Letting The Cat Out Of The Bag: Is Freelancing Really For You?

Letting the cat out of the bag
Freelancing and working from home is a dream to many. Designers, bloggers, social media experts and many other careers that didn’t exist a couple years ago have now become a comfortable means to earn a living for some.

Freelancing sure does sound great, but ask anyone who has been doing this for a while and they will tell you that the cons are usually higher than most anticipate. Sure, you get to take a break anytime you want. Working in your pajamas sounds great, but the stakes are much higher than most imagine.

In this article I want to look at some of the downsides of freelancing, and take a sobering look at some realities that every freelancer needs to confront.

Never a Guaranteed Income

This may not be true for some, but for most this is the case. Ask any freelancer and they will tell you that one of the biggest cons of working from home is the uncertainty of it all. There are a few freelancing gigs that offer a consistent income, but working from home is usually one of those deals where you can go from rich to poor within days.

If you’re single you can survive on the bread and butter, but if you have a family to feed make sure you do the research before you dive in. Remember to look into the future not just the present — you might be able to earn thousands this month but once the contract is over it’s back to the basics.

Life On The Web Can Be Lonely

Most freelancers are dependent on the internet. We all know that networking on the web is all about social media these days. Twitter, Facebook, LinkedIn and others all have started replacing the need to hang out at a coffee shop, and Friday night bar outings are frequently replaced by podcasts.

No matter how much fun it is to socialize on the web, real life socialization is important, and often difficult to find as a freelancer. You will have less opportunities to just be around people than you would at an office. The reason being that your participation on the social web directly affects your business and we can’t let the business die. Socialization on the web isn’t only a matter of choice when working from home, it becomes a necessity, an integral part of your work — but there aren’t too many socialization opportunities at home.

Time, The Devil

Seriously, managing time while working from home is one of the toughest aspects of freelancing. If you are single you might not have a lot on your plate, but anyone who has family knows what I am talking about. When you work from home there are expectations and you might feel a heightened sense of responsibility. Kids running around, nagging relatives, or a couch potato spouse might make the job even harder.

Many freelancers end up working late hours since they are so tied down with household responsibilities and other things that you can usually avoid if you work in an office. Time management isn’t an easy task and many freelancers fail to manage time effectively. This can cause problems not only in your work life, but in your personal life as well. This is one of the key things you need to analyze before you jump onto the freelancing bandwagon.

Different Roles, Different Outcomes

Being a great designer or an awesome writer isn’t good enough when you decide to become a freelancer. A freelancer has to be the best in a lot of other fields. For example, you may be the best designer out there, but what’s the point if no one knows about you. You need to be a good marketer too.

Whether through social media participation or a campaign of some sort, you have to be able to sell yourself to the clients. Freelancing isn’t about being good at one thing, it is being good at many things. You have to be the productivity guru, financial planner, a good salesman, smooth talker and above all the best damn time manager there ever is. Freelancing is about putting all of your eggs in one basket and making sure they stay in there.

Too Much, Too Little

If you are a freelancer, I am sure you can relate to this. One of the things most freelancers battle with is what to charge and whether to charge hourly or by project. If you are a designer, you can either charge by hour or the finished work. Same thing with writers and other freelancers.

It’s a thin line between getting that dream job and losing it because of pricing. Ask for a higher amount and they might bail out, ask for less and they might think you are not good enough because it’s lower than industry standards. The biggest problem arises when you take on a job and find out you are actually charging way less than you should be for what you have been doing. You will go through a lot of different stages when freelancing, and trust me, most of the time you never get out the “too much or too little” situation.

What do you think?

What do you think? Are you ready to be a freelancer? If you are a freelancer, do you agree with what I had to say? Are there any other difficult realities that I missed?

Share your thoughts in the comments.


  1. says

    I can empathize with most of these freelancer’s woes. You are expected to wear many hats as a freelancer, more indeed, if you have a family. Besides being a mommy, wife, and writer, you must also be a bookkeeper, secretary, marketing exec and lawyer. It’s hard to play that many roles in life, but therein lies the reward. Challenging as it may be, those who survive and are successful to a perceptive degree are the happiest. It is ultimately satisfying to realize every dollar you make comes from your own ideas, creations and hard work, all the way through the project. The career is not for everyone. It takes discipline and tenacity on a level people who do not run their own business (and design, create and market the product) can never understand. It can be a learning experience for many people, and can teach responsibility and foster a work ethic that might otherwise have been overlooked or missing in the corporate world.

  2. says

    Freelancing is definitely not for everybody. It takes a lot of guts and a certain amount of non-conformity to venture out on your own.

    All the downsides you described are correct. But for those of us who actually enjoy freelancing, the benefits outweigh the negatives.

    It’s tough and it’s still work, but I like it.

  3. ClayZirkle says

    Kudos to @TrinaLgrant ‘s comments. I’ve been working as a real estate agent – in commercial leasing – for about 5 years now. It’s essentially this – every day, I wake up unemployed. So – my income lives or dies not so much on my ability to find tenants or get leases signed – it’s longevity and increase lies in the success of my “marketing” .

