Be your own boss … set your own hours … choose your own clients. The allure of freelancing is very strong for many of our career coaching clients, particularly those considering a career shift.

If working as a freelance professional sounds appealing, you’re in good company. According to a recent survey commissioned by Upwork and the Freelancers Union, entitled Freelancing in America: 2015, nearly 54 million Americans are engaged in some sort of freelance work. That equates to 34% of the U.S. workforce.

The term “freelancer” casts a wide net, encompassing a variety of independent workers. For some people, freelance work may involve supplementing a traditional “day job” with a side gig to augment their income — think Uber drivers. Others have traded in their corporate badges for a home office, where they pick and choose clients and projects, building a lucrative career along the way.

insights for freelance work

The Freelancing in America study categorizes today’s “freelance workers” as follows:

  • Independent contractors (36%)
  • Moonlighters (25%)
  • Diversified workers (26%)
  • Temporary workers (9%)
  • Freelance business owners (5%)

According to Forbes, the top ten careers for freelance work include: Marketing, Business Project Management, Web Development, Writing, Accounting, Insurance Inspection, Teaching/Tutoring, Social Media, Graphic Design and Administrative Assistance.

But before rushing into your boss’s office with a letter of resignation in hand, our career coaches recommend exploring the potential benefits and drawbacks of working as a freelancer.


There are plenty of advantages to freelance work:

Unrivaled flexibility — You are your own boss, which means you report directly to … you! Decisions about where to work, what hours to work, what to wear to work … are all yours to make. Of course you’ll still need to respect deadlines and deliver clients’ projects within an agreed-upon timeline, but as a freelancer, you have the luxury of budgeting your time according to your commitments, obligations and priorities.

Increased happiness — Whether it’s due to an increased ability to strike a work-life balance, the lack of typical office stressors or a sheer passion for what you do, freelance work tends to correlate with an increased level of happiness.

Financial rewards — According to the Upwork survey, 60% of the freelancers said that they earn more as freelancers than they did before freelancing. Part of the reason: You set your own rates based on what you deem to be your current market value. Moreover, you earn what you make. No profit-sharing between you and a company or agency as middleman.

Demand — America’s workplace is changing, and the freelance landscape stands to gain from the shift. According to the Intuit 2020 Report, which examined trends likely to affect consumers and small businesses in the current decade, more than 80 percent of large corporations plan to “substantially increase their use of a flexible workforce in coming years.”


Of course, to every yin, there is a yang. By its nature, freelance work comes with its share of challenges, among them:

Unpredictability  If job security is uncertain in a traditional work environment, take it down a few more notches in the freelance world. Clients may need your services one day, and manage just fine without them the next. Feast or famine is often the name of the freelance game: You may experience periods of time that put your task-juggling skills to test, and others that lead to a drought — in work and income.

Lack of support  As a freelancer, while you are your own boss, you are also the marketing, accounting and information technology departments. Whatever your line of business, you will likely have to spend a good portion of your work time marketing your brand and services — on an ongoing basis. Keeping accurate work logs, sending client invoices and collecting payments are all your responsibility, which can pose a challenge for creative types who would prefer a root canal over managing finances.

Isolation — In a traditional office environment, for better or for worse, people (co-workers, your boss, the mail clerk, etc.) are around. Our career coaches emphasize that as a freelancer, you need to be especially proactive in developing and maintaining a professional network. Depending on your field, this may also mean seeking opportunities for professional development — and footing the bill to attend conferences or workshops.

Tax burden  The Internal Revenue Service (IRS) requires that people who earn more than $600/year from someone other than their employer report (and pay taxes on) that income. If you work for multiple clients, that could mean reporting income from a variety of sources, and having enough reserves on hand to pay taxes owed come April 15. Self-employment taxes (including Social Security and Medicare taxes) also come into play at certain income levels.

pros and cons for freelance careers

Career Coach Insights: weighing the possibility of freelancing in your future

Freedom and flexibility were tied as the number one driver for freelancing, according to the 2015 Freelancing in America survey. Other freelancers cited the ability to pursue their passions, build their skills, broaden their experiences and take advantage of opportunities in specific industries geared to independent workers.

While enticing, these advantages don’t make freelance work right for everyone. It requires a high degree of discipline and accountability that many people find come more easily in a traditional, structured work environment.

Freelancers are optimistic about the demand for their work, with 83 percent of respondents saying that “the best days are yet to come.” Will you be joining their ranks?  

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