This is part of a series of stories we’re sharing about independent workers. Since February is Black History Month, we’re recognizing the unique stories of Black independent workers. We spoke with Chantay Hadley, a publisher, author, and delivery driver to learn more about her experience as a Black independent worker.

Jessica shares how she knew it was time to leave her day job to focus on her business. If you’re considering a similar move, there’s a lot you can learn from her story.

This post is part of a series focused on the unique stories of independent workers. We spoke with Stride member Matthew about his experience as an Instacart shopper and his advice for other 1099 independent contractors.

Tax time doesn’t have to be stressful. Here are some of the common mistakes that rideshare and delivery drivers make at tax time, plus how to avoid them.

This qualifying life event allows you to enroll in health insurance outside the Open Enrollment Period if you have a low income at or below 150 percent of the federal poverty level. Here's everything you need to know about it, plus how to get covered if you're eligible.

What is Special Enrollment Period? Stride is here to answer that question and all your other SEP related questions. While SEP can be confusing and frustrating, it may also be your ticket to better health insurance after a big life change. Here’s what you need to know.

If you're an independent worker, you'll likely need to pay quarterly taxes. Here's what they are, how to pay them, and deadlines to know to avoid paying a fine.

To figure out if (and how much) you owe in quarterly taxes, you’ll need the Form 1040-ES. Here's what it is and how to use this form to file your taxes.