    It has been difficult at best – the payoff is forthcoming – and as I endeavor out on some other opportunities as a freelancer – I expect the same.

    Today’s tools however – social media – are significant differentiators. Am scrambling as quickly as I can to learn the best, proper and respectable uses of tools like Twitter, WordPress, Digg, Vimeo and YouTube to name a few – – – and paying attention to articles such as this.

  4. says

    These are all great points, and things that a lot of people don’t realize they’ll encounter once they start freelancing. In many ways freelancing is often glamorized. That idea that we have these super flexible schedules, work in our pjs and get to be our own boss is nice, but once reality sinks in, that flexible schedule gets packed with projects and the business side of things. To people that don’t realize this, though, our job looks easy, and I think that’s one of the most difficult parts of freelancing, that our work can be under appreciated if people don’t understand where we’re coming from.

    I addressed some of my other “pet peeves” about freelancing on my blog if you’d like to share some of yours! http://www.nmaldonado.com/blog/?p=169

  5. says

    You definitely have to be OK with a little chaos, late payments, instability, time management, accounting, etc. etc.

    You also have to get used to work requests (email and phone calls) coming in at all hours of the day, evenings and weekends!

    If you can handle the responsibility and the chaos, the pros definitely outweigh the cons

  6. says

    If want to do it because you don’t want to work hard then it may not be for you. The only good thing [IMO] about a regular job is that – in theory – you’re there 9-5, Mon-Fri, and can turn off the rest of the time. With freelancing you may be up and working at 6am and still getting things done before you go to bed, on a weekend.

    Aside from contacts and clients, learning how to set limits on your new-found freedom may be one of the biggest challenges over the first few months. It took me maybe half a year to get over the novelty of being able to what I want, when I want.

    Oddly enough, after trying out al kinds of schedules and systems, the one that works best for me is essentially 9-5, Mon-Fri, with clear deadlines keeping me on track.

    So…while freelancing probably appeals most to lazy, undisciplined people, these are the ones who should avoid it unless they’re willing to change.

  7. says

    If you are going to see the big picture, you shouldn’t neglect these cons because it will determine your contentment as a freelancer. Anybody who is thinking to be one should first evaluate if he understands what he is entering. It isn’t easy of course. Indeed, for singles it will be less worry but for people with family it’ll be a job requiring a lot of demands.

    Discipline is a must for freelancers, in terms of time, money and job quality. Learning to manage these will make it less burdensome. It may sound complicated but expecting what awaits you is better way to prepare.ss

  8. says

    What you need to do, if you’re feeling bad about the “cat” is to find residual income streams. Just like R.Kiyosaki suggests-income streams that will produce income while you’re sick, on vacation, sleeping, etc.


  9. says

    As a freelancer I recently had the following worry; when it comes to apply for a full time job at certain company, Will they consider you less worthy because most of your experience is Freelance? Will they preffer someone that has worked for several years in an office environment instead of a home / office?

  10. Jane says

    This is absolutely right. To be a freelancer, you have to be ready to commit everything. I’m doing a favor for a friend which turn out to be my freelance job. Having a full time job and freelance, it’s really really tough. It’s like you need your brain to work 24/7. And YES, time management is something that I have to work out. But doing freelance is like freeing your soul to do whatever you like, your style for the customer. You can explore and don’t have those boundaries or the company image that they always want to portray.

  11. says

    I agree. Freelancing definitely has some downsides. I jumped in because I thought it would be great to sit in my office at home and work on the computer, taking a break anytime I want. I soon realized that my previous gig, commissioned sales in the truck parts and equipment industry, infected me with something of a wanderlust attitude and the need for human contact.
    So I’m back on the road doing something that I really enjoy and working at the freelance jobs as I find them. I’m lucky. I have marketing skills and I’m accustomed to an irregular income so I will be able to transition to full-time freelancing when life on the road finally makes me crazy for the last time.

  12. says

    Thanks to all for sharing your thoughts. Freelancing certainly is something I can’t move out of but it does take quite an effort to get comfortable with it as well. Like PS said in the comment, many people view freelancing as an easy way out and that’s far from the truth.

  13. says

    Hi Ritu:
    I’ve been freelancing for more than 18 years and can attest to the truth and wisdom of every single point you make.

    Freelancing may be a little easier and less stressful for singles and married people who rely on freelance earnings as supplemental income. It gets considerably tougher when you have children and your family depends heavily–or entirely–on your freelance income.

    Another freelancing con: As small business owners and sole-proprietors, many freelancers find their business hard to scale. Even if you’re glued to your desk 8-10 hours a day, YOU are the only person who can do the work.

    This makes success a double-edged sword: In an effort to maximize income many freelancers burn the candle at both ends; we may juggle too many projects at one time and feel incapable of saying no to new jobs even when we’re fully booked.

    The pressure takes its toll with long work hours, isolation and lack of healthy exercise –see Jonathan Fields excellent post http://www.jonathanfields.com/blog/fat-bottom-bloggers-is-your-blog-killing-you/

    Not what any of us had in mind when we opted for the freedom and flexibility of freelancing!

