Why Freelancing Is Freakin’ Hard

Rock climbing is hard, and so is freelancing.Despite how magnificent it can be to work for yourself, there are some things about freelancing that just plain suck. And no matter where you specialize, these vicious drawbacks usually find a way of asserting themselves.

What drawbacks am I talking about?

  • Dealing with the feast & famine cycle
  • Managing every aspect of business entirely on your own
  • Finding time to market yourself, do client work, deal with clients, keep up the administrative stuff, and still grow the business
  • Balancing work and life (and often family) while dealing with all of the above
  • Getting sick, going on vacation, or otherwise not working 24/7 while still dealing with all of the above

Now if you only look at these negatives, freelancing seems like a pretty bad idea — that’s definitely not the case. It’s important to acknowledge the challenges of freelancing, though, so that you can manage them and learn to free yourself from the usual limitations.

And that’s what we’re going to do in this article.

The Feast and Famine Cycle

This is a problem that most freelancers deal with painfully at the beginning of their career — and usually still manage later on too (hopefully with less pain).

It starts when you have lots of free time and very few clients, when the obvious thing to do is to market a lot. After marketing for a while you’ll get clients and eventually start running out of time — and then you’ll stop marketing (because you’re packed with work and have no time). Finally, when you’ve managed to hammer through those client projects and finish all of the work, you’re left with very few clients again, and the cycle repeats.

What to do about it
The feast and famine cycle is primarily a problem of time. If you can shave a bit of time off of your client work, and automate some of your marketing, you’ll do a lot to alleviate the stress. You can also even things out by building alternate sources of income that are steadier than client work.

Managing Everything Yourself

Like the feast and famine cycle, this is the hardest at the beginning, but the problem never fully goes away. Truth be told, managing every aspect of a growing business is incredibly difficult to do on your own, regardless of how much experience you have.

The root of the issue is that there is simply too much information for any one person to handle. It’s like trying to view an entire atlas at one time — you can’t do it unless you flip to the front and look at the “general” map that doesn’t have all of the details.

It’s the same for freelancing. Very, very, very few people can think about the accounting, legal, marketing, customer support, industry, and strategy/growth aspects of their business at the same time. Trying to plan, manage, and schedule all of these by yourself is a recipe for disaster.

So don’t try to do it alone.
The solution to this problem is an easy one — get help from other people. You shouldn’t do your own accounting, let an accountant do it for you. If you can delegate the less important tasks, and only focus on what’s important to you, then your business is likely to be in much better shape.

Doing Everything Yourself

If thinking about and managing everything is a problem, than actually doing it is much worse.

Let’s say you’ve found help from an accountant, and you’re using some tools to help with the marketing. That still leaves an enormous amount of work to be done by you — enough that you’ll eventually run into an earnings plateau and have a hard time making more than that. How happy you are with that number and how much time it requires to maintain it will depend on how well you’ve handled the other problems.

But what if your income weren’t time limited? What if there were ways to leverage your time so that you get more work done with less effort? There are…

The way to beat these time and earnings limitations by working with other people. You could outsource some of your work, you could work with other freelancers, you could find partnerships. You can create an entire distributed team. With these concepts time is no longer a limiting factor on your income.

Maintaining a Work/Life Balance

The hardest part about all of this is that freelancers don’t work in a vacuum, separated from everything else. We have lives, families, hobbies, and many other things that demand our time. We just can’t work all day and all night.

Not to mention, freelancers who do work all day and all night typically end up burning out in a spectacular ball of flames (yep, I’ve done that).

How to keep a healthy balance
The trick to keeping a good work/life balance is pretty easy, at least in theory. It tends to be very difficult to actually put into practice.

The ‘secret’ is to set limits. Only work during set hours. Deal with clients during designated periods. Take breaks at regular intervals throughout the day.

Unfortunately, there aren’t many ways to make it easier, though having more time overall will help. So in a way you’re lucky: dealing with the other problems we’ve mentioned will help alleviate this one too :-)

Planning for emergencies

Perhaps the worst thing that can happen to a freelancer is getting so sick that they can’t work. Losing the only employee of a one-person business is devastating, and it can happen without warning.

So what can you do?

There are a few ways you can deal with this. The first is to have someone ready to answer emails or take phone calls in your absence. It doesn’t have to be a good solution, it just needs to work in an emergency.

