Freelancing Your Way to Felicity and Financial Freedom: Part 1

by | Nov 18, 2021 |

This blog post is the first in a series of eight adapted from a talk given at TOS-Con 2021. Learn more about TOS-Con here.

Freelancing is not for everyone. It’s really difficult to both build a career that you’re passionate about and to make good money doing it, but if you’re willing to put in the work and refine your strategies over time, the results can be enormously rewarding.

Please note that this article assumes you’re based in the United States. If you live elsewhere, the general principles of being an awesome freelancer still apply, but your local laws and regulations may differ.

Pros of Freelancing

In almost any industry, freelancers live in a world of extremes. Traditional jobs typically offer most things in moderation—moderate pay, moderate benefits, moderate opportunities for advancement, moderate frustration with your coworkers. Freelancers, in contrast, tend to either succeed magnificently or crash and burn hard.

Increased Earning Potential

Some freelancers simply monetize their passions without investing considerable time and effort to learn the science of business. There’s nothing wrong with that—plenty of freelancers are happy with a modest income as long as they get to do what they love. But if you’re willing to become a businessman, there’s almost no limit to how much you can earn.

Flexible Schedule

When you freelance, you are, by definition, some sort of contractor—and contractors, by U.S. law, set their own work hours. Your clients have no say over when you work. Typically, you’ll deliver goods or services in accord with deadlines, but other than that, it’s up to you when you get the work done. Clients can ask you to work at certain times, but you’re not obligated to do so.

Choose Your Clients and Projects

Don’t like the work you’re doing or the people you’re doing it for? Both are in your power to change. Of course, you should never leave a client hanging mid-project unless they’ve done something so egregious that you can’t overlook it, nor should you violate a contract or work agreement without a fantastically good reason. But, nonetheless, you’re free to cut ties when appropriate and seek better opportunities.

Broaden Your Horizons

When you work in a traditional job, you typically spend most of your time with the same group of people. There are upsides to this, but it’s not a great way to expose yourself to different ideas, strategies, and tactics. As a freelancer, you’ll get to see how different companies employ different business philosophies. You’ll have a much more expansive frame of reference by which to judge what works and what doesn’t.

Increased Independence and Confidence

As a freelancer, you don’t have the same support network you’d probably have in a regular job. You’ll have to work a lot harder to achieve your goals, but when you do achieve them, you get to take all (or at least most) of the credit. Although being fully in charge comes with a lot of responsibility, it comes with great psychological rewards, too.

Cons of Freelancing

Freelancing has drawbacks that can be comparable in magnitude to its advantages. As long as you have a realistic idea of how daunting these challenges can be and come up with a strong plan to mitigate them, they are manageable.

Huge Taxes

Depending on how much revenue you bring in, you’re likely looking at a tax burden of anywhere from 15 to 40 percent. In most cases, you’ll pay significantly more taxes than if you made the same amount of money doing the same kind of work for a traditional (W2) employer. Filing your taxes also becomes much, much more complicated.

No (Traditional) Benefits

You have no employer, so you have no employer-subsidized health or dental care, no retirement plan, and no paid time off. Any and all benefits you want to extend to yourself have to come out of your own pocket.

Feast or Famine

Until you gain some degree of recognition as an expert in your field, your workload and income will be hard to predict. You may go weeks or months with no income at all. Make sure you price yourself accurately to ensure that your high points are high enough to mitigate the inevitable low points.

Cash Flow Challenges

When you work for a traditional employer, you (hopefully) get paid on time, every time—without having to personally do anything to make sure that happens. But as a freelancer, you are your own billing and accounting department. Some clients pay late, incorrectly, or not at all. Getting paid can sometimes be a major headache.


Most freelancers work alone, and most of those who collaborate do so long-distance. Spending most of your working hours alone can take its toll, even for textbook introverts (although remote working in the post-COVID era has made this true for many traditional employees as well).


In a traditional workplace, distractions are everywhere, but they’re generally easier to overcome. Being physically present in a location exclusively associated with work goes a long way toward keeping your mind focused on the job at hand, but when you work from home, or when there’s no supervisor looking over your shoulder, staying on task gets a lot harder. You’ll need to actively cultivate discipline and create a work environment conducive to your particular field to be successful, and both of those things can be difficult.

Ultimate Responsibility

At the end of the day, you get most or all of the credit for your achievements as a freelancer, but the same is true of your failures—and you will fail a lot. There will be days—at first, probably a great many days—when you feel totally convinced that you’ve made a huge mistake. Impostor syndrome will rear its head, and you’ll probably feel a strong temptation to return to the relative safety of a traditional job. Depending on your values and priorities, that may ultimately be the right decision, but I’d encourage you to ride it out for a while before deciding that freelancing isn’t for you. Everyone sucks at everything when they first start doing it, and freelancing is no exception. Give yourself enough time to start gaining mastery and traction before you throw in the towel.

In my upcoming posts, I’ll detail a series of strategies for becoming a successful freelancer.

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