The Pros and Cons of Becoming a Freelancer

The Pros and Cons of Becoming a Freelancer

Freelancing is on the rise. But is it for you? 

According to a 2022 Upwork study, more than 60 million people in the U.S. freelance. Freelancers are most likely to be skilled professionals, with 51% of freelancers providing skills such as programming, marketing, IT and business consulting, according to the study. 

Some freelancers decide they want total ownership over their work. Others are disgruntled by full-time jobs in companies. Some are forced into freelancingmaybe they’ve been laid off or they can’t sustain a full-time job with a family or disability. 

Whatever your reason for considering the freelance life, here are the ups and downs to consider.


The flexibility is truly limitless.

A freelancer by definition is free and untethered. Depending on your industry, freelancers often have the flexibility to choose their projects, and therefore their bosses, time off, commute (or lack thereof), rates, scope of involvement, hours and everything in between.

Some freelancers straddle many different careers

a photographer may also be a consultant and an interpreter, for example, whereas a staff worker may be limited to one function.

You’re not necessarily dependent on one income stream.

In the past, stability meant a steady paycheck at a full-time job. However, with many industries collapsing, like journalism and manufacturing, freelancing has become a critical financial buoy. Freelancers can enjoy a diversity of income streams, so that the fall of one job does not mean the demise of their entire livelihood. 

In fact, some freelancers report that they make more money than they did at full-time jobs because they have varied income streams. After developing strong contacts, these freelancers have the ability to increase or decrease their workload at any given time. 

There’s a healthy distance from office culture.

Working on staff usually means that you are mired in an office culture. This can be a great thing if the office culture is healthy. However, many office cultures feature problems from toxic structures to ageism to annoying colleagues who chew their food too loudly. Freelancers tend to have a distant relationship with their employers in which the interaction is limited to the project.

You own your brand.

Freelancers are generally able to use their personal names and brands as they wish. For example, if you want to be an activist and fight for a cause, you do not have to worry about representing a company.

You can go hog wild on Twitter and call yourself whatever you want – a “Glitter-tacular Woo Woo Happiness Coach” or “Financial Consultant for Animal Rights Radicals.” No matter what you want to be, no HR department can come after you, and no company can misrepresent who you are. 

The Cons

No built-in insurance or benefits.

One of the most glaring problems for freelancers is that they do not receive benefits like health insurance, unemployment insurance or matched 401ks. This is an undeniable downside in a country where premiums for things like health insurance are at an all time high.

In an ideal situation, you have a spouse who can add you to their benefits, or perhaps you qualify for a government-subsidized program. Otherwise, there is sadly no silver lining to this issue right now. You will need to save considerably for insurance and health visits.

The paperwork is intense.

Full-time employees usually have everything automated, whereas freelancers have to stay on top of their income, taxes, expenses, retirement and invoice payments year-round. Freelancers on 1099s have to pay taxes four times a year, whereas full-timers on W2s only have to think about it once.

Freelancers might have to chase down a client for payment, whereas full-timers get paid biweekly. No doubt about it, the paperwork for a freelancer is brutal. You’ll need a good accountant, and a new way of organizing your finances.

It’s up, down, and non-stop.

Many freelancers experience feast or famine, which means a period of success, followed by a period of professional dips. One has to become accustomed to a lack of control and predictability. 

Over time, freelancers learn to hustle constantly and own the fact that nothing is permanent. Looked at a different way, this makes freelancers more nimble than full-time workers who lose their stable jobs after many years.

Boundaries are less clear.

Freelancers have to set their own boundaries. Whereas full-timers have weekends off, paid vacation and hours of operation, a freelancer could work around the clock if they aren’t careful.

Beware new legislation targeting independent contractors.

There is a new slate of legislation targeting independent contractors. The fight is complicated and ongoing. If you live in California, the AB5 law has already passed and is constantly being amended, whereas other laws are being considered throughout the country, including the federal PROAct. For more information about your state and national efforts, head to

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  • January 16, 2023