Menu Join now Search

In It to Win It: Tips for Successful Freelancing

Working from home, being in control of your income, seriously freelancing may be the best job (duh I'm doing it now). However, it's also risky. Follow these tips and you'll be heading toward success instead of want ads.


When I graduated from college, my head was buried so deep in the sand about my career path that it’s a wonder I even joined the American workforce at all. Even better, I found a job at a company I actually liked—so much so that I stayed there happily for seven years. But when I finally became restless and took stock of what I wanted to do next, I realized that I couldn’t find it in an office. I was sick of the daily grind: hitting the snooze button on my alarm clock until the last possible minute, only to sit in traffic, eat lunch at my desk, and feel guilty about all the exercise I wasn’t getting. On top of that, the freelance editing I’d been doing on the side was becoming too time-consuming to balance with my day job, and I knew I’d have to sacrifice one or the other soon. The more I thought about it, the more self-employment seemed like the right path for me to take. 

Three years later, I don’t regret my decision at all. Being a full-time freelancer taught me invaluable lessons about organization, multitasking, self-discipline, and work/life balance. It afforded me the flexibility to work for a wide variety of different companies and meet inspiring people, and it broadened my professional experience in ways that working for a single employer never could have. But that’s not to say self-employment is for everyone—people who thrive on routine may never get used to its irregular hours and erratic paychecks. And even if you think you’re well suited to the freelance lifestyle, you’ll need to make a commitment to approaching it as professionally as you do your full-time job. The following tips will give you a head start.   

Establish a Routine
One of the biggest pitfalls of self-employment is that it’s dangerously easy to be undisciplined about your schedule. Temptation lurks everywhere and in myriad forms—the full fridge, the beautiful day outside, the errands you need to do, and, of course, the Internet. But if you ever want to see a paycheck in your mailbox again, you have to learn to resist all those distractions and focus on the work tasks at hand, particularly when you’re just starting out as a freelancer and are trying to develop a reputation as a prompt, reliable professional. 

To set up a schedule that works for both you and your clients, begin by thinking about what you do in a typical day. Questions to consider include:

  • How many hours of work per week are you hoping to do?
  • What are your clients’ business hours? Do any of them work in another time zone?
  • How many meals do you eat each day, and for how long?
  • How much time do you spend exercising every week?
  • If you have children, how much time do you need to spend each day feeding them, getting them ready for school, playing with them, and so on?
  • If you don’t count working out as your “me time,” how much time do you need for relaxing—watching TV, reading, bonding with your spouse or friends—each week? 

Once you have a better sense of your time requirements, type up a schedule and stick with it. Getting into a rhythm not only will make you a more efficient freelancer, but also will help you through the inevitable moments when you’ll wonder, Am I crazy for doing this? Professional obligations should comprise the bulk of each workday, so be frugal with your allotments for meals and relaxation time—after all, just because you’re working from home doesn’t mean you should be going out for brunch or taking a long siesta every day. However, don’t underestimate the importance of stepping away from your desk for a good workout or a healthy meal, as you’ll find yourself reenergized and more focused afterward. Remember, balance is key. 

Be a Hustler
You never know when you might meet a potential freelance employer, so always remain open to the possibility. Look online or in the newspaper for organizations or clubs devoted to your line of work, and attend their events. Volunteer for companies that can use your services; even if you don’t get paid, you may meet people who can direct you to paying clients. Keep your resume in up-to-the-minute shape and create a Web site for yourself so that you can give prospective clients a link to it the moment they express interest in your work. And when you do have a regular stable of clients, always strive to keep them happy, because they may prove to be your greatest advocates down the road—nothing beats word-of-mouth referrals as a means of securing new gigs. 

Learn to Say No
Saying no to freelance work may seem counterintuitive. Contracting is inherently unpredictable—you never know when you’ll be assigned your next project, or if one of your clients will go out of business, or if the paycheck for your last assignment will even show up at your house—so turning down work when it’s dangled in front of you can make some self-employed people very uncomfortable. (Believe me, I’ve been there.) And while it behooves you to be readily available to your clients, especially when you’re newly self-employed, biting off more than you can chew during your workweek won’t help anyone involved. If you’re rushing through projects because you’re overloaded, the chances of your doing sloppy work will increase, which in turn will risk your employers’ disappointment in your subpar performance. Producing better-quality work at a slighter slower pace, even if that means sacrificing a little bit of income, will ultimately keep your clients happy and keep you in business (not to mention sane). 

Avoid the Money Pit
If you’re accustomed to having a fixed amount direct-deposited into your checking account twice a month, the “patchwork paycheck” can be a rude awakening. Not only are many companies not required to pay their contractors at regular, predetermined intervals, but they often wait months before cutting freelancers’ checks. Given these potential delays, every day you wait to invoice a client means another day you’ll wait by a mailbox filled with nothing but coupons. Even if you’ve submitted an invoice promptly, you’ll generally end up needing to follow up on it; if you haven’t received payment within thirty to forty-five days (unless the company has specified another payment time frame in writing), send your client an email that includes the original invoice and a polite reminder that you’re still waiting for your check. Always save any money-related written communication that you send or receive—you don’t want to wind up empty-handed in small-claims court someday. 

Getting used to a new tax structure is another big change for people transitioning from full-time employment to contracting. As a self-employed person, you’ll be responsible for paying estimated taxes (based on your projected annual income and your eligible deductions) four times each year. The bad news is, you’ll have to set aside about one-third of each freelance paycheck you receive in order to cover those quarterly payments to the IRS. The good news is, freelancers are able to deduct all kinds of expenses, including work-related meals, office supplies, some transportation, and home-office square footage. Get in the habit of saving your receipts for every purchase you suspect you can write off, and when it comes time to estimate your annual taxes, consult a certified accountant about exactly what deductions you’re eligible to take. 

You’re Not the Boss of Me
Sometimes it seems as if the expression “the grass is always greener” was invented by people struggling with career indecision; there’s no doubt that neither freelancing from home for a variety of clients nor working onsite for a single employer is ideal all the time. Nine-to-six officegoers love to live vicariously through the work-from-home crowd; they never get sick of making comments like, “It must be so nice to go grocery shopping on Tuesday afternoons” and, “I can’t believe you only have to commute from your bed to your desk.” And even happily self-employed people who frequently accuse their full-timer friends of “selling out” or giving in to The Man still fall victim to the occasional pang of jealousy when they hear about those people’s amazing benefits packages or three-week paid vacations. Either way, you can’t really know how the other half lives until you’ve tried it, and while the odds are good that almost all self-employed people have held a full-time job at one point or another, the opposite can’t be said of most Americans—though that may be changing. For the 10.2 percent of the U.S. labor force that was unemployed as of October 2009, taking on a few contract gigs from home is probably looking a whole lot better than another year of ramen and daytime TV.  

More You'll Love