The second part is to have someone you can call to take over some of your work if it becomes absolutely necessary. I recommend working with other freelancers on a regular basis anyhow, which makes setting up a situation like this even easier.

If you have those two pieces standing by, unexpected emergencies will be a lot easier to deal with.

So what’s the big answer?

As we hinted at throughout the article, the answer to these problems is to treat your freelancing more like a business and less like a job. Start building systems that save you time, start working with other people where it’s valuable to you, and start to build assets that bring in some steady money.

Of course, doing all of this can be very difficult, and there’s not a lot of information out there. Which is why, I’m happy to say, we’ve been working on an ebook for the past several months that outlines exactly how to do all of these things — in detail. If you find yourself dealing with these problems, I highly recommend you check it out.

You can get more information by signing up for the early notification list

Update: the book is on sale! Click here to learn more…


  1. says

    Very nice list. I find myself most falling into the whole “one man army” do everything hole. Only recently have I had to reach out in order to keep from being buried in unrelated work.

    Great post!

  2. says

    Great post, Mason. The section about hiring an accountant is especially good. I think it might be worth adding a section to the Forums listing different professionals in the different fields (accounting, writing, etc) so that we can take advantage of the collective minds of everybody who reads this blog.

  3. says

    Excellent article and very true. It’s not often you get people posting the truth about just how hard being a freelancer can be and all the obstacles we face. We do it because we love writing and for those of us that do make it big it is because we start to see our writing as a business.

  4. says

    @Zach — Yea once you hit a certain amount of work the one-man thing starts to get very difficult very quickly. Congrats on getting there though, that alone can be pretty difficult :-)

    @David — That’s a great idea. I have to consider how to phrase it, and how we would moderate that, but I think a services or some other type of forum would be really cool.

    @Amanda — Very glad you enjoyed it. Freelancing is definitely difficult in a lot of ways, and I think it helps to acknowledge that and consider other ways of doing some things.

    Thanks for the comments!

  5. says

    It is hard! Excellent article, you would think now on my second or third attempt at entrepreneurship/freelancing that I would have some of these aspects nailed by now. It is so easy to succumb to some of these issues, especially when you are out on your own. Trying to do everything yourself, letting clients creep into what would normally have been your hours off or getting so wrapped up in your work that you loose sight of why you started freelancing in the first place.

    You hit it on the head the with this article, the trick is to identify the problem and learn how to overcome or at the very least manage it. I recently set out to start solving these problems in my own freelance career and your article was just the push I need to move forward, thanks.

  6. says

    I think managing the work life balance is the hardest. Not only is there no “clock out time”, but your personal life is constantly blending with your work life. Setting some boundaries and not letting your work bleed over too much into your personal time is key.


  7. says

    Health is a biggie. I had surgery on my thumb and was using my four fingers to type. My thumb swelled again. Turned out I was overworking it. So now I have to type one-handed until Jan 6. Ay yi yi.

  8. says

    The feast and famine cycle is something that we all go through.

    The best way to deal with this (based on my experience) is to either a) limit yourself to a few clients per month, b) recommend a colleague, or c) outsource some of the work you feel isn’t too mission critical (e.g. XHTML/CSS for example – or if a client needs a blog, you can find a design-to-wordpress service).

    Work/life balance is also crucial – it helps to set a schedule (e.g. every 4pm, you stop for a while, and do something for yourself).

  9. says

    Great list. One important thing I learned is to try and find prospects who are already, actively, trying to find services you provide – as oppose to trying to convince a company that they need your services. People are so immuned to sales that they’ll turn down anything, even if it benefits them.

  10. says

    Freelancers, whatever you do, don’t sit back in your chair, slouch and stretch your arms toward the keyboard while you work. It seems comfortable at first but the pain that you will get in your back and shoulders doing this for too long is brutal. There’s a right way to sit and this is not it.

    When there’s no mandatory breaks, trips to the water cooler or end of the working day at 5, a bad habit can easily become a health crisis. And my insurance at the time would not cover trips to the chiropractor!

  11. says

    Good post – thorough and well thought out. Yes, everyone thinks about how easy it is to be a freelance and all the perks that go with it, but there are so many hidden unknowns and tough lucks that you really have to perservere.

