How to Overcome 20 Reasons Not to Become a Freelancer

We recently published an article covering 20 reasons not to become a freelancer.

The idea was that there are already a ton of articles out there talking about how great it is to be a freelancer, and all the benefits, but there are very few posts that talk about the flip side of all that.

Freelancing is not for everyone. It’s an important decision that not only affects your career, but can also affect your personal life and financial well-being. Of course, a lot of readers thought we were being way too negative about it all.

So here’s a follow-up to that article, covering ways you can overcome the potential pitfalls of freelancing if you’re still sure it’s a career move that’s right for you.

The good news is that virtually all of these things are manageable if you’re willing to put in the time and effort it takes to deal with them.


1. You Think It Will Be Easier Than a Corporate Job

Image by ste3ve

This one requires a change in your mindset. For the most part, freelancing isn’t going to be easier than a corporate job (though it doesn’t necessarily need to be harder). If you go into it knowing it’s going to be hard work, just like any other job, then you’re going to set yourself up for success and you’ll already be ahead of many other freelancers.


2. You Don’t Have Much Experience

It’s not too hard to figure out how to overcome this one: get more experience! And there are some relatively simple ways to do so. Start a couple of personal projects. Get in touch with a local community group or non-profit about designing a website for them on a spec basis and in exchange for a testimonial. Don’t forget about any projects you completed in school. Those can all be used to bolster your portfolio.

Experience doesn’t necessarily have to mean paid experience. Any project that you complete for a satisfied client (even if that client is yourself) can be used as an example of your work.


3. You Have No Business Sense

There’s a difference between having no business sense and having no business knowledge. Some people, no matter how hard they try, just suck at making business decisions. In those cases, find a partner who does have a mind for business. Or a mentor who will help guide you if you don’t want to take on a partner (or can’t find one).

In the case that you just lack business knowledge, then head to the library or the local bookstore. There are tons of business books out there. Pick up a few on being an entrepreneur or starting a small business (particularly small, service-based businesses) and start reading. Also check out business- and freelance-related blogs, like these:

There are plenty of other business and freelancing blogs out there, so feel free to share your favorites in the comments. The point is that there are plenty of ways out there to gain the knowledge you need to be successful in business. It just takes some time and effort to learn.


4. You Need Benefits

Image by foxypar4

This can often be one of the scariest things for freelancers who are used to having paid holidays, paid sick days, and things like retirement plans and health insurance (in countries where employers often provide insurance).

For sick days and paid holidays, simply figure out how many of these days off you want or are likely to need. Let’s say you’re going to take five holidays a year, and that you think you’ll need five sick days. If you’re average weekly pay needs to be $1,000 (we’re going to use that number because it’s easy to figure things based on, but adjust according to your own needs), then that’s $200/day based on a five-day workweek. So for ten paid days off each year, you’ll need to come up with two weeks worth of pay. If we break that down over the remaining 50 weeks in the year, that’s only $40/week that you need to put into savings to cover your own paid sick days and holidays.

Other benefits like health insurance and retirement plans are a bit trickier. You’re going to lose out on things like employer-matching of retirement contributions. That’s just a sacrifice you’ll have to make if you want to freelance. But you can still set up private retirement plans. You’ll want to work with a qualified financial planner on these things to figure out the best plan for your particular situation and goals. It’s way too much to cover here. But be assured there are plenty of options out there.

As far as health insurance goes, check with professional organizations both locally and nationally, especially Chambers of Commerce. It’s common for these organizations to have group health insurance available for members. You’ll still have to pay for it out of your own pocket, but the group rates can make it much more affordable. Depending on your health, you may want to set up a high-deductible plan and a health-savings account to cover costs until you actually reach your deductible. Again, those are things you’ll have to consider based on your own situation and your own needs. Call local insurance agents and get a quote for health insurance and then compare that to the group plans available to you. Many health insurers also provide rate quotes on their websites.

