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Building Your Own Benefits as a Self-Employed Person

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Being your own boss means that you should ideally be providing yourself with employee benefits, which can be daunting. After all, having a retirement package, health insurance, paid vacation time and an HR department to help is a major reason why people stay traditionally employed. As your own boss, you need to figure out how to fund paid time off, insurance, and pick the right retirement plan. As a sole proprietor, you need to figure out what accounting and tax options might benefit your situation the most. Optimizing your financial strategy might significantly improve your short- and long-term outlook while making it easier to focus on your writing.

Join us for a panel discussion with Rafael Espinal, executive director of the Freelancers Union, and Lee Frisari, tax consultant at Brass Taxes, moderated by author Erin Lowry.

A Q&A will follow the presentation; you can pre-submit a question when registering for the event. A recording will be made available for those who cannot attend live.

The event will take place via Zoom with automatic closed captioning. To request any other accessibility features, please email and we will make every effort to accommodate.


Rafael L. Espinal Jr. serves as the executive director of the Freelancers Union. Born and raised in Brooklyn, New York, he started his career in public service as a New York City Council Member representing the 37th District. During his tenure, Espinal demonstrated his dedication to supporting working-class communities by championing legislation focused on workers’ rights, sustainable development, and environmental justice. In January 2020, he transitioned from the City Council to the Freelancers Union, where he has been instrumental in expanding the organization’s reach and impact, advocating for the rights of the growing independent workforce. Under his leadership, the organization has made strides in providing its members with valuable resources and support networks, lobbying for policy changes that benefit freelancers, and promoting public awareness around the importance of the freelance economy.

Lee Frisari is a tax consultant at Brass Taxes. When not at the finance and tax desk, Lee is usually playing percussion instruments or playing in nature. He is a musician and meditation coach, and has freelance hustled as a grant writer, carpenter, fisherman, tour guide and LGBT educator/advocate. He currently resides in Los Angeles, California.

Erin Lowry, moderator, is the author of the four-part Broke Millennial series, including:Broke Millennial, Broke Millennial Takes On Investing and Broke Millennial Talks Moneyand her soon-to-be-published Broke Millennial Workbook: Take Control and Get Your Financial Life Together. Erin’s been featured in The New York Times, Wall Street Journal, and on CBS Sunday Morning, CNBC and The Rachael Ray Show. She has written for The New York Times, USA Today, and is a columnist for Bloomberg Opinion. She publishes a twice-weekly Substack newsletter called Broke Millennial with Erin Lowry.

Special Thanks to Our Supporters and Partner Organizations

With support from the National Endowment for the Arts, Penguin Random House, and our donors, the Authors Guild Foundation is pleased to make Business Bootcamps for Writers free and open to the public.

Several writers organizations have partnered with the Authors Guild Foundation to help shape these programs. Our deepest appreciation to these organizations.