problems freelancers face

7 Common Problems Freelancers Face — and How to Conquer Them Like a Boss

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The life of a freelancer can seem very inviting. There’s no dressing up for work, no long morning commutes, no boss breathing over your shoulder — what’s not to like?

But having freelanced for several years, I can attest this life isn’t always easy; it has its share of bumps in the road.

Here are seven of the most common problems freelancers face, along with tips for overcoming them to live your best freelancing life.

Freelancer problem #1: Finding enough work

One of the biggest freelancer concerns is maintaining a continuous flow of work. When you go freelance, it’s completely up to you to find projects and book clients.

Sometimes you put in a ton of work only to have a client disappear without an email or phone call. Then you have to put yourself out there yet again to find new leads.

This constant hustle can be a deal-breaker for many. And not finding enough work isn’t the only problem freelancers face — something you have too many assignments coming your way.

Whether you’re a writer, graphic designer, digital marketer, or translator, you might find yourself buried neck-deep in work. While this situation is obviously preferable to its opposite, it can still be tough to turn down work when you don’t have the bandwidth to take it on.

How to overcome this obstacle

Be in touch with clients

Don’t wait for clients to call or mail you. Instead, take the initiative, get in touch with them, and show your new work constantly.

And don’t limit your communication to showing off your portfolio either. Reach out to say hello or to send best wishes on New Year’s.

By nurturing your relationships with clients, you’ll build a sense of trust. This trust could lead to a long-term working relationship that’s beneficial for both of you.

Plus, the more you put yourself out there, the better luck you’ll have. By approaching lots of clients, you’ll give yourself even more chances to get work.

Don’t put all your eggs in one basket

Don’t limit yourself to one or two clients. If they go MIA, you’ll end up with empty hands (and empty pockets). Instead, try to work with multiple clients and websites, particularly those that offer a regular workflow.

If your field allows, you might also book clients both online and offline, so your income isn’t limited to the sometimes fickle virtual world. By working with multiple clients, you’re more likely to have some work and income to carry you through the dry spells.

Market your services

Although marketing yourself might feel unnatural at first, it’s so important to being a successful freelancer. Advertising your services is key to attracting clients and building loyalty.

So create content, whether audio, video, or written, to advertise your services. And remember that new content is constantly popping up online, so try to post at least one thing every day to remind people you exist.

Get active on social networking sites

Engaging with online communities is helpful for showcasing your portfolio and discovering new opportunities. You can connect with other freelancers and make valuable connections (just don’t get stuck in a Facebook rabbit hole of your college friends’ wedding pictures).

You can also use social media to inform friends and family about your services and ask them to spread the word Don’t be afraid to toot your own horn, as this proactive approach will help you be successful in your field.

issues with freelance work

Freelancer problem #2: Getting taken for granted by friends and family

When you work from home, your friends and family might start asking for all kinds of favors during the day. Or your significant other, while they understand and support your work, might still ask you take care of chores during the daytime before they get home from the office.

I can speak to this personally; from changing a light bulb to taking the dog for a walk, there isn’t one hand-me-down task that hasn’t come my way. What’s more, friends and family might try to request your services for a lower rate, or even for free.

While you might want to help, working for free isn’t going to pay your bills or make others value your services as much as they should.

How to deal with these freelancer concerns

Learn how to say no

I received one of the best freelancing tips from my mother: “If you keep pushing your boundaries, absolutely no one will end up being happy.”

Since she passed on this advice, I only do the things I have the resources to do. I’m okay with a little favor here or there, but when I’m busy, I’ll say so.

Even if you struggle with setting boundaries, remember that if your friends and family really care about you, they’ll understand.

Treat friends and family as clients

Don’t let people assume you’re grateful for any project that comes your way. Treat friends and family just like any other client. Ask them for a proper brief, as well as the price.

Devaluing your work by offering it for free or a reduced rate doesn’t do anyone any good. They’ll get the message and won’t ask you to give away your time, energy, and work for free the next time.

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Freelancer problem #3: Having to be a jack of all trades

Having to work as a one-person business is one of the most significant issues with freelance work. As a freelancer, you don’t just have to work on assignments and projects.

You also have to juggle other business activities, from acquiring clients to chasing them down for payments to marketing yourself to managing your finances — the list goes on and on.

You’re a boss, brand manager, financial executive, IT person, and even the coffee guy. While freelance work can be very fulfilling, it also involves a lot of work for one person.