The main difference in regard to benefits between being employed in a corporate environment and being a freelancer is that as a freelancer you’ll need to pay for your benefits out of your own pocket. But with some advance planning, it’s completely within the grasp of most freelancers to continue to enjoy the same benefits they did when employed by someone else.


5. You Think the Pay Will Be Better

This is another one where you’ll need to adjust your perceptions going into freelancing. In all likelihood, the pay will not be as good, at least in the beginning. And even if you’re earning a similar amount, remember that you’ll be paying for more things out of pocket, too. Things like insurance, utulities, software upgrades, and taxes will all come out of your own personal income.

One way to combat this is to cut back on your expenses as much as possible before making the switch. If you need less money to live on, earning less won’t be such a big deal. And the less money you’re spending on living, the more you can reinvest in your business, which can often translate into being more successful in the long run.


6. You Have No Self-Discipline

This is probably one of the most difficult things on this list to overcome. The truth is, there’s no easy way to learn self-discipline. Sometimes you can develop it out of necessity, but oftentimes things need to get really bad (like being evicted or having your car repossessed) before you actually develop it.

The best advice here is to set goals for yourself on a daily basis and make sure you meet them before you finish work for the day. If you set goals that are too big, you’ll come up with excuses not to complete them. Set goals that you know you can accomplish during the day. And set consequences for yourself if you don’t meet them.

Another option is to get someone else to hold you accountable. A significant other or friend is one option, as are other freelancers. Find someone you can email each day with a list of what you have to accomplish or what you have accomplished, who will hold you accountable if you don’t do your work. Sometimes just having someone to report to is enough to keep you motivated. Offer to do the same for them.

Again, learning self-discipline isn’t easy. And it’s one of the few things on this list that a lot of people might not be able to overcome well enough to become successful freelancers. If this is an issue for you, think long and hard before giving up a corporate job.


7. You Don’t Love Your Work

If you don’t love your work, or at least enjoy it, you’re going to find it hard to stay motivated to complete things, even if you’re normally a very motivated person. The best advice here is to find something you do love and then start freelancing in that field instead.


8. You Think the Hours Are Better

Image by PresleyJesus

A shift in perception is needed here, too. You’ll likely work longer hours as a freelancer, especially when you’re starting out. It won’t be uncommon to work 10, 12, or even 16 hour days sometimes. And you might find yourself working 6 or 7 days a week.

Be careful about not taking on too much work. Sometimes we feel as if we need to take on any work that comes our way in the beginning for fear of not having any work later. But if you take on too much, you’ll just burn yourself out and produce inferior work. Carefully think out how much you can work without overdoing it and then be aware of how much time the different projects you accept are going to take. You’ll still have to work a lot of hours in the beginning unless you’re very, very lucky, but you need to balance it with your own well-being. Remember that a few very happy clients is going to beget more work than a whole bunch of dissatisfied ones.


9. You Have No Space for an Office

The good news here is that there’s almost always room for an office unless you live in a closet (and even then there might be a way). A dedicated desk is the simplest form of an office. Your desk doesn’t have to be large, and you can tuck it into the corner of your bedroom, living room, or kitchen. If you have an unused room in your house, or even an unused closet, consider locating your office there. It’s nice to have a space where you can close the doors at the end of the day to shut out your work.

Think of unconventional spaces where you might be able to locate your office. Do you really need a dining room? Or a guest room? Don’t worry about what you think your house or apartment should have for rooms. Instead, worry about how you can best utilize the space you have.

As a last resort, if you absolutely can’t find a dedicated workspace, consider renting a space or finding a coworking space. See if you know someone who would be willing to rent you their extra bedroom for use as an office. Or even their garden shed. Basic, one-room offices in smaller towns and cities can often be rented for only a few hundred dollars a month. It might be worth it if you’re finding you absolutely can’t set up a dedicated workspace in your own home.


