We’ve all read countless articles on the reasons you should consider freelancing.

They often make it out like anyone still working in the corporate world is just a schmuck with no ambition. But the truth is, there are plenty of reasons not to start freelancing.

Below are twenty such reasons, all laid out so you can make an informed decision about whether freelancing is really something you want to do in your career.

There’s nothing wrong with staying in a corporate job, just as there’s nothing wrong with setting out on your own. But it’s a choice every designer and developer needs to make for themselves.

One note: when we talk about “corporate jobs”, we’re talking mostly about design firms with multiple employees (whether they’re corporations or not), but most of it also applies to in-house design teams at large companies.

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

A lot of people considering freelancing think it will be easier than their current corporate job. After all, they’ll only have to take on projects they want to take on, they won’t have a boss or coworkers to deal with, and they’ll be able to set their own hours.

But most freelancers, when the first start out at least, aren’t able to be too picky about the work they take on. And while they don’t have coworkers or a boss to deal with, that means they also don’t have anyone to turn to if they get stuck on a project.

There are still clients to deal with, too. And the whole thing about setting your own hours pretty much just means you can choose which sixteen hours in the day you want to work when you’re getting started.

2. You Don’t Have Much Experience

If you’re just getting out of school, you may not have much experience to draw on. And there are a couple of reasons why experience is more important when you’re a freelancer.

First of all, you’ll need a portfolio to show prospective clients if you want them to hire you. While you can always use personal projects, it’s also good if you have at least a few sites in your portfolio that you completed for other people (bonus points if they’re not friends or family). This shows a prospective client that you’re legitimate, and that you’ve had happy clients in the past.

The other reason is that experience proves to both you and the client that you’re capable of finishing projects. If you’ve never done anything but personal projects, there’s no indication that you’ll be able to finish a project.

Freelance designers need to be able to handle client requests and revisions, as there will almost always be things your client wants to change, no matter how great your initial design is. And until you’ve finished a client project, you don’t even have any proof that you have what it takes to work with clients.

3. You Have No Business Sense

When you’re freelancing, you generally don’t have anyone around to handle invoicing, collections, marketing, PR, and the myriad other tasks that corporate design firms handle for you. These are all things you’ll need to deal with yourself when you start freelancing.

Of course, you can always outsource some or all of these functions, but you may find it prohibitively expensive when you’re starting out. It’s better if you know how to do all of them yourself.

Keeping your own books is especially important, as it gives you a clear picture of how much money you have coming and how much is going out (and where it’s going). That’s important if you want to stay in business.

4. You Need Benefits

Some people can’t get by without benefits. If you have existing health problems, you’ll almost certainly need health insurance. And even if you’re healthy, that’s no guarantee you will be in the future. Plus, if you have kids, you’ll likely want health insurance for them, too.

This is one of those issues that’s not going to matter in countries with universal health coverage, but even in those countries there are other benefits you may not want to lose.

If you’re self-employed, you’ll no longer have employer contributions to your retirement plans. You won’t get paid sick days or personal days anymore. All of these things will need to be built into your budget or schedule.

5. You Think the Pay Will Be Better

Many considering switching to freelancing think the pay will be better. After all, they’ll get to keep all the money they’ve billed out, without sharing any of it with an employer. And that’s true. But you’ll also be responsible for paying all of your own taxes (in the U.S., at least, that amounts to an extra 7.5% in payroll taxes that you have to pay that would otherwise be paid by an employer).

You also have all sorts of other business-related expenses you’ll need to pay. Things like office supplies, new equipment, software, and all those other expenses that go along with running a business will all have to be paid by you.

There’s also the difference between hours worked versus billable hours to contend with. Not everything you do will be billable work. Time you spend on administrative tasks aren’t billable.

If you screw up on a project and have to take time to fix it, that’s usually not billable either (at least not ethically). At a corporate job, you generally get paid either for the hours you actually work or on a salaried rate, regardless of how much the client is billed.

6. You Have No Self-Discipline

If you can’t discipline yourself to actually work, then you’re not going to make it as a freelancer. If you find you’re spending hours playing video games or on Facebook instead of working, you’re going to have a very hard time finding enough billable hours to pay your own bills.

