Challenges That Freelancers Face and How To Solve Them

Last updated on July 11, 2020

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“At least you can sleep in, probably until 10 a.m! I so wish I could do that!”

This is the response that Betty, a friend of mine who works for a local bank, gave me, right after I had told her that freelancing isn’t for everyone. She had been complaining about the latest antics her mean boss had done  the previous day. As far as she was concerned, she had the boss from hell while I had it easy peasy!

I laughed, because I don’t wake up at 10 a.m. I don’t have the luxury to do that. But this just exposed the fact that people aren’t aware of the challenges that freelancers face.

Read: How Do You Identify a Difficult Client

Freelancing is the best career choice that I ever made. I said goodbye to the stone-faced boss, some cheeky, ever-talking and gossiping workmates, a fixed salary, and lengthy morning commutes. I, however, said hello to new things; things that elevate and demotivate me at the same time. Now that we are clearly aware of the benefits that freelancing has awarded us, allow me to highlight the biggest problems that freelancers face and how you can solve them.

1. Self-discipline

I am a member of several freelancing Facebook groups and when I asked in one of these groups, “What is your biggest challenge as a freelancer” this came up as number one!

At the office, you had rules that said you had to be at work by 8 a.m. or you had to meet some benchmarks, or, sometimes you had to work overtime. What about now? Do you at times sleep until the sun is hotter than your pans? Do you binge watch 4 episodes of Blacklist (or your favorite series) from 9 a.m.? Do you allow your friends to stop by at any time and endlessly chat about the latest trending stories? Or do you leave your workstation whenever you mind suggests so? Well, all these are instances where you lacked self-discipline!

Read: Sure Ways to Fail In Your Freelancing Career

Rather than punish you for I was once a victim, let me help you out. Keyword: be strict with yourself. Create a schedule like a school timetable, complete with time and rules. Indicate when you will be at your “office” working, set resting times, decide when to wake and retire, then set targets. If possible, print this out and fix it right next to your workstation. I’ve done it and it works like magic!

2. Time Management

The internet is an angel and a devil at the same time, what with all the catchy headlines bombarding us everyday.


You quickly click on the link only to realize that you have wasted your precious 15 minutes reading yet another nonsensical story. Remember that if you were at the regular 8 to 5 office, all of these would not be possible.

What to do? Make use of the schedule that I previously mentioned.

A things to do list is a must-have for every freelancer. I cannot overemphasize this.

Once you have set your working hours, do nothing but work! Have the courage to resist any distractions such as your TV or a friend. You can allocate your leisure time to such.

3. Lack of Self-motivation

I am the kind of freelancer who doesn’t miss having a boss. But maybe you do. Maybe you can recall those days when you had to work with a cold or do some extra hours because you had not met your benchmarks. The point is, you had a boss and you had to meet the targets so that you received your dues.

I, at times hold meetings with self and I argue about taking one day off my routines. “It’s my choice, anyway!” I at times say. When you find yourself inventing excuses not to work, classify that as lack of motivation. What to do? You can cure this by having a friend or a group of freelancers to share with. If you realize that other people are working hard as you watch a movie, you will probably be challenged to work. There are plenty of freelance groups on Facebook and LinkedIn that you can join.

Read: What Are Some of The Freelancing Commandments That You Should Follow

Here’s another one solution. Ask yourself, “What is my ‘why’?

Why did you decide to become a freelancer? Probably because you needed extra income or for many freelancers, because you wanted to be in charge of your own time. Keep your why in front of you and it’ll keep you motivated.
You can also calculate the amount of time that you waste and convert it into money form. For instance, if you earn $10 an hour, that means you’ll lose the same amount for every hour lost. That should get you really motivated!

Lastly, set goals – time-based goals and see how motivated you become as you attain them one by one.

4. Fast, Reliable Internet

Slow internet is another problem that freelancers face, especially in developing countries. Without good internet, everything stops. In fact, slow internet was listed as one of the most annoying things on the planet in 2014. Unfortunately, human or natural errors will always cause this problem.

