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“Freelancing is tough. It can be very difficult, in fact. It can wear people down, making them lose sight of what they used to love because they have to do everything else just to get by.” – Mason Hipp, The Unlimited Freelancer

Recently, a friend of mine switched to become a full-time freelancer. Although I’ve been hearing horror stories regarding the profession, he was among the lucky ones who received a good gig just two weeks after quitting the usual day job. However, he also now has to take care of his benefits, manage his own pay, and go after clients who don’t meet their end of the bargain.

It sounds like a lot of headache, but for many freelancers out there, it’s just another day at work. Being the boss has its perks – the biggest of which is being able to own your time. Unlike people with jobs from 9 to 5, you decide who to work with and for how long. After that, you can either go on vacation OR take on another project.

As a tribute to all diligent freelancers out there – including my friends – I compiled the top problems they face in their chosen career, along with tips on how to combat them.

#1. Poor Time Management

Time Management

One of the easiest traps to fall into once you become a freelancer is thinking that work-life balance will just come naturally. After all, you are the boss now.

As you have no one to answer to but yourself, it can be tempting to take on one job after another. Until you realize that you’re back where you started: slumped at your desk at 2AM in the morning, writing reports or picking web fonts. Whatever happened to healthy work-life balance? Shouldn’t that be easier now that you work alone?

Solution: A freelancer once said “work anywhere – except at home”. He could be right. It’s easy to drag your job anywhere with you, even when you shouldn’t. If you enjoy working at home, make sure to setup a special place that’s similar to an office scenario. This should prep your brain into full focus.

Then when it’s time to logout, simply leave the space and do something else. It will take a while to get used to, but if you want that work-life balance so badly, you’ll manage to break bad habits.

#2. Work Overload

Work Overload

Many freelancers choose their predisposition because they want absolute freedom in pursuing their passion.

Whether it’s writing, web design, or consulting, they can often work for hours while forgetting to eat. Although it’s alright on occasion (after all, who doesn’t enjoy being busy at times), taking on too much tasks will eventually wear you out. Not only do you create a high-stress environment for yourself, you go back to problem number one.

It’s true that you won’t be earning much during your first few weeks as a freelancer. But that doesn’t mean you should overbook yourself just to pay the rent.

Solution: Time-management isn’t the only thing you need to master as a freelancer – but also budgeting skills. Take note of your expenses so you’ll know how much work you need to pay off bills (and have some for little pleasures, too). Choose from among the numerous mobile money management apps to easily keep track of your cash. If it gets too complicated, ask a friend for help.

#3. Late Payments from Clients

Almost – if not all – freelancers experience this at least once in their careers. While third party platforms like Elance provide protection, there are still some bad apples out there. Aside from the hassle you get, now you need to take on more duties to cover for lost income.

Solution: Know how you can protect yourself early on. If you decide to work alone, prepare contract templates so all parties have a written agreement. Invest in professional legal advice if you have to. Some freelancers advice on splitting payments based on the project’s progress (i.e. payment during startup, another one after mockups are delivered, and the final sum upon completion).

If a client still refuses to pay – and it’s too expensive for you to take legal action – let it serve as a lesson. You can warn fellow freelancers about this particular client so they can avoid him like the plague.

#4. Isolation


One of the greatest myths about freelancing is that, as you have more time on your hands, your calendar would be full of social events.

Definitely NOT true. You’re lucky if your friends are freelancers as well – but what are the odds? Most likely, your circle consists of average office employees who work when you don’t. While you can certainly spend all that free time scrolling through your Twitter Feed, in the long run, that’s not healthy for your eyes or your social life. So aside from your pets, who can you talk to about that exciting new gig you landed?

Solution: Work hard but play hard. Remember that work-life balance you’re so eager to get? You can’t achieve that without healthy relationships. If your friends are all busy during weekdays, ask them to grab lunch or dinner with you instead.

Block certain holidays in the year so you and your friends could all hang out together. Try services like to get to know new people in your area. Visit your parents. Go to freelancing forums.

Once you become a freelancer, being productive while staying at home is going to be one of the first challenges you need to overcome. Whatever you do, don’t limit yourself to that path between the coffee shop and your apartment. You’re a freelancer now! The world is your oyster.

Posted by Cris Antonio

Cris Antonio is the Chief Editor of She’s currently focused on helping healthcare workers find better career opportunities through Locum Tenens. Aside from writing, Cris also enjoys painting, collecting toys, and reading German novels.

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