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5 Tips to Succeed as a Freelancer


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Freelancing sounds like the burnt-out worker’s dream come true. Freelancers are able to set their own hours, choose their own jobs, and be their own employers. Unlike some type of fantasy, however, freelancing is indeed very real work that comes with many challenges, in addition to its obvious benefits.

A wise step into freelancing requires a careful self-examination of your personality, strengths, and weaknesses to ensure that self-employment is right for you. Before you take the leap into freelancing, make sure you’ve done your homework so that you can be successful and self-actualized in your endeavors.

What Is Freelancing?

Freelance workers (or independent contractors) are employees who are not committed to any particular company or agency for the long-term. They provide goods or services to companies in exchange for a pre-determined payment, usually specified in a contract or bid.

Although freelancers hail from many different educational and career backgrounds, the work most easily lends itself to positions that provide an easily measurable good or service. For instance, many freelance workers are writers, designers, artists, event planners, or consultants. Freelance workers usually set their own schedules, pay their own taxes, and cover their own overhead in exchange for working independently from traditional employment.

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Important Considerations

Freelance work isn’t for everyone – the most successful at it are those who thrive with independence and flexibility. If you’re considering freelance work, you need to be a self-starter and risk-taker, and you need to be comfortable with the following realities:

  • Paychecks Are Variable. One of the only things you can count on as a freelancer is an uncertain paycheck. The nature of working by contract means that there are meager months and months of great reward. You can mitigate the effects of this uncertainty by keeping a well-stocked savings account to tap into as needed, and by being able to embrace risk and challenge. You also have to plan on spending some of your paycheck to keep your business afloat, which may further reduce your take-home totals.
  • Freelancing Is a Business. Even if you’re a great writer or musician, freelancing may not be a good fit for you – you need to feel comfortable setting boundaries and making assertive choices to safeguard your income. If you’re not good at the tasks that accompany business ownership, such as invoicing, financial tracking, and chasing down payments, then it may not be a good fit for you.
  • Flexibility Is Key. Flexibility is both a benefit and a drawback of working as a freelancer. The flexibility may allow you to pick your kids up from school on time or start a pot roast mid-morning, but it may also mean that you have to drop your family responsibilities at a moment’s notice to assist a client. Many freelancers find that the benefits of increased flexibility counteract the annoyances, but a varied schedule may not work well for everyone.
  • Clients Are Your Boss. If you want to go into freelancing because you hate your boss, you may be dismayed to realize that you suddenly have many bosses. Each client becomes a manager and employer who expects excellent service. If you dislike your traditional job because you dislike authority, freelancing cannot provide the escape you long for.
  • Freelancing May Not Pay Well. Many folks make the move into freelancing after working in their respective industries for several years. However, many actually take a cut in pay compared to their peers in traditional employment arrangements. In addition, you won’t be eligible for any company-based benefits – which are usually worth thousands of dollars.
  • Working From Home Doesn’t Mean Not Working. People who work from home often put in more hours than people who work in a normal office setting. You may have to work just as hard as a freelancer – if not harder – than you work at a traditional job.

Many freelancers find that all of the aforementioned drawbacks are worth the increased flexibility and personal fulfillment that comes with the transition. You just need to carefully weigh whether the benefits outweigh the drawbacks according to your personality and the needs of your family.

Important Considerations Successful Freelancing

Tips for Successful Freelancing

Above all, a successful freelancer knows how to run a business. A passion for writing or art isn’t enough to make it in a cutthroat world that functions with contracts, low-ball offers, a quick succession of innovations, and fierce competition. To make it as a business, you have to think like an entrepreneur and manager, even if your passion and skills aren’t necessarily in those arenas.

1. Diversify Your Portfolio

There’s a reason why financial advisors suggest a diversified investment portfolio. A portfolio that includes multiple investments inevitably has low performers, high performers, and performers in the middle of the pack. When you’re a freelancer, a portfolio of active contracts and work can provide a measure of stability when one or more income streams dries up. A freelancer needs to prepare for the ups and downs of contract work by buffering against lost or poorly performing gigs with multiple streams of income. For instance, if you’re a writer, make sure you have a portfolio of websites, schools, or companies that you write for rather than putting all of your financial security into just one contract. And if possible, diversify across industries, as well.

2. Streamline Your Overhead Time

One of the main challenges of freelancing is that you must spend hours each week on overhead, which you usually can’t bill for. These hours are often spent invoicing, writing contracts, and pitching ideas to clients. If you’re planning on a 40-hour work week, it’s probably a good idea to count on having only 30 billable hours each week, simply due to the sheer volume of clerical and managerial work required to run a successful business.

