Top 7 Freelancer Challenges You Ought to Know About

Top 7 Freelancer Challenges You Ought to Know About


Ayesha Saini

Ayesha Saini

509 week ago — 5 min read

With top-notch companies contemplating abolition of the 40-hour work week; and CEOs openly acknowledging about not having it all, the lure of breaking free from the 9-to-5 mechanism has been a trigger for many.


Undoubtedly, freelancing has its befitting perks. 


Right from sitting in the driver’s seat (looking onto a wide open windscreen), to earning more sans the approval of your commissioning boss, or relishing the perils of solopreneurship –reasons why people have ditched their regular job to kick-start their freelancing careers are aplenty.


Having said that, freelancing is not always about sitting under the sun, getting a beach tan, ummm! sipping on coconut malibu–and working on the latest projects. It is infused with major challenges (willingly or unwillingly) that even the most seasoned self-employed freelancers have faced. 


Henceforth, to help you sail through the choppy waters of freelancing woes, here are some top freelancer challenges you ought to know -


  1. Finding Clients and Staying Upbeat About Your Work. Finding the right niche of projects, and getting your foot in the door genuinely takes time, care and attention (and a lot of patience), particularly if you are dealing with a new client.

    While establishing an initial connection with a client can be vexing, as it might involve hitting the ‘send’ button on your mail copious amount of times, making inane phone calls and handling knock backs and silences aesthetically. But, what outweighs the deflated zeal is when you start to build on your portfolio, are able to build your client base steadily, and subsequently grow your reputation with it. 

  2. Forgetting To Sell. Most freelancers believe that they can do it all by themselves if they but keep their quality intact; nevertheless what most end up overlooking is the concentrated efforts one must focus on while selling their products or services in front of potential clients. Freelancers generally tend to harvest work relentlessly by giving a royal miss to seeding their business in the form of marketing or selling their brand name. Simply put, when they harvest, they stop seeding!

  3. The Collaboration Catastrophe. Juggling with ones skills and talent when you are a one (wo) man show might be one of the toughest challenges for you. Most singleton freelancers can’t help but think that they can do all the work by themselves. Yet you can change this challenge into an opportunity by joining hands with juniors or associates in the same business and spreading the daily duties evenly, and as a result, increase the value of your service. 

  4. Time: The One Entity You Just Cannot Control. Depending upon the non predictability of their line of work, freelancers generally face a hard time jettisoning between their not-so-good-paying clients, and good ones, thus adding to their work woes. Apart from this, meeting during effective work periods or skyping at ungodly hours, especially when one works with different time zones, can at times be extremely demanding. There will be times when you would find yourself muddled between a host of tasks; and you won’t be able to take your eyes off your laptop for hours together.

  5. Procrastination Is A Silent Killer. You bag that much-awaited project, but still keep on (repeatedly) convincing yourself that you’d sit on it super soon only to discover that the luxury of time is no longer by your side and the slated deadline is breathing down your neck. This stands true for not only freelancing, but for other aspects of life too. The trick here is to be a stickler for the phrase – ‘work first and play later’ – and you shall never go wrong.

  6. Not Every Hat Fits. Freelancers of a case-specific field might find themselves wearing multiple hats all at once. Right from marketing, accounting, client servicing to providing your own skilled creative freelancing services. Wearing varied hats can be a major challenge for a creative personnel, as he or she may not be strikingly good at making compulsive to-do lists, managing finances, keeping record books and marketing their brand, all at once.

  7. Bright Shiny Object Syndrome. While trying to carve their own brand/niche, when freelancers get easily distracted, face trouble in finishing projects, bounce around in a disorganised fashion, spin themselves all over the place and scratch head in-between multiple ideas – what they suffer from is called the Bright Shiny Object Syndrome. Often considered as scattered or flaky, such freelancers fail to formulate a fixed strategy for their work, or even if they do develop one, fail to stick to it in the long run. So keep re-inventing. 

    There you have it, a quick pick of top challenges self-employed freelancers face.

    What’s been yours?

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Ayesha Saini

Digital Writer and Blogger. Accidental Entrepreneur.