The Pitfalls of Freelancing and How to Overcome Them

The Pitfalls of Freelancing and How to Overcome Them

Handling clients from hell, juggling tasks and deadlines, bidding for new deals, having the freedom to work in your underwear, sharing your workspace with your cat that’s also your coffee-break buddy, and last but not least – convincing your mother it’s a real job and not “a passing phase“: if you’re a freelancer, then most of this must sound familiar. All of it is just part of a regular workday in the freelancing world.

The freelance market is on the rise and business independency and proactivity in this sense are definitely gaining momentum.

The largest independent workforce survey commissioned by Upwork and the Freelancers Union has shown some insightful results: an astonishing 55 million Americans are freelancing (that’s a growth of 1 million people, in comparison to 2015), making their annual economic contribution an estimated $1 trillion! An earlier report, called “Future Working: The Rise of Europe’s Independent Professionals“ showed the same growth tendencies for the EU labor market: the numbers have increased by 45% (from 6.2 million to 8.9 million freelancers) in the period between 2004 and 2013.

79% of workers think freelancing beats a traditional 9-5 job, making them feel more motivated, respected, and career-satisfied.

The global freelance community is also steadily growing, which has been cause for speculation that it will be the leading workforce by 2020. According to this data, business owners that offer full-time office jobs will have to come up with competitive salaries or other ways to attract qualified talent. The survey has shown that 79% of workers think freelancing beats a traditional 9-5 job, making them feel more motivated, respected, and career-satisfied.

However, with the obvious advantage of doing a job you love and enjoying the perks of being your own boss, there comes a set of not widely discussed pitfalls. The good news is that, when you get to map out the usual difficulties, you can find your way of coping with them and work on reducing the way they might affect you.


It can get a bit lonely

Having the freedom to work from home or anywhere else means you can enjoy some peace and quiet, but it also means you are left to your own devices at all times. According to psychology experts, socializing with colleagues is important for personal growth (upgrading the level of emotional and social intelligence), as well as for building meaningful relationships and having a sense of belonging. The market of independent workers has evolved, but so have the traditional businesses making an office environment-friendly and inviting, while strongly nurturing a sense of community.

The undeniable freelance alienation can be overcome in three ways:

  • Joining a coworking space
  • Finding a virtual community
  • Real life mingling and networking

A coworking space will make you feel less cut-off from the rest of the world. In addition, it gives you a sense of professional environment without any distractions you usually encounter at home. Another perk is pointed out by the Harvard Business Review

Working in a co-working space will make you feel like your work is meaningful, which then helps you get better at it and increases your productivity.

Freelancers share a similar mindset because of the specific way they lead their work lives and tackle everyday problems: it’s not that hard to connect with other people online through forums, blogging, social networks, or even passively by reading a comic that will make you chuckle and sigh while thinking “so true“.

There are also support structures and real-life groups of freelancers and entrepreneurs which can relate to the things you go through on a daily basis. Do search for one in your local community: most of them offer workshops, seminars, or open debates.

Flexibility: a double-edged sword

Having flexible working hours can be great: no need to set the alarm and you are free to organize your day the way you want to. However, it can also mean you can fail at time management and fall into a hectic work schedule that leaves you with a feeling you’re working 24/7. The struggle with procrastination is real, which makes learning the basics of self-discipline mandatory. Luckily, technology’s got your back and there are many tools and apps you can use to keep yourself organized while respecting deadlines.

Here are the top three to consider:

  • Timely: with a smooth design and a user-friendly interface, Timely tracks time automatically in the background of your desktop, making it easier than ever to calculate your working hours and get the most of your day.
  • Harvest: in addition to helping you with time management, this tool allows you to send invoices and track your expenses; you can also connect it to your other business tools.
  • Focus Booster: it’s like you have a mother that’s constantly reminding you to clean your room, but a bit less annoying; jokes on the side, Focus Booster is a great tool that support staying on track by ticking things off your to-do list and helping you break work into time intervals.

Another important thing to point out: you have to let your clients know when you are available, especially if you work for the international market. Take time zones into consideration and set some boundaries if you don’t want to receive a call from a client at 3 AM on a Sunday. It would be the best if you manage to get a clear structure in your day and set working hours for yourself that you’ll actually stick to.

Freelance flexibility

You’re on your own, kid

While being an employee in a traditional working environment means you enjoy health benefits, superannuation, insurance – in the freelance world you’re totally on your own. Generally speaking, freelancers are on no man’s land when it comes to laws and legal policies.

When it comes to EU states, most of the laws for the self-employed are actually just an adaptation of existing policies, instead of being specifically designed for this group of people. Due to the lack of an efficient system of monitoring, many of those who are self-employed are not entitled to unemployment insurance: there is no way the government can be sure a person is truly left involuntarily unemployed. The same goes of sickness and disability, which is why many freelancers complain about not getting the adequate support they pay for. Freelancers have a vague place in the tax and social security framework, falling somewhere in between individuals and businesses.

To keep your finances in order and ensure you’re paying your taxes right, try using online tools, such as QuickBooks Self-Employed, while tools like PayPal are great for receiving payments, and Expensify is awesome for tracking income.