There are a couple of ways to combat or account for this inevitability:

  • Be Efficient. Do whatever you must to make all of your un-billable hours as simple and straightforward as possible. Use invoicing software such as Freshbooks, and organize your contacts so you don’t waste valuable time. As opposed to other areas of your business, efficiency with overhead is key so you don’t use all of your time on tasks that don’t translate into dollars. When it comes to these tasks and others that you can’t easily monetize – such as meetings or continuing education obligations – it may be wise to set aside an entire day each week to take care of them.
  • Count Un-Billable Hours as Part of Your Bid. Try to work the cost of overhead into some of your bids, as long as you remain competitive in your pricing. If you have 30 billable hours and 10 un-billable hours of work each week, then you may want to consider increasing the price of your work by 25% to account for the hours lost to overhead.

3. Build Your Support Team

Freelancing can prove to be lonely at times, especially if you work from home. You need to build a solid support team and make time for friends during the week so you don’t burn out. The people you rely on ideally should be able to offer different perspectives on your work and help with managing your daily tasks.

  • Count on Outsourcing. Don’t waste any of your valuable time with tasks you don’t know how to do or aren’t very good at. For instance, if your computer breaks down, you could spend an entire day trying to troubleshoot it by yourself – or you could have a PC repair company troubleshoot it within an hour. Have a list of people to call when you need help with anything business related. It’s worth the money, and you can write it off on your taxes too.
  • Connect With Other Freelancers. Freelance work can feel isolating and confusing, especially when income ebbs and flows and you’re not always sure what to do. Join a support network, such as Freelancer’s Union, for advice, assistance, and additional networking opportunities. You can also find local help on, and answers to your tax- and employment-related questions on the government’s Small Business Administration website.
  • Consider Coworking. If your main challenge with freelancing is the sense of isolation, consider coworking as an alternative to working from home. A coworking arrangement allows you to rent office space for a small fee so you can mingle with other freelancers, share ideas, and go through the motions of traditional work life.

4. Learn to Be a Referee

You need to become an excellent setter of boundaries when you work as your own boss – boundaries for others, and for yourself. Make sure you formulate rules about how you spend your time, including your night and weekend hours. Give yourself time for vacations too.

It is also important to clearly define certain boundaries for those who would use your services:

  • You’re Worth the Money. Freelancing is the land of low-ball offers. An offer of $5 for an hour-long gig is ridiculous – don’t take it. You’re worth the money, and if you’ve taken the risk of going out on your own, you deserve the reward of a decent payment.
  • Don’t Work Hours You’re Not Paid For. Once again, bill for everything. If a potential client suggests that you forgo billing for certain aspects of a job or wants a substantial amount of meeting time “off the clock,” you need to say no.
  • Don’t Answer Your Phone and Email All the Time. Once you set limits on when you do and do not work, you need to feel comfortable telling your clients no. Enforce your no-call times. If you’re a good enough worker, your clients cannot begrudge you for abiding by your own rules.
Provide Self Benefits

5. Provide Yourself With Benefits

You need to have a plan for benefits. As a freelance worker, you won’t have access to health insurance, disability insurance, or life insurance through any of your clients. You also won’t be able to count on the security of regular paychecks. Each of these challenges is surmountable, however, as long as you plan ahead.

  • Provide an Income Buffer. First of all, account for the ebbs and flows of income by having between three and six months’ worth of savings in your bank account. This buffer can help in months that work is scarce, and you can build it back up when the work pours in again. Additionally, you should start and build up an emergency fund.
  • Insurance Coverage. Insurance should be considered part of the cost of doing business. It’s wise to seek out medical, short-term disability, and long-term disability plans as a bare minimum of coverage. Depending on your age and health, it may also be prudent to purchase dental and vision insurance. Freelancer’s Union has options for dental, medical, and vision at a group rate to residents of participating states. Also, consider health plans through your state’s (or the Federal Government’s) health insurance marketplace. You might qualify for subsidies that you wouldn’t get applying elsewhere.
  • Retirement Benefits. Finally, make sure to plan for your future. The government provides nice tax breaks for both traditional employees and freelancers who contribute to traditional IRAs and Roth IRAs, and as a self-employed person, you can also open a SEP IRA or an individual 401k plan. Which one is right for you and how much you contribute depend on your personal and business circumstances. In addition to your own research, a financial advisor can help you make these decisions, and an accountant can help you understand the tax implications of any avenues you’re considering.

Final Word

If you’re thinking about making the leap to a freelance career, don’t look at it as an escape from the rat race of traditional employment. Freelancing comes with significant risks and challenges, and you need to be sure you’re prepared for the inevitable difficulties that arise. However, with an independent personality, a little planning, and a lot of creativity, you may find that freelance work is the perfect mixture of flexibility and self-fulfillment for your career path.

What additional tips can you suggest to thrive as a freelancer?


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Mary McCoy, LMSW is a licensed social worker who works closely with individuals, families, and organizations in crisis. She knows first-hand how financial choices can prevent and mitigate crises, and she's therefore passionate about equipping people with the information they need to make solid financial decisions for themselves and their loved ones. When Mary isn't on her soap box, you can find her hiking, jogging, yoga-ing, or frolicking with her family.