10. You Don’t Know Where to Find Clients

There are a few answers to this one. First of all, you can check online job boards for clients who are looking for designers. Realize, though, that often you’ll be competing with overseas vendors who can often compete a lot better on price. The good news is that there are also often clients who only want to deal with vendors in their home country.

Another option is to network locally. Carry business cards with you everywhere. Join your local chamber of commerce or other professional organizations. Don’t be afraid to approach local businesses and offer your services. You might be surprised at how many people are receptive to listening to a proposal, or who know someone who’s been looking for design work.

In the beginning, your best bet for getting clients is to put yourself out there. Make sure everyone you know is aware that you’re now freelancing and taking on new clients. Personal referrals are often going to be your best source of business. Take the time to thank those who send business your way and you’re likely to see even more business from them.


11. You Have No Project Management Skills or Experience

Image by koalazymonkey

There are plenty of blogs and books out there on project management. A few hours spent online can at least give you some basic information on how to manage simple projects.

There’s also a lot of great project management software out there. While these apps aren’t going to do the job of project manager for you, they will make it a lot easier to keep everything organized and on track.

Take the time to learn how to effectively manage projects and make sure you don’t take on projects that exceed your skills, both as a designer/developer and as a project manager. You’ll get better at it with practice.


12. You Don’t Want to Deal with People

The bad news here is that you’re going to have to deal with people as a freelancer. The good news is that you can often choose how you deal with them. You might opt to only work with clients who are outside of your local area so you don’t have any face-to-face meetings. Or you might try to direct all your clients to only communicate with you via email. It’s likely you’ll have to talk on the phone every once in awhile, but you can minimize it by letting people know you prefer email.


13. You Can’t Stand Up for Yourself

This is probably one of the hardest things to overcome on this list. It’s often deeply rooted in one’s personality, and therefore not something you can simply read a book to overcome.

There are a few options here. You can take an assertiveness training course. You can pick up books on how to be more assertive and then put into practice what they tell you to do. Or you can just practice standing up for yourself more often. Start small. Don’t get defensive. And don’t let people walk all over you.

Being able to stand up for yourself to clients is something you really need to learn if you want to be a successful freelancer. While many clients wouldn’t take advantage of you, there are plenty out there who will realize you never say no or fight back and will use that to their advantage. They’ll fight with you over deadlines, over price, over when to pay you, and over getting you to do work for free. And if you don’t know how to stand up for yourself, you’ll probably let them win and end up having to do all sorts of things that undercut your business.

So learn to say no and learn to stand up for yourself if a client is giving you grief about something.


14. You Have No Time-Management Skills

Time management is a tough one for a lot of people, whether they’re freelancers or employees. Figuring out how much time to spend on different aspects of a project, or on different projects, as well as managing the distractions that invariably creep into our workday is challenging.

But there are plenty of ways to more effectively manage your time. There are tons of apps that can help by both tracking your time and by helping you to track what you need to get done. There are paper-based systems, too. Something as simple as scheduling regular breaks in which to check your Facebook and Twitter, or working on things in one-hour blocks and then reassessing how much time you’re spending at the end of those hours can go a long way toward making sure you’re effectively using your time.

Spend some time reading up on time management and then explore the available tools to find something that works for you.


15. You Can’t Self-Motivate

Image by pink_fish13

This is right up there with a lack of self-discipline as far as dealbreakers go. If you can’t get yourself to start (or finish) a project, to go look for clients, or to otherwise build your business, then you’re going to have a very hard time becoming a successful freelancer.

One trick that might work for a lot of people is setting up a goal/reward system. When you reach a particular goal, treat yourself to something. This could be taking a break and going for a walk, going out to dinner, taking a mini-vacation, or buying something you’ve been wanting for awhile. Make sure the reward matches up to the importance of the goal (taking a mini-vacation just for sending out a proposal probably isn’t the best idea). Using a reward system is a great way to motivate yourself if you’re finding you lack motivation otherwise.