  12. says

    A growing trend for freelancers is coworking. Coworking allows you to mitigate many of the problems you mention in your post. Coworking is mainly about independents working in the same physical space as other like-minded independents. This proximity helps create a collaborative environment that lends itself to accelerated serendipity and unexpected ideas. Marketing and networking are a natural, unforced byproduct. Work/life balance strains are relaxed as work no longer remains exclusively in the home domain; additionally social interaction while working reduces the stagnation and isolation that can crop up working alone. Find a coworking location near you to check it out: http://coworking.pbwiki.com. And, if you are in Austin, we’d love to see you at LaunchPad Coworking when we open!

  13. Matt says

    The easiest way to help yourself and others is to simply hire someone as an employee. You will gain free time doing drudge work while increasing sales and gaining additional revenue. Turn a one person operation into a business.

  14. Sertys says

    Freelance is anything but business. It’s a great adventure, no matter what your area of expertise is, just because you tend to improve yourself regardless of the standard set of rules. You dig wherever you want and please the client the way you feel coolest. I’ve been a freelance software developer myself for a few years of my humble existence and the “thrill” of a project near completion is still filling up my mornings from time to time.
    I miss the nights in front of the monitors, exploring the depths of the linux kernel or trying to figure some javascript routine for fun or profit. My perl days were the greatest though :)

    I’ve changed since then by means of mentality and wealth. I now know that i’m not necessarily obligated to work for my living. There’s lots of people who would do that for beercaps.. The catchy thing with freelancing is people thinking they’ve left the rat race of life, but it’s just to find out they’ve entered the rat olympics of existence. It gives you a unique freedom of act but puts you in the position of responsibility for lots of un-casual things.

  15. says

    Awesome list!

    Marketing is my biggest problem / challenge. Even though I have the technical ability, it just seems to be hard for my potential clients to find me.

  16. says

    I worked freelance for 10 years. When a corp job fell into my lap, I figured I would give it a try. I kept a few of my best clients and moonlight for them.

    It is great not having to worry about money, and working for the man is easier in that when I f-up, they pay for the mistake. But boy do I miss the freedom and the pride of knowing I, as in no one but me, made a project happen.

    Thanks for reminding me of the struggles I dealt with as a freelancer. Makes the corp job a little easier to suffer.

  17. says

    When people ask me what I do for a living, I tell ‘em I’m “self-unemployed” as an aircraft broker on the internet. Working at home, you do get to work all the time, and it is hard to set hours when your website invites prospective buyers to “call you now” to discuss a plane. So, whenever I leave the house, the calls transfer to my cell, and it isn’t unusual for me to be talking to a client while I’m trying to get groceries through the checkout lane.

    But, I love what I do, and after wearing a suit and tie every day for 30 years, I now often work in my pajamas and slippers until afternoon when I head downtown to run errands.

    A big break came for me a couple of years ago, when I moved from a desktop to a laptop computer with a Sprint wireless card, so I can be anywhere and still run the website and get my email. So, now I get to work out of a Nevada casino hotel room or similar, when it is snowing and blowing back in Minnesota.

  18. Doug in Seattle says

    I’ve been solo for 20 years now. Your assertion, “Perhaps the worst thing that can happen to a freelancer is getting so sick that they can’t work.” is close, but not THE WORST. The worst thing a freelancer can do is not pay their taxes. All of them, including unemployment. I’ve seen folks try to slide for a while. When the IRS finds out, they are like a dog on a bone. Good luck keeping any worthwhile assets!


  19. says

    Some things that help me to feel a little bit better (as web developer)…

    1) Stay structured: Keep clients projects, files, emails, documents as much organized and categorized as possible.
    2) Set small milestones every day.
    3) Set strict work time (I know.. is very difficult) in order to stop working every day at the same time, and take a good lunch, do some sports, etc.
    4) Use productivity oriented tools (software in my case) like: Project management tools, Tasks & Calendars tools, etc.

    But.. anyway… this is easy to say, but really difficult to make.

    Excellent post Mason!

  20. says

    You can smooth out the feast or famine greatly by having others marketing for you. Specialize in excellence at one thing and make sure others in a position to send you work know about you. Referral clients are pre-sold and far more likely to be satisfied with your work.

  21. says

    Nice post. Regarding the famine/food cycle something else that alleviates this is if you do commission work for some of your clients, especially if you do freelance programming. I.e. setup/maintain a shopping cart and you get 30% of the profits etc.
    I’ve found that this really helps as when you find that your normal work has dried up you are still getting some income from other sources.

  22. says

    Great article.

