The Pros and Cons of Freelancing: Cards On the Table Time

Straight talk about the freelance life.

Many people see the freelance life as glamorous and alluring from the outside. To be honest… those people aren’t entirely wrong.

But it would be dishonest to suggest that there are no downsides.

Is the freelance life the life for you?

Here, we lay all the cards out on the table and examine the ups and downs of being your own boss.

The Pros and Cons

PRO: Freedom and flexibility

It’s one of the first draws freelancing has for most people. We decide our work hours. We decide where and how we work. We decide how much we work. We could hustle every day of the year, or we could make is a seasonal sort of thing. It’s entirely up to the freelancer to decide based on their needs and desires.

CON: Dealing with irregular income

Some months are better than others. There could be months where a freelancer makes thousands of dollars, there could be months when it’s hundreds. There might even be periods in which nothing is coming in at all. A freelancer must be prepared and learn how to budget so that even during slow periods, the bills can still be paid.

PRO: Freedom to choose clients and partners

You get to decide who you work with and work for. Back in my straight-job days, I often had to work on campaign materials for politicians I despised. I did not have a say in our clients. As a freelancer, I am in a much better position to refuse projects I have objections to. I can choose not to partner with a vendor I don’t like. A freelancer is better positioned to be true to themselves.

CON: No benefits except what you can manage yourself

Vacation. 401k. Health care. These were all benefits I left behind when I went freelance full-time. I don’t regret my decision, but the lack of benefits can hurt from time to time. I don’t get a vacation unless I’ve budgeted for the time off. I’m responsible for my own retirement plan.

And health care?

For too many years than I care to recall, my health care plan was, “I either get better or I don’t.” (This experience may only be familiar to fellow Americans. The rest of the developed world seems to have a better handle on this issue.)

I have insurance now, but it was tough to get to the point where I could afford it.

PRO: You’re the boss

Bad bosses suck, don’t they? They can make a bad work situation worse in ways that stagger the imagination. That’s no longer an issue when you’re freelancing. Unless you’re also a jerk, bad bosses need no longer haunt your days and nights.

But you have to be a responsible self-boss. As much as you’re the one calling the shots, you have to be responsible enough to make sure work is coming in and getting done.

But you also know how to cut yourself some slack when you need to.

CON: You’re on the hook for your own business expenses

Your old office or workplace paid the rent, utilities, Internet, and materials. Now you have to make sure those costs are covered. While you can declare a lot of those expenses on your taxes, it can still be a hefty amount to pay out until you’re bringing in enough income to comfortably cover all your freelance business expenses.

PRO: No more commute

Instead of driving twenty miles to a workplace I dreaded, I’m now taking 20 seconds to get from my kitchen to my home office. My car needs less maintenance. I’m spending less on gas and not contributing as much to road pollution. I’m not waiting for busses in the rain and snow.

I get to spend more time with my family, and I’m not so rushed in the mornings.

This could be you as well.

CON: The taxes are pretty onerous

Where a traditional employer would pay half the cost of Social Security and Medicare taxes, as a freelancer, this is all on you. You will also have to file taxes more often, manage your own paperwork, and figure out sales tax where appropriate.

You might even find you’ll have to pay for a professional to help keep it all straight. It’s probably the least glamorous aspect of being a freelancer, but one you’re going to have to deal with, whether you like it or not.

PRO: Pursue the projects that mean the most to you

You get to choose the projects that fire you up. Maybe this was something you wished you could do at your old straight job but were never allowed to do.

Now you can give it a shot. Apple founders Jobs and Wozniak both worked at computer companies that had no interest in personal computers. As soon as they were able, they left those jobs to pursue their passion. The rest is history.

I’m not saying you’re going to have the same success, but you have the freedom now to try.

CON: It can get lonely

Chances are that if you’re freelancing, you’re working alone. That means no more office mates or co-workers. Human beings, generally, are social animals. Even if we didn’t always like our co-workers, the interaction was still necessary. After a while, the isolation might get to you.

To combat this, try to schedule some extra time with friends and family. If it’s possible, you could even look into co-working opportunities with other freelancers.

Weighing both sides

Personally, I can never see myself leaving the freelance life.

That said, it has its downsides. For me, they’re worth it.

I would not dare speak for you, but I would want to make sure that you were aware that there are upsides with every downside. You have to determine what you’re willing to trade off so you, too, can enjoy the freedom of freelancing.

And if you decide it’s not for you, more power to you.

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