When you work in a corporate environment, there’s always the threat of being let go if you goof off too much. When you work from home, you don’t have that same threat lingering. But if you don’t get client work done on time, you’ll have unhappy clients and, eventually, no clients.

If you can’t discipline yourself to work when you need to, you’ll be better off sticking with a corporate gig.

7. You Don’t Love Your Work

So many people who work the usual 9-to-5 don’t really love their jobs. They don’t wake up in the morning looking forward to going to work. But they do it in order to earn a paycheck and put food on the table. Sometimes this is because of the work environment itself, but others times it’s because they don’t really enjoy the work they’re doing.

If you don’t love what you’re doing, you’re probably not going to love it any more once you’re freelancing. Freelancing is hard work, and if you’re already struggling to find the motivation to get your job done, you’ll probably struggle even harder once there’s no boss there to motivate you.

8. You Think the Hours are Better

When you own your own business, you’ll likely end up working twelve- to sixteen-hour days five to seven days a week, at least for the first few years.

Freelancing is like any other business. Sure, once you’re established, you’ll likely be able to reduce your hours and only take on higher-paying projects. But in the interim, you’ll probably have to take on any work you can get to build up your reputation and a stable of regular clients.

It’s also likely that your workflow won’t be as efficient as it could be for your first few months, or even years, in business. You’ll spend time on unnecessary activities. You’ll end up repeating things because you don’t have good methods for keeping track of everything.

And because of this, you’ll spend more time than is necessary on a lot of things. Time and effort will eventually fix these issues, but they’ll still have to be dealt with for a little while.

9. You Have No Space in Your House/Apartment/Bedroom for an Office

You’ll need a dedicated space for working. This doesn’t have to be an entire office, but you should at least have a desk that’s only used for your work. The idea that you can do everything from your kitchen table is likely just going to cause you headaches. As will the idea that you can do all your work from the local coffee shop.

The good news is that most people can find a quiet corner in their house, apartment, or bedroom where they can set up a permanent workspace. If it’s in a room shared with other activities, an armoire-style workstation is often preferable, so you can “close up” for the day and not have to stare at your unfinished work.

10. You Don’t Know Where to Find Clients

You’ll likely need to seek out some clients when you first get started. If you have no idea where to look or how to contact potential clients, you’ll probably have a hard time finding work.

Come up with a plan before you start making the transition to freelancing. Tip: Stealing clients from your previous employer is not the best way to find clients.

11. You Have No Project Management Skills or Experience

Freelancers need to be able to manage a project from start to finish.

When working in a corporate environment, you may have only had to deal with certain aspects of a design project. But if you’re freelancing, you’ll need to be able to manage every aspect of the design and development process. This includes outsourcing specific portions of design or development, finding out what the client needs and wants, working within the client’s budget and timeframe, and managing problems that will inevitably crop up.

If you’ve never managed a design project from start to finish, you’ll likely have plenty of missteps on your first few projects. Either get some experience with project management, or read a lot of books, blogs, and anything else you can get your hands on to learn the ins and outs.

12. You Don’t Want to Deal With People

When you freelance, you’re going to have to deal with clients. And while you often have more control over how those interactions go, you’ll still have plenty of face-time with other people. Don’t freelance in order to escape dealing with people.

13. You Can’t Stand Up for Yourself

You’ll almost certainly end up with difficult clients at some point in your freelancing career.

If you can’t be assertive and stand up for yourself, you’ll end up getting walked all over. You need to have the confidence to stand up to a client who tries to get you to work for free, or who tries to bully you into reducing your price once the work is complete.

You also need to be able to handle clients who don’t pay their bills or make unreasonable demands.

14. You Have No Time-Management Skills

Time management can be one of the most challenging aspects of freelancing. It’s also one of the most important. But most designers find it easy to spend too much time on a certain project or aspect of their business (or personal life) to the detriment of other parts of their business or life.

Time management for freelancers consists of two important things: time you spend on your work versus time you spend on your personal life, and time you spend on one project versus another project. Setting regular working hours helps with the first one, even if all those regular hours consist of is only working until 4pm (and getting up earlier to allow yourself more working hours) or only working 8 hours a day (regardless of which 8 hours).

