The Top 15 Problems that Freelancers Face

Freelancing has taken the world by storm in recent years as a viable alternative to the 9-to-5.

Technology is leading the push, allowing people to fill needs for employees in different time zones and on different continents. 

Employers love the idea of paying contract rates rather than the more significant cost of on-boarding a new employee, and self-employed workers love the freedom and flexibility.

A 2017 report filed by freelance marketplace Upwork showed 57.3 million Americans freelancing either part- or full-time, with that number expected to reach 86.5 million by 2027, a higher population than the non-freelancing population of 83.4 million.

For all of its positive benefits, freelancing does come with its own unique set of problems as well. Without proper preparation and reaction skills, these problems can turn into disasters. 

Freelancers don’t have to worry about rush-hour traffic, co-workers that they don’t get along with or whoever keeps stealing their lunch out of the break room refrigerator. But things like tracking invoices and payments, paying for their health insurance, and time management are all real and threatening.

Here’s a more in-depth look at 15 problems only freelancers face, along with hacks to keep them from affecting your business in the long run.

Paying for insurance. Most standard employers offer discounted health and life insurance to their full-time employees, along with prescription plans and wellness incentives. Freelancers have to find their own health insurance plans or risk running afoul of the law and paying out of pocket. Fortunately, several big insurance companies, such as United HealthCare, have begun offering self-employed health plans that take care of your basic needs at a lower premium.

End-of-the-Year Slowdown. Depending on what industry you’re in, you might notice a slowdown of incoming work as November and December roll around. There are a few reasons behind these trends. A lot of companies reduce their output during the holidays as employees take time off and sales dip. Others want to cut off expenses at year’s end for bookkeeping purposes. The end of the year might be a time to lower your rates and seek out new work to get you through the lean months.

Getting Undercut. Someone, somewhere is willing to do the same job as you for less money. It’s the very nature of business. Do not get into a bidding war that leaves you working for a rate that doesn’t afford you the ability to pay bills and care for yourself or your family. Have faith in your rates and your talents. Companies will recognize your value and the smart ones will ignore the low-ball offers.

Scam Artists. Scam artists are alive and well in the freelance community, placing ads that offer a lot of money, long-term commitments, and great benefits. Some of these are extremely well done and can lure in even the most cynical freelancer. Whenever you see an offer that seems too good to be true, do your due diligence on the company behind it to ensure it is legitimate.

No Payment. Every freelancer has a story about getting burned by a client who took the finished work and disappeared. It is a painful but an education experience. Every time you have a new client, put in writing the terms and conditions of the work being done, and have both parties sign it. This gives you a legal framework from which to work with if things go south. You can also consider requesting a “hiring bonus” – say 25-50% of the final bill – as a down payment for your services. You’ll be able to separate the scammers from the serious clients based on who is willing to pay upfront for your time.

Stressing on Finances. A continuation from the last item, being a freelancer often means trying your patience as you wait on clients to approve work and make payments. We all want a consistent schedule of payments, but that doesn’t always happen when freelancing. Your best bet is to build up a reserve of savings so you’re never out on a limb if a client is a day or two late with your payments.

Sick days are painful. When you work 9-to-5, you have at least 5-10 days in reserve for the mornings you wake up with a fever or the flu. That’s not the case for freelancers. They usually have to power through colds and headaches when they’re on a deadline. For the days when you’re too sick to get out of bed, contact your employers to tell them what’s going on. Most of the time, they will understand and help you establish a new deadline. 

Boredom. Being home all day long can make you jumpy and irritable. Treat your home workday just like you were at the office. Take scheduled breaks, step away from your workstation for lunch, take a walk outside, or even a power nap. If you can’t stay focused on the task at hand, a break usually helps you reset. 

Balancing Work and Family. If you’re married with children, establish hard and fast parameters for when you’re the work version of yourself and when you’re the home version. Be present in whichever role you’re currently inhabiting. Establish physical barriers between your workspace and your home life.

Clients asking for free work. How many times have you finished a project and gotten an email back saying it all looks good, but can you just edit this 1,000 introduction I whipped up? You may feel pressure to do the extra work for free, but that sets up a bad precedent for your relationship. Your time is important, and your work is to. If clients want extra work, let them understand what your rates are. Most will have no problem

Unbilled Hours. Some clients will ask for more than they’re paying for. Solution: When you take a job with a fixed rate, estimate how much time it will take and make that is part of your agreement with the client. If they ask for more work that isn’t a correction, charge them for it.

Missing Deadlines. It will happen eventually, be it because of a hurricane, a car wreck, a sick child, or a stomach bug. When you know deadlines are going to be missed, contact your client as soon as possible, give them a real date of when you can finish the work, and give an apology from the heart.

The Client Who Hates Everything. We all have had a run-in with a client who is never satisfied with our work. It’s too long, too short, doesn’t convey the message, looks sloppy, doesn’t use enough color, uses too much color, or just doesn’t work for them. Make sure to convey upfront how many iterations your cost implies. If the client keeps wanting more or if their demands are unreasonable, it’s time to be transparent and disengage from the contract. If money is owed, try to find a middle ground to stand on.

Ownership. When you’re producing creative work such as a logo, a graphic, or a blog, you have to establish upfront who owns the finished product. Does an article carry your byline forever or are you giving up rights of ownership? Does a logo earn you residuals each time it is used or are you signing complete control of it away to your client?

The All-Nighters. Staying up until 4 a.m. to cram for your Chemistry final was acceptable in college, but let’s face it, you’ve aged a lot since then. Staying up past your bedtime is OK once in a while, but when you start burning the candle at both ends, you’re damaging your own brain capacity as well as the quality of your work. Your body tells you when it’s time to sleep. Do yourself a favor and listen.