16. You Don’t Want to Maintain a Professional Image

This is a tough one. If you’re going to have your name tied directly to your work, as is almost always the case when it comes to freelancing, then you need to maintain some professionalism online. But there are ways around this.

First of all, take advantage of privacy settings online. Then make sure you’re not friending your clients on Facebook if your profile is littered with drunken photos or other compromising materials.

Don’t be afraid to delete things that friends post on your profile if they’re potentially offensive to clients or other professional contacts, or otherwise inappropriate. This includes untagging yourself from photos or asking people to remove them altogether.

Use an alias for some things online. Don’t want your clients knowing about your passion for stamp collecting (or mud wrestling)? Then make sure your real name isn’t associated with any of your activities surrounding those things online. That doesn’t mean they’ll never figure out the association, but it makes it less likely that a casual Google search will turn up anything incriminating.

Basically, use common sense. If you wouldn’t want your mother (or grandmother, or first-grade teacher, etc.) to see something online, then you probably don’t want your clients or prospects seeing it either. So don’t put it out there.


17. You Want Paid Vacations

Image by Tomas Fano

This one is actually easier to overcome than a lot of freelancers think. If you want to have a paid vacation, then you need to set aside money to pay yourself for it. Let’s say you want to take two weeks off every year and your average weekly income is $1,000 (to use the example from earlier). You need to set aside $40 every week to replace the income from those two weeks off. Then, when you take the time off, tap into that savings to pay your bills.


18. You’re a Workaholic

This is one of the most difficult things to overcome when it comes to freelancing. It’s easier if you have a significant other to remind you to take time off or to call it quits for the day. But if you live alone or are single, it’s tougher.

There are a few tricks you can employ, though, to keep yourself from working too much. First, get out of the house/office. Take a walk, go for a drive, go visit a friend or relative. Remove yourself from your work environment.

Turn your cell phone off and disconnect from the internet at the end of the day. Try not to check your email and other messages when you’re done work for the day. It’s only going to entice you to go back to work.

Take a day off every week. Try to disconnect completely. Don’t even check your email. Let people know that you’re taking the day off so they don’t contact you, or at least are understanding when you don’t answer your phone or email.

Have office doors you can close. Even if this is just an armoire in your living room that contains your “office”, having doors you can physically close is a great way to mentally finish work for the day.

Find a hobby. Preferably one with regular meetings or events that will get you to stop work for a little while. The best part about a hobby or activity is that it often gets your mind off of work, in addition to physically removing you from your work environment.


19. You Don’t Want to Keep Regular Hours

There’s no good way around this one. You’ll need to at least be accessible during somewhat-normal business hours in most cases, especially if you deal with clients in your local area or in your time zone. While international clients are likely to be less concerned about this, in many cases you’ll be working with people who at least live in the same country as you, if not nearby.

But being accessible doesn’t necessarily mean you need to be working during those hours. It means you need to be answering phone calls and emails, but you can probably do that from almost anywhere with a good cell phone. If you work better at 2am, then do you actual work then. Just make sure clients can get in touch with you during the day if they need to.


20. You Don’t Like Being Alone

Freelancing is often a solitary business. But there are a number of ways you can get around this. First of all, seek out clients in your local area where you can have actual meetings on occasion. Find another friend who works from home who might want to get together for lunch once a week.

Volunteer in your community one or two days a week and work it around your regular work schedule. Most community organizations are desperate for volunteers and it’s a great way to get out of the house a couple times a week.

Join a club or organization. It could be a book club, a sports team, or some other organization related to one of your interests. You can find plenty of these kinds of things through sites like if you don’t know of any.

Take a class at your local community college or adult learning center. It doesn’t need to be related to your career. Just pick something that sounds interesting or that you’ve always wanted to learn about. Most classes aimed at adults meet only once or twice a week, often in the evenings, so it’s easy enough to fit them around your schedule.