The second one is a bit trickier. Track how much time you’re spending on each project and be aware of what you quoted to the client. Try to estimate how much time each part of the project will take, and then try to stick to that estimate.

15. You Can’t Self-Motivate

This one is closely related to self-discipline, but takes it a step forward. Discipline is all about doing the things you have to do. Motivation is finding the wherewithall to do things you want to do.

There should be things related to your freelance business that you don’t have to do, but want to do or will make your business stronger or more enjoyable.

If you only ever do the bare minimum, you’re kind of missing the point of freelancing and being your own boss. Self-motivation means you can do things above and beyond what’s required to improve your freelancing business.

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

When you work for a corporate design firm, you may never have to deal with clients directly. Clients might not even really know who you are. And that’s okay, because usually they’re more interested in the company than the individual designer.

When you’re freelancing, though, it’s your name that gets tied to your work. That means you need to keep a professional image for the best business results.

If a client Googles your name and all they find are drunken photos of you from spring break, it’s going to damage your reputation. You need to be willing to keep your private life private, and to act professionally in public. Hint: use the security settings on social networking sites to limit who sees what.

17. You Want Paid Vacations

As a freelancer, you don’t get paid vacations. You’ll need to either budget accordingly throughout the year to cover your vacation expenses, or make a big push right before a vacation to get everything done. Of course, the longer your vacation, the more advanced planning you’ll need. And in many cases, you might still have to deal with client emergencies while you’re away.

If you’ve become very accustomed to having four weeks of paid vacation each year, that can be a big adjustment to make. The main thing you’ll need to do is to notify your clients well in advance that you’ll be taking a vacation if you’re going to be gone for more than a couple days.

18. You’re a Workaholic

When there’s no one telling you to stop working at the end of the day, it’s easy for some people to just keep working. This can be just as detrimental to many as not working enough, though, as it can quickly lead to burnout.

If you’re not able to limit the hours you work, you’re probably going to have a short-lived freelancing career. Your work will suffer if you’re overworking, as will your family and personal life. It’s important to set limits to the number of hours you work, and to only take on projects that fit within those time constraints.

One possible solution is to let yourself be a workaholic for three or four days a week, but then not working at all on those other days. This can help to satisfy those workaholic tendencies while still allowing you enough time to recharge.

19. You Don’t Want to Keep Regular Hours

The freedom to work when you want to is one of the biggest draws for many freelancers. The idea of not having to work 9-to-5 is a huge plus. But that doesn’t mean you don’t need to keep regular working hours.

First of all, most of your clients probably do keep regular 9-to-5 hours. You’ll need to be available when they’re working and want to get in touch with you.

The other issue is that if you don’t have a set work schedule, you’ll probably find you have a hard time getting everything done. Figure out what time of day you work best, whether that’s from 6pm till midnight or from 3am till noon and then work those hours. But make sure you’re available during at least some regular business hours so your clients can get in touch with you when they need to.

20. You Don’t Like Being Alone

Freelancing can be a lonely business. In many cases, you’re not meeting clients in person very often. You don’t have coworkers around. And you’re probably working out of your house. If you don’t like being alone for long stretches of time, you’ll likely find you’re not well-suited to freelancing.

Of course, there are solutions to this. You can work out of your house some days (from a coffee shop or coworking space). You can foster non-work relationships so you’re interacting with people when you’re not working. Or you might want to set a regular lunch-date with other friends who freelance or work from home.

The Bottom Line

Freelancing is not for everyone. And there’s nothing wrong with that. So often in creative fields we feel like if we’re working in a corporate environment that we’re somehow not as creative as those who have set out on their own. But there’s very little truth in that.

Freelancing is a career choice and something that every designer and developer has to decide on in respect to their personal situation.

For some, freelancing is a dream come true. But for others, it’s like a prison sentence. Don’t feel ashamed to stick with your corporate job if that’s where you’re comfortable and it’s fulfilling to you.





Written exclusively for WDD by Cameron Chapman.

For the seasoned freelancers out there, what kind of challenges have you experienced and how did you solve them? Please share your own tips below so that future freelancers can learn from your experiences…

