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  • Writer's pictureChristy

To Freelance Or Not To Freelance?

Updated: Jan 22, 2023

If you are dreaming of setting your own schedule, working from anywhere, keeping more of your hard-earned cash, choosing your own projects, or simply reclaiming your commute time, you are not alone. According to MBO Partners, the number of full-time #freelancers in the U.S. grew 25 percent in 2021 to 3.4 million, or 35 percent of the workforce. That number was just 17 percent in 2014, and the trend is continuing to rise. Statistica predicts that by 2027, a whopping 50.9 percent of the workforce will be freelancers.

The pandemic surely had something to do with this meteoric rise in self-employed remote workers. “This year may be remembered as the seminal moment when work forever changed,” said Miles Everson, CEO of MBO Partners. “An undercurrent that has been simmering reached a boiling point when people were forced out of the office and into alternative work arrangements. This is the largest shift we have seen in the workforce in decades.”

If the pandemic taught us one thing, it is that working from home is pretty great. It’s easy to understand the reasons why employees love the freedom, flexibility and cost savings of remote work. But here are some pros and cons to consider before taking the plunge into the self-employed world of freelancing.

A woman smiles in front of a camera like she is interacting with a virtual audience from her kitchen.


1. You can make more money. According to Upwork, 60 percent of freelancers who quit a full-time job earn more. The 2020 average hourly pay for most freelancing jobs was $28, which is more than 70% of workers in the U.S. How much you can charge depends on your industry, level of expertise, and whether or not you use a third party to find customers. But you really can make more money full-time freelancing, providing you are willing to work hard to fill your calendar. If you want advice on how to calculate your hourly freelance rate, this is an excellent resource.

2. You can have a more flexible schedule. It makes sense to work when you are the most productive and will have the least distractions. George Orwell and Anne Rice were night owl writers, while Earnest Hemingway and Sylvia Plath started their day with the sun. A mother might need to work while her young children are napping or in bed for the night. A West Coaster with all East Coast clients may need to get up early and finish by late afternoon. In a recent FlexJobs survey, 62% of respondents said work schedule flexibility was a top motivator in choosing freelance over traditional work. Being able to run an errand or take a walk midday is appealing to those of us who desire a better work-life balance.

3. You can be your own boss. As scary as it might be to launch out on your own, the power you can regain by having control of your own career destiny might be worth the risk. People who choose to freelance say they love being able to choose their own projects, work at their own pace, and avoid office politics. When you are your own boss, you get to decide on everything from the design of your website to the dress code. No more clocking in and out, quarterly reviews, cubicle drama, useless meetings, Hawaiian shirt days, or stolen staplers. Sounds good, right?

4. You can save money, time, and stress. A LinkedIn contact of mine noted that he and his wife, after quitting their teaching careers and getting remote work, are making the same salaries, but have an average of $1500 more in their pockets each month. They sold one of their cars, taking away a car payment and insurance, they spend less on gas and childcare, and they eat out less.

When you freelance from home, you not only save money, you also save time by being in charge of your own schedule and working smarter, not harder. And all this savings adds up to less stress. It’s no wonder Payoneer notes that 83 percent of freelancers say they’re satisfied or very satisfied with their freelancing lifestyle.

5. You can be more productive. In the same FlexJob survey listed above, 36% of respondents said their desire to be more productive in their jobs was a major contributor in their decision to freelance. How much time and energy is wasted in a traditional work setting trying to “look busy” when your brain’s peak productivity has expired? Think about it. When you are the one choosing the projects, you tend to take on work that is interesting to you. If you are setting your work schedule, you can take brain breaks when you find your productivity waning. And when you are the sole revenue generator for your business, you will have the motivation to complete more tasks in less time (the very definition of productivity).

A man sits at a table outdoors on a busy summer day, working on his laptop.


1. There are no benefits. This probably goes without saying, but if you leave a traditional job, you may be walking away from company subsidized health insurance, and a 401K. Depending on the generosity of the employer, it may be easier or harder to turn down these benefits. For some companies, the plans you can get from are comparable in cost and coverage to the plan your employer offers. And you can always open up your own Roth IRA to save for retirement. You just won’t receive any matching funds, or be forced to contribute monthly. If you are considering moving from traditional to freelance work full-time, it might be wise to do a cost analysis to determine whether you can pay for insurance and contribute to a retirement plan, while maintaining the lifestyle you are accustomed to.

2. There are no paid days off. If you don’t work, you don’t get paid. It’s as simple as that. You might find you don’t need as many days off because you can work your doctor visits, and hair appointments into your new flexible schedule. And if you’re doing what you love, you most likely won’t need those mental health days either. But gone are the days of paid vacations and holidays. With some creative planning and saving your pennies, you can take time off, but most freelancers say they tend to bring their work with them, even when they are sitting on the beach.

3. You have to hunt down your own business. This can be the biggest barrier to getting a freelancing career going. Most freelancers aren’t sales people. They are IT specialists, graphic designers, or copywriters. For many, it is difficult to drum up new business, especially at the beginning when they are freelancing as a side hustle while working a 9-5. Marketing yourself is a necessary evil in the freelancing world. But the good news is, sites like Upwork, Fiverr, and have made it easy to find work. The downside to using a third party is that, of course, they take a cut, but you might find it worth the cost for the peace of mind they provide.

The other good news is, freelancing isn’t going away any time soon. Upwork reports that 71 percent of decision-makers want to continue or increase freelance contracts in the coming years. It is advantageous for companies to hire freelancers who have specialities they need, and who won’t cost them extra taxes or benefits.

4. You are a team of one. While it may be appealing to strike out on your own for the reasons shared above, it can also be overwhelming and time consuming. You will be the receptionist, the office manager, the accountant, the sales and marketing team, the IT team, and on and on. You may get to the point where you can hire some of these tasks out to other freelancers, but for a while, it will just be you.

You will also need to build a network of people in your field to share ideas and learn from, as you will no longer have a team. It might be a good idea to check out professional freelancing associations aligned with your industry or expertise. And of course, LinkedIn is an excellent resource for networking and professional development. We are living in an age where online networking and learning has never been easier, but it is crucial that you avail yourself of these resources as a freelancer.

5. You will pay higher taxes. Ah, yes. The dreaded self employment tax. You will need to put aside around 25-30 percent of your income for Uncle Sam, as you will not only owe self employment taxes, but also income taxes. (This is compared to between 12 and 24 percent depending on your bracket for traditional workers.) Be sure to keep track of business expenses like internet service, technology, subscriptions, and mileage, as those will all be deductible.

The Balance has some great tips for managing taxes as a freelancer, but it will probably be best to hire a tax professional to make sure you are paying what you owe, and nothing more.

Freelancing isn’t for everyone. Some have tried it, and gone back to traditional jobs for a variety of reasons. But if you decide to take the plunge and move from side-hustler to full-time freelancer, you will be joining millions of other Americans who are taking the reins of their career, and changing the workforce landscape forever.

What are your freelance ideas? Share them in the comments below.

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