In the End…

If you really want to freelance, you can find ways around any obstacles that stand in your way. The important thing is to go into freelancing with your eyes open to the potential pitfalls that can stand in the way of your success. If you have plans ready to deal with the things above, then your chances of success are much greater than if you just dive in with rose-colored glasses.

Written exclusively for WDD by Cameron Chapman.

Please feel free to share any additional tips or insight in the comments.

  • Timmy G

    I actually read this list on another site but this one has more steps. I’m a beginner freelancer and so far I’m doing alright. This list just tries to bring me down.

  • Austin Knight

    Freelancing seems like a scary plunge! I think the biggest fear is that people feel that they just aren’t ready, but that is something we all just have to get over and just go for it. Don’t waste your time making sure everything is perfect because you will never be satisfied! It is a hard thing to start but the thrill of taking a risk is so much fun :)

  • Chris Kirkman

    I have spent man years freelancing and also many years in the corporate design world so a lot of these points I can relate to. Great post!

  • wpBlast

    The more I read about freelancing, the more I realize it’s what’s right for me. I’m still in college, so I’m trying to get an early start and learn as much as I can. Despite how difficult freelancing can be, the benefits seem to greatly out way any of the negatives.

    Great follow up post btw.

    • Andrew

      Kudos to you, sir. I, too, am a college student that’s freelancing. I worked at a web design company for a few years and realized I was pretty much doing everything from design to building – why not just do it minus the low pay grade? I must say, for someone who hasn’t actively sought out clients – I’ve been getting a good stream of 3-4 clients/month based on word-of-mouth alone.

      • wpBlast

        That’s inspiring to hear. Congratulations!

      • Mieshia

        Yeah, I get a lot of word-of-mouth clients too, but I’m still struggling with a few of these :/ I think it’s more like… I’m afraid I’m not ready to take on the amount I know I’m going to get. But it’s not like I won’t know how to do the work or something like that.

        Fear of success is a weird one, yeah? >n<

  • Buy My House

    What a mind boggling and prolific informative article. Thanks for sharing it.

  • Najam Siddiqi

    Its really a good article . I m also a freelancer its really help me alot

  • Brandon Bender

    Man the best thing I have done to date (besides marrying my wife) was go solo!

    If you take the jump, the highs and lows are worth it. Your free!

    Simple as that.

    Brandon Bender

  • weberica

    I ‘ve tried to work in small firms and big corporations and I just couldn’t. Waking up early, regular hours, chefs, regulations, 3 weeks holliday, no smoking … I felt like prisoner every day and I was deeply depressed. Freelancing is freedom ! :)) And another thing.. life is cheaper if you work at home, think how many things you will not pay as a freelancer – transportation, parking, restaurant food, clothes, baby sitter, cleaning lady… (time is money)

  • abhishek

    This is really nice one….
    I read your previous article about not to be a freelancer. I was waiting for this article.
    Thanks for motivation…

  • Kaspar

    Great read :) A lot of good information!

  • Jesmond

    I’ve been working in a corporate business for quite some time now and I really hate it. I hate being confined in an office for 9 hours of the day with boring people. Freelancing is the right job for me and I’m confident that I have enough experience to make it work. Thanks for these pointer, they finally helped me set my mind on leaveing the corporate environment :)

  • Sergio Ordonez

    I usually don´t comment, but this one actually deserves it.

    Very good reading!

  • Polly

    Anybody can be a freelancer if they have the guts to do it.

    Moreover, I think everybody SHOULD try it at least for a while, just to prove themselves they can deal with being on their own.

    Yeah I get it – scary stuff, but you know what? Nobody cares, so grow a pair and deal with it, because who knows, someday you may HAVE TO.

  • Laura

    I enjoyed the list last time because I could see that it was a warning to all those considering freelancing, but were taking the whole thing light-heartedly. So I didn’t find it negative.