The good, the bad, and the ugly of variable income

Another setback of freelancing includes financial uncertainty, especially if you’re project-based. You cannot count on the same amount of money each month. Sometimes you get swamped with work, which means you have to work long hours, but eventually – you feel accomplished with money piling up on your bank account. At other times, there is a sad tumbleweed rolling across your to-do list and you’re getting anxious about whether or not you’ll be able to close a deal soon.

Sarah HorowitzIndependent workers, by the very way they are working, this new way, are the vanguard. they’re the ones who are showing us the future.Sarah Horowitz, executive director of the Freelancers Union

There should also be a special place in hell reserved for clients who don’t pay on time: if you’re a freelancer, hitting that refresh button to see if your PayPal balance has changed certainly sounds familiar. The Freelancers Union Survey has found that in 2010, 44% of independent workers had some sort of problem with payments. This issue needs to be a priority for lawmakers because this malicious behavior is also stripping the government of taxes.

Dark side of freelancing: the skill rot

Today’s traditional workplaces usually offer many different types of training for their employees. While an average freelancer can devote some time to working on professional development, too often are skill levels left to lull themselves to sleep. You get cozy with your usual orders, it becomes easy money, and you just stop upgrading professionally. Not having enough challenging projects or doing the same thing over and over again can be a bit tiring at times.

Don’t let yourself fall into this dark hole: constant learning is crucial for maintaining your value on the market and keeping personal work satisfaction. Do your research and find out what skills are in demand. You have to keep up.

Once you’ve determined that, embrace the perks of the internet: thousands of free online courses (check out Coursera, edX, or Iversity), materials, textbooks and guides. Knowledge has never been this accessible, so make sure you take advantage of it.


Problems of putting yourself out there

When you’re a freelancer you have to learn to swim with the big fish, instead of sleeping with the little ones. The market is huge and growing, which means you need to convince your potential clients of your value and talent. This is why you need to create a high-quality portfolio, no matter what niche you work in. And, shockingly – the best way to do it is to create a personal website.

A portfolio is the key to sealing the deal and here’s why:

  • It shows your potential clients you have relevant experience
  • It is a direct display of the quality of your work
  • It helps people determine whether or not you share the same mindset
  • It testifies to the level of your creativity and shows how innovative you are

When making a portfolio, make sure you include only the highlights (your best work), make it versatile, and follow the basic rules for creating an eye-catching one.

In addition to ensuring your virtual presentation, you must not neglect real life networking. Seize every opportunity you can to promote yourself, but avoid being too pushy. There’s an art to estimating to whom you should flash your business card and who is just a lovely interlocutor. Use the power of social media not just for making personal connections, but for building business ones, too. The sooner you realize you have to be very proactive, the better.

Problems with safety: handling clients and protecting yourself

In addition to the obvious need for technical skills, freelancers need great interpersonal skills too. This especially applies to networking and negotiating the salary and terms with clients. The most challenging thing for a newbie in the freelance world is to figure out how much should he charge for his work. There are three things to consider:

  • The average pay for your niche (consult online forums)
  • The current state of the market (perhaps there is a lack of available talented workers in your niche?)
  • Your own personal value on the market (experience, clients you’ve worked for so far, quality of your work, flexibility, ability to meet client’s need, etc.)
Call.Me is an instant messenger and video/audio platform with the utmost level of privacy, the best encryption and the tightest security tailored especially for you.Call.Me

To avoid being played, make sure every single detail of your agreement is stated in the contract. Negotiations can be a great insight to the type of client you’re dealing with. Can you trust them to pay? Do they even know what they want? Are they reputable or do they have a shady history? Never be too desperate to accept every deal! Learn to say no.

This is a slippery slope and another pitfall for freelancers: sometimes, your assessment might be wrong and you could miss an amazing opportunity to work with someone that could launch your business. However, you should follow your instinct and stay away from offers that don’t meet your criteria. If the legal stuff scares you a bit, consult a lawyer a couple of times until you gain the confidence to handle these things on your own.

freelance paperwork

In addition, make sure it’s clear you own your intellectual property and protect it wisely. Not to get too paranoid, but the internet is not a very safe place. Have you seen all the drama about Mark Zuckerberg taping over his webcam? This is why you should be cautious about how you virtually present yourself and what data you are leaving unprotected. There are numerous cases of freelance work being stolen over the web, so maybe it’s better to be safe than sorry.

Consider using protected communication (encrypted messages and files) provided by Call.Me so no one can trace you while you’re online, making you and your work safe during negotiations or any other form of communication. It’s available both as a web app and a mobile one.

As the last takeaway, to cite the great Charles Dickens: freelance has the best of times, and it has the worst of times; it has its share of wisdom, and it has its share of foolishness; it makes you believe, and it leaves you incredulous. Ok, he never actually wrote that – but it’s close enough.

Freelancing has its pitfalls, but it is exciting and liberating. There are setbacks in traditional jobs too: it all comes down to how well you can handle them.



Sarah Green

Sarah Green explores the latest web trends and covers stories related to technology, startups and digital life in general. Writing professionally since 2012, she has developed a sixth sense for trending topics in these fields.

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