, you can build a small shed or detached room. This can be costly up front, but cheaper in the long run than renting.

There are a lot of ways to tackle coming up with a space to work. Be creative, account for finances, and make it comfortable and functional.

There are several things you have to think about before you commit to going full freelance. These are just the main points that I think are most important. If you've already made the jump, what were some of the things that helped you make your decision?

© 2018 Rebecca

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