The Freelancer's
Essential Guide to
Business and Taxes
By Justin Gomer
& Jackson Hille
Who Should Use This Guide?

Who Should Use
This Guide?

Because the Gig Economy now occupies up to 40% of the workforce, anyone can utilize it if they either want to know more about the changing economic dynamics of freelancing or how to become a more successful freelancer. Whether you are an Uber driver, a newly minted PhD, a career consultant, a salaried professional, or simply between full-time jobs, this guide will serve as a helping hand while you navigate or start your career in the freelance world.

Why Use This Guide?

Why Use
This Guide?

The inexorable headwind that all freelancers face is instability. Working as an independent contractor on part-time projects or as a full-time freelancer for a Gig Economy startup will always carry a consistent level of risk of your next paycheck being smaller than the previous one. Therefore, this guide is here to provide a concise, yet comprehensive reality check, so that you are fully prepared to protect, build upon and succeed in this new freelance-centric economy.

This guide is educational, inspirational and practical. It will teach you why the freelance economy is growing and how, as a freelancer, you can take advantage of that growth. Additionally, it provides multiple examples of freelance success stories, ranging from the world of journalism to startups. Most importantly, the guide concludes with a step-by-step tutorial to tax season for freelancers, helping you protect what you have earned over the course of a year.

How Should This Guide Be Used?

How To Use
This Guide?

We formulated this guide to work for all categories of workers and freelancers.

For new freelancers, we propose you read the guide from beginning to end, in order to completely understand the framework of the Gig Economy and how you can carve out a workable space for yourself as a freelancer.

For seasoned freelancers, while we think it is certainly beneficial to be familiar with the macroeconomic, business and organizational architecture of the freelance economy, feel free to scroll down to the sections on which you need more information, maybe sections specific to your type of freelance work (e.g. academia). Maybe you just want to check out our tax tips and tax templates. We encourage you to jump around as you wish!

Table of Contents:
  • 1 An Introduction to the Gig Economy
  • 2 The Gig Economy and Its Freelancer Components
  • 3 The Core Values of Freelancers
  • 4 Independent Academics
  • 5 Multimedia Freelancers
  • 6 Freelancing & Startups
  • 7 Concluding Thoughts on the Freelance World
  • 8 The Essential Tax Guide for Freelancers
  • 9 About the Authors and Online Tax Forms
TOO MANY WORDS, TOO LITTLE TIME?
Check out The Essential Tax Guide for Freelancers and try out our Online Tax Forms

introducing The “Gig” Economy

The last decade has witnessed an explosion of independent contractors in the US labor force. New personal technologies allow folks to connect with people who need a lift or place to stay for the night, for example. While ridesharing companies like Uber and Lyft certainly did not inaugurate the “Gig Economy,” the meteoric rise of these and similar companies mark a fundamental shift in the American economy and its workforce. Freelance work offers flexible hours and the ability to work from home. In exchange, companies shed many of the costs of a full-time employee-health and unemployment insurance, retirement benefits, salaried pay, paid vacations, etc.

number of americans self-employed according to the bureau of labor statistics

2015 - 15.5 million
2020 - 60 million
40% of the workforce

The independent contractors that comprise this growing sector of our country’s labor force work in a variety of industries and across all levels of the corporate hierarchy. While ridesharing drivers dominate news headlines, there are also, for example, legions of Ivy-League-educated consultants drawing six-figure salaries working remotely on a per-contract basis throughout the globe. Even within industries, wages and benefits among freelancers vary significantly. For example, a recent study found that the hourly rate of Uber drivers ranges from $15-$53 per hour.

Emerging legal challenges have called into question the legality of how some companies classify and compensate independent contractors. Most notably, Uber is currently appealing a decision issued by the California Labor Commissioner’s Office that established Uber drivers as employees, rather than independent contractors. Should the ruling stand, Uber, which “employs” less than 1,000 people but “contracts” with around 200,000 drivers, could see its overhead rise by an estimated $4.1 billion, annually. Similarly, courts have found several other companies hiring independent contractors liable in a host of other violations including insufficient wages.

Uber
Driver’s
hourly rate:
$15-$53
per hour

As such, attitudes toward the gig economy remain highly ambivalent. For every corporation or contractors praising the flexibility of contract work, the lawsuits of others suggest little more than worker exploitation. And it is undeniable that corporations increasingly turning to contract workers do so first and foremost to increase profit margins.

Despite the emerging challenges to the legality of the manner in which some companies compensate independent contractors, as mentioned above the Gig Economy is undeniably on the rise. Therefore, the purpose of this guide is to help contract workers maximize their opportunities in the Gig Economy and protect their earnings. While some freelancers may very well win classification as full-time employees in the courts, this guide is your safety net, so that if you have to remain a freelancer long-term you can successfully navigate the Gig Economy and make a worthwhile living.