In the light of this, I try my best to have the best connection. Yes, slow and unreliable internet is inevitable, but you can minimize the disappointment. First of all, find out which network provider is the best in your area. Do not use any provider just because your friend says it works well. Second, find a reliable provider, i.e. one who is stable. Last but not least, do not go for the cheapest because, in most cases, cheap internet will disappoint you.

5. Lack of Steady Workflow

Regardless of what you are: data entry assistant, academic writer, transcriber, binary trader, graphic designer and all else, we have low and high moments regarding work. Today, you might have tons of work to do, then, tomorrow, you have to fight for the few low-payment jobs available. That’s feast and famine for you. Again, this is inevitable but not overwhelming.

What to do: One, work with sites that have regular work flow. This way, even during the dry spells, you’ll have a bone to chew. Second, diversify. Don’t put all your eggs in one basket. I bet there is more than one website where you can get your freelance work from.

Third, maximize on the times of plenty harvest. Work as much as you can then store the surplus for the drier times.

If the ants can do it, so can you, dear fellow freelancer.

6. Longer Working Hours

I know you eagerly waited to hear about this. You must be a unique freelancer if you never worked in the dark or exceeded your set working hours. It happens! At times, your body is in overdrive and you just feel like working and working and working. Other times, it’s simply because you bit off more than you could chew. Sometimes, though, some of us have to work during the wee hours because of time difference: the clients might be up when we should be asleep!

Read: Tips To Help You Quit and Freelance Full-Time

What to do: Don’t take on more work that you can handle but if you do, outsource to qualified affordable freelancers. Believe me, they are there. Adhere to your schedule so that you don’t push work forward that would have fitted into your regular working hours.


As you can tell from this blog post, freelancing is not as easy as it appears. Being your own boss doesn’t mean reduced roles, more comfort and getting rich quick. Freelancing means an expanded role, deeper self-control, extra self-discipline, better time management and potential alignments from the normal working routines. What we have discussed are simply the challenges that freelancers face: they should not scare anyone.

In conclusion, I would suggest that you love freelancing together with its challenges. Remember what Confucius said? “Choose a job you love, and you will never have to work a day in your life.”

Over to you. What are some of the key challenges that you are facing right now?


About the author

Virginia Nakitari is a work from home mom passionate about making money online. She's here to show you legitimate companies offering full-time, part-time and remote jobs from home! Stay tuned!

  • Thanks Sheeroh for the very informative piece. My greatest challenge is self discipline. There is always something “pressing” that comes my way. I know what my goal is and believe if I apply some of what was in your piece then I can achieve my goal

  • I identity with most of those problems. Any pointers as to the “best” internet provider. I seem to be spending a lot on internet, about 1500 a week yet i have the worst connection. I would like to know how others are coping and what their experiences are like.

  • Lack of motivation can be a big challenge to a freelancer at times. I shall briefly share my story here. I stay alone in a relatively quiet place. As one would expect, I work from home. Now, the serenity of working alone in a quiet house can be attractive. One gets all the time to concentrate and produce really amazing work but at times, having to stay indoors and alone from Monday to Friday can be quite monotonous. The good news is that I discovered a trick. Whenever I feel like doing it, I go out for meal or a cup of coffee. I also make a point of going out to restaurants every weekend. I carry my tools and work from a restaurant throughout the weekend. Interesting but it works.

    • As I was reading your comment, I was thinking, “Just carry your laptop to a restaurant or library near you” But you took the words right out of my mouth. I don’t do that but I’m very active in several freelancing groups and that keeps me very motivated.

  • Thanks Sheeroh,

    These are truly motivating gems.

    This is my second year and my biggest challenge remains “Lack of Steady Workflow” but from a different angle. You get a good client who for example wants 6 quality pieces daily, so you fear taking another client least you compromise on quality or on delivery. Then your “good client” goes missing for 2 or 3 days! You take on something new, then he/she resurfaces!


    • Dilemma indeed! That is why you need to have at least two great freelancers, who are reliable and who can deliver high quality work. That way, when you get additional work, you won’t have to let the other client down.