If you don’t allocate your time right, you could end up spending too much time lost in the weeds and missing deadlines as a result.

Freelancing tips for finding balance

Adhere to a fixed schedule

To avoid becoming overwhelmed, start by organizing your schedule. Create a to-do list, and prioritize your tasks. Set a fixed number of working hours, and make sure you complete your work during those hours.

If Facebook or Instagram notifications are a big distraction, consider keeping two cell phones (one for professional contacts and the other for personal), and keep the latter on airplane mode during working hours.

You might also use an anti-procrastination app to block these time-sucking social media pages and any other distracting websites on your computer while you’re working.

Make use of time management apps and other helpful tools

If you want help operating your business, use tools such as Zoho, Basecamp, and Asana to manage projects, Toggl to manage your time, and Freeagent (an accounting software) to handle invoices, expenses, taxes, and receipts.

You can even contract a virtual assistant to answer your calls. In fact, if you have lots of projects coming your way, it could make sense to sub-contract freelancers yourself to handle smaller projects so you can bid on and make more time for larger ones.

Set a day aside to dedicate to busy work

Mundane tasks can take over your entire week if you let them. Instead of getting lost in busy work, set aside one day per week to manage your extra tasks. That way, the flow of your actual work won’t be interrupted and you can focus deeply without worrying about administrative tasks.

Plus, you’ll end up with big chunks of time to dedicate to what you enjoy doing — writing, design, web development, etc. — while making money.

issues with freelance work

Freelancer problem #4: Working for yourself can get lonely

While freelancing gives you the freedom and flexibility to work for yourself, it can also be a lonely experience. Humans are social beings, and life can get daunting when you’re not around like-minded people to brainstorm ideas with or teammates to meet for coffee.

Along with feeling isolated, you might get bored with certain projects and have trouble motivating yourself to get stuff done. That said, my “boring” projects are still far more engaging than my previous 9-5 job!

How to deal with these freelance woes

Take on projects you enjoy

One of the best ways to avoid boredom is to take on work you’re actually interested in. You’ll be a lot less likely to lose focus if you’re working on something you care about.

If you’re a travel writer, for instance, you probably won’t enjoy writing an article on data science. So search for projects that make you excited, and be choosy about what you accept (if you’re financially able to do so).

Join a coworking space

By joining a coworking space, you’ll have a quiet place to work, as well as a built-in community of like-minded remote workers. A lot of coworking spaces hold happy hours, invite speakers, or host other events so you can get to know your fellow coworkers.

With a coworking space, you might get the benefits of an office — a quiet environment where you can be productive, enjoy unlimited coffee, and have people to socialize with — without feeling like you’re trapped, since you can come and go as you please.

Meet your clients

Whether in-person or through video chat, meeting your clients is a great way to stay connected to your purpose and counteract feelings of loneliness. Platforms such as Zoom, Skype, and ClickMeeting make it easy to set up virtual meetings.

By meeting your clients, you can brainstorm ideas, share meaningful feedback, and stay inspired.

Create your own team

Depending on your field, it could make sense to team up with other freelancers to offer collaborative services. With this approach, you’ll still have the independence of freelancing but have the built-in social network of your team.

Freelancer problem #5: Dealing with difficult clients

Difficult clients are the ones who aren’t clear about their goals, don’t respond on time, set unrealistic deadlines, or are just plain unpleasant. Some clients even becomes intrusive and call you in the middle of the night for updates or revisions.

And the worst ones fail to provide timely payment, so you have to keep following up to get compensated for all your hard work. More often than not, the ones that want you to fire extra cylinders to complete their task are the same ones who take three months to complete a minute’s money transfer. Oh, the humanity!

How to deal with these freelancer problems

Communicate

Get clear on what you can and cannot accomplish, and stick to these boundaries. Be transparent with clients from the beginning about your working hours, the time zone you live in, how many revisions you’ll do, and the payment date.

If a client calls you at odd hours, don’t answer and send a courteous email later on instead. Consider putting your phone on ‘do not disturb’ mode during out-of-work hours. If a client still expects you to fly to the moon and back again, it could be time to professionally disengage.

Always craft a written agreement with the client

The best way to avoid chasing clients for payments is to have a contract in place. Charge a late fee if the client misses the payment date. Refer to the agreement just in case the client refuses to pay, tries to pay too little, or demands you go beyond the scope of work both parties agreed to.