The Reach of the Gig Economy

  • Core Values

    Just how dependent have workers become on freelancing? Recent data from researchers at Stanford University suggests that nearly 60% of workers derive at least 25% of their total income for the Gig Economy.

    Not only is the number of workers taking on freelance work on the rise, the Gig Economy has infiltrated virtually all sectors of the US economy. Here is an overview of what freelancing in a range of industries looks like. For each industry, we offer key strategies independent contractors pursue in order to optimize their careers in their given industry. While obviously different workers bring different priorities to their participation in the Gig Economy, we’ve focused our recommended strategies around a few core values we think most freelancer’s share.

    Recommended Strategies Around Core Values

    1. Maximizing earning potential - Who doesn’t want to make as much money as possible?
    2. Positioning oneself for stable and reliable employment - Generally speaking, freelancing offers workers flexibility in exchange for stability and employment benefits like health care. Yet, most freelancers live lives that require a certain degree of stability and reliability in order to, for example, pay the rent and other monthly bills. Therefore, it is essential that workers entering the Gig Economy familiarize themselves with ways other independent contractors in their industry establish stability in their careers.
  • Academia

    The Great Recession led to draconian budget cuts and hiring freezes at many of the nation’s colleges and universities. As a result, thousands of newly minted PhDs are finishing graduate school and entering a dismal job market. With bills to pay and not enough tenure-track jobs to go around, many young academics are turning to the Gig Economy to provide the economic security no longer available in higher education.

    Last year, The Chronicle of Higher Education, academia’s leading periodical, published Katie Rose Guest Pryal’s, “A Manifesto for the Freelance Academic,” detailing how new PhDs can successfully navigate the new realities of the academic market and “take some power back.”

    Pryal’s Manifesto Consists of a Five-Pronged Mantra:

    1. Get paid for your work - Academia is notorious for demanding young scholars to compete significant amounts of unpaid work--writing, editing, etc.--in order to earn promotions or employment within academia. Pryal says no more. Freelance academics must only take on work for which they are paid.
    2. Live in a place you love with the people you love - Given the distribution of institutions of higher education throughout the country, it was standard practice that new PhDs would move hundreds if not thousands of miles away from their home for their first job. The freelance academic therefore has the advantage of prioritizing location in ways unavailable to traditional academics.
    3. Stop applying to academic jobs - Applications for academic positions are incredibly labor intensive and costly. Given how unlikely candidates are to earn those positions in the current academic climate, freelance academics should focus their efforts on building a career in the Gig Economy.
    4. Remember that you are not alone - There are numerous resources to help build your career as a freelancer, and many other scholars doing the same thing. Build community, share resources and knowledge, and everybody wins.
    5. When you find yourself being lured back to your department for a temporary gig, remember: They’re never going to let you in the club - A temporary job is just that: temporary. While it is easy to fool yourself into thinking that a temporary job will lead to a permanent one, the reality is that in academia it almost assuredly will not. As with #3 on this list, the key here is to focus on building a stable and secure career; part-time adjunct work is not the way to do so.
  • Multimedia

    Writers, photographers, designers, etc. worked as freelancers long before anyone coined the phrase, “Gig Economy.” Yet, with a precipitous decline in what few stable jobs there were in various multimedia fields, workers in these industries have come to rely more heavily, if not entirely, on freelance work.

    The most important tool for freelancers in this field is their familiarity with various forms of media. It is essential, therefore, to use that knowledge and literacy to leverage various technology and media platforms--e.g. Facebook, Twitter, LinkedIn--to promote yourself and your work and build your own personal brand.

    More specifically, the Freelancers Union, which “promotes the interests of independent workers through advocacy, education, and services,” advocated that workers in media fields market themselves as a resource, demonstrate the diversity of your interests and talents, maintain relationships with past clients, and always listen.

    Shea Serrano is one of the more impressive examples of successfully navigating the freelance economy as, in his case, a writer. Serrano has no formal training as a writer. He was a teacher that only began to write seriously in 2008 after his then pregnant wife was put on bedrest, forcing him to find additional work to supplement their income. He found work writing about popular culture--rap music, in particular--for a Houston Newspaper which led to a job at Grantland, which led, most recently to a New York Times Bestselling book entitled, The Rap Year Book.

    In an interview with GQ Magazine, Serrano, when asked about his start as a writer, explained that he literally Googled “work from home jobs” and “writer” was a common answer. He then found a need in that industry--local newspapers hardly covered rap music (a topic he cared passionately for)--and found various ways to leverage his knowledge of the music genre into paid labor and eventually national notoriety. Additionally, Serrano has taken the notion of personal brand building via technology, specifically Twitter, to heart; on Twitter, Serrano constantly interacts with fans in a lighthearted and personal manner, simultaneously increasing his personal brand of authenticity and his customer base of millennials who are constantly perusing social media during their workdays. Serrano’s personal brand building worked wonders during the launch of his most recent work, The Rap Year Book, in which he prompted his followers, through jokes, challenges and giveaways, to make the book number one on Amazon - a strategy that not only worked, but propelled the book to the New York Times Bestselling list, as aforementioned. In short, Serrano presents an example of how, regardless of education or professional training, freelancing can pay enormous dividends for those willing to dedicate their lives to crafting their passions into their professions.

