These Are Freelancers’ 6 Biggest Challenges — and How to Overcome Them

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It’s not so easy being self-employed. But you can take steps to work through the challenges you encounter. 

Some people make the decision to go freelance because they want more flexibility. Others do it because they find that they’re able to increase their income by venturing out on their own.

No matter your reason for going freelance, you may find that it poses its share of benefits as well as challenges. And if you’re struggling with the latter, you’re by no means alone. In a recent Everly survey, these were the biggest challenges freelancers are facing.

1. Difficulty building in vacation time

A good 42% of freelancers say working in vacation time is tough. That’s understandable, because freelancers don’t get paid time off. One option, however, is to put money into your savings account every week for vacation purposes. And that sum should be enough to cover not only the cost of a trip, but also, the cost of not earning any income for a week or so.

2. Clients who don’t always pay or pay on time

For 40% of freelancers, clients who are late with payments or don’t pay regularly are a problem, and understandably so. After all, you have bills to pay. And you can’t just tell your credit card company “sorry, my client paid late” and expect to be let off the hook with regard to things like interest. One solution, however, is to start asking for upfront deposits, and then payments at different intervals instead of at the end of a project. That way, you’re assured that some money is coming in while you do your work.

3. Paying for health benefits

Health insurance can be very expensive when you have to pay for it in full on your own, so it’s easy to see why 38% of freelancers cite this as a major challenge. But it does pay to shop around for health insurance every year during open enrollment for marketplace plans, because you may find that your needs and costs can change from year to year.

4. Difficulty finding regular gigs

A good 37% of freelance workers say they struggle to find regular gigs. One option is to offer discounted rates to clients who use your services regularly. That might incentivize them to give you a reliable stream of work. And also, don’t hesitate to ask satisfied clients to refer you to others. You can even consider rewarding them for helping you drum up more business.

5. Doing taxes

Many people have a hard time tackling their tax returns. But it’s not shocking to hear that 36% of freelancers struggle with this necessary but potentially painful task. When you work freelance, you have to keep precise records and know what expenses you’re eligible to write off. It pays to hire an accountant for tax help. That investment could pay off in the form of tax savings and minimized stress.

6. Feelings of isolation

When you work freelance, you often lose the camaraderie of office life. And not surprisingly, 34% of freelancers struggle with feelings of isolation. If you have the same challenge, force yourself to work outside your home. Find a coffee shop to work from twice a week, or look into renting co-working space if the cost isn’t prohibitive. And if it’s not feasible to work from anywhere other than your home office, at least try to keep your social calendar active, whether by attending professional networking events, volunteering, or spending time with friends.

Being a freelancer isn’t always smooth sailing. While these challenges may be fairly common, the good news is that they’re all solvable in their own right.

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