    However I did find reading the flip-side very inspiring. And some very nice points about how to meet clients and people, including people who are not associated with business or work. It’s always good to have a way to get away from it all, and having friends with different interests or jobs than you is a great way to give your mind a rest.

    I thought the point about having someone to report back to every day, another freelancer, friend or spouse, was a FANTASTIC idea. And one I shall be implementing. I already use the mini-reward system and find it works very well.

    Thanks for the great read as always Cameron

  • DaveK

    There is nothing quite like working for yourself, I have never been happier, I think it all comes down to passion, you gotta love what you do coz you WILL be putting the hours in :-)

  • Chris Mower

    Work hard and smart and you’ll be successful. As you go, you’ll figure things out. Don’t feel like you have to have it all worked out before you start, or you never will. Great article, thanks for sharing!

    @Timmy G… did you read the article or just the headlines? The headlines are doubts that people who want to freelance have. The body contains the solutions written in a positive, easy-to-understand way.

  • Melody

    Some of the biggest things to overcome deal with personal habits, self discipline, procrastination, motivation, etc.. You can essentially learn all the business skills you want but if you aren’t motivated at the end of the day then you’ll get no where..
    Good read..

  • Rachel

    Great article..really helpful..thanks for post…

  • Jordan Walker

    Great list of reasons not to become a freelancer.

  • adam

    Good post but I think I saw this somewhere else before as well.

  • Joel Emberson

    An excellent article – some good tips here!

  • Juan Pablo

    Fuuuuuu , que buenas lineas.
    Verdaderamente no existe camino facil en esta vida. Tomes el que tomes tienes que ser para que te haga feliz.
    Gracias por compartir esto,

  • katerwater

    Many items start with “This is probably one of the most difficult things…”

    That’s not really motivating. The writer also claims you can easily learn the basic management skills via books and blogs, but I don’t believe that counts for every country. The bureaucratic chaos in some European countries is way bigger than in the US, where you can basically start a company in your own backyard…

  • jaidi

    here at work in agency, everybody be a workaholic without hour to go our home for our confortable room! all this point here is IF you dont have experience, skills, etc… basically, you can do your work easy like working for agency. if you have skills and experience for years working in agency, why dont try be a freelancer? or working in agency AND some many projects free! the world is so complicate.. and we need a little bit more money ; (

  • Robert

    Freelancing has good and bad points. I’m the opinion that you must think for yourself if freelancing is the right thing for you. Some people are better with corporate jobs, some are better as freelancer. As you stated in your article are many aspects to be considered before starting to freelancing.

  • Ben Stokes

    Great article, I think you covered everything there. . . I would say freelancing is quite hard especially if you are not used to working on your own, can be quite hard to motivate yourself also. . . we all know what it is like to stare at the monitor :)

  • miguel antekera

    i dont like to be alone…

  • Martina

    I think freelancing is good. Your points in the article are good and match the perspective of a freelancer.
    If you have the motivation and the necessary skills, you can work better and easilier as with a corporate job.
    I’m a freelancer because i’m making more money that way, i love my work and i can plan when i want to work.

  • Brett Widmann

    Veyr nice info. Can’t agree more.

  • steve

    My tip for maximum freelancing return is use 1 to 3 channels to find clients. Build up active profiles (for social type sites) that show your status in the network and strive to be the best. I did 57 projects in 15 months on 1 popular freelancer site (channel).

    The YOU CAN’T STAND UP FOR YOURSELF one can be costly though, many clients will try to nickel & dime things, know when to say ” I need to be compensated for that time”.

    To be able to stay home I run 3 personal sites, maintain to good freelancer portfolios on freelancing networks, flip domains and when that is all slow, pluck jobs from sites like Craigslist.

    My toughest part is – #20 Not liking to be alone. I am married but if I wasn’t I am sure they would have found my body slumped over the computer by now because I am a compulsive #18.

    Great list BTW…