  • Freelancing in Tech Startups

    As with academia, community is imperative, and the internet provides the best resource to connect you with startups looking to hire freelancers, and other freelancers successfully navigating the startup world who can connect you with employment opportunities and help you build relationships that will bear fruit down the road.

    Union IconThe Freelancers Union is also an important resource. Joining the organization is not only free, but the union provides a variety of resources to help connect you with freelance work. They also offer health care benefits members can buy in to! Moreover, the Union publishes a large amount of content on their website regarding securing freelance employment in fields tailored to their membership.

    The success of Kiip--a mobile phone app that enables companies to reward clients for virtual achievements--illustrates the entrepreneurial potential for freelancers to leverage their work into a major commercial success. Kiip was started in 2010 by a then nineteen year-old Brian Wong. Wong began his career as a freelancer, designing ads using Photoshop on his personal computer. His experience freelancing in digital advertising sparked ideas about how to improve mobile game advertising. Those ideas became Kipp, whose clientele now includes Disney, Carl’s Jr, Kodak, PepsiCo, and Sony.

  • Conclusion

    As the above examples illustrate, freelancing combines a host of variables and considerations. Many of these are consistent across fields but many more are specific to your chosen field. What unites freelancers, in our view, is a desire to maximize your opportunities, strengthen your position in the Gig Economy, and connect with other freelancers and organizations in your field that will allow you to build community and networks that will grow your career.

Nearly 60% of workers derive

Get Paid

Academia is notorious for demanding young scholars to compete significant amounts of unpaid work—writing, editing, etc.--in order to earn promotions or employment within academia. Pryal says no more. Freelance academics must only take on work for which they are paid.

The most important tool for freelancers in this field is their familiarity with various forms of media. It is essential, therefore, to use that knowledge and literacy to leverage various technology and media platforms--e.g. Facebook, Twitter, LinkedIn--to promote yourself and your work and build your own personal brand.

RAP

Shea found that local newspapers hardly covered rap music (a topic he cared passionately for) and found various ways to leverage his knowledge of the music genre into paid labor and eventually national notoriety.

The success of Kiip--a mobile phone app that enables companies to reward clients for virtual achievements--illustrates the entrepreneurial potential for freelancers to leverage their work into a major commercial success.

What unites freelancers, in our view, is a desire to maximize your opportunities, strengthen your position in the Gig Economy, and connect with other freelancers and organizations in your field that will allow you to build community and networks that will grow your career.

Classifying Freelancers For Tax Filing

Freelancers are self-employed and therefore required to make quarterly tax payments, in addition to filing an annual tax return.

What sorts of taxes are we talking about?

    Self-employed workers have to pay two kinds of taxes:
  1. Self-employed tax (SE Tax) - to cover Social Security and Medicare contributions.
  2. Income Tax

Are all self-employed workers subjected to taxation?

Essentially, yes. There is, however, one exception, which relates to the profitability of your work or business. Here’s the formula:

How do I make my quarterly SE tax payments?

You’ll need to fill out a 1040-ES form in order to calculate the payment amount. Remember, the quarterly SE tax payments covers the

Social Security and Medicare portions of your tax obligations. Your annual tax return covers the income tax bill.

What form do I use and how do I file my annual return?

Depending on the nature of your contracting and self-employment, you’ll fill out a 1040 form.

What about 1099s? 1099 forms are sent by companies to contractors reflecting the payments the company made for contract work. They are not, however, documents independent contractors submit to the federal government. For example, an independent contractor who has done work with several companies throughout the year will receive a 1099 from each company. They will then fill out a single 1040, reflecting their total freelance income, and submit it to the government.

1099
1040
  • Used to file tax with the IRS. Used by a company to reflect a miscellaneous expense to an individual (which is an earning to the individual for services or work done)
  • 1099 form details are among the listed items

Source: http://theydiffer.com/difference-between-1040-and-1099-forms/

  • Used by a company to reflect a miscellaneous expense to an individual (which is an earning to the individual for services or work done)
  • Does not include details of a 1040 form.

Source: http://theydiffer.com/difference-between-1040-and-1099-forms/

How do I minimize the tax burden?

Two important deductions as a self-employed worker

When calculating your self-employment tax obligation, you can subtract half of the self-employment tax before calculating your tax rate. Follow the example below for someone with a net self-employment income amounts to $40,000:

You can claim half of your SE tax obligation as an income tax deduction on your 1040. Follow this example for a $1,500 SE tax payment.

Taking advantage of both of these deductions will insure that you minimize your tax burden and maximize your earning potential as a freelance worker.