  • Hi Sheeroh,

    It is like you have been reading my mind, some of these challenges I must say I struggle with most of the them. Now that my house is my office, I get visitors whom you can’t really avoid but most of the time I only sacrifice at most 30mins then I excuse myself to get back to work.
    Time management is another one but with time I am coming up with ways to crack it and progressing well.
    These tips are very practical and I will work on them step by step. So far so good though it is not easy, as you say this is not for every body although it is workable.
    I will work hard and strive higher.
    Thanks for sharing.

    • That’s a very practical way of dealing with unexpected visitors. They are able to understand that they cannot take a whole hour chatting away. With time, they will cut down on the ‘we were just around the neighborhood’ talk. Trust me, it will come to pass. 🙂 When that happens, you will have all the motivation to indulge them a whole Saturday afternoon!

  • Hi Sheeroh,
    I just love your posts like always.
    You will agree with me that all the points above not only apply to freelancers but all online business.
    I find so much education here though am not a freelancer 🙂
    Thumbs up for such a great piece.

    Best Regards.

  • Well put, my spouse and I work online and guys think we are a cool family, but only God knows what we go through. In a nutshell those challenges are spot on, somehow my Spouse ended up being an introvert yet she had always been this outgoing lady, but hey, at least we have a hustle, right?

    • And an awesome hustle at that! I think it’s important to schedule some days, like weekends, where you can go visit friends and family. That should keep the ‘introvertness’ at bay.

  • hi Sheeroh. I identify with the challenges you listed above. One of the interesting thing that challenges me is that previously I had my boss so I had to play by the books. Now I am my own boss and having no book to play by really takes a lot of discipline to work as required. Working towards it though. Thank you.

    • Exactly. You are your own boss now and success (or failure) is entirely up to you. That should motivate you and help you stay on track. 🙂

  • Nice post. Let them that have eyes and internet connection read and understand this post. Working online is not a walk in the park, as some 8-5 workers think…some quit working online one day after venturing into it. However, working online is rewarding if only people follow all the tips you have adviced and managed their challenges.

    Keep up the excellent work.

  • Hi Sheeroh

    This is amazing piece you put out there. I had to comment

    “At least you can sleep in, probably until 10 a.m! I so wish I could do that!”
    Being the netpreneur that I am. I always laugh out when someone mentions something like that to me.

    It goes without a doubt that many people do not understand how much time we spend
    trying to make a living online. I have spent like 18-20hrs a day before which was an overkill.

    Self discipline is indeed one of the core challenges like you mentioned as the lack of it could
    lead one (even the oldies) down the drains of destruction.

    It is worth mentioning that I have also found a healthy diet and personal workouts to do quite
    some BIG lifetime magic.

    I now do not work for longer hours like I used to do and besides I can accomplish my to-do-lists much faster. 8-10 hrs And Boom!! (Instead of the previous 18hrs)

    Workouts have indeed contributed a ton in my self discipline so far as it helps shape the mind
    and the body.

    My experience with number 4 goes way back. What I did is look at my internet connection as one of the core investments. It is worth spending 5k -10k on a super speed connection.
    Give NO room for downtime either using a Backup connection as it gives you the peace
    of mind to work.

    The Benefits far outweigh the challenges when you accomplish your goals. How sweet!!

    • That’s such a great point, about backup connection. It’s very important for every freelancer to have a plan B. Working out is a great way to stay healthy, given the fact that we spend so much time sitting down. Thanks for your comment. Highly appreciated!

  • Hi Sheeroh,
    Your blog post is spot on. I used to agonize over slow internet connectivity. Eventually, I dealt with it. Exit connectivity enter power disruption. Kenya Power guys seem to dislike me and this affects my productivity. You’ve really challenged me on self-discipline; I now know better. As for steady workflow, that messed me up totally. I signed up for an academic writing site and was on cloud nine until low season struck. I had to go back to employment (so sad) at least to get the bills paid.

    • Hey Nicholas, A lot of freelancers seem to have issues with KP, myself included! That got much better when I bought a laptop. The only challenge is when there isn’t power for a long time and eventually the battery goes of. Sorry about the low season bit. That is where diversification comes in. Academic writers can try article writing, transcibers can also learn captioning etc etc. We need to put our eggs in several baskets! 🙂

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