    I think a lot of people believe that as a freelancer, I spend all day in my bunny slippers chatting on Facebook….but contrary to that belief, there is a LOT of work that goes into freelancing. Best things I ever did to help my freelance career (and sanity)? Hired a CPA to manage my taxes, hired a cleaning person to clean my house. That way, when I finally do get some down time, I’m not spending it reading IRS code or sweeping up dog hair. :)

  23. says

    Really great post Mason!

    In the last paragraph you really summed it up with “As we hinted at throughout the article, the answer to these problems is to treat your freelancing more like a business and less like a job.”

    Thanks for the read,

  24. says

    Now that I have a baby boy, the work/life balance thing is even harder. If you’re away in an office downtown somewhere, you can’t be asked to change a diaper. At home, you can be asked. The point I’m trying to figure out is how to benefit from the flexibility of freelance life while still being disciplined and focused on building my business.

  25. says

    It’s hard – but completely worth it. One of the things I find most important is to pay yourself a regular paycheck, don’t treat every project like your personal income. So for example you would pay yourself $600 a week, and even when you get that elusive $20,000 project you still continue to pay yourself $600 a week, this results in having enough money in the bank to get you through the “hard times” mentioned above. Just my 2 cents.

  26. says

    It sure is tough to work as a freelancer and handle all this but once you get the hand of it the rewards can be great. A nice way to grow your freelancing business is to try and get a virtual online assistant to help you get your things done

  27. says

    in every part in life, there are some good side and bad side. freelancing is also has some positive side and negative. overall freelancing is challenging than regular job, but it has more fun. and each day the confident will grow.

  28. says

    Great post. I can’t agree more with the first point: automate your marketing. You should work to build an online presence for search terms related to your expertise in your local market, and have a website with an autoresponder that will do the “selling” for you. You don’t have to cold call or even “network”, because the Internet can get you plenty of leads. Now you can concentrate on serving your clients and doing what you love. Outsource the back office things like bookkeeping/accounting or get a virtual assistant. You can even get an answering service to handle customer calls, so you won’t even have to stop working to pick up the phone. I share how to do this in my free report: http://www.rainmakerorlando.com/FreeReport

  29. says

    Great post. I can’t agree more with the first point: automate your marketing. You should work to build an online presence for search terms related to your expertise in your local market, and have a website with an autoresponder that will do the “selling” for you. You don’t have to cold call or even “network”, because the Internet can get you plenty of leads. Now you can concentrate on serving your clients and doing what you love. Outsource the back office things like bookkeeping/accounting or get a virtual assistant. You can even get an answering service to handle customer calls, so you won’t even have to stop working to pick up the phone. I share how to do this in my free report:free rap music downloads

  30. says

    Thanks for sharing the nice information , yeah its right that freelancing is tough but doing freelancing is lot of fun. Also , sites like eZdia , has made freelancing very easy, as here you just have to post your expertise and employers will search you for their work . Isn’t is a good one for freelancers , just try at eZdia.com

  31. says

    Nevertheless, if you’ve never spent time freelancing before, it can be difficult to find work on freelancing websites teeming with qualified workers. Consider using a site such as Fiverr or Gigswood, which allow you to offer small services and get paid

  32. says

    Very good advices, I remember writing a similar blog post in 2006. But you’ve done a much better job than me.

    It is slow to start with but with constant hard work and maintaining relationships with good clients, it pays off well. Eventually, if you are anything like me, I just cannot do 9-5 job (getting experience is an exception).

    Keep it up! :)

  33. says

    Hi all, I will like to introduce everyone to freelance domain marketplace, it’s a freelance jobs marketplace where service buyers post jobs that they need to be done and freelancers submit bids to win the job. It’s totally free to post jobs. Our services include web designing, programming, writing, translation, software development, engineering, seo, marketing, advertising, copywriting, proofreading, data entry and more


  1. […] Freelance Folder: Alright, alright we don’t exactly get up at noon and take fifteen breaks a day. Freelancing is pretty damn hard because… “Despite how magnificent it can be to work for yourself, there are some things about freelancing that just plain suck.” […]

  2. […] Freelance Folder recommends finding someone that could fill in checking email and answering phone calls while you’re out. Or someone that could pick up your work  for a few days. This all sounds well and good, but if you’re really so down and out that you can’t work … will you be able to bring someone totally out of the loop up to speed? This seems like it would be just as hard as doing the work yourself. […]

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