  14. says

    Brilliant article! I couldn’t agree more… Excellent point on being forced to become a renaissance guy by knowing, doing and being good at a number of things at the same time.

    I’m a family man, and managing the little time I’ve got left is really really hard. There’s no day during the week in which I don’t find myself wishing there were 72 hour days.

    Rat racing gigs, a day job and having a family is quite a challenge. I’m 31 and don’t mind my hair going gray. I guess this is where passion and survival instinct merge.

    My conclusion is: Freelancing – don’t fear it, go for it! Only time and experience can tell you if this is your deal.


  15. Fedor says

    It’s a great article and it’s true.

    Inestability, some times fears may drive you through ways you don´t need in this job, but definitely outweigh the cons. Family time is unvaluable, time for diferent projects, great expirience in diferent field as you describe, etc.

    It takes a lot of self-discipline and organization but it’s something you will value in diferent areas in your life.

  16. says

    I totally agree that you will need a lot of self discipline if you want to do freelancing. There will be many distractions in your house that will pull you away from your work. Knowing when to steer clear of those distractions is a necessary skill if you are going into freelancing.


  17. says

    What I’m most curious about is to see what happens to the freelance “tide” as the economy picks back up. We got flooded with out-of-work 9-to-5ers (or so it seemed) when the recession started making the unemployment numbers up–just my perception—but will the level of freelancers stay higher even after the economy climbs back to a respectable level?

    I have a funny feeling the answer is yes. What really intrigues–10 years ago the dot com bust ruined freelancing for many but this time around it was the opposite–the cubicle workers got the boot and the stay-at-homers seemed to prosper…ahh how times have changed.

  18. says

    I have been working from 8 to end in an office and as a freelance for many years, having an stable incomme and a plus via the freelancing is very safe and very stressful, as a graphic designer I need to be creative, but the imagination have no standard hours of work, we are more creative in the morning but going to work dealing with rush hour traffic kills you dose of imagination in the morning, you are already stressed when you reach your desk and most of the times ending doing someone elses ideas, thing you relly hate. And no doubt sitting in you home desk 9, 10 or 12 at night is not the best for creation, now I’m totally freelance, I can create right when I wake up, i’m always fresh to talk to clients, I can go shopping for grocery’s at unconventional hours, last year was stressful to go shopping in my way home after work, and I can say that I feel more creative and effectibe now.

    In the other hand some times you hit bottom financially, and two days later you are making it big, earning more than you have planed, paying the cost of opportunity at a high rate. Some days you have nothing to do, and some times you have no idea how to squeeze more time in a day, and I must say that when you have so much to do you need backup, in my case other freelancers to push or pull a proyect with me and finish it.

    And the need of wear all the hats at the same time is difficult, marketing, accounting, negotiation, collecting payments, paying bills (God bless internet banking) and do the job at the same time took all your stamina and you think “Oh my God is just monday”,you can say reading this “freelancing is hell” buy you know there is onething that make me do this every day with no regrets, at the end of the day I have done my vision, followed my rules, gave the best I can give, make my own choices, at the end of the day I am happy and proud of myself!!

    Do your best, Follow your dreams, Be free!!

  19. says

    I am reminded of a quote from a famous writer, some of the stature or Hemingway or Steinbeck. The quote is: “If anything can keep you from writing, let it.”

    As we all know its not an easy road, and you better be on Mission or it will eat you alive.

    Great post! Its an important reminder that those of us who do this should be very proud of it. Thanks

  20. says

    Great article, and nice to actually see some cons for once! Mental preparedness is definitely one of the keys to living the life as a freelancer. From early experiences as a freelance motion designer, mind games would always enter the foray. I had to learn right away that working hard and believing in myself was the only way to combat the many negative thoughts that crept into my head. I look back and for the most part all the effort I’ve put in has paid off in one way or another. This includes pro-bono work and all those hours of marketing that felt like time wasted.

    Despite the negatives and external perception of a freelancer, I wouldn’t want it any other way. The experience is what you make of it.

  21. says

    I couldn’t agree more,

    When I was still a single I have spent 5 years in Thailand working as freelancer for western clients, I could afford a great appartment with swimming pool, restaurant meals, air tickets, treckings and travels with ease.

    Things are very different now, back in the UK married and wid a children. From one side it is great to be father and can spend lot of time with your family but when it comes to managing your time/clients it can be really hard…I have to work late nights when the kid is sleeping in order to find the right concentration……if I try it during the day it will most probably end with my daugther watching cartoons or playing with my PC.


  1. […] Letting The Cat Out Of The Bag: Is Freelancing Really For You? is a really interesting article, that talks about what us freelancers (often) think about. Is this really for me? Will I really make a good living just by writing and live happily ever after? Will I bring home a paycheck every week by writing? Freelancing is rewarding, but it is not easy. I also dislike very much when people tell me how awesome working from home is. It can be nice. The niceness is not guaranteed. Just like earning a full-time income with freelance writing is not guaranteed. […]

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