If you’re connected to the client through a freelancing platform such as Freelancer.com or Fiverr with no written agreement in place, always ask them to set up a milestone payment before accepting their offer.

issues with freelance work

Freelancer problem #6: Filing taxes

Filing self-employment taxes is by far one of the biggest freelancer woes. The struggle gets even more real for new freelancers who are not aware of their unique tax situation. Nothing lowers the high of working on your own terms like a hefty tax bill from the IRS.

Freelancing tips for filing your taxes

Keep track of your income and expenses.

As a freelancer, it’s incredibly important to keep a clear record of your income and expenses. Your records will help you estimate your profit, tax liability, and refunds, as well as protect you from penalties.

I learned this the hard way after losing two important receipts and having to pay $1,000 in fines and interest (sigh). Learn from my mistakes and keep a separate bank account for your freelance income. And don’t forget to send an invoice before you get paid.

Take advantage of digital tools so you don’t lose important records. Services such as GoDaddy Bookkeeping, Shoeboxed, Wave, and Xero can help you convert receipts into a classified digital archive, which you can send to the IRS when the time comes.

Set aside money to pay your taxes

When you’re an employee, your company takes taxes out of your paycheck before you get it, so you don’t have to worry too much about overspending. But as a freelancer, you’re responsible for paying your own taxes at a later date.

So set aside 15-20% of each check aside immediately after you get it and don’t spend that money until tax season comes around. If you don’t budget and save for your taxes, you could get hit hard with a big bill you can’t afford to pay.

Pay your taxes quarterly

The best way to avoid ending up with a massive bill every year is to pay your taxes quarterly. As a freelancer, paying taxes quarterly will help you avoid penalties. While you’ll still have to file at the same time everyone else does in the spring, you probably won’t get hit with a big tax bill if you’ve been keeping up with your taxes throughout the year.

Although quarterly taxes can be a pain, it gets easier with practice. Plus, you might get to claim a whole bunch of deductions as a freelancer, such as deductions for your business expenses and home office.

Hire an accountant if things get too complicated

If you’re feeling totally lost with your taxes, it’s a good idea to hire an account or tax advisor. Even though tax preparers cost money, this fee could end up saving you a lot of time, money, and headaches. Your accountant might even discover tax write-offs you never knew about.

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Freelancer problem #7: Managing an irregular income

Freelancers don’t have the safety and security that comes with a regular salary. You might make $200 today and $2,000 tomorrow. While your income is inconsistent, sadly your bills probably aren’t. Not knowing when your next pay cheque is coming in can leave you stressed if you don’t take a proactive approach to managing your personal finances.

How to deal with this common freelancer problem

Create and follow a budget

Crafting a budget is key to handling your finances as a freelancer. Even if your income fluctuates from month to month, calculate an average to get a sense of what you’re working with.

Add up your regular monthly expenses so you know your necessary expenses. Write down your savings goals, too, and try to set aside a little bit of money into an emergency fund each month.

Figure out how much discretionary income you have to spend on entertainment and other non-essentials each month, and make sure you stick to your budget so you don’t end up in the red.

Maintain a healthy cash reserve

Regardless of how long you’ve been in the business, you must keep some backup cash in your accounts for those quieter periods when no work is coming your way. In fact, I would only recommend taking the plunge to freelance work once you’ve saved up enough to cover your bills and other expenses for the next two to three months.

Consider setting up a separate savings account for your emergency fund and funnel a certain amount each week or month into it. As you build your savings, make sure not to touch that account unless you find yourself out of work or run into an unforeseen emergency.

Avoid impulse buying

Although it’s tempting to increase your spending when you start making more money, avoid this impulse to inflate your lifestyle. Continue following your budget, whether that involves preparing your own meals, traveling during off-peak season, or finding cheap or free activities in your area.

You might want to splurge on a shiny new car when you get that first big check, but you’d probably be better off putting that money aside for bigger goals like buying your first home or saving for retirement.

issues with freelance work

Are you up for the challenges of freelancing?

There’s no shortcut to freelancing success, and the challenges that often come with working remotely make some new freelancers give up the ghost before they taste success.

But with the occasional freelancing woes, this career path also comes with exceptional advantages, such as total control over your work and schedule.

Plus, you can pursue your passions and work on projects you love while building an impressive portfolio. To be a successful freelancer, it’s critical to set realistic goals, actively market your services, and manage your time in a way that works for you.

Once you become a practiced freelancer, these problems freelancers face won’t seem nearly as monumental, and you’ll instead get to savor the freedom that